101 Leadership and Life Lessons for My 11-Year-Old Self

1 hr. read

“And bad mistakes
I’ve made a few
I’ve had my share of sand
Kicked in my face
But I’ve come through”

I trust you’ve recognized these lyrics from “We Are the Champions” by Queen in 1977!

That very same year, my eleven-year-old self was trying to figure out his role in life. Would I become a secret agent, a pilot, or an explorer?

Unaware of my achievements and mistakes to come, at least I already knew I was quite attracted to roles requiring strong leadership.

By leadership, I mean the attitude, the mindset, the way of life that brings people together and keeps them engaged.

Fast forward forty-five years and thirty years working in and with Corporate America. 

I’ve learned a lot about leadership and corporate life in general. I’ve seen what worked and what didn’t. I remember the hundreds of great – or not-so-great – leaders I’ve worked with. 

So, as I’ve come to appreciate what stellar accomplishments are made of, let me share my view on their most significant enabler: leadership. I’ll do it using my own lens, with values and principles that are mine.

Sometimes, I wish I’d understood these when I was getting started. But isn’t learning and improving what the whole journey is all about?

Your view of leadership excellence might differ and that’s OK. We’re all conditioned by our own environment. Still, I trust you’ll find value in these 101 leadership and life lessons

It’s all part of the modest contribution of The Product Sherpa: helping leaders who want to progress and achieve stellar results through proper levels of engagement.

Now some warning. It isn’t my typical two-minute-read article. You’ll likely need more than one hour to review this whole post. So, make sure you bookmark this page to return to it at your leisure.

For your convenience, I’ve grouped the 101 lessons into five core categories:

You can also go to the table of content and navigate to each lesson individually. Each of them is a quick read. You have probably seen most of these already, but they’re now in one place. Enjoy and spread the word if any of these resonate with you!

CORE VALUES

core values

1. Be obsessed with customer problems.

“You need to get to the future, ahead of your customers, and be ready to greet them when they arrive.”

This quote from Marc Benioff, CEO of Salesforce, is one of the best I’ve come across on this topic. It all starts and ends with the customer, indeed.

Today’s leaders need to know how to identify and translate customer problems.

Great leaders listen intently and let customers articulate their problems in context and their own words. They rely on their product teams to apply such customer–centricity during product discovery and execution. They keep driving decisions with the customer’s and the company’s best interests in mind. It’s the only way to build products that will delight your customers while making economic sense for the company.

Such customer orientation is an absolute must for any business leader to succeed. Of course, most CEOs focus on the customer, but the ones with a product management mindset go the extra mile. They build intimacy with what’s on their customers’ minds. They anticipate what will delight them once the right solution is there.

2. Be authentic and engage.

In many companies, managers now hold the key to establishing more authentic leadership. They’re reaping the associated benefits of more engaged teams:

  • It all starts with truly understanding what’s motivating their team members and using this knowledge as the base for their proposals.

  • They know how to persuade team members by embedding their arguments in compelling stories that speak to their audiences.

  • As importantly, they’re not operating in a vacuum and don’t fear the positive confrontation of ideas. They’re not superheroes who get it right all the time. They need forums to exchange and build from there.

  • To enable such forums, they nurture learning communities. All participants safely exchange and enrich the pool of ideas.

  • Teams value the sharing of critiques and challenges with their leaders. It’s the foundation for inventing and generating more impactful solutions that people can relate to.

Although not pervasive, authentic leadership is picking up in the corporate world, and the movement keeps growing because everyone wins: goals are clear, teams are engaged, and results are strong.

3. Put real effort into your best vision and mission.

As a leader, you have the moral obligation to drive the vision for your business. In other words, where the company is heading on a time horizon. To illustrate what a great vision and mission can be, let me use Tesla’s example:

Tesla’s Mission

“To create the most compelling car company of the 21st century by driving the world’s transition to electric vehicles.”

Tesla’s Vision

“To accelerate the world’s transition to sustainable energy.”

Their mission clearly states Tesla’s focus. How they want to compare with others, and what their timeframe is. It’s bold yet credible.

Their vision is taking it to the next level and is quite inspirational. It reveals that Tesla is much more than another car company. They want to bring their expertise in sustainable energy to more domains to make a more profound impact.

A solid mission and vision are undoubtedly the best foundation for a great business.

4. Learn from failure and build resilience.

For a while, experts have been arguing about how necessary planning is. My take is that it’s worth it. Despite the pain, the alignment you gain from planning is priceless. But planning needs to come with the ability to monitor execution continuously and timely revise the plan if the results are not the expected ones.

Resilience is about progressing on your goals even if things do not go as planned.

I’ve seen the most resilient teams sticking to their vision even when things repeatedly didn’t go as planned. The past, for them, was more guidance than resentment. The team’s experience from a series of failures was helpful when making bold, decisive moves came.

Here are a few of the fundamental principles we kept top of mind when things didn’t go the way they should:

  • It takes a LOT of minor setbacks to influence the big picture.
  • Failure is OK. Own it, learn from it and expand from there.
  • When trouble looms, make sure you ask for help and seek advice.

And by the way, the question is not whether we’ll fail or not, but more about how we will approach failure and what we’ll learn from it. Failure is an opportunity to learn, progress, and improve.

5. Don’t wait for others to create meaning for yourself.

Some might argue that life has a meaning that is superior to what humans can even comprehend. 

Possibly, but with my business hat on, let me respectfully disagree. 

We, humans, invented that concept of meaning. And that’s great news! Instead of wishing that mother nature or others will bring you meaning on a silver plate, you can build it for yourself.

The secret to creating more meaning for yourself is to move out of “auto-pilot” mode and be fully present and mindful.

It can be as easy as picking a few minutes in your day and try to experience them as if they were totally new. Usually when doing something for the first time, we’re quite present and engaged. By fully living the moment and being 100% present, you’ll notice things you didn’t when you were on auto-pilot. 

You’ll capture ideas and opportunities you wouldn’t have noticed otherwise. They all add up to creating purpose and more meaning that you can actually control.

6. Have an exponential mindset.

We live in a world of exponential evolutions. Look around you; everything is accelerating. Yet, the way most of us keep thinking is still very linear. Such incremental thinking is what’s causing us to get blindsided eventually. 

An exponential mindset will help you anticipate accelerating mutations and ease the transition from one paradigm to the next. As Mark Bonchek highlighted in a 2016 HBR article on this topic:

 “The incremental mindset focuses on making something better, while the exponential mindset is makes something different.”

One way to get started with it is to assume that what took five years to happen will now only take one year. So, look at your market or category, imagine the consequences of such acceleration, and what impact it would have on your plans.

7. Balance big audacious goals with Zen.

Let me share what I found works for me:

I make a point always to have one impossible goal going on. Big plans stimulate my creative and critical thinking. Not only do they get my adrenaline up, but they are extremely rewarding, too, even if I fail.

I’m liberal with goal planning and continuously consider my options. There is such a thing as a Plan B, and it will likely” lead you to Rome too.” So I make sure I consider different scenarios and regularly assess the state of progress against the goals. Course correction is always acceptable – actually, the earlier, the better.

I balance my impossible goal with periods of absolute randomness. I can spend hours with no predetermined objective. Letting my mind and body wander and doing just what I love. It’s where I make my best discoveries.

Being only bold-goal-driven would make me a terrible person. But I also know that becoming 100% Zen is impractical. 

By applying these balancing principles, you can start to integrate better two radically complementary approaches to life: goal-driven vs. Zen. 

You’ll get the excitement of working towards outstanding achievements while enjoying the beauty of this world – yes, there is some! – whatever path you take, wherever you end up.

8. Demonstrate humaneness and courage.

I have found the best way to assess where you stand on these two core values is to reflect and ask yourself the following questions:

  • How good are you at demonstrating respect for those you interact with? Don’t limit this to your team. Think of peers and even competitors- adversaries.
  • How much confidence and decisiveness are you projecting in the face of adversity and challenges? 
  • How well are you mobilizing teams despite mounting pressure in times of changes and uncertainty?

With practice, you build courage by stopping creating issues that don’t exist. You realize the present inconvenience will pass and get sorted out. Here’s how I have progressed there:

  • First, I’m training my mind to recognize when uncertainty hits. I avoid jumping to conclusions (positive or negative, as I highlighted above).
  • Second, I’m consciously accepting the situation without losing my nerves. It’s here, and that’s a fact.
  • Third, I’m trying to establish a state of non-resistance. Good or bad, reality can’t be undone, and resisting it will not help. Of course, if someone is stepping on my toes, I should defend myself. But accepting it has occurred will drive a better answer.

9. “Humility” is your magic sauce.

To help your team get to the right level of critical thinking and have them truly solve the problems at hand, you need to create the right kind of culture and environment. That’s where some form of humility comes into play.

I don’t mean you should have a “low opinion” of yourself. Instead, make it clear to others that you don’t have all the answers. Recognize the expertise where it is and invite team members to engage in problem resolution with the same mindset. The expertise that lies in your teams is your goldmine. That’s how you can solve the most challenging problems. So, make sure you leverage the collective brainpower.

Interestingly, such humility can co-exist with very different leadership styles and personalities. A fascinating combination is probably Steve Jobs 2.0 (after getting fired the first time from Apple). It shows that ‘humble narcissists ‘can become the best business leaders. Despite his “aggressive” style, Steve Jobs clearly understood the power of the team. 

“Great things in business are never done by one person. They’re done by a team of people”. Steve Jobs

10. Be constantly willing to improve.

The best leaders never stop learning! Your worst enemy is complacency. 

No matter how overwhelming or painful it can be, you should genuinely try to understand people and situations by asking practical probing questions to get to the bottom. 

Along these lines, the best leader is never afraid of asking for help to ensure continuous progress.

This quest for improvement also comes with a structure of habits carefully built. Routines and rituals define us. We are what we do! I know I’m a runner, an author, a Sherpa because that’s what I’m doing – almost – every day. I “just” Do It!

11. Be optimistic yet selective.

Even in the most screwed situations, seeing some good can be a life savior. It helps you persevere and reach your untapped potential. 

