Coaching is a powerful approach to helping people solve their challenges and supporting their growth. To implement a coaching practice, it’s important to learn how to steer a coaching conversation and what concrete questions and tools can be used in each conversation phase. This post provides a concise and hands-on model and toolbox of the coaching questions and tools I gathered over the years. I compiled everything into a cheat sheet called the “Coaching Steering Wheel”.

TL;DR: Cheat Sheet for Steering Coaching Conversations

The PDF can be downloaded here. I printed the cheat sheet and put it on my desk so I always have guidance during conversations.

Introduction

Disclaimer

I don’t consider myself a trained coach with official titles. But over the years of coaching people as a manager, reading books, attending courses, and being a coachee on my own, I learned a lot about hands-on coaching and could apply many coaching tools in practice.

Coaching as a Manager

There is a lot more to say about coaching as a manager. However, in this post, I like to focus on the basics of coaching. Those basics can be applied in any coaching conversation (without a hierarchy between the participants). I will cover the manager-specific bits in another post.

For now, it’s important to note that coaching is only one way to help somebody. Instead of coaching them, you could mentor them, train them or “manage” them (being more tactical and directive). It all depends on the situation. Keep that in mind when reading about the coaching approach described in this blog post.

Definition of Coaching

As there is no official definition of coaching, people have different notions about it. To ensure a common ground for this blog post, I share my working definition:

Coaching is guiding people to find the answer on their own and developing new skills and insights without telling them what to do. The path is already there - but they have to find and follow them. In a session, I want to

• activate my coachee,
• keep the thinking bubble over their head,
• point them to positive solution-oriented thinking,
• and make them aware of their power and responsibility to change something.

The Coaching Steering Wheel: How to Steer a Conversation

There are many different coaching models on different levels of granularity, but they tend to follow a similar pattern, which I call the “Coaching Steering Wheel.” It gives the coach a mental model to steer a coaching conversation. There are four steps:

1. 🔎 Problem: Problem Analysis, Information Gathering, and Reflection
2. 🎯 Result: Desired Result and Goal Definition
3. ⚖️ Options: Brainstorm Options
4. 🚀 Actions: Required Actions and Support

Next, we look at each step and present hands-on question techniques and conversation tools that help you in each phase of the conversation.

🔎 Problem Analysis, Information Gathering, and Reflection

What’s on Your Mind?

An excellent opener for a conversation is the question

What’s on your mind?

Often, your coachee now tells you about a problem they have.

Now, it’s about revealing information and digging deeper into the problem by asking questions that make the coachee reflect deeply on the problem.

What is the Real Challenge Here for You?

What’s the real challenge here for you?

This question helps to reveal the real problem and direct the focus on what matters most. It also helps to slow down the rush to action.

What Kind of…?

What kind of…?

This question helps to become more specific and asks the coachee to become more concrete which can reveal new insights.

And What Else?

And what else?
Is there anything else about…?

While the “What kind of…?” question helps to dig deeper, asking for “and what else?” is about broadening the view. It aims to create more insights, self-awareness and lead to more options.

Embrace Silence

Resist the urge to fill the silence with your talking. Learn to endure - and finally embrace - silence. Silence often means that your coachee is thinking, which is exactly what we want them to do. Don’t interrupt their reflection process by talking.

Remember that coaching is about the coach helping the coachee get new insights and perspectives on their own. It’s not about you telling them what to do and what your solution is. Hence, your input is not as important as you may think. So be silent.

Don’t talk. And then, don’t think about talking. Instead, listen carefully.

Summaries, Paraphrasing, and Labeling

Repeating what your coachee is saying is a simple but powerful tool to keep your coachee thinking and talking. There are different styles, which vary in how much and what you repeat and how much you change the original phrasing (mirroring, labeling, summaries, paraphrasing). However, the most simple and hands-on advice is to use the following words to start your sentence:

It seems like…
It sounds like…
What I am hearing is…

… and then either:

• repeat what you have heard in the client’s words (summaries)
• or repeat what you have heard in your own words (paraphrasing)
• or label your impression of their situation or feelings (labeling).

In all cases, the coachee will continue to think and talk. They will either confirm or correct your impression, which leads to more insights.

Moreover, the coachee will feel heard and that you have understood them. So those techniques are also powerful tools for building relationships and trust.

Tell Me Where I’m Wrong

Tell me where I’m wrong, but it sounds like… What do you think?

You ask the coachee to consider something without becoming defensive. You just share a hunch without it being an insinuation. It’s just you wondering.

Example:

Tell me where I’m wrong, but it seems like you are struggling with interpersonal conflicts. What do you think?

Scaling

On a scale of 1 - 10, …

You ask the coachee to rate the situation on a scale of 1 to 10. This is useful for getting clarity on the severity of an issue, the difficulty, or the impact of something in a more objective way.

On a scale of 1 - 10, what is your stress level?
On a scale of 1 - 10, how satisfied are you with your work?
On a scale of 1 - 10, how committed are you to taking this action?
On a scale of 1 - 10, how difficult is this task for you?

One insight might be that an issue or situation is not bad at all, which helps to put things into relation.

If you repeat this exercise, you can track the progress of your coachee.

In any way, good follow-up questions are:

How can you improve the rating by 1?
How can you get to the next level?

But we’ll cover how we reflect on possible action in a later section.

Perspective Change

What would Peter think about X/you?
How would you do in Peter’s situation?
Why has Peter reacted that way? What do you think?
What if the situation would be the other way round?
How would you describe the situation if you see it through the eyes of X?
What is Peter’s intention?

