Executive Coaching & Coach Training for Leaders

How to have a coaching conversation (for leaders)

Here are eleven tips for successful coaching conversations with your employees. It all starts with the first three. Nail those and you're on the right track.

Be present 

Presence in coaching is everything. The more present you are, the better you can listen, the better your questions will be and the more cues you will pick up from your coachee. Presence sounds easy but we all know it’s not. Removing all potential distractions (phone, laptop etc) and a focused/conscious effort to be present are a great start.

Be curious 

Curiosity leads to better questions, which have the potential to lead to new awareness and learning for your coachee. The most effective mindset shift here for a leader is to move from teacher to learner. Don’t just be curious to the topic/challenge your coachee brings, be curious about the person in front of you and how they see the world.

Actively listen

I asked a group of leaders this week what they believe active listening is. "Listening not to respond but to actually hear what is being said" was a brilliant answer from one of the group. Our aim when we actively listen is to listen to the words that are being used and everything else that is 'filling the space'. It's important that we listen beyond the normal surface level listening we do in life. Our typical listening involves waiting for a pause so we can jump in and add what we have to say. In coaching skills programs, I get leaders to come up with a list of things that we can potentially ‘listen’ for when we’re really tuned in to our coachees. That list is a BIG one and includes words, tone, language, energy, body language, behaviours, attitudes, limitations, emotion, wisdom, experience, strengths, values, assumptions… the list goes on. 

Believe in the person you’re coaching

This is essential to a good coaching outcome. If you believe that your coachee is capable, creative and resourceful then you’re good to go. If you don’t, then coaching just isn’t gonna work (reach into your leadership bag of tricks and choose another tool).

Choose your moment 

Leadership presents many different opportunities for coaching. It might be a dedicated coaching session with a member of your team (i.e. a monthly 45 minute 1:1 coaching catch-up), a new project being handed over or maybe a coachable moment in the hallway when you’re discussing a challenge they’re facing.  

Use a coaching model to guide the conversation 

If you’re new to coaching, get your hands on something like the GROW model. It’s hard to know how to coach without knowing how to structure a coaching conversation! Coaching models can also be useful for plucking one or two questions that might come in handy for a coachable moment with an employee.

Have a clear outcome 

Explore the outcome that your coachee wants from the coaching session/conversation. Keep exploring until you’re both clear. Coaching sessions that lack a clear outcome go around in circles and they’re confusing (and unsatisfying) for coach and coachee. 

Ask good questions 

Powerful questions are the ones that arise in the moment and have the potential for your coachee to see themselves and the challenge they’re facing in a new and fresh light. Asking good questions is easy when you’re present, curious and actively listening. If you believe something is worth exploring, in the context of the outcome your coachee wants from the conversation, then be curious and ask.

Keep it simple 

When asking questions or offering observations, keep it short. It’s not easy answering three questions that are stacked on top of each other (think football journo), or responding to a 100 word observation. Don't dilute your message.

Step back (in a metaphorical sense)

After a question or observation give your coachee space to reflect/process and speak. Challenge yourself to hold your silence a little longer than usual and you’ll likely be rewarded. Try not to hold your silence to the point where it gets awkward… you’ll get better at getting the balance right over time.

Allow your coachee to create and own their next steps 

And support them to find a way to be accountable to themselves (rather than to you). This can be as simple as “how will you be accountable to following through?” 


One of the best things about coaching is that it encourages and permits the person being coached to experiment with new behaviours, skills and thinking. That permission to experiment also extends to the coach in practising and exploring coaching skills!

Sam PattersonComment