As you try to identify these upsides, you’ll become better at solving problems and reap greater rewards than most.

A lot is going out of control around us, however. So, the key to keeping your sanity and maximizing impact is to focus on what you can control and learn to be indifferent to the rest.

Selectiveness in such a noisy world was the hardest for me in 2021. Yet, I’ve kept progressing by limiting my exposure to social media and general news and seeking more targeted insights.

I’ve made the best out of the past year, choosing problems to address and taking a bold and positive approach to their resolution. 

12. Be an unconditional giver.

We’re all used to seeing negotiations and give-and-take in our relationships at work. Yet, the best leaders know they’re demonstrating formidable strength by giving without expecting anything in return.

So start by giving more than you take. Share with others. Give them your time, your thoughts—no need to be the smartest in the room. Just kindly and genuinely share. Good things will come from it.

Such an unconditional approach might be unsettling initially for those who are used to constant negotiations. Still, it is the key to building the most robust relationship and winning allies for life.

13. Establish vulnerability-based trust.

A dear German friend introduced me to the work of one of the best experts in the field, Brené Brown. She further associates vulnerability with courage and, therefore, the ability to lead.

Brené Brown recognizes that vulnerability can be uncomfortable, and it takes courage to expose yourself. Still, leaders need to “create a culture where discomfort is normal.” When things become edgy, you’re doing what you need to be doing.

Showing vulnerability is first about investigating and accepting imperfection. You’re willing to own your mistakes and ready to handle criticism. You’re also refusing the conformity that still prevails in the workplace.

As such, when you’re willing to show vulnerability, failure becomes an option. With it, you are opening the door to innovation and outstanding outcomes.

Along these lines, you must be unequivocally clear that anyone’s shortcomings, fears, and failures won’t be used against them.

It has to be mutual. It can feel very uncomfortable, but that’s the only way to build genuine trust.

14. Don’t be a victim, ever.

This one saved me more than once. I learned to take responsibility for everything that happened to me at work – and in my personal life.

It’s been hard, especially when I perceived some decisions or events as unfair. Yet, I never resorted to blaming or being a victim. Instead, I focused on shaping my reality and forging my destiny.

15. Meet new people, experience more places.

The pandemic threw a monkey wrench into many of our travel plans and dreams of exotic destinations. Yet, even in a more virtual way, 2020 was one of the richest years I’ve had when it came to meeting new people. As for physical activity, be deliberate about it, and it will soon become second nature.

I always keep my dog in mind when I’m about to meet new people. Romeo is an adorable little Boston Terrier who expects magic in every encounter. Although it doesn’t always end up that magical, sometimes it does, and it pays off.

Meeting new people and discovering new places have increased empathy, emotional intelligence, and creative thinking. If you want to find the interesting side of others and get something valuable from them, don’t be afraid to engage with them and ask open-ended questions. Chances are you’ll capture someone’s frame of mind, dig deeper and learn a lot.

So, build the habit of reaching out, making new connections, and reconnecting with your network. 

Meet at least one new person, rekindle with two people in your network and go to one new place weekly. It doesn’t have to be far. You can keep exploring your district, your city, your county.

16. Forge strong discipline.

The following questions can help you gauge better where you stand with discipline:

  • How strongly are you preparing your teams to address unknown and uncertainties?
  • What are you ensuring to adequately reward your best players?
  • How clearly are you articulating the consequences of poor performance?

17. Step back, reflect, and think.

You don’t need a therapist to do so. You don’t even need to adopt fancy techniques of meditation. Just spend “me” time with your thoughts and dig into what you haven’t fully processed yet.

A trigger might help, like reading a book, watching a movie, listening to a song, or meeting that old friend or previous colleague.

But once you develop your mental clarity, you better understand where you are going. You also add meaning to your actions and your work.

So if you want to be at the top of your game, ensure you’re not just spending all your energy on sole productivity. 

18. Know how to apologize.

Here’s some real-life experience that you might find helpful:

A few years ago, I was the General Manager of a business unit developing audio software. We had just done a gate review, where all the indicators the team had communicated were green.

My boss, the Sr executive VP, was quite pleased with the status, and we moved into the next development stage. He happily shared this outcome with the rest of the executive team.

The next day, my engineering leader came to me, extremely embarrassed. He shared a batch of unsolved issues, a.k.a. bugs, that fell through the cracks. The status was not green; it was purple red!

I shared my disappointment but also apologized to the team. After all, if our process didn’t catch such issues, there was a flaw. A flaw that I – as the leader – carried some responsibility for. We needed to deconstruct the process and fix it for good.

In addition, and importantly, I asked for an immediate plan of action to mitigate the situation of the newly discovered bugs. The team worked on it at night and gave me their analysis and proposed action plan that we reviewed first thing in the morning. 

At that stage, I had enough elements to go and break the news and what we were doing about it to my boss. Guess what I did?

I reached out to him. Then, I apologized for the oversight. I made NO excuse, expressing we would get to the bottom of the process flaw to fix it for good. Finally, I shared the immediate mitigation plan to address the newly-found bugs.

It didn’t go very well. At first, my boss felt betrayed and quite disappointed. But eventually, after some time, he acknowledged that our approach was demonstrating drive and ownership. He even thanked me for my leadership on this.

The moral of this story?

Of course, don’t fail too often, and don’t over apologize! But the next time things don’t go as planned, make sure you own the problem, discover its roots, and drive its resolution.

19. Focus on sustainability.

Here are a few approaches you can take, from the most practical to the visionary ones:

  • Eliminate plastics and other non-sustainable materials from your product and packaging – as much as possible. If you can’t avoid plastics, work on using post-consumer recycled plastic, not virgin materials, and avoid single-use plastics.
  • Think smaller in how you design your products’ inner parts and focus on a smaller footprint. Every component counts: from electronic circuit boards to screws, magnets, and accessories.
  • Focus on renewable energies for each part of your operations. Look at ways you can influence the shift away from fossil energies in your factories or offices. It’s trickier for your supply chain, so focus on which transportation will be the least impactful. For example, do you need to expedite with airfreight, or can it come on a slow boat from China?
  • Participate in reforestation and afforestation projects. It is a longer-term shot, but you don’t need to create it all from scratch. Your company can join existing initiatives that already have a proven impact. Just Google it! You’ll be amazed at how many projects are at your fingertips.

These are just a few ideas to get the ball rolling. Future generations will thank you for that! Keep it going.

20. Slow down to avoid burnout.

Here’s a little experiment I recently did that can shed some light on how to adjust your speed best:

I’m running the same 7-mile route along the coast in Santa Cruz two to three times a week. In the beginning, I used to push as hard as possible, all the way down. I arrived exhausted and out of breath, and it would take me forever to recover. My time was about 55 minutes. 

Soon enough, I wasn’t enjoying that run anymore, so I decided to take it easy. I mentally set my pace at half the normal one. The run was pure joy. I rediscovered all the beauty of the East Cliff shoreline. I arrived fresh and relaxed. Want to guess my time? 57 minutes!

You read it right! 

A minor adjustment in your execution speed can make a difference in the quality of your perceived experience.

So, whether it’s in business or personal, make sure you experiment too. Adjust your execution speed, don’t take on more than you can chew, and find your happy “pace”!

21. Let go of perfectionism.

It is an important nuance between many founders and CEOs. Most founders are typical overachievers and tend to be perfectionists. But perfectionism and extensive responsibilities don’t do well together.

If you wish to be a successful leader, let go of your involvement in all the tiny details. Strive for cohesion and mutual trust. 

Perfectionism is the enemy. Excellence is the goal.

22. Get ready for the unexpected.

When you prepare for the Antarctica Marathon, you focus your training on adapting to cold environments with extreme and sudden changes in conditions. With the mild Californian winters, it wasn’t easy for me, but I got as ready as possible.

After an epic couple of tumultuous days in the Drake passage from Argentina, we eventually hit Antarctica. Given the limitations, less than 100 visitors could be on land simultaneously. The Vavilov and Ioffe expedition boats were following each other for a day. We were on the Ioffe. 

The Vavilov team went first for the Marathon: temperatures in the ’20s (Fahrenheit), gusty winds, hail, and snow. These were pretty typical conditions, and several runners suffered from hypothermia. Some even were not able to finish.

I woke up on the Ioffe expedition boat the following day, mentally prepared for a tough day. I was pleasantly surprised to see the sunny skies and calm seas. The ice on the ground was probably the only sign it had been quite cold that night.

The course was a four-loop path (you don’t do point-to-point in Antarctica if you want your runners to finish alive!). The weather proved to be remarkably mild and bearable in the ’30s. But, after a couple of loops, I noted the deterioration of the road conditions as the ice started to melt. 

I would have never expected it under these latitudes: we were glued into fields of thick mud. One of my shoes even entirely disappeared in the sucking brown mass. It took all of us longer to finish. Yet, we invented new ways of running on our heels and even took an extended cut to avoid the deepest mud areas altogether.

Bad stuff tends to come in the most unexpected ways. No matter how great your planning is, you must build agility in your execution to prevail. Creative thinking and improvisation do best when coupled with solid planning. 

23. Nothing is static, you can invent the future.

“We’ll never succeed unless we continue to open up new vistas.” Chuck Geschke – 2008

Chuck Geschke and John Warnock founded Adobe in 1982. They could not imagine they would someday receive the National Medal of Technology from the very hands of President Barack Obama. But they did! Twenty-seven years later. After almost three decades of continuous invention, Adobe had become a major tech player. 

Earlier, the duo had spent years at Xerox Park, researching graphics and image processing areas. Together, they developed a promising page description language (PDL), but their management wasn’t into a bold implementation of the idea. So, the two left Xerox to start their own company, Adobe. Their first product was Adobe PostScript, an innovative computing language sold to printer manufacturers. PostScript provided a radical new way to print text and images on paper. It also sparked the desktop publishing revolution, transforming the professional printing and publishing industry in just a few years. Soon, Adobe diversified into more applications. Some even became a “verb,” like Photoshop. I’m sure you know most of them by name.

