I talk with coaches every week through my bookkeeping service at letsdothebooks.com. Over time I've distilled three questions whose answers reveal more about where a coach is in their practice than almost anything else — not because of what the answers say, but because of how confidently and clearly a coach can say them.

Timestamps

[00:00:00] Introduction — I describe the conversations that led to these three questions, and introduce the core idea: confidence and clarity in the answers matter more than the content of the answers.

[00:00:48] Question 1: How will I meet and enroll my next coaching client? — This question has marketing and sales baked into it. A boring answer is a good sign. A hopeful or hypothetical answer signals a practice still in an exploratory season.

[00:02:02] What a mature answer looks like — I use my own practice as an example: referrals and podcast listeners. No drama, no hypothesis. An answered question.

[00:03:06] What the answer reveals — Confidence in this answer gives me a strong read on where a coach is in their practice, independent of whether they're a good coach or what their timeline looks like.

[00:04:13] The confidence edge — Where my own confidence becomes hypothetical: scaling enrollment, moving from a handful of clients per year to dozens. That gap is diagnostic too.

[00:05:11] Question 1 as a standalone heuristic — If there were only one question to ask, this would be it.

[00:05:38] Questions 2 and 3 — Why they matter: coaches can really lose the thread of a healthy practice here, and the answers reveal mental and emotional state as much as business strategy.

[00:06:06] Question 2: What structure and deliverables will I follow to support my next client? — I describe my own model: block of sessions, Zoom calls, no homework, no portal, no between-session access. Simple and settled.

[00:07:43] What an unsettled answer looks like — A coach adding and subtracting from their delivery model could signal confident growth, or it could signal burnout trying to disguise itself as a structural problem.

[00:08:58] Structural solutions to mental-emotional problems — The tell: a coach building a portal because they're tired of repeating themselves versus a coach building one because they're excited about a new dimension of service. Same idea, very different implications.

[00:10:57] Reading the tone — Bored and matter-of-fact, or excited and energized: I trust the answer. Deep sigh, fatigue, hoping something will fix something: I dig deeper.

[00:11:32] Question 3: What will happen when your next client is finished with the engagement? — The question most coaches haven't thought through. My answer: invite them to continue in almost an identical engagement.

[00:12:36] What a hypothetical answer signals — Wishing, hoping, and wondering here carries the same diagnostic weight as in Questions 1 and 2.

[00:14:13] The grandiosity of "I don't want to create dependence" — I push back on this framing directly. What's more likely: insecurity about asking for the renewal, or a belief that renewals are predatory.

[00:15:20] Why renewals matter — The first yes is the hardest thing in any business. Subsequent yeses are much easier to clear. If you're not set up for renewals, you're in an eat-what-you-kill business.

[00:15:58] Big promises make renewals harder — Coaches who oversell a specific result in the initial sales process anchor clients to a finish line. That makes the second yes harder or even impossible.

[00:16:44] Eat what you kill vs. reap what you sow — The two business models, and why one becomes easier over time and the other doesn't.

[00:18:17] Closing — I don't believe there are wrong answers to any of these questions. What I'm listening for is confidence and clarity in whatever path a coach is on, because that's what keeps a practice in productive motion.

[00:18:49] The three questions, restated — A clean summary before the close.

Links

• letsdothebooks.com — My