Recommended Insights
Recommended Insights

How to Have a Coaching Conversation

How to Have a Coaching Conversation

The ability to start — and hold — a coaching conversation is a transformational leadership skill. Through coaching, you help people become more self-aware. You turn experiences into learning opportunities. You reinforce strengths and explore challenges. You help people take responsibility for their actions and their development.

As more and more people in your organization develop coaching and conversational skills, you instill a coaching culture, which increases:

  • Employee engagement
  • Job satisfaction and morale
  • Collaboration
  • Teamwork
  • Bench strength

Coaching isn’t just for specialized professionals. In fact, nearly anyone can conduct a coaching conversation. Coaches can help people who are ready to identify problems and find solutions. And being a coach — developing others — is part of leadership.

Some of the most powerful coaching experiences are informal exchanges in hallways, cafeterias, workspaces, and over video calls in the course of everyday work.

When enough people at an organization begin coaching one another, something powerful begins to happen. As a critical mass of people having coaching conversations is reached, relationships strengthen, engagement increases, and performance improves. Interactions across the entire organization, both in-person and virtually, become more effective, and together, as we explain in our white paper on the subject, all these conversations start to create a better culture.

First, Recognize When to Hold a Coaching Conversation

First, identify when there’s an opportunity for a coaching conversation. Not all conversations lend themselves to coaching. Make sure you know whether it’s the right time and you’re ready to try and coach your people. To recognize when someone is open to having a coaching conversation, pay attention to the following cues:

  • “Can you help me think things through?”
  • “I’d like to bounce some ideas off of you.”
  • “Could you give me a reality check?”
  • “I need some help.”

In these moments, you can turn a typical conversation into a coaching opportunity.

Follow These 3 Steps to Have a Coaching Conversation

At that point, remember these 3 guidelines to hold a coaching conversation:

  1. Listen carefully.
  2. Respond thoughtfully.
  3. Resist imposing your own solution.

1. Listen carefully. Don’t assume what the conversation is about or what path it should take. Truly listen, allowing space for others to think, reflect, and express themselves. Start with building your active listening skillset, but know that truly listening goes beyond active listening, to listening to understand.

Listening to understand focuses on the idea that there are multiple levels of information we must tune into during conversations. One level, of course, is the factual information being presented — most of us tend to pay attention primarily to that. But listening for the values behind the topic at hand and the emotions that people bring to an issue is an important part of a better conversation.

That’s where we often find unstated objections, sensible reservations, and concealed barriers that might torpedo new initiatives. Stronger and more robust solutions to business challenges emerge when people are really listening to understand one another.

2. Respond thoughtfully. Coaching isn’t about the quick fix or first solution. It’s about uncovering answers through inquiry, openness, and exploration. Start by asking powerful questions that draw out more information or stretch the other person’s thinking, such as:

  • What else could you do?
  • What else occurs to you?
  • Who else have you talked to about this?
  • Who else is affected in this situation?

Beyond creating mutual understanding about facts, asking powerful questions like these can help uncover insights that wouldn’t have come to light otherwise.

A non-directive prompting question like “How do you want your team to feel when you announce the new initiative?” is likely to spark more reflection and lead to greater insights than asking “When are you announcing the new initiative?” While the latter question might be helpful in getting the person inquiring up to speed, it isn’t particularly powerful and isn’t likely to add any real value for the person answering, as they simply repeat a straightforward fact they already know.

Be sure you set a comfortable tone, maintain eye contact, and give plenty of time for them to think and respond to your questions. Encourage them to express themselves — without you agreeing or disagreeing.

3. Resist imposing your own solution. Shift away from the common and natural tendency to want to problem-solve or give advice. There are times to direct or give answers, but coaching conversations are about the other person’s learning — not about your opinion or expertise.

Informed by neuroscience, the real art of conversation is balancing an appropriate mix of challenge and support. Providing support includes assuring people that they’ve been heard and, especially, that their feelings and values are understood. It provides an important sense of psychological safety, builds trust, and encourages honesty and transparency.

When that ratio is right — and practiced in an authentic rather than formulaic way — the challenge is received and actually fosters more constructive dialogue, rather than triggering defensiveness.

When you’re able to listen carefully, respond thoughtfully, and resist imposing your own solution, you have the basis of a coaching conversation.

So whether that conversation was a planned coaching session or an impromptu moment, you’ve opened the door to new thinking, new action, and valuable learning. And when coaching conversations start to happen all across your organization, you have the foundation for a strong organization-wide coaching culture.

Ready to Take the Next Step?

Upskill your team so they understand how to have a coaching conversation and listen to understand one another. Our conversational skills solutions can equip your team to hold better conversations every day and help you scale a culture of feedback across your entire organization.


Subscribe to our eNewsletters to get the latest on cutting-edge, leadership insights & research.
November 23, 2020
Leading Effectively Staff
About the Author(s)
Leading Effectively Staff
This article was written by our Leading Effectively staff, who analyze our decades of pioneering, expert research and experiences in the field to share content that will help leaders at every level. Subscribe to our emails to get the latest research-based leadership articles and insights sent straight to your inbox.

Related Content

image of people standing on painted venn diagram representing concept of virtual collaboration
Leading Effectively Articles

How to Improve Your Organization’s Virtual Collaboration

With remote and hybrid work on the rise, effective virtual collaboration has never been more important. Success requires more than technological solutions – don’t overlook the importance of interpersonal skill development, too.

Use Active Listening to Coach Others
Leading Effectively Articles

Use Active Listening Skills to Coach Others

You don’t have to be a coach to use these 6 active listening techniques. Go beyond active listening and truly listen to understand, turning a casual chat into a coaching conversation.

image with microphone and lead with that podcast episode title, What Naomi Osaka Can Teach Us About How Leaders Can Support and Manage Mental Health

Lead With That: What Naomi Osaka Can Teach Us About How Leaders Can Support and Manage Mental Health

In June, 23-year-old Naomi Osaka, the No. 2 ranked tennis player in women’s tennis, withdrew from Wimbledon. This happened in the wake of Osaka withdrawing, in the second round from the French Open in a storm of controversy caused by her decision to skip mandatory post-match news conferences. In this episode we explore how Osaka’s acknowledgment of her own anxiety and depression is helping to normalize the conversation around mental health, and what leaders today can do to lead with that.

Transforming Your Culture With Conversations

Transforming Your Culture With Conversations

As the single activity that touches every aspect of your business, conversation is critical to the success of your priorities. Watch this webinar on how to transform your culture with conversations.

Accelerating Leadership Development at Market Speed
Leading Effectively Articles

Accelerating Leadership Development at Market Speed

Leadership development is no longer just for individual leaders at the top. Follow these 3 steps for accelerating leadership development and scaling learning and skill-building across your entire organization.


Please update your browser. requires a modern browser for an enhanced and secure user experience. Internet Explorer is no longer supported or recommended by Microsoft. The Center for Creative Leadership recommends that you upgrade to Microsoft Edge or similar.