In my opinion, the most transformative invention Chuck and John enabled remains Acrobat PDF (Portable Document Format). I participated in the European launch of Acrobat in June 1993 in London. We didn’t know it yet, but we had pure gold in our hands. Acrobat would soon become the absolute reference for universal rich documents you can share on any device, any platform.

24. Be disruptive yet patient.

Still, in the Adobe example, Chuck Geschke knew how to leverage opportunities. He practiced it during the early days at Adobe. The company had successfully developed its PostScript language. It soon became apparent that PostScript had a unique way of handling typefaces.

The only caveat was that the leaders in the typeface industry were very traditional and entrenched. As Chuck and the Adobe team kept hearing “no” from the typeface industry leaders, they soon became experts in going to their hungry competitors. They secured great deals and eventually disrupted the whole category.

When we launched the first version of Acrobat in 1993, we had a particular niche market in mind. We thought it would primarily benefit professional publishers and their clients as digital proof before going to press. We even sold the PDF Reader for $50! Understandably, initial sales were slow, and the technology was not going anywhere. Acrobat was probably out in the market three years too soon. But then the Internet took off. After much debate, Chuck and John decided we would distribute the PDF reader for free.

With the emergence of the Web, PDF became mainstream and became the standard for distributing rich electronic documents. It didn’t contribute much to the financial bottom line at first. Some teams in charge of the high-revenue applications and systems even highly criticized why we’d keep such a money-losing solution. But the perseverance and continued investment eventually paid off, and Acrobat was a pivotal contributor to Adobe’s $15B revenue in 2021.

25. Always keep an open mind.

On a personal note, I experienced the truly open mind that characterized Chuck Geschke at Adobe. It was back in early 1994. I had met Chuck only once at that time, but he already knew who I was and what was driving me. 

We had just announced our intent to acquire one of our competitors, Aldus. I was in charge of the Iberica market in my twenties and probably too excited by the acquisition prospect. I regularly talked to the Spanish press and shared more than I should have about plans.

My enthusiasm endangered the deal at a critical juncture and slowed the negotiations. Many executives would have used the opportunity to fire me. Chuck didn’t. He backed me up, believed in my potential, and trusted I wouldn’t make the same mistake again. By doing so, he and Adobe got the best out of me for the next ten years. 

At some point, everyone in your team will fail. What makes the difference is how you, as a leader, react to it and help them learn and rebound.

26. Become a lifelong learner.

The daily whirlwind of corporate life can be challenging for any leader, and you’ll soon find yourself putting out fires all day long.

You will regress if you don’t step back with a deliberate effort to learn something new every day. That’s a fact of life.

You might not experience the higher cognitive decline rate older adults face. Still, you’d better make mental acuity a key priority. Numerous psychological studies have proven that learning new skills is the best way to go about it.

So don’t wait for your HR organization to build the perfect learning plan for you as a leader. Be proactive and dive into it! It has never been more accessible these days. The pandemic eliminated commutes (for now) and triggered new behaviors that are here to stay. We have traded many “busy” time for “quality” time. Spend some of it with your loved ones, but make sure you keep a portion for learning too! Online learning quality is still, but new best-in-class experiences are emerging and leverage the power of communities.

On that point, I recently participated in a Product Strategy Sprint online training offered by Section 4, Scott Gallaway’s latest venture. This fast-paced two-week online program gave me much hope that education is going toward the correct transformation. It struck the perfect balance between lecturing, break-out rooms, workshops, time for practice, and a final report. 

Check it out. I trust more education programs will start to follow this path!

27. Stay physically active.

By now, we all know the correct dose of physical activity is essential at every stage in life. So don’t wait until you’re retired to establish a rock-solid routine! It will pave the way for stronger mental and physical health.

The essential notion here is “routine.” I typically handle my physical activities like any critical meeting to make sure they stick.

I’m diligent about marking my calendar with daily exercises. It means blocking times in my work calendar where I specifically call the name of the activity, like “Tuesday morning, 7 am – 8 am, Speed Session – Intervals 6x800m”.

OK, I know, I’m a marathon runner. You surely don’t need to go that far to get noticeable results. But make sure you mark down your work calendar with these daily activities, even if it’s 20 minutes walking around the block. 

You will feel better, energized, and stronger at addressing your challenges 

COLLABORATION

28. Know how to handle key decision-makers.

Every executive team, board, and customer has unique protocols, challenges, conflicts, and alliances. Understanding these is essential before you try to sell your ideas. 

How to interact with each of them? Who are the biggest influencers? What’s critical to each board member? What tensions or disagreements exist? 

As you get ready to bring your topic to any agenda, it’s critical to assess each decision maker’s position on it before you walk into the room. Do they already have strong views on the desired outcome? How much education do they need on the issue? What’s its relative importance for them?

Finally, be clear on what you precisely ask for with key decision makers. There’s a significant difference between informing, consulting, or asking for a decision on a topic. I’ve learned to be clear upfront on what I expected the board to do with the matter brought to them.

29. Beware of group consensus, and explore divergences.

Many decisions tend to be made by groups as they seem to represent diverse points of view. The issue is that, even if you correctly state the problem, once a consensus starts to take shape, it has its momentum. 

Group wisdom takes over, and getting people’s honest perspectives is getting harder.

Instead, you should use group meetings to address divergences. You’ll likely know even before your group meeting where the consensus is. But what matters is for you to explore the areas of divergence between the stakeholders. 

That’s the key to any great decision: understanding why well-informed individuals might have diverging views on an issue. Go to the roots of such divergences, educate and get educated about these.

30. Ignore the critics, seek selective constructive feedback.

The last thing you need is a bunch of critics of your work. Anyone can be a critic. It’s an easy trap. 

Remember, your path to success is uniquely yours and highly experimental. So, be sure to seek feedback from your target audience and validate – or not – how they understood your intent. 

Then, educate, adjust as needed and keep soliciting proper feedback.

31. Know how to delegate.

Too often, I’ve fallen into the trap of being overly descriptive about a task I needed to delegate and how to do it. That’s fine with a precise sequence of events that doesn’t vary much.

But in most cases, I’d benefit from describing my desired outcome. 

Something like: “I need you to put together a weekly summary of our project status meetings, highlighting key takeaways, timeframes, and owners.” 

My EA would take it from there and decide on the best ways to go about it.

32. Don’t use emails for teamwork.

With the lack of in-person communication during the pandemic, I’ve seen the use of emails grow to communicate just about anything. That’s a problem!

While emails are probably still the best tool for external communication, they’re not practical for team collaboration. It’s hard and confusing to designate owners, set deadlines, or establish frameworks by email.

The best communicators prefer specialized tools or channels to collaborate, like Asana, Jira, or Monday.com. You can use them to assign responsibilities and manage projects effectively. 

Such tools help track the essentials and enhance transparency and accountability.

33. Don’t spend the whole day on Zoom.

For many, remote work has become a fantastic opportunity to become more productive. It has eliminated office distractions and allows for more thinking time.

But the fear of missing out leads us to fill our days with new types of meetings to feel still connected.

That’s OK!

Belonging is essential, and one-to-one calls will go a long way to help you there. Yet, the most effective communicators keep these calls short and informal. They ditch the camera and pick up the phone instead.

34. Build alliances and alignment.

Building alliances and seeking early wins is critical when starting a new role.

Establish some relationship capital inside and outside of your team. As you build alliances, look for the most impactful early wins. They don’t have to be big, but they’ll matter in establishing your credibility.

Along these lines, identify potential misalignments and develop a plan early to address them, including your team. 

Also make sure you properly manage expectations with your boss and align on the definition of success and the required resources.

35. Keep stakeholders aligned with your vision.

Inevitably, you will have some tension or conflict of interest between different groups. The short-term imperatives driving most sales teams often clash with some longer-term views of the product teams. 

You can live with it as long as you unequivocally communicate to key stakeholders what you’re working on and what you’re not working on.

36. Get the best out of procrastinators.

If you struggle with procrastination within your team, here are a few tips to help you manage it.

  • Help the fearful by playing to their strengths. Some team members would instead work on something they know they’re good at. They fear the stretch challenge and failure. So make sure they’re not constantly pushed outside of their comfort zone. You can still help them grow; choose their challenges wisely.
  • Give milestones and short deadlines to the thrill-seeker. The secret with this type of procrastinator is to break the time horizon of a project into chewable chunks, with regular checkpoints and a short-term. You don’t need to unveil it all at once and can give smaller assignments sequentially.
  • Build a culture of accountability. The best leaders know how to probe where their teams stand with open-ended questions. They act as a coach, letting the team solve the problems they own. They show support yet help clarify the consequences of everyone’s actions.

Lastly, here’s an effortless technique I’ve used myself while struggling with procrastination: the 10-minute rule

Quick example: “Instead of saying you’re going to work on your business plan, say you’re going to use the next 10 minutes to work on your business plan.”

37. Master difficult conversations.

As business leaders, we tend to struggle with difficult conversations. Soon, our lack of decisiveness leads to a growing pile of challenges. We think issues will sort out themselves, and things will improve. Yet, in most cases, things get worse. And, we carry the weight of an underperformer and toxic culture.

Most leaders proactively address underperformance and start with empathy to solve challenges. It’s a great way to be in someone else’s shoes. Yet, by doing so, they end up over-indexing on how people feel and can lose sight of why they’re having a difficult conversation in the first place.

One of my stays at the Emergency Room showed me how doctors could master difficult conversations.

My simple case was, “We have analyzed your X-rays and didn’t see any conclusive obstruction. We recommend you undergo an endoscopy to add certainty to the diagnostic. There’s a chance of 1,000 for a complication requiring further hospitalization. Do you have any questions about this?”

In business, interacting with a team member who didn’t do all their homework on a project could translate as:

 “I have read your analysis on why our product A is underperforming. I’m concerned that I do not see enough of the root causes. I recommend you consult our marketing team to form a complete view of the situation. There’s a small likelihood they will push back and escalate, but we need to get the situation under control. Tell me what you think.”

I trust you get the notion.

Know how to observe without judging, rationalize without (too much) feeling, and request without demanding.

38. When you’re lost, ask for help.

It was a cool morning in the heart of the Maasai territory in Kenya. We were ready for an epic race through the hills, canyons, and river beds. The itinerary markings were rudimentary, with orange chalk on random stones through the path. Elevation was around 6,000 ft.

