“Why bother to have this coach/coachee relationship at all?”
At the top of an engagement you should look your client square in the eye and ask this question. Why?
All too often the answer is taken as a foregone conclusion, and why wouldn’t it be? Coach knows what’s on his brochure, the sort of things he says he can help with and the outcomes that working with him tends to support. Having made the decision to kick things off in earnest, client does, too.
Asking this question forces clarity of intentions for THIS particular client. Your brochure might be crystal clear about the “why” in the abstract. But it says nothing of how that maps on to the particular ambitions and situation of the individual before you.
Granted, this can be a scary question to ask! It’s like putting them on the spot to justify that working with you actually makes sense and is worth doing, and that’s a test you very much don’t want them to fail.
But this question is just the lead into a brief interview, whose purpose is to clearly establish:
What would you like to have accomplished by the time we’re done in 4, 6, 12, or whatever N number of weeks?
The time-bounded part of N weeks is essential. It’s not to say you’ll necessarily stop working together after those N weeks over, but clear intentions have to be bounded in time (otherwise this exercise devolves into a “someday” fantasy). If your overall engagement isn’t time bounded, or it’s longer than, say, six months, break it into segments.
This interview will be a peppering of questions like:
- What project will you complete?
- What outcome will you have caused?
- What will be so in the world?
- What do you want that number (metric) to get to?
- How will we know it’s done?
- Why does accomplishing that matter to you?
- What will that make possible?
These questions will apply to each of the accomplishments that your client intends to fulfill on. Ideally there will be several, to give variety and depth to the overall intention. If it’s one big thing, you can (and almost certainly should!) break it down into sub-parts: probe your client to discover whatever distinct, interrelated pieces contribute to the whole.
As your client speaks and grapples with these questions, encourage them to look deep for all the areas of life that they could and should pursue results in (do this with three simple words: “And What Else?” Michael Bungay Stanier calls this the AWEsome question), and guide them to describe desired outcomes in specific, measurable terms (as in it needs to be clear during a later reckoning whether it was met or not).
Properly executed, this interview feels to us clients as a luxurious experience: one where we’ve been really heard. You are nailing it when we get excited to imagine what it will be like to be supported in fulfilling these things that matters to us (we may or may not share this excitement with you outright, but you’ll know whether or not it’s present either way).
Ultimately your job is to capture these desired outcomes. These are the clear, up-front intentions of your working together. These are the real reasons to have this coach/coachee relationship, and these need to inform and guide your coaching as the arc of those subsequent weeks play out.
As your clients’ intentions for the “why” of working with you evolve, update this Whiteboard with your client watching. Having this present for both of you to see and remain present to powerfully anchors and keeps alive their excitement to work with you. Their diligently showing up to the process and doing the work naturally flows out of this.