You ask the coachee to consider a problem from a different perspective to discover new insights.

How & What (Instead of Why)

Avoid asking questions with “Why”. They often feel like an accusation and aggressive. Instead, use “How” and “What” questions.

“How come?”
“What are we trying to accomplish?”
“What’s the biggest challenge you face?”

Facts Vs. Stories

Especially when your coachee talks about an interpersonal conflict with another person or is very emotional, it’s crucial to listen carefully and spot when your coachee mixes up facts and stories.

• A fact is objectively provable. Peter said X. Julia walked out of the room.
• A story is the meaning we give a fact. It’s our interpretation of the facts. It often bases on assumptions that might be inaccurate. They don’t have to be true, and - even more important - we can decide how we think about the facts and change that way of thinking.

In a coaching conversation, it is insightful to nudge the coachee to separate the facts from their stories and thoughts. Next, talk about other possible interpretations of the facts.

What are the facts?
And what is your interpretation and assumption?
How is Peter’s behavior making you feel and think?
Is there any other interpretation of what happened?
What might be the intention of Peter?
Why would a reasonable, rational, and decent person do that?

🎯 Desired Result and Goal Definition

After understanding the problem better, we want the coachee to define their desired result or goal. Goal setting is the essential first step to getting them active and realizing their self-efficacy and that they can do something about their situation or perception.

The Problem Trance or “Resisting What is”

Some coachees get lost in thinking about the problem or situation over and over again. They continuously loop and spend much energy talking about the problem (e.g., how unfair, stupid XYZ is.) without moving on to acceptance, solutions or actions. That’s called the “Problem Trance.”

Another word for this pattern is “Resisting What Is” which often happens when people go through a change. Their thoughts can get stuck on the why and should. They pay a lot of attention to the problem and not the solution. Thus, they can’t move forward and resist the current reality.

As a coach, you can detect that pattern and try to make them recognize what is beyond their control.

What is in your control?
Can you control XYZ?

Shift to Positive Thinking and Proactiveness

People tend to focus more on the negative side. It can be a spiral to the bottom, and hard to flip them to a positive frame gain. A helpful question to accomplish that is:

What would you like to have happen?

When a coachee tells what they want (goal, result), it flips them to positive thinking and lets them think about positive things.

Alternatives are:

What is your desired result?
What is your goal?

⚖️ Brainstorming Options

After defining the goal, we brainstorm options to achieve the goal.

Discover Options

Here are some questions to discover options:

How can you achieve X?
What is your suggestion?
What are the alternatives?
How have you handled similar situations in the past?
What have you tried so far?
With whom have you talked so far?

You can ensure that your coachee has thought through all possibilities and did a risk analysis:

What can happen in the worse case?
What have we overseen?

🚀 Required Actions and Support

Finally, we move to concrete actions and the required support.

Discover Actions and Support

To talk about the coachee’s actions, you can ask something like:

What is your first step?

Mind that this is about the coachee and their action and how they can change their situation. Make them aware of their power and responsibility to change something.

To let the coachee reflect on possible support and help, they could get, ask:

What do you need to do to get there/the result?
Who can support you?

Especially as a coaching manager, you can additionally ask:

How can I support you?
What would you do if I wouldn’t be around?

Ensure Commitment: Document and Follow-Up

Ensuring commitment to the goals and action is always important but especially crucial if you are the coachee’s manager. Take the following steps:

• Document the goals and agreed actions. A good approach is to have a shared document (e.g. Google Docs) and write down the goals and action items during the session.
• Follow-Up. Agree that you will talk about the actions and the progress in the next session again. Schedule the next session if it’s not recurring anyway.

Contribution and Further Readings

No tool in this blog post is new. I only collected everything I learned and reorganized it into a structure and model that works for me in my daily conversations. Therefore, I like to give credits to:

• “These 4 Questions Will Drastically Improve the Way You Lead”. An article based on Michael Bungay Stanier’s book “The Coaching Habit”.
• Coursera course “Coaching Skills for Managers” by Kris Plachy. The tools “Resisting What Is” and “Tell me Where I’m Wrong” have been covered in the course “Coaching Practices”.
• Clean Language, that David Grove developed, contains the questions “What kind of…?” and “Is there anything else about…?”. I learned them in a course on Agile Leadership conducted by the leadership coach Olaf Lewitz.
• The book “Never Split the Differences” by Chris Voss is about negotiation but it contains many techniques that are also useful for coaching conversations. For instance, it covers the power of summaries, labels, and why you should avoid asking Why. I summarized my lessons learned from his book in my post “Manager’s Summary of the Book ‘Never Split The Difference’”.
• From the executive coach Hanne Dinkel, I learned the notion of the “Problem Trance” and that I should avoid asking Why (again). Moreover, she thought me the questions “What can happen in the worse case?” and “What would you do if I wouldn’t be around?”.
• I derived the tool “Facts vs. Stories” from the book “Crucial Conversations”. But a similar tool is presented in the already mentioned course by Kris Plachy (called “Fact vs Thoughts”).
• The GROW model is an alternative conversation model. Thanks to the leadership coach Shivani Buchner for pointing me to it.
• The question “What would you like to have happen” is also part of Clean Language. I learned this one from my colleague Sherilyn Ooi.
• I took the notion of “keeping the thinking bubble over their head” from James Stanier’s book “Become an Effective Software Engineering Manager”.