Around mile 24, I was on my way to being the first non-local runner to finish. As I feared, crucifying cramps were impacting my legs. Lost in my thoughts, I found it harder to focus on the path. I soon checked for the orange marks. They were gone!

I checked again and couldn’t see any orange stone around. I ran back a few hundred yards, but still, no sign was on the horizon. After going back and forth a few more times, I had to admit it: I was lost!

I noticed a hut in the distance. I ran there, hoping to find someone to show me the way. Children were playing outside the place. I tried my luck with them, but none would speak English.

I only said two words: “Finish line?”. Suddenly, a giant Maasai man surged from inside the hut. He didn’t say anything but started running barefoot among the forest of acacia trees. I followed him, and I was back on the right path after half a mile.

Eventually, I crossed the finish line. I was late but ended up finishing, thanks to that massive help from my new Maasai friend.

The lesson is an obvious one. But we often fail to realize it in business before it’s too late. 

So, the next time you and your team lose sight of your destination, swallow your pride and ask for help. It will save you from much trouble.

39. Consistently probe what’s happening with your team.

Assume you have given enough guidance to your team and set the proper context. You now need to keep the pulse on how they’re doing. You have ample opportunities to ask for feedback. It ranges from informal daily chats to 1:1, business reviews, or annual assessments. 

Be consistent and continuously seek feedback. Don’t wait for the quarter’s end or yearly evaluations to do so!

It can only help if you also ask the right questions. To understand what’s happening, there’s nothing better than open-ended questions starting with “What” or “How.” Such questions invite your team members to elaborate and go beyond a yes/no response. I try to avoid questions starting with “Why.” Some people feel more pressured or “interrogated,” and it won’t elicit much dialog.

Here are some examples of great open-ended questions:

  • What are your big goals and areas of focus right now?
  • How is project X going? Tell me more.
  • What are the top challenges you currently face on project X?
  • What has not been working so far?
  • What’s your biggest takeaway on project X so far? 
  • How is it impacting your approach moving forward?

There is a causal effect between the number of relevant questions you ask and the levels of accountability in your team. So don’t be shy! Ask as many as needed to get a solid grasp of the situation at hand.

40. Resist the temptation to solve your team’s problems.

Most leaders are natural problem-solvers, but you should avoid solving your team’s problems.

I know this is hard because you want your team to succeed. You probably have reasonable potential solutions when your team shares their top challenges with you. But if you wish for proper team accountability, they need to own the resolution of their problems. The solution is actually to ask more open-ended questions!

So, the next time you uncover a team member’s primary challenge, don’t try to solve it. Don’t even suggest a solution! 

Instead, ask more questions like: “What options do you think you have”? Such questions will act as a natural filter. If your team can genuinely solve the problems independently, they will. If they have dependencies that require your help and decision, you’ll be already on top of it.

As you practice the art of not solving all of your team’s problems, you’ll notice more substantial commitment and accountability from them. Eventually, they will thank you for your empowerment.

41. Help your team focus on outcomes.

If you consistently ask the right questions to your team, you will help them own the outcome and feel more accountable for the consequences of their choices. The more questions you ask, the more you will uncover performance issues. That’s why you need to continuously educate the team on the consequences of their actions. 

Hypothetical open-ended questions are a great way to help them preemptively avoid disasters in the making:

  • What if event Y happened? 
  • What impact do you think it would have on project X? 
  • What options would you consider then?

In most cases, a truly empowered team will self-correct such issues before they get out of control. 

Yet, in some cases, the situation won’t improve. It’s where reflective open-ended questions can help the team build their takeaways and identify better strategies for the future:

  • What do you think caused issue A?
  • Knowing what you know now, what would you have done differently?
  • How does it impact the way you will approach upcoming project X?

Your approach must be supportive, empathetic, and not default to anger or blame. You will likely experience awkward moments out of frustration or even embarrassment. It’s OK. It is a crucial step for your team members to build personal responsibility.

42. Juggle conflicting interests.

Another key lesson I learned from my Adobe days. One memo Chuck Geschke sent internally in 1998 summarized most of these. In it, Chuck refers a lot to leadership values. 

One that stood out for me relates to collaboration and the need to juggle all constituencies with interest in the business – shareholders, customers, employees, vendors, and communities – and the unavoidable conflicts that come with it. 

He was years ahead of stakeholder capitalism when he stated:

“The job of a leader is to juggle these conflicting interests without letting any of them dominate the others because they’ll drag your company down.” 

43. Let your team figure out the “How.”

As a leader, you’re here to let your team understand their impact. Have everyone internalize the values and beliefs and make the mission crystal clear. You need to ensure you set the destination. 

From there, as we say in Southern Europe: “all roads lead to Rome.” It means that you will achieve the same result, whatever your methods or how you do something.

It’s always been an essential dimension for me as a leader: letting my team figure out how they will contribute to the overall organization’s success. 

In the world of knowledge working, no manager should ever tell you how to do things. Your team should own how they operate. Otherwise, they would face quite an uphill battle to feel accountable and would be just executing then.

Instead, let your team own the “how,” and chances are they will collectively come up with brilliant ideas you would never have considered. Let them surprise you; they will connect the dots and bullet-proof the execution of the plans. 

Most importantly, they will own the outcome. It’s your best insurance for both top performance and a motivated team.

44. Influence more than the chain of command.

Addressing the chain of command and getting executive buy-in is necessary to get things moving, but it’s not enough. Both starting businesses and established corporations have their chains of influence. They differ, but it’s equally critical to understand and master them. 

Let me share a sadly familiar story in big corporations. 

I had tried to move the needle for months with my latest business turnaround plan. Back then, I didn’t understand why I wasn’t getting much traction. I thought I had the chain of command under control: I had monthly the CEO and a few key executives attention. The business plans I presented made perfect sense to them. Yet, I wouldn’t get the execution I needed.

The answer was simple: I did not understand how the chain of influence worked.

 It took me a deliberate effort to deconstruct and understand who the key stakeholders were and how much attention they needed to get things done. Most of these enablers were middle managers across different functional areas. The lesson learned is that addressing the chain of command alone isn’t enough.

Whether large or small, businesses can have a rather complex chain of “influence.” And if leaders don’t understand it, they’re likely wasting their time. 

So, pay specific attention to the enablers in your company. They’re here for a reason. They are protecting what the institution is standing for. They’re the guardians of the company’s cohesion and survival. They will likely meet any of your disruptive ideas with an eyebrow. 

It doesn’t mean you should not take the initiative. It doesn’t mean you shouldn’t innovate. You need to understand how to find the keys to get them on your side or neutralize them with some senior executive help. 

45. Over-index on communication and transparency.

It’s time for leaders to be incredibly transparent and over-communicate about what’s at stake for their business and where they stand with challenges and opportunities. We often think such communication is vital for team members. And it is. But don’t underestimate its power to all stakeholders: customers, partners, analysts…

Transparency is hard, especially when things don’t go as planned. But, it’s an excellent opportunity for you to review your business vision. Is it still on target? Should you revisit your desired destination? Once clear, over-communicate the whole package from your WHY to vision, mission, and strategy to all stakeholders.

Communication is a two-way street. As you engage, consider it the perfect opportunity to check on your team members, customers, and partners. You should assess how they fare, what they’re struggling with, and what keeps them excited.

46. Enable and trust your team’s critical thinking.

Some things never change: “great” leadership is about true empowerment, bringing inspiration, developing others’ strengths and creating engagement. With experience, we realize there’s rarely a right or wrong answer. 

But, I’ve seen the best outcomes when team members come to me with a problem, not asking me to solve it, yet soliciting the right questions from me. It takes practice and trust, but this is the best thing you can do to help open their minds and explore more options before THEY conclude.

One example was the launch of a new generation headset at Plantronics. The product was a substantial evolution from an already very successful franchise. We had pressure from partners to launch it at the same price as the older version and replace it. That was the plan of record. The product was exceptional, and the first reactions were highly positive. The team was quite uncomfortable with the situation. We all felt we were leaving opportunities on the table.

So, I made it clear there were no “sacred cows,” helping the team consider “What if?” scenarios combining different price points and channel strategies. After analyzing for a few weeks, we decided to go with a higher price of 20%. Double-win! It was a smashing success, and the older version stayed in the market for many years.

This story’s moral is that once the team was “allowed” to open up their options, they baked a decision through proper analysis with their critical thinking. They took in much information and evaluated its relevance and impact. They handled ambiguity and reached the best conclusion they could with what they had at that moment. 

As a leader, I didn’t have to weigh in anymore. I had coached them to worry less about coming first hand with the correct answer and focusing more on asking themselves the right questions.

DECISION-MAKING

decision-making

47. Know your biases and seek different perspectives.

If I agree with someone else, does it make it true? Not really! We’re all conditioned by the environments we’ve lived in, the people we met, and the teachings we learned. So when I see I’m starting to align with an idea, I turn suspicious. 

That’s why it’s so critical to study radically different perspectives than yours.

Whether I agree or disagree with an idea, I’m trying to articulate why. By doing so, I start challenging my biases and their influence on my thinking. 

Particularly helpful is for me to dig into why someone would have a radically different perspective. 

48. Handle advice-givers with care.

Most advisors have good intentions. They sincerely want to help. Yet, they cannot connect all of the dots for me. 

So, whenever I receive advice, I dig deeper— trying to get as much data and context as possible. I go beyond good Intentions.

Along these lines, there’s a reason why we tend to hear more about failures than success stories. There are way more failures. So, whenever I receive advice, I try to understand which outcome the advisor reached when facing a similar situation. 

Then, I can apply my lens based on my experience, values, and intended results.

49. Don’t follow your competitors.

Most of us obsess over our competitors. We follow their every move. When they seem ahead, we overreact by adjusting our product roadmaps or go-to-market strategies.

We shouldn’t.

Don’t get me wrong. You must genuinely understand your competitive landscape and correctly anticipate the moves from potential disruptors.

Don’t obsess over it.

