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How to Ask More Powerful Questions

“I got this.”

This was my go-to line when I knew what I was doing and wanted to get my boss off my back. What I couldn’t see was how it highlighted a major mistake. I wasn’t evaluating the situation – I wasn’t asking questions. I assumed I knew all the answers and I was usually wrong.

I didn’t realize the error in my ways until a major client rollout flopped and I had no one to blame but myself, my own stubborn belief that “I got this” even though I clearly didn’t.

In a debrief with my boss, he said, “Aaron, when you say I got this and have no concerns about a situation, that is exactly when I get concerned.”

What he meant was as soon as I stop asking powerful questions, I assume I know what’s going to work and stop evaluating potential outcomes and solutions. It’s a tendency we all have when we want to take the quick route. It’s what holds us back from being powerful leaders.

Why is asking powerful questions a key leadership habit?

It provides leaders with a means to mitigate their confirmation biases and dive deep into the evaluation of a situation, a person or their team as a whole.

I had biases for how the rollout was going to play out. I’d done this before, I knew what was going to happen, so why should I look further into it. I wish I could say this was unique to me, but we all do this. Our brains are wired to jump to outcomes, to look for shortcuts.

Not sure this relates to you? Watch this quick video to test yourself.

Daniel Kahneman, Nobel Prize winning behavioral economist who was the first to highlight these biases states, “Confirmation bias comes from when you have an interpretation, and you adopt it, and then, top down, you force everything to fit that interpretation.”

This bias can be fatal for leaders, it can hinder their decision-making ability and blindside them completely. Asking powerful questions is our way around it, it can help us avoid this common miscalculation.

What does a powerful question look like?

I’m going to share a definition and criteria (this sounds funny) of what makes a powerful question but I also want to be clear there is no script for asking a powerful question. Powerful questions evoke clarity, create greater possibility, reveal new learning and generate action. Here are a few ways to determine if a question is powerful or not.

A powerful question…

  • Is open-ended. Ask what, when, or how instead of asking a yes or no question.

  • Comes from a beginner’s mindset. Start by telling yourself, “I don’t know the answer.”

  • Is clear and succinct. Keep it simple, don’t use too many words.

  • Is impactful. It’s important to remember that not every question in a conversation should be powerful. In a 30-minute conversation aim for 2-3 powerful questions.

  • Happens in the moment. This is probably the most important point to remember about powerful questioning. You can’t plan it! Formulaic questions planned before the conversation won’t work. You have to be in the moment.

There is no script for asking powerful questions. There is, however, an often-overlooked trait, which will set you up to ask powerful questions in any situation.

What’s the trait?

Curiosity. Want to discover a master at curiosity? Find any 3-year old and watch them for an hour. They ask what, why and how to nearly everything they see in the world around them. They want to know more and do not limit themselves by the societal expectations of what’s right or wrong. They just ask. As we get older, we are trained to lose our curiosity when it becomes clear it’s not acceptable to ask all the questions which come to mind. Instead, we go about our days having surface level conversations, rarely digging deeper with a co-worker, client or even a friend.

The secret to asking more powerful questions is digging deeper, it’s triggering our 3-year old selves and reconnecting with our curiosity.

I found it hard to come up with a way to share this concept with you. I realized it’s so hard to explain because as adults there are very few situations where we are curious. Then I remembered riddles, they are a great way to bring the curiosity right back. Try this one out…

“What has a head, a tail, is brown, and has no legs?”

As you are reading this, trying to figure out the answer, your mind is swirling with questions and possibilities.

What kind of animal has no legs?

Is it an animal?

What else could it be?

What sort of things have tails?

The series of questions running through your head is your curiosity showing up. It’s the little kid inside of you wanting to understand, to know. Curiosity is the genuine desire to learn more – to explore.

To be able to evaluate people, teams or situations with greater fidelity – go back to the curious part of you that wants to explore. Instead of restricting yourself, open yourself up and allow your mind to ask any question.

Allow yourself to ask the powerful questions. You already have them in you.

Sometimes it may take priming yourself with a riddle to get you there.

“What has a head, a tail, is brown, and has no legs?”

A penny.

Published on Forbes, December 19th, 2017.

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