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Improve Your Question Skills: Understand Your Role

This lesson is a part of an audio course 5 Ways to Improve Question Skills by Dean Heffta

Our position affects our performance.

If we're playing point guard on the basketball team, our actions will be very different than if we were the center. If we are the foreman on the construction site, our behavior to be effective will be different from that of the welder.

Our position affects our performance.

The same is true when it comes to asking questions of others – the position we take on will affect the questions we use, and how they are heard.

In this lesson, we'll identify the four different roles we may take on when asking questions.

Here we go…


Or, you may call it the Sage or even Guru. Regardless, it's the wise one who is there to help you discover things about yourself.

We may take on this role when we find ourselves in the role of mentor. While we have plenty of experience in a given area, rather than giving answers when asked – the Guide knows that the real role is to help others to uncover the right answers for themselves.

Maybe a younger cousin is considering attending your Alma Mater and studying the same major. She asks if you think it's a good idea. Our instinct may be to give a yes or no answer, but in the mentor role… we know it's not that simple. We embark on questions that help our cousin to uncover the activities she finds most rewarding, the type of life she hopes to live, the people she enjoys meeting, and so on. In our conversation together, our questions are less about what we think and more about helping her on how to think.

We see so often that people believe their own conclusions more than the answers that are given to them. Because of that, we guide others through thinking rather than giving an answer.

Done poorly, we may be seen as avoiding taking a stance or even being political. But done well, you'll see the energy grow as the cousin begins to think more and more clearly on what's right for her.


It may be the formal title of leader, or it could be when we find ourselves as the de facto person guiding a group conversation. Questions from the leader position follows a theme of what's essential.

From this mindset, the leader's questions are focused on getting to what's most important.

Uncovering what the limiting factor of our business is.

Defining the next most crucial market to pursue.

Determining who is ready to take on greater responsibility and which action is most urgent to take.

If we are leading a group conversation – we may be using questions to determine the most important problem to tackle or conclude the meeting by finding out what each person's key action will be.

It is the application of questions to determine the highest and best – regardless of the topic.


Some years ago, I was startled a night with a loud crack. Looking out my window, I see my neighbor's garage on fire. Immediately I'm over the fence to knock on their door as flames pour out the large window in the back of the building. Moments later, the first fire truck and firefighters arrive. As they begin attacking the garage door with their axes, I say to one of them that the source of the fire is in the back, where there is a large window. His immediate response was, "Sir, please leave the premises. We are professionals." Obviously, he wasn't interested in my "help." I obliged and returned to my side of the fence to watch the rest of the story unfold.

This is an example of me trying to be helpful – but not first finding out if there was an interest in help. I was bursting with advice that was quickly dismissed.

Would I have gotten a different response if I had first asked a question like "Do you want to know where the source of the fire is?" or "Would you like to see the easiest way into the garage?" Remember that when we hear questions, our brains are compelled to engage. I may have opened the captain's mind to the information.

The flip side is when people come to us, asking for advice or help. We may quickly jump into the mode of telling them our opinion or taking over the project. But if we are in the helper position – the most important question we can ask is, "How can I be most helpful?" At that moment, we are defining the expectations of our relationship – essentially establishing: what success is.

When we ask that question – we set our assumptions aside from how we think we should help – and allow the other person to define it. The questions we ask in the helping role are typically oriented towards helping the other person with their thinking, their decisions, and their conclusions. We aren't there because of our technical expertise or decades of experience. We have to rely on questions like "If someone came to you with this same situation – what would you suggest they consider?" "Fast forward 10 years and look back at this decision, which path will you be most proud of?"


Think back to the medieval royal courts. They had people whose job was to entertain and lighten the mood but also speak truth to authority and help them to see the folly of their plans. Call them fools, jokers, or jesters – they played an important role as advisors.

Often charged with delivering bad news, they could use questions to lighten the impact. Either by enlisting the royal to ask questions or in doing so themselves.

Today, we may turn to comedians as our closest example. Jerry Seinfeld is famous for asking "Why" questions that get the audience thinking. "Why do they call it a 'building'? It looks like they're finished. Why isn't it a 'built'?"

When we play the jester, we can use questions to get people to see the world differently, to point out the absurd, and perhaps just get people re-engaged in the discussion.

So, think about the role you are playing – and then consider the questions that would serve the situation.

The Guide – getting people looking deeper in themselves.

The Leader – orienting the group to what's most important.

The Helper – uncovering how to be most valuable.

The Jester – using levity and questions to soften the blow or change a perspective.

Your assignment is to look for one example where you can apply each of the four roles in your life.

In our next episode, we explore what goes into the crafting of questions.

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Written by

Dean Heffta

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