Focus your passion on solving your customers’ most significant problems. It might not prevent you from being disrupted. Still, the customer-centric foundation you build and enough agility will help you adapt to ever-changing market conditions.

50. Clearly define problem statements.

I’ve been in too many situations where a leader and his group tried to solve an issue. Still, they were not aligned on the exact definition of the challenge. 

So, ensure you spend enough time framing the problem for your group and have everyone aligned on what’s at stake and the consequences.

And before you consider setting a group meeting to solve a complex challenge, collect your stakeholders’ views on the problem at hand independently. Collate their answers and group them into agreement and divergence areas.

You’ll save much time and avoid many sterile debates.

51. Challenge simplistic Yes or No choices.

Our brains love finding a shortcut and reaching peace of mind with a clear outcome. But a simple YES or NO just doesn’t fit most complex issues.

A binary approach is acceptable – and effective – for simple situations, like choosing that healthy salad over a highly processed meal.

But it shows its limitations for more complex issues. Such issues require upfront work to ensure alignment on the challenge, a more balanced view of the pros and cons, and a deep look at alternatives.

Handling complex issues requires strong leadership. The kind of leader who’s not afraid of respectfully probing the real questions first, prioritizing the issues at hand, and helping creative ideas blossom.

The answers will be less divisive and bring more alignment.

To start, make sure you:

  • Challenge any simplistic Yes or No choice on the next complex issue you face.
  • Respectfully qualify the problems at hand.
  • Enlist help from the best talent.
  • And build alternative plans and scenarios. When facing complex issues

52. Beat the experts at forecasting.

Here are a few lessons that helped me spot the “prediction imposters” and tune my approach.

#1 Nothing is certain until it happens.Regarding future outcomes involving human behaviors, the scenarios multiply; beware of certainty. You’d better put your “critical thinking” hat on and ask yourself deep and probing questions. Stay humble and open-minded.

#2 Cluster big questions into smaller chewable ones. Think about everything that would need to be true for an outcome to materialize. Also, ask yourself what would need to happen for this same outcome not to occur. Even on considerations – like “What’s our revenue forecast for the next quarter?” – I’ve seen success when we distilled the main question into smaller chunks. 

#3 Keep progressing and tune as things progress. It’s always better to be directionally correct than precisely wrong! The best forecasters I’ve worked with were the ones who would adjust their thinking as new events happened. We’d start with various possible outcomes, be more precise, and provide the best results.

#4 Luck is a crucial part of the equation. A more precise definition of luck is the sum of all the events you have no control over, affecting a result. Over time, it all regresses to the mean. One can more easily discern what role true expertise or sheer luck played in the outcome. From there, you can work towards influencing what was just luck and have more control over your destiny.

Superior forecasting is complex, but you can grow from the experience with practice and some humility, whether your predictions were right or wrong.

As Enrico Fermi, the famous atomic physicist once said: 

    “There are two possible outcomes: if the result confirms the hypothesis, then you’ve made a measurement. If the result is contrary to the hypothesis, then you’ve made a discovery.”

53. Develop your inquisitive mind.

Don’t fall for the most logical solution based on curated facts presented to you. Ask yourself what other piece of information you could obtain. 

Challenge the data set, inquire for more, and put it in context. You will soon elevate yourself from the equation by being more inquisitive. Keep asking open-ended questions and look for alternatives.

Chances are, you’ll discover the problems worth solving, and your solutions will achieve better outcomes.

54. Apply your vision magic filter to all upcoming ideas.

Having a solid and clear vision for your business is the best tool you can think of to make the right decisions down the line.

Once clear on your vision, apply it as a filter to every idea. There is always some interpretation at play, but in the spirit of the 80/20 rule, the goal is to have most ideas sorted out. 

Keep pursuing the ideas that help your vision in an obvious way. Put the other ones aside and keep revisiting the dilemmas if they exist as things evolve.

55. Take action with first principles.

In short, first principles help you stop thinking by analogy. Instead, you genuinely attempt to deconstruct how things work and how they uniquely apply to a situation at hand.

Philosophers like Aristotle introduced first principles. Centuries later, entrepreneurs apply them with success. Take Elon Musk’s Space-X, who had to completely rethink the way to build rockets without spending R&D to NASA’s “astronomic” levels.

When dealing with a complex situation or innovating, first principles help you avoid the “conventional wisdom” trap. You don’t let others define the problem for you. You’re the one framing it.

As importantly, first principles get you unstuck. They help you go to the essential and into action mode with a simplified mental model.

So, the next time you have a potential solution to a complex situation, dig into why you think that way. Look for evidence, and consider alternatives and their implications. Make sure you challenge your assumptions.

56. Learn how to say no and be selective.

Learning to say no can be challenging, but it’s a lifesaver. Limiting your exposure to time-wasters allows you to dedicate more of your energy to what truly matters.

The key is to ensure you clarify your priorities – activities or people. From there, you can draw the proper boundaries and dedicate more time to what really important to you.

So, trim down any unrewarding activity. And shield yourself from non-constructive or toxic encounters.

57. Use critical thinking to reframe failure.

The next time you need to make a complex decision, make sure you apply your critical thinking. It will help you:

  • play multiple scenarios and their respective outcomes,
  • assess risks in relative terms, not in “doom-and-gloom” mode,
  • discern what to measure and what not to measure.

Most importantly, critical thinking will help you reframe failure for what it truly is: a wisdom accelerator.

With the correct critical thinking applied, chances are one of the scenarios you predicted will happen. 

Even if it’s the worst case, you’ll be prepared to take action and won’t lose your precious energy commiserating on bad luck or an upcoming pink slip!

58. Solid instincts can beat business theory.

Another key lesson I learned from my days at Adobe. In a fascinating interview with the Wharton School, Chuck Geschke gave a brilliant answer when asked about why Adobe continued to invest in Acrobat and the pdf format for so long:

“Your instincts. You can’t analyze a market that has never existed”.

Instinct was a crucial part of the equation for Chuck. He and John saw the digital world coming. It started with desktop publishing and then expanded into imagery, video, and any form of rich content. Most interestingly, Chuck and John were not big on business literature. In that same interview with Wharton School, Chuck admitted he had only read one business book as of 2008. And the only chapter he remembered from it was entitled “Market Gap Analysis.” 

“The one idea I remember was that it is easier to build a business if you find a new solution to an already perceived problem that no one has come out with before — because you instantly are [at] 100% market share”.

It’s an excellent summary of what Adobe accomplished under Chuck and John’s leadership.

Be the first to create solutions to well-identified problems. Educated instinct is the way to progress in uncharted territories.

59. When facing a problem, acknowledge it and understand the situation.

Over the years, I’ve had to handle quite a few unpleasant conversations with senior executives and colleagues when we got hit by the unexpected. The good news is that, like 99.99% of you, I never encountered life-threatening situations in the office. It helped me forge an approach that I used as my golden rule:

Never, ever lose your calm. Not even when an angry customer or executive would yell at you to a deafening point. Not once.

Being disappointed is understandable, but getting upset will not change the problem or make things easier. Murphy’s Law and obstacles are a fact of life, and when you face such setbacks, you’re better off taking some distance and coming back to it when everyone on the team has calmed down. So don’t hesitate to cut any escalating heated discussion, even if it’s just for 15 minutes.

From there, gathering people who understood the problem was the best thing I’ve seen happen. They would start assessing the situation together and reach alignment. Here are a few key questions that served us well:

  • How can we best state the problem we’re facing?
  • What are the root causes of this situation?
  • What are the most likely consequences and their impact?
  • What was under our control vs. out of our control?

60. Know how to reset expectations and assess your options.

There is a hierarchy of problems in every situation. Start by making sure you properly reset expectations. I’ve been trying to anchor such a reset by looking at how far we needed to go. 

So, I’ve typically started by looking at the current VMSA framework: 

  • Vision: what’s our desired destination?
  • Mission: what are we about? What’s our WHY?
  • Strategy: how do we make it work given our constraints and imperatives?
  • Actions: what specific actions are we taking, and which key performance indicators?

Then, given the nature of the problem, we’d ask ourselves at what level we needed to act. 

Let’s take an example. Suppose just one channel partner doesn’t want your product anymore. In such a case, you might stick with the current vision and mission and adjust your channel strategy and actions. But suppose the issue is a more pervasive recall of your product with severe consequences on the nature of your offer. In that case, you will have to reconsider your mission and vision.

There’s rarely one single winning approach to a situation. You always end up choosing one strategy over the others. It’s true in the product and business world too. Yet, it’s best to consider your options upfront and build a good-better-best or worst-neutral-rosy set of scenarios.

PSYCHOLOGY

psychology

#61 Know how to handle smart sociopaths.

Sociopaths do exist in the business world. They can and will destroy any goodwill and engagement from the rest of us. They will cause heavy frustrations, departures, and business failures in no time.

So, how can you handle them without losing your sanity?

Be preventive and reveal as little as possible. Knowledge is power, and the smart sociopath will want to charm you to extract what they need from you. So if you suspect a colleague has such tendencies, keep the revealing to its strict minimum.

Be patient and let them expose themselves. Trying to confront a smart sociopath will likely backfire. Don’t forget how much effort they put into crafting their image to attain power. So instead of directly pointing at their lies, play the “innocent” questions game that will eventually have them engulfed in their contradictions.

Finally, use the weapon of “reasonable.” In many cases, you can’t avoid engaging with the smart sociopath throwing an unreasonable request at you. Just say no, as gently as possible. Give them a reason by letting them know how unacceptable their ask is and illustrate what a more reasonable approach would look like.

62. Recognize and proactively handle your team’s insecurities.

Leadership is about securing engagement. Yet, study after study, the numbers keep showing that the number one reason people leave their jobs is the lack of recognition for their contributions.

One way to improve this is to handle your team’s insecurities better. With experience, I learned how to discern better when someone was mainly looking for constructive feedback they could use to grow. I also better identified when it was more about channeling insecurities and getting a self-esteem boost.

Both situations should elicit feedback that is fact and evidence-based. But for insecure team members, I’d go beyond the project at hand, provide a clear judgment call – positive or negative -, and open up the dialog on possible evolutions.

