How to Start a Coaching Conversation

Two people talkingI’ve been writing about the need for leaders to improve by helping employees to think better and improve their abilities to problem solve. Until leaders learn to do this, they will continue to contribute to employee disengagement.

Starting a coaching conversation is an ideal way to encourage self-directed learning. How do you initiate a coaching conversation?

Posing questions allows you to focus on your employees’ mental processes. Asking them to share their thoughts:


  • Helps them find connections in their minds
  • Makes them more self-aware
  • Encourages them to take greater responsibility for solutions

As they process their thoughts, they’ll begin to search their mental maps for insights and potential solutions.

The following questions can facilitate a constructive coaching conversation:

  • How long have you been thinking about this?
  • How often do you think about it?
  • On a scale of 1 to 10, how important is this?
  • How clear are you about the issue?
  • How high a priority does this issue have?
  • How committed are you to resolving this?
  • What might be the gaps in your thinking?
  • What impact is thinking about this issue having on you?
  • How do you react when you think of this?
  • How do you feel about the resources you’ve invested thus far?
  • What could be a plan for shifting this issue?
  • How can you deepen your insight on this?
  • How clear are you on what to do next?
  • How can I best help you further?

You will notice that none of these questions focuses on the problem’s specific details. Notice how the questions avoid suggesting what employees should think or do. They’re designed to help your people become aware of their own thinking.

At this point, your employees will begin to contemplate key issues on a much deeper level, which allows them to see things more clearly. This often leads to new connections in their brains that create fresh insights.

We need to abandon our need to find behaviors to fix and problems to solve. Concentrate on identifying and growing people’s strengths and abilities to think things through.

What questions work best for you in your coaching conversations? I’d love to hear them! Leave a comment in the box below.

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