Bad at Asking Questions? Follow These Three Rules.

2-min. read

My first fifteen years in the corporate world felt like a whirlwind. 

Too busy getting the “job” done and climbing up the ladder, I rarely stepped back to ask deep and insightful questions.

I realize now how bad I was at asking questions at all, too preoccupied with proving myself and getting my – often – pointless points of view across.

But I wasn’t alone. The vast majority of people I worked with were like me, too self-absorbed and busy running the rat race.

Then, one day, a significant product failure forced me to rethink how I could bring real value. Gone were the days of false certainties. I suddenly realized that I needed to become much better at asking effective questions to make a positive impact.

I’m constantly working on it, but it’s already been a lifesaver. With practice, I’ve become a much stronger leader. As significantly, I’ve helped my teammates develop that critical skill, and we all benefited from it. 

Brilliant questions don’t need to be too elaborate. They don’t even need an answer.

Yet, you’ll know you’ve asked the right ones when they open up new avenues, ways of thinking, and actual dialog.

So, how can you take your questions to the next level and bring superior insights to help with your decision-making?

Here are three rules I always keep in mind

#1 Create a trusting environment

If you intend to get into a deep and meaningful conversation, ensure you have established enough reciprocal trust and goodwill with the other person. It doesn’t happen overnight, so keep reaffirming positive intent and genuine interest in each other’s perspectives. It will go a long way.

#2 Choose the right open-ended probing questions

Open-ended questions are a fantastic tool if used properly. Here’s a quick recap of which ones to use and when:

  • Avoid questions starting with “Why,” as these might sound too inquisitive.
  • Use “What” questions to get started and explore ideas or situations.
  • Use “How” questions to better understand the mechanics of specific actions or thoughts.
  • Build scenarios and explore possibilities with “What If” and “When” questions.

#3 Keep your questions to the point and evolutive.

There’s nothing more confusing than long multi-dimensional questions like:

“Did you realize our top customer received a partial shipment on April 2nd that triggered a penalty clause, and our finance team wasn’t even aware of the miss, which made it harder for us to avoid a rating hit with our bank?

Hard to follow!

Instead, break it down into an evolutive set of shorter questions like:

  • What do you think happened to our top customer shipment on April 2nd?
  • How did the penalty clause get triggered?
  • What made the finance team miss that event?
  • What could we have done differently to avoid a rating hit with our bank?

You get the point. These open-ended questions trigger a real conversation that will give you much more robust insights into what happened and opens up avenues for problem resolution.

There are other rules to keep in mind, like what pace to adopt with these questions or how to leverage silences to instill confidence. 

But if you start with these three rules, you’ll be much better than most business leaders.

Good luck!

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