So, recognize and proactively handle your team’s insecurities while putting them in the driver’s seat. It will go a long way for them to see that their contributions are appreciated. They’ll enjoy their work more, stay motivated and even solve impossible problems for you!

63. Don’t waste your time criticizing even your worst enemies.

When you see something you don’t understand or disagree with, try to deconstruct it. 

Get to the root causes. Put yourself in the other person’s shoes and look for why she should think or act the way she does. 

In the end, you might still disagree, but you will have gained a more solid and defensible perspective.

64. Excel at difficult conversations.

Proactively and timely putting uncomfortable topics on the table is a recipe for gaining respect and mitigating catastrophic outcomes. 

As a leader, ensure you openly share your feelings about a situation and what’s on your mind to sort things out.

65. Know how to handle the ups and downs.

It’s OK – and desired – to set bold expectations if you want to win big. But it’s also dangerous if you’re not ready to manage the pain that goes with the down periods.

So make sure you focus on making the most of each day at work and cherish every small win. It will help you graciously approach the unavoidable downtimes.

66. Don’t think everyone will like you; they don’t care.

At first, I thought popularity was important. I had the mentality of a king and queen of the prom. 

What a waste of time and energy! 

The reality is that, while being liked may be comforting at times – it simply isn’t the point at work. Instead, focus on what you fundamentally believe is best for the business. 

Accept that some people will look at you incredulously. Keep charging ahead.

67. Use the magic question in your 1:1’s.

I’ve learned to get the best out of team members in our 1:1s. All by asking a simple question: “What’s Top of Mind?” 

Their answer could be a significant issue, a creative idea, or a personal challenge.

I usually would not offer advice or try to solve the problem. But I would use this first question as the opportunity to dig deeper with follow-up questions, keeping them as open-ended and probing as possible.

Conversation after conversation, I built the level of trust needed for the team to come to me with impactful topics proactively. They used me as a sounding board for critical thinking. I got great insights. We all won.

And more often than not, they’d leave these 1:1s with a clearer sense of how to address their top issues without having me do any command and order.

68. Envy is the enemy.

No one is immune. We all experience envy at one stage. So how should we handle it?

One simple trick I use is to follow some of the stoic philosophers’ wisdom. Whenever envy hits me, I remember this saying from Epictetus: 

“An ignorant person is inclined to blame others for his misfortune. To blame oneself is proof of progress. But the wise man never has to blame another or himself.”

There will always be a competitor with more revenue or positive customer reviews. There will always be someone with more money, power, and prestige.

So, focus on what you can control and set yourself free. Stay healthy and delight the ones who truly matter: your family, friends, and customers!

69. Be a positive energizer.

I recently stumbled on this quote from a Harvard Business Review article written by Emma Seppälä and Kim Cameron.

Its title: The Best Leaders Have a Contagious Positive Energy.

“The greatest predictor of success for leaders is not their charisma, influence, or power. 
It is not personality, attractiveness, or innovative genius. 
The one thing that supersedes all these factors is positive relational energy: the energy exchanged between people that helps uplift, enthuse, and renew them”.

A great reminder that the best leaders are energizers.

70. Master distorted realities.

I’ve learned to deal with reality distortion and accept that being a leader increases the chances of being misinterpreted and misunderstood.

It’s human nature: your every move, mood, what you say, and what you don’t.

It’s all going to be scrutinized and exacerbated.

But it doesn’t mean you should stick to a pedestal and do nothing about it. You’d better establish the right “contract” with your team to achieve excellence.

So
for you and your team to do your best job, you have to be unequivocally
clear that anyone’s shortcomings, fears, and even failures won’t be
used against them. 

Patrick Lencioni, the author of “The Five Dysfunctions of a Team,” captured it best. The notion here is that you can’t both put your energy into doing your best job and trying to protect yourself. You need to choose one. 

 

It has to be mutual. It can feel very uncomfortable, but that’s the only way to build genuine trust.

Leading can feel lonely. You know you cannot share everything and that challenges with your team will often feel unsolvable. 

 

But, accepting the reality of skewed perspectives and establishing genuine trust will go a long way in addressing your self-doubts and lack of objective feedback.

71. Build mutual accountability.

As a leader, you must create clear standards for performance and behavior in your team. Every team member has to commit and hold each other accountable to meet those standards. 

It’s difficult, especially when you care about team members and don’t want to damage your relationship. 

But if you stick to these standards and accept some uncomfortable conversations when things go off, everyone will win.

72. Build contextual awareness and credibility.

Whether you’re just starting a new job or have been there for twenty years, it’s critical to understand what’s happening with the business.

While many questions should be asked, I have learned to focus on the following four. They’re deceivingly simple, but the answers are not always obvious:

  • How much do you understand the core needs and challenges surrounding you and your business? 
  • How well do you know where your organization stands vs. its market and competitors? 
  • How good are you at staying humble and deeply curious?
  • How well are you adapting your competence to your organization’s unique situations? 

73. Don’t be authoritarian; clarify context and consequences.

I still vividly remember my days in the French Army. Our boss, Colonel Meyer, was a perfect example of a non-authoritarian leader. Not once did Colonel Meyer use the words “should” or “must.”

In place, he provided ample context and left enough room for the team to bring added value.

I recall one specific example of his approach: our group was in charge of organizing think-tank reunions between the military and representatives of civil associations. 

In one instance, we were four days from the next meeting, and attendance confirmations were very low.

Colonel Meyer could have been pretty direct, instructing that we should reach out to the list of invitees to remind them of the meeting and secure their attendance.

Instead, he gave us context and options: “I’m concerned our upcoming meeting is not getting the interest we sought from the civil groups. General Ferrand is attending this next reunion. Not having a full house would damage our reputation and limit future credits. Please find out what’s going on and report on how we can fix it.”

Colonel Meyer’s clarity on context and potential consequences made the real difference. We knew why the boss was concerned, and we had ample opportunity to solve the problem at hand creatively.

74. Let your team self-manage.

At one point in my career, I realized that my job as a boss was to turn every team member into a true leader, no matter their role. We’d all benefit from this.

Interestingly enough, the current Great Resignation crisis highlights the need for pervasive leadership and the self-management that comes with it.

We, as knowledge workers, can “self-manage” ourselves. We’re done with incompetent managers. Flatter organizations with fewer layers are welcome.

And when we have a boss, we expect her to help us blossom to do extraordinary things. We want our boss to help us turn into great leaders.

The time for self-management has come. Organizations that embrace this leadership principle will keep attracting the best talent like magnets and see their success grow.

75. Document and share your thinking in narratives.

Remote working and distributed teams have exacerbated the pain of poorly managed meetings and long hours going through presentations.

But, great leaders also know they have to be effective communicators. They don’t wait for meetings to get the ball rolling, consistently documenting and sharing their thinking into narratives with the rest of their team. 

Everyone who needs to be involved helps refine the thinking and can contribute by reviewing or commenting offline. 

When they happen, meetings are more focused on a real conversation or deeper dive between informed professionals. And when they’re unsure their colleagues have taken the time to review the thinking, they go the Amazon way. I mean, making sure the first part of the meetings is silent and dedicated to reading the narrative.

It can all be done with modern office software (Google, Microsoft) and on any document type (like product requirements, business plans, marketing campaigns). 

76. Keep your questions short and go one at a time.

There’s nothing more confusing than facing a series of long-winded questions all wrapped into an unnecessary context. 

Let me give you an example I experienced more than once:

“Mary, you are a top performer, and I believe you can have even more impact on our business. Would you be interested in taking Bob’s role as VP of Product, or is that not something that interests you? It’s OK if you don’t want to do that, but I believe you’d be a great fit, and Bob is leaving, so we need to fill that role. I know you are ambitious and mentioned changing responsibilities, so I’m not sure what’s next for you in your career. What do you think?”

How confusing! What about:

“Mary, what would you think of taking the VP of Product role when Bob leaves the company?”

Please note that I’m not asking for a yes or no answer. I’m initiating a conversation and using this first question to step into more digging to understand what’s on Mary’s mind truly.

77. Be persuasive with positive storytelling.

I made the most significant impact when I realized that we all love stories and react better to positive persuasion.

The notion, in a nutshell, is to build a storyline that establishes common ground and makes people want what you offer because they can see their interest.

Here are the ten concrete steps I typically take when preparing a pitch for optimal persuasion:

1 – I create an unequivocal title that clarifies the topic and desired outcome. 

2 – I establish trust by finding one common ground with the audience.

3 – I articulate the problem at hand that needs to be solved.

4 – I give some hope that current approaches have their benefits.

5 – I demonstrate why they won’t work by showing their limitations.

6 – I share my proposed solution and how it addresses the identified issues.

7 – I provide proof points on its feasibility.

8 – I explain the required Calls-to-Action for both the audience and myself.

9 – I remind the audience of the early benefits.

10 – I end with a more aspirational view of the long-term benefits.

That’s it!

A story that flows through this ten-point narrative and keeps positively reinforcing the benefits of the outcome for all.

78. Practice rational compassion.

These days, you need to pro-actively gauge what’s going on in your colleagues’ minds more than ever. 

Engage in open conversations about why they should stay with you. From there, consistently keep the pulse and care for their success. It will soon become reciprocal and maximize your chances of success.

That’s what we call rational compassion. It’s close to, but not precisely like, empathy! A nuance makes rational compassion particularly adapted to the business world. Psychologist Paul Bloom highlighted the difference between both best:

“Empathy is feeling what others feel whereas compassion is simply caring for people, [and] wanting them to thrive.”

79. If you feel too much pressure, take a break.

The tennis player Novak Djokovic crystallized this notion for me at Roland Garros in 2021. The world’s #1 player evoked the psychological benefits of taking a break in the heart of a disputed final. 

He didn’t do anything else than change clothes completely and take deep breaths. These few minutes gave enough time outside the court environment to reset his mind and turn him into a new player.

Eventually, he prevailed and brought the Trophy home for the second time. With that new title, Djokovic became the first player in modern tennis history to have won twice each of the four Grand Slam competitions.

Now, think of the times you’ve stumbled into heated conversations during meetings, feeling forced to make decisions because of the perceived urgency others imposed on you!

