Meet Derek – The Best Boss I’ve Ever Had

3-min. read

I went through a fascinating mental exercise the other day, trying to recount all the bosses I’ve ever had and ranking them from best to worst.

Evaluating these 30+ bosses soon turned into significant work! 

What could best sum up outstanding leadership? What criteria should I use for it? How could I be as objective as possible?

After some back and forth, I ended up with one critical proxy for best leadership: the boss I had respected the most.

Interestingly enough, my top ten bosses were a mix of young and more experienced leaders, men and women, with various leadership styles.

I won’t spend much time telling you about my worst boss. To make it short, he was a crook!

Yet, one of these leaders stood out as the best. His name was Derek. He was my boss when I led European product marketing at Adobe in Edinburgh, Scotland. Derek was the managing director for our European operations. Like all of us, he was far from perfect.

So, what made me respect Derek more than any of my other bosses? Were these the long evenings spent conversing around a few pints of beer or glasses of scotch whisky?

Not really, and although it’s been twenty-five years now, what still sticks with me about Derek’s leadership are the following behaviors he showed and helped develop in others:

1 – Derek was straightforward

A truth seeker, Derek knew how to ask the tough questions and could articulate aloud – sometimes with brutal honesty – what most of us had in our minds.

Although he rarely caused them, he wasn’t afraid of confrontations and constantly sought to get to the heart of the matters. It helped us save a lot of time and energy.

2 – Derek didn’t take things – too – personally

He had stellar emotional control and demonstrated maturity in the most challenging times, like when we concluded to close our European Headquarters.

In the heart of adversity, Derek stayed calm and level-headed. It had a soothing effect on all of us and helped us stay highly focused.

3 – Derek “ignored” the negative vibes

Like other great leaders, he wouldn’t allow much “drama.” Yet, he didn’t react angrily to negative behaviors

Instead, he subtly disregarded them into irrelevance while actively rewarding all the positive actions with his attention.

4 – Derek set the pace for success

I rarely felt in a rush when Derek was around. His unique combination of high energy and calm demeanor generated a more serene environment for the whole team. We felt we were in control.

It allowed us to focus on the most critical matters instead of constantly being thrown into the whirlwind of urgency.

I’m forever grateful to have worked with Derek during these formative years. I became more conscious of how such behaviors set the tone for optimal team performance and forged massive respect for him as our leader.

Most interestingly, Derek’s approach was not all about innate character traits. Any aspiring leader can hone these skills and improve over time.

So, give it a try! List and rank all the bosses you’ve had since you got started. 

You might find different criteria than the ones I identified. That’s ok. At any rate, I trust you’ll end up with a clearer view of what your best bosses had that others lacked.

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