How to Kickstart a Great Coaching Conversation

This article is an excerpt from the Shortform book guide to "The Coaching Habit" by Michael Bungay Stanier. Shortform has the world's best summaries and analyses of books you should be reading.

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How should a coaching conversation begin? How can you start a session on the right foot?

The Coaching Habit by Michael Stanier discusses seven questions that all coaches should ask. The first question sets the stage for the coaching conversation, so it is crucial. It fits well with the book’s underlying principle to say less and ask more.

Keep reading to learn how to kickstart an effective coaching conversation.

The Coaching Conversation Starter Question

For some managers, the spirit may be willing but the conversation skills may be weak. You may have all the best intentions to coach your team members, but you just can’t seem to find a way to start a coaching conversation without any awkwardness. So, you fall back on small talk, mere troubleshooting, or weekly meetings with the same old agenda, leading to meandering, time-consuming, and unproductive coaching conversations.

Questions about the weather, sports teams, or weekend plans rarely lead to something that can help your direct reports grow. However, questions that seem like they come from a coaching manual may feel too formal or uncomfortable to address. 

What you need, then, is a question that hits just the right balance, one that’s casual and non-threatening while being direct and meaningful. The first essential question, “What’s on your mind?” is informal enough to encourage openness but focused enough to draw out the exciting or worrying things that have been occupying your team members’ thoughts.

Why This Question Is a Good Coaching Habit

Asking, “What’s on your mind?” not only starts a productive coaching conversation and session but also helps relieve cluttered thoughts. 

Science has shown that even holding a thought in the back of your mind uses a decent amount of your brain power and can influence your work, for better or for worse. 

  • For example, if you’re mulling over a friend’s recent betrayal, you may approach vendors with an attitude of distrust—this may result in missing out on deals you’d usually be able to close. 

When you ask a team member about something that’s been taking up space in his mind, you allow him to bring those thoughts to the surface and release them—therefore helping him let go of subconscious influences on his work.   

How to Make It A Habit

First, recognize your bad habit—when someone comes to talk to you, do you get caught in small talk, jump to giving advice right away, or talk about some other work topic that isn’t really the issue? All these habits prevent the other person from effectively releasing their cluttered thoughts. 

Then, determine what usually prompts you to jump into these bad habits. Often, this trigger looks like a team member or colleague popping in to ask if you’ve “got a minute” or instant messaging you to ask if you’re busy—in other words, when someone approaches you with an issue, you react by doing what feels the most helpful or least awkward. 

Once you’re aware of the different ways team members approach you, you can consciously respond by performing the good habit of asking the right question: “What’s on your mind?”

Make sure you really understand what they’re saying, instead of steering the coaching conversation towards what you think they’re saying. It helps to keep in mind that every issue involves one of the “3Ps”:

  • People: Relationships that may be causing friction or tension
  • Patterns: Repeated behaviors that may be detrimental to a person’s growth. Talking about patterns leads to coaching that focuses on development and helping your team members reach their potential. 
  • Projects: Obstacles like technical challenges and other hindrances that keep a team member from completing a task—often, this is all you’ll need to talk about because it’s what people are most focused on in their day-to-day work. 

When your team member tells you what they’re thinking about, look for the “P at the center of the issue: Think about the relationships, behaviors, and technical obstacles involved, and ask your team member which one they’d like to discuss.

How to Kickstart a Great Coaching Conversation

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Here's what you'll find in our full The Coaching Habit summary :

  • How to turn coaching into an informal, effective daily habit
  • Why you should practice listening instead of speaking for 10 minutes a day
  • The seven essential questions to ask your team members

Elizabeth Whitworth

Elizabeth has a lifelong love of books. She devours nonfiction, especially in the areas of history, theology, and philosophy. A switch to audiobooks has kindled her enjoyment of well-narrated fiction, particularly Victorian and early 20th-century works. She appreciates idea-driven books—and a classic murder mystery now and then. Elizabeth has a blog and is writing a book about the beginning and the end of suffering.

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