I’ve always made my best decisions by stepping back and looking at the problem with a fresh perspective.

If it means you need to leave the room for a few minutes or even adjourn the meeting, do it! Your decision-making will improve, and your business will benefit from it.

So, next time you think there’s no good solution to a problem at hand, and you feel the pressure to conclude, remember Novak Djokovic’s technique and take a break!

80. Give a sense of purpose to your team.

The absolute majority of us want to have a positive impact on the world. We want to own it, be truly impactful, earn respect, deserve that promotion, and bring in the additional income that comes with it. It’s our primary motivating factor to succeed at work.

So how do you nourish that sense of purpose in your team? 

By providing a clear vision and a why! It is the motivation toward a positive future. No matter how small or big, your intended destination and values shape such a sense of purpose. Practically, it means you’d better ensure your team is crystal clear about why they’re coming to work every single morning. And to be clear, it has to be more than paying the bills! 

Successful whys focus on the value your company brings to the world. It’s not about making money. Revenue growth, profit, and large bonuses are the (positive) consequences of a well-articulated why.

81. Become an effective mentor.

“Your success is my success.” can be the most fulfilling yet challenging achievement in our individualistic society. Think of how you can make a difference as a leader for your whole company by helping your team members or even colleagues in other teams.

That can be quite difficult though when you’re in a leadership role. Team members often won’t dare reach out. 

You need to volunteer your help and be strategic with your questions. The point is to extend such an offer and have a proper mentor mentality. 

Here are a few ones I’ve seen make the most significant impact:

  • “What does success look like to you?” It pushes people to consider their goals and desired outcomes. It gives context to their current situation, whether in the big picture or a particular case. 
  • “What top three challenges are you facing?” The simple fact of spelling out your top challenges gives you a better sense of what you can influence or not and where you should put your energy. By narrowing things down to the top perceived obstacles, you help people prioritize what’s getting in the way and have them think harder about what they control or not.
  • “What options have you already identified?” Here you make sure people take further ownership of how they’ll address their identified challenges. As you let them elaborate, have them explore the different aspects of such options. 

If they’re stuck, keep asking open-ended exploratory questions like “Tell me more…”. It helps expand their horizon and practice their critical thinking.

82. Take your active listening to the next level.

Most human beings on earth want to be accepted and understood. With this in mind, active listening is a powerful technique you can use to demonstrate compassion. 

Leaders can all take cues from experts in negotiation like Chris Voss on active listening. He explains that the best negotiators are not overwhelmed by the typical back-and-forth you typically see in talks. They take the time (literally) to discover as many insights as possible from the other party. 

That, in itself, is a fantastic lesson: 

Negotiation starts by validating the other party’s concerns and emotions, building trust, and creating a safety net that allows for honest conversations. It takes time, patience, and agility.

Chris Voss also highlights the importance of creating and maintaining a positive frame of mind and shares some simple mirroring techniques that can be very powerful. Mirroring is simple and consists of repeating the last few words or the most critical ones the other party just expressed. 

It helps strengthen the bond, encourages them to talk even more, and eventually unveil their strategy to your benefit.

83. “Label” the other party’s feelings when negotiating.

Labeling is probably the most powerful lesson I got from Chris Voss’s book about negotiation. It reinforces empathy and helps de-escalate tension. 

Once you’ve spotted a strong emotion (negative or positive), you want to express it in a non-aggressive, non-judgmental way back to the other party. Sentences starting with “It seems like…”, “It looks like…”, and “It sounds like…” will help there.

As you acknowledge the other party’s feelings with labeling, you diffuse negative emotions and reinforce the positive ones. 

Along these lines, summarizing and repeating the other party’s concerns is a sure way to reach some breakthrough in the negotiation. In other words, a vocabulary like “That’s right” associated with a good summary that labels the other party’s feelings will go a long way.

84. Transform conflict into collaboration.

When negotiating a deal, persuading the other party that they have something to lose if the deal falls through is paramount. People will take more risks to avoid any loss than to realize some gain. So, make sure the other party sees that there is something to lose by inaction.

The way you can do it is by “anchoring” their emotions. Let them go first with their offer and provide a range of options to them with credible references. Non-monetary terms are also essential (like payment terms and add-ons…). So, offer more of them, especially if they’re not so important to you (yet, critical to the other party.

The next step is to provide the illusion of control. A recommended approach by experts like Chris Voss, which belongs to the typical arsenal of compassion techniques, calibrated questions to transform conflict into collaboration. 

Using open-ended questions starting with “what” or “how” (not “why”!), you take the opportunity to educate the other party on what the problem is, rather than being too directive. Here are typical calibrated questions Chris Voss is referring to:

  • What about this is essential to you?
  • How would you like me to proceed?
  • What brought us into this situation?
  • How can we solve this problem?
  • What are we trying to accomplish here?
  • How am I supposed to do that?

I particularly like the last one! It’s perfect for making the other party feel like they’re in charge while you’re the one driving the conversation!

PROCESSES

85. Know what tasks to eliminate.

It is worth considering whether you need a task in the first place. One way to test this is to stop that task for some time and see whether it has any impact.

Tim Ferriss said it best in his 4-Hour Workweek bestseller:

“Never automate something that can be eliminated, and never delegate something that can be automated or streamlined. Otherwise, you waste someone else’s time instead of your own, which now wastes your hard-earned cash.”

86. Automating doesn’t always beat delegating.

If a recurring task proves critical for the business, it’s tempting to automate it. 

Some of the most automation-obsessed companies have built empires with that mindset – think of how Amazon became an e-commerce giant! 

But automation doesn’t always make the most sense. Suppose you put your best engineers on building and supporting some task automation. It might cost you more than just delegating this task to your EA. 

So do the math!

87. Reflect on the failures and successes of the year.

It can be daunting to remember everything from the past year, personally and professionally.

So, I’m usually soliciting help from my digital life to boost my remembering. I typically block a couple of hours and browse through all the photos I took. Bonus: I will eventually use this as the basis for a photo album I’ll share with friends and family. I also review my calendar, the emails, and the text messages I sent (way less than what I received).

Then, I block about 30 minutes and try to answer a series of questions along these lines:

  • What were the highlights and lowlights of the year? 
  • What surprised me the most? 
  • What felt hard or easy? 
  • What am I the proudest of? 
  • What made me feel hurt, angry, or sad? 
  • What new things do I now know about myself, people, and the world? 
  • What went according to plan? 

It all starts in a free flow. But very quickly, highlights, lowlights, and critical learnings become clear.

88. Put things in perspective.

After reflecting on the past year, it’s essential to step back further and assess how it helped the critical aspects of your life. 

It’s like a life audit, but I’m keeping it simple by focusing on just the dimensions that matter to me.

Using a scale of 1 to 10 (1 being the poorest and 10 being the strongest) to gauge my state of fulfillment and a -/+ to indicate if I feel I made progress in the past year, I’m assessing the following dimensions:

  • My love (and only one!)
  • My health and well-being (physical and mental)
  • My fitness level and activities
  • My friends and family 
  • My explorations and learnings
  • My creative, coaching, and mentoring contributions
  • My finances

Putting all of these in perspective will help you better prioritize your efforts for the future.

89. When transitioning, quickly understand the situation at hand.

Each time I transitioned into a new role, I referred to the very useful advice found in the book The First 90 Days from Michael Watkins. 

Take a break if needed before the transition and set up a plan to help accelerate your learning. It means identifying all the key stakeholders and preparing for discovery conversations with them in the first few weeks on the job.

Once in the place, quickly understand your business situation and adjust accordingly. There’s no “one-size-fits-all” approach that works. 

You need to understand if the business is in a startup, turnaround, accelerated-growth, or continued success mode and adapt your strategy to it.

90. Improve your mindfulness at work.

With experience, I’ve learned how to add more mindfulness to my work life. Here are the three principles I keep following:

1 – I live in the moment—no need to rehash painful memories or think about hypothetical future problems. I was a different person then and will likely be another one tomorrow. 

2 – I avoid multitasking— not looking at my emails, social media accounts, or any other distractions using blocks of time. We all have our internal clock. For me, 15-minute blocks work well, followed by 5 minutes of mindful breaks to assess how I’m progressing.

3 – I nurture my curiosity. To optimize my productivity and creativity, I take the time to observe the world with a critical mind—asking myself open-ended questions like a 4-year-old child!

So, take a few minutes. Step back and think of how you, too, can improve your mindfulness at work. It will boost both your productivity and creativity. 

91. Create “me-time” to stay balanced.

Despite constant solicitations from your life stakeholders, unplugging is paramount if you want to build resilience. I do it daily by creating “me-time” in my schedule. 

It’s there, just like any other meeting. Whether for a run, meditation, or time with friends, you must mark it down and commit.

It’s not enough, however. I’ve long learned the benefits of taking time off and truly unplugging. My pre-pandemic Antarctica or Africa travels taught me one important thing: being away for at least two weeks without any connection was the best way to regain perspective and strengthen my vision for the business.

And guess what? My team thrived in my absence, and the world didn’t collapse!

92. Life is short; focus on executing the vision.

It just took a few hours in ER to remind me that nothing’s for granted. The bus you get under, the stroke that hits you, that aneurysm that ruptures. You simply never know what life has in store for you. 

I’m no exception; most people who make it through the emergency room shift their perspective. They realize they have little control over the bigger scheme. So, they start acting on their lifestyle, that dream hobby they’ve always wanted, or that family trip they kept postponing.

Similarly, the best business leaders keep the ER dynamics in mind. 

The best leaders know nothing is for granted, and they must embrace the unexpected. There’s so much outside their control. At the same time, they put things in perspective and elevate from the daily grind. 

They achieve a state of controlled chaos and focus on essential questions, such as:

  • What’s our vision and mission? 
  • Why does our business even exist in the first place?
  • What key goals are we trying to achieve? 
  • What legacy do we want this team to leave?

93. Know how to enable the vision.

Product management is one of the functions that produce the strongest leaders. One of the reasons for this is the way they approach a vision.

Product management rarely creates the product vision on their own. They participate in it with the rest of the product team and soon become its guardian.

