How to start a coaching conversation?

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How to start a coaching conversation?

I was once a part of a business coaching group, whose aim was to find small businesses to coach, to help them with their growth. One of the striking things about this group was there was very little attention to the actual coaching session. Lots of stuff about business growth, tools and spreadsheet, but precious little about coaching. One of the newer coaches asked, “how do you start a coaching conversation?” The answer was given “Say good morning and see what happens.” This always struck me as poor advice! Let’s spend today’s blog looking for better advice than that…

Coaching conversations: purpose of the start 

Most coaches will be clear about the beginning of each individual coaching session (assuming this is not the very first session between coach and coachee.) They will say that it is where the topic is agreed, and some outcomes from the session are decided. That’s true, and pretty clear. We’ll look in some detail at how that’s done. 

Coaching conversations: start before you start 

Often coaching sessions are planned in advance. There is a date in the diary, a relationship already established, and the coachee is expecting to be coached. In that case, the coachee can be prepared for the upcoming conversation in advance. In particular, we want them to decide what topic to bring to coaching. It is good if they are ready, and that they have started mulling over the topic. There are a few ways to do this, including: 

  • Email the week prior. A brief but clear email, reminding them of the time of the session, and encouraging them to have a topic to bring to coaching. This simple act generally stimulates enough thinking to make sure a topic is ready and available. 
  • Set expectations at the outset. In the initial meeting, discuss with your coachee what the expectations are. Let them know that a topic is needed for every session. Then leave it to the coachee to make sure they bring a topic along. It may be a fresh one, or a continuation of one already started. 

Informal coaching conversations

Plenty of coaching conversations are informal and arise on the spur of the moment. It may be a colleague, a friend or a team member who comes to us with a question, a topic or a challenge to talk through. Here are a number of ways we can tackle this, using coaching: 

  • Let them say their initial piece. For some, it will be just the headlines… “I really want to talk about an upcoming project”. For others it will be the full story. Either way, it’s fine. Let them talk. 
  • Check whether they want coaching or something else.  “How can I help?” “What are you looking for from me?” “So, you want some advice, or would you prefer me to coach you to your own answers?” These are all useful ways of tackling this phase. 
  • Make sure you understand the topic. “Have I understood that you want to talk about xxx?” 
  • Establish an outcome. “Where do you want to get to with this, in the next xx minutes? (Give the timeframe that you have available) 

This approach or similar, using these questions, or versions of them will help. They will get the coachee clear, focussed and ready to talk through their topic. And the structure works just as well if they are calm or have strong emotions. 

Planned coaching conversations 

If the coaching session has been booked in advance, then some of the above can still apply. What is different is that there is an expectation that you’ll put in time on finding out what the topic is. This will be an important part of the coaching process. The structure would be something like this: 

  • Review the actions from the last session – or not! (See below) 
  • Ask for a topic and let the full details come out 
  • Ask for an outcome from the session: “where do you want to get to in the next 30 minutes?” 
  • Ask further questions, not about the detail, but about the outcome: Some favourite questions I have heard coaches ask include  
  • “Why now?”  
  • “What impact will be resolving this have?” 
  •  “What feelings do you have about the topic?”  

All of these will start to deepen the coachee’s thinking, even at this early stage. 

Reviewing actions agreed in the last session 

When starting session 2, 3 or onwards, there is another aspect that is open to debate. That is the question of whether we start the conversation by reviewing the actions and learnings that the coachee took from the last session. There are two schools of thought about this – yes and no! The yes group, amongst which I am one, say that it is a useful opportunity to review how they got on with their actions. Also, it holds the coachee to account, and it provides all sorts of learning opportunities for the coachee from talking it through. The no group say that the actions lie with the coachee, that unpicking them brings in hierarchy in the relationship, and so should be avoided. Take your choice of an approach. Make sure you contract with the coachee on the approach. 

Final thoughts 

Starting the coaching session does much more than just establish what the topic will be. It’s there to build trust, to show your coaching style, to let the coachee feel comfortable in the role of talker. Getting this part of the session strong is an incredibly useful thing to do. It creates a great starting point for the coachee to work well on their issue. Invest in making the beginning of the session solid, and the rest is likely to flow more easily. 

Happy beginning, and happy coaching!

Charlie Warshawski


If you were stimulated by this article and want to know more about how to use coaching for your career, your organisation or your life generally, then get in contact. Email us at or book in a time for a 30-minute phone or Zoom call  

We look forward to hearing from you! 

Charlie Warshawski is a leadership coach and coach trainer. He runs an accredited coach training organisation, Love Your Coaching, offering coaching qualifications. In his coaching, he works 1:1 with leaders, business owners and entrepreneurs, supporting them on topics that are both professional and personal – according to their needs 

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