Three Types of Coaching Questions to Include in Coaching Conversations

In a previous post, I wrote about the types of questions to avoid in coaching conversations. This week, I think it only natural that this week I focus on the types of questions that we should ask in those same coaching conversations. We’ll be looking more closely at three types of questions: curiosity, context, and unexpected.

Curiosity-Based Questions

I feel like curiosity is something that I talk about a lot here (remember that Picard post about curiosity and one impossible thing at a time from a couple of months ago), and yet here I am again, still climbing this wall. Of course, it is right about now that I bumped into this Pascal quote about curiosity

“Curiosity is only vanity. We usually only want to know something so that we can talk about it.”
― Blaise Pascal, Pensées

Of COURSE we want to know more so that we can talk about it! Isn’t that part of the point of coaching? (But yes, this did make me laugh, and more than a bit.)

Curious questions are humble and come from a desire of wanting to know, not wanting to judge. Curiosity-based questions are important because they keep us (okay, me) in wonder and out of judgement, the focus on the client, and out of solutioning. These questions help me to anchor in curiosity.

• What do I see? What do I hear? What is coming up for me?

• How am I judging, and how can I shift to observing?

• What is it like from their perspective?

• How does their experience help them to see things differently?

• What is important about this question? Am I asking this question for them or for me?

True curiosity is genuine wonder, and it comes from a place of joy, not fear. It will make all the difference in the world for your coaching.

Tips for Staying in Curiosity-Based Questions

• Ask questions that serve the client, not you. Shallow questions are useless. Focus on asking humble, of-service questions.

• Talk less, listen more. My more powerful coaching sessions are always those where I have an open mind, open ears, and an open heart, not an open mouth.

• Stay out of judgement, avoiding questions that confirm your own beliefs and biases.

Contextual Questions

Recently, a client came in with the topic of what to do next with their house and possessions. The person and their spouse had downsized from a larger house to much smaller house a few years ago, retaining only the things that they absolutely loved and found to be beautiful. But now, they were continuing to age, and they were worried about the beloved momentos of a life well-lived being lost to natural disaster. They didn’t know what to do next.

I then asked this question, “What is it like to live amongst beauty?” The response from the client was immediate and powerful: tears.

But do you see what happened in that question? I used the client’s language about beauty and their home to ask a powerful, meaningful question. I played off their words, their imagery to deepen the context of the conversation. The strength of that first question helped us to have a meaningful, productive session, culminating in a course of action that brought them immense joy. I doubt that we would have gotten there, however, without that first, great question.

Here is a small definition of contextual questions:

The contextual questions usually contain reference expressions to refer to previous questions and their answers. We address the reference resolution in contextual questions by finding the interpretation of references so as to maximize the cohesion with knowledge.

I think of contextual questions as the “Yes, and…” of this realm. The client plays an integral role in this type of question because as a coach, you use their experiences and descriptions to ask question to help them go more deeply into that experience. You say “yes” to their question or answer, and then “and” to even more excavation.

Tips for Using Contextual Questions

• Get really, really good at powerful questions, so good that you don’t even have to think as to how you want to construct them. Practice this skill so that it becomes second nature.

• Level up your listening. In coaching, we talk about being at levels two or three in coaching conversations. To use contextual questions effectively (or honestly, at all), you’ll need to be listening at level three.

• Use their language, meaning that as much as possible, use the clients’ own words and metaphors. Stay in their realm, stay in their world.

Unexpected Questions

And last but not least….unexpected questions. The question you never saw coming. The question out of left field. The question that borders on ridiculous. What is it about this type of question that makes them so effective?

Think of it this way. The human brain is a pattern-making machine, and it is always looking for shortcuts, things to automate, things to make easier. And that includes the way that you do things, the way that you think. That unexpected question derails old patterns and habits and ways of thinking, making it possible for a person to find new ways forward.

Take Doug here, for example. He was entrenched in giving his “My name is Doug and I love you” spiel when the expected happened, a squirrel, and it rocketed him to a new way of acting and being.

Here are some examples of unexpected questions:

• What would it be like to think about this from your motorcycle’s perspective?

• What would your dog do in this situation?

• How would your eight-year-old self handle this problem?

• What is the theme song for this relationship?

See—you’re already thinking in a different way, wondering how you might answer these questions. Give them a try in your next coaching or mentoring session.

Tips for Asking Unexpected Questions

At first glance, it might seem difficult to generate unexpected questions on the fly, so here are some tips to help you get there.

• Play to the outrageous, even if the question seems ridiculous to you. The question isn’t for you, it’s for the person you are coaching and mentoring. A question that is ridiculous or outrageous to you might be just what they need.

• Use your intuition, leaning into level-three listening. Pay attention to what is happening in you to better inform what question you ask next.

• Lean into bravery. It takes courage to ask any good, powerful question, but an element of bravery is needed to ask the unexpected question. Be daring, be brave, and ask the question no one expected to hear.

Wrapping It Up

This post originated as a conversation between Kerri Sutey and me. I was driving north to Montana, and we spent an hour on the phone, talking this topic through. Originally, we were thinking that we might use it as the basis for a conference talk (and we still might!), but for now, it deserves to be its own blog post. But don’t worry—you’ll see either or both of us sooner rather than later on a stage, talking about coaching or the Agile Coaching Circles.

The image used for the title of this blog post was captured by Linda Nickell. Connect with her on Instagram as @coznlinda, or join in for the next Happiness Hour. Details and schedules can be found on her site.