Product managers seek deep insights from well-identified customer problems. Their role is about helping everyone else understand that product vision and constantly communicating it. They also act as the guardian of such vision when the time comes to execute and conflicting views unavoidably appear.

Along the same lines, one of the critical responsibilities of a CEO is to shepherd – not necessarily define – a strong vision for their company. A company vision is essentially where the company is heading and what the timeframe to reach the destination looks like. 

Defending a product vision is the perfect path to learning how to do it for a company vision. 

You will need to know how to facilitate and align different perspectives. It requires a deep understanding of your context to be credible. You also need a strong sense of prioritization because you cannot do it all. It also demands a true sense of collaboration and communication, as you can’t do it alone.

94. Learn how to make (a lot of) decisions.

Again, product management is an excellent illustration of this leadership quality. 

Product management isn’t for the faint of heart! The best product managers I’ve known worked an insane amount of hours. They would tirelessly align teams behind the product vision and ensure proper execution. They had to find more hours in their week to stay on top of constantly evolving customer and market problems.

Yet, thanks to their role’s intensity, width, and breadth, product managers quickly learn how to optimize their decision-making processes. They have no choice. If they don’t, they’ll soon be overwhelmed and fail. 

Assessing the right metrics for product success and always being on top of their analysis. It’s about turning a lot of data and inputs into insights. It involves building strong critical thinking, digging into the root causes, and creating the right systems for market visibility, customer behaviors, and retrospective learning from executed projects. 

Along the same lines, the best CEOs I’ve worked with would understand how critical the correct data is for proper decision–making. Knowing what to measure and how is a crucial skill that helps build scenarios, measure execution, and course-correct as needed. 

Great product managers and CEOs know how to turn data into a framework of solid insights and use it to make the right decisions.

95. Design the proper compensation and incentive model.

Although every team and context are unique, here are a few principles to consider:

  • Make the bonus count. Most product team members end up with a 10-15% bonus. That’s not enough to move the needle. Make it 25-30% of total compensation uncapped, and you will start to move the needle.
  • Align with broader company goals, but make sure you focus on the team’s impact on these goals. Total company revenue or EBITDA is hard to assign to a platform feature team. While you can consider the broader company goals as necessary thresholds, you need the team to own tangible goals they know they can execute.
  • Supplement with non-financial incentives. I’ve always been fascinated by these sales-masters programs that would reward the best sales contributors and send them – and their significant other – to an exotic destination. You don’t have to go that far! You can still build such a kind of recognition for your high-performance product teams. 

Ultimately, make sure you are rock-solid with your team’s impact goals so everyone knows what to achieve.

96. Don’t focus exclusively on strategy.

It’s an area where entrepreneurs often have an edge because they need to alternate between higher strategic levels and everyday execution constantly. As leaders grow and progress in established businesses, they typically steer away from the pure execution part and operate at higher strategic levels. I’ve seen them fail when they became disconnected from how things got done. 

Successful leaders would still keep “doing” in addition to guiding their teams. They were the ones who could effectively switch back and forth between operating at “stratospheric strategic altitudes” and executing the most mundane tasks at “sea level.”

It doesn’t mean you should micro-manage every single aspect of your business. Just look for where you’ll have the most significant impact. 

For instance, I’ve always paid specific attention to how my product managers generated Product Requirement Documents (PRDs). These deliverables are critical to the ultimate success of a product. I took the time to dive in, commenting, challenging the thinking and the assumptions. I eventually guided the managers to deliver the best possible deliverable.

Whatever the size or maturity of the organization, the best leaders challenge the status quo, get their hands dirty, and genuinely understand how to get things done. It is not the same as micro-managing, however. 

Every team member deserves the right to drive their part. But the right leader will build enough intimacy with how things get done to form an informed judgment on how aligned everyone is. 

97. Stop obsessing over planning and experiment.

Once you have found a winning formula and know how to replicate it for your business, your focus is naturally on perfecting and tuning this great foundation. That’s fine. 

The trap is to fall victim to the planning you establish and not try things out anymore. It’s where most established businesses have a big lesson to learn from startups. They shouldn’t assume the winning formula is here to stay and that all they have to do is plan the execution steps. They’ll be better off accepting that the winning formula still has ways to go and is under constant threat. Instead of taking months to plan, they’d maintain some form of paranoia about the disruptive forces out there. 

So, whatever the state of your business, you’ll gain in experimenting with new approaches, learning from these, and adjusting as you build a better understanding of what works and what doesn’t.

It’s one of the best lessons I’ve learned from the entrepreneur and startup world: don’t spend all your energy preparing the perfect plan. It doesn’t exist. 

Instead, find ways to iterate and continuously improve your execution by experimenting in small increments. It requires some tolerance for failure. The good news is that more established businesses are now opening up to such a philosophy. If you’re still facing resistance, start by incorporating tiny experimental chunks in your plan and progressively expand these vs. solely focusing on building that perfect plan. 

The best leaders I’ve seen were those who try new ways and approaches on a small scale and then assess how these can expand if they start to see traction.

98. Fight against bloated processes.

Once a business meets success, there is a tendency to build an organization and processes that will protect the franchise at all costs. Some believe that such approaches are making it harder for innovation and disruptive thinking to happen. The increased complexity makes it harder and slower indeed.

But processes are here for a reason, and they’re not the source of the issue. The real cause is how bloated some of these processes are and how opaque organizations can be. It makes cross-functional collaboration harder. 

Sub-goals are put in place and become so specialized that you’d think some teams are working against each other. How do you overcome such tension?

Suppose you have a common language for the definition of success. In that case, you’re better off choosing relevant metrics for success that won’t contradict each other. The strength of a unifying vision and its impact on operational planning and organization comes into play. The key here is collaboration, transparency, and shared accountability. 

It takes leadership courage to challenge the status quo and dysfunctional processes, but it’s a necessary move. The startup world is more straightforward, as no function has had time yet to build its “castle.” It’s all fresh. You’re still on a mission to discover what will work. In any case, don’t forget to keep it simple. 

What led you to success was your ability to keep things simple and execute with minimal means and time. Keep that hunger in mind when you revisit your processes as an established business. 

Processes are not evil, but they tend to bloat over time, and the worst red flag is when no one in the company can explain why they put a specific process in place. It means it’s time for an overhaul.

99. Learn how to handle expenses well.

Great leaders know how to drive a P&L (Profit & Loss) and will work with all the relevant teams to save and optimize costs. 

When a crisis comes, you have a plethora of options to consider. But this can quickly become overwhelming and turn into cost micro-management. The most effective approach I experienced was focusing on the top suppliers and expense areas. From there, we would study what should be fixed costs (like salaries) vs. variable costs and optimize.

There’s no right or wrong answer, but the fundamental is that fixed costs help when you can scale, but they don’t offer much flexibility if you are struggling. Variable expenses are likely not as effective when you scale up, but they bring much more flexibility. It’s a good idea to see how you can convert more costs into variable costs in times of crisis. I’m not advocating that you lay off your whole team and hiring great consultants instead! Still, look at how you can increase your flexibility by selling some of your assets and leasing them back, for example.

The principle also applies to your COGs if you manufacture products. You can seek how to turn more of your non-recurring engineering costs (NRE) into variable costs. The levers will differ if you’re a SaaS-only business. 

Still, the principle of cost optimization remains the same. Take an audit of your key suppliers. Apply the 80/20 rule and focus on the top suppliers under your P&L responsibility. Reconsider your major cost items with them for present and upcoming developments.

100. Know how to optimize revenue.

Too many leaders tend to obsess over cost management. When things don’t go as planned, it is tempting (or requested) to go and cut costs to improve your net income. It reaches a point of diminishing return. 

So, make sure you pay attention to your business fundamentals. You will minimize the risk of cutting too far, leading to reduced innovation and irrelevance.

I struggled with cost savings too, until I realized my most significant leverage on the bottom line of the P&L was how to optimize the revenue line. 

Here are the following four top approaches I’ve seen work well:

  • Analyze your portfolio and eliminate “dogs”: in other words, your least profitable products, especially the ones that are in declining categories. I’ve seen too many instances where we didn’t have the courage to end-of-life a money-losing product line. There was always a good reason like a significant customer still relying on it, but it dragged us down.

  • Rethink your distribution strategy: you don’t need to sell your products everywhere! So, please work with your sales team on clearly articulating your channel landscape, the key players, their operating mode for success, and your expected penetration. Once aligned on the destinations of choice for your customers, do they map to your current channel strategy?

  • Be strategic about pricing. You worked hard, creating value and differentiation with your products. Value-based pricing is the way to extract maximum profit, as it forces you to rethink your segmentation and adapt your offering and price structure. You will maximize your impact by working with sales and marketing to align a credible story with your pricing model.

  • Lastly, along these lines, you should also optimize your customer lifetime value by identifying the best ways to up-sell or cross-sell your customers. The goal is to keep improving your revenue and profit by focusing on your existing customers. They are your lowest-hanging fruit.

101. Methodically prepare for the following year.

Over the years, I have perfected my approach when planning for the following year. After proper reflection on what happened in the past year, I’m trying to think of everything I want to accomplish, contribute, and become across all these critical dimensions in the next year.

It quickly bloats into a long list, so I’m applying an essential filter to it: What matters? It helps narrow it down to three to five big goals that I’m articulating precisely, thinking of what success will look like.

As importantly, I’m looking into what I’ll need to do to get there: what I need to start or stop doing, habits I need to form, which milestones, turning these big goals into chewable chunks. In other words, I’m creating my plan for the year.

I keep things simple, so the whole reflection, assessment, and year plan fit on one page. Most importantly, I’m trying not to overthink it. I know things will evolve throughout the year, and I’ll have to adjust for the unexpected.

Reflecting on top lessons from the past year and putting them in perspective makes my new undertakings more meaningful and in tune with whom I am.

Table of Contents

SO, WHAT DO YOU THINK?

Now that I’ve shared these 101 rules of leadership, I want to hear from you!

How much does this list resonate with you?

Which items are definitely on the top of your own list?

Which ones are not?

Any I might have missed?

Either way, let me know by leaving a comment below!

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