Want Better Insights? Go Straight to the Point!

2-min read

Years in leadership roles have taught me one significant learning: leading with the right questions beats leading with command-and-order any time.

By asking the right questions, you help clarify the situations at hand. You empower people and increase their ownership of the problems to solve. You also understand much better what’s on people’s minds, their values, their drivers. 

It’s an invaluable and universal tool you can use in almost every aspect of your life, not only with team members, partners, or customers.

Yet, asking the right questions to obtain the best insights is tough!

In past articles, I already highlighted the importance of active listening. I celebrated the power of open-ended questions that start with “What” when exploring a topic. I also evoked the trap of leading questions.

But there’s more to it, and it has to do with how you simplify your approach. In other words, how to 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 okay 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 you’ve 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 truly understand what’s on Mary’s mind.

Some of us – especially the extrovert type – might argue that shorter and more straightforward questions will lead to awkward silences. Most extroverts hate such silences and tend to keep the conversation active, filling in more contextual – unnecessary – details to avoid discomfort.

I know. I’ve been there too, but now I understand that silence is my friend! It gives time for thinking, and you will obtain a more thoughtful answer to the question you just posed. 

Once you become more comfortable with silence, you’ll become better at asking shorter and more straightforward questions. Think of it as proof that you asked the right way.

I’ve been practicing it for years. Although I’m still far from perfect, I know I’m getting much stronger insights from my shorter, simplified questions.

I trust you will, too, so step back and think about how insightful your questions are, how you can improve and how not to fear silence!

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