Twenty Minutes and a Pricing Document
Marcus, founder of a 30-person software firm, has had four sessions. He arrives with a 14-page pricing strategy document and says: "I've got 20 minutes and I need you to tell me whether this pricing model works. You ran product at a SaaS company, right?" You did, and it is on your public bio. He also wants to move sessions to 6:30 a.m. and to "keep it loose" - no goals, no agenda, just a sounding board. Meanwhile his board has asked for evidence of "coaching outcomes" in eight weeks, and Marcus has forwarded you that email without comment. Session five of ten is due to start in two minutes.
1. How do you handle the request to evaluate the pricing document in this session?
Read the worked answer
Decline the consulting task, but do it in a way that keeps the relationship intact and redirects to the coaching work.
Name the difference plainly and without apology: "I could give you opinions on pricing, and I have them - but the moment I do, I'm consulting, and you lose the person whose job is to help you think. That's a bad trade for both of us." Then test whether the real request is for a decision or for relief from the anxiety of deciding. Ask what he would do if I were not in the room, or what he is most afraid of getting wrong.
If he genuinely wants an expert review, say so explicitly: it is available, it is outside this contract, and it would need a separate arrangement and probably a different person so the coaching is not contaminated. Then use the remaining time on the coaching question underneath - how he makes high-stakes calls, and what he notices about how he is making this one. That is the work he hired you for, and it is also what the board is actually paying to see.
2. Marcus wants to drop goals and "keep it loose," while his board wants evidence of outcomes in eight weeks. How do you re-contract?
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Treat the two requests as a single negotiation rather than two separate problems. "Loose" and "evidence" are not necessarily in conflict, but they cannot both be served by an agreement nobody has stated out loud.
Ask Marcus what he wants from the remaining six sessions and what he is willing to let the board see. Then propose a workable structure: sessions can be open in content, but each one ends with a sentence he chooses about what he is taking away, and every third session reviews progress against two or three outcomes he names. That gives the board substance without turning sessions into a report card.
Be clear about the boundary: you will not manufacture outcomes to satisfy a board timetable, and you will not describe him in ways he has not agreed to. If eight weeks is too short for the outcomes he wants, say so now rather than at week eight. Get the revised agreement confirmed in writing, including the 6:30 a.m. change and the consequences if he cancels late.
3. He forwards the board email with no comment. What do you make of that, and what do you do with it?
Read the worked answer
Forwarding without comment is data, not a neutral administrative act. It may be a request for help, an invitation to take sides against the board, a test of whether you will collude, or simply haste. Do not assume - ask, and ask early in the session rather than at the end.
A useful opening: "You sent me the board's email and didn't say anything. What were you hoping I'd do with it?" That question surfaces the unspoken contract before it hardens. If he wants you to advocate for him, say that advocacy is not your role and explain why that protects him. If he is worried about looking bad, that worry is coachable and probably more important than the pricing document.
Watch the triangle risk: coach, client, and a third party who pays and evaluates. Triangles erode honesty unless the coach stays clearly aligned to the client while being transparent with the sponsor. Name the triangle out loud, agree what you will and will not do with the email, and keep the agreement current.