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How To Develop Confidence In Your Questions

By Toku

In many ways, questions are the core of coaching. So much so, that if you search for coaching questions you’ll get an ENDLESS list of 50 great coaching questions, 100 powerful questions, 1001 questions for any client.

Don’t get me wrong I LOVE reading list of questions as much as the next person.

But these lists never address the KEY challenge I see most coaches face.

Sure knowing good questions is helpful, but knowing which ones to ask and when is even more important, and trusting yourself to do that is perhaps the most important thing of all.


So how do you develop confidence in your questions? It’s possible to feel confident when you ask a question. Even if you’re not 100% sure it’s the right question to ask. The key to this is a combination of curiosity, humility, and practice.

I’m going to share with you the top 3 things I keep in mind when I’m coaching to help myself feel confident in my questions.


#1 I’m willing to be wrong (aka I practice not needing to be right) 
When I was a new coach I REALLY wanted to be right about . . .
 – What was going on with my client.
 – What the real problem was.
 – What solution would help the most.

 – What the right thing was to say.

Ok if I’m totally honest I still want to be right about this. But I’m not committed to it. I notice that stuff and then I set it aside. I practice a willingness to be wrong.

Why it helps. . . 
The reason this helps is that there’s less on the line when I ask a question. Because my goodness as a coach doesn’t hinge on the answer. When I’m humble enough to be wrong I can ask whatever I dare because the answer doesn’t scare me.


# 2 – I trust my client
I trust my client to answer the question to the best of their ability. I trust my client to tell me if the question doesn’t make any sense. I trust my client to do the work of being coached.
When I trust my client there are no wrong questions. There are only the next questions and follow up questions.

Why it helps. . . 

If you trust your client to do the work of being coached you trust them to find a way to make the question work. This doesn’t mean I don’t try to ask good questions. It simply means I trust them to help make my questions good.


#3 – I hold all questions as a form of practice
I used to think of questions as a sort of performance. I’d try to be clever in my questions. I tried to be really dramatic. (Ok. Again, I might still do this sometimes.)

For the most part, I try to hold each question as a practice. I’m practicing insight with my clients, I’m sitting at the center of inquiry and waiting for the answers to arrive.

Why it helps. . . 
Quite simply: when I practice, I get better. Not just over several sessions but even in a single session.
When I practice, I often ask myself . . .
 – Did that work?
 – What worked about that?
 – What was missing?
 – What could I do better next time?
If I ask a long question and the client gets confused, I reflect.

What was missing? Simplicity. What could I do better next time? Ask a shorter simpler question.

So, I take my time. I simplify the question in my mind first and then I ask.

By turning each session into practice I can coach the client as they show up TODAY, not last week or last month. And I get better over time at asking questions.

Ok, that’s it, now you have my 3 focuses.

So go out, ask questions, be confident, PRACTICE.

You might be amazed at how much better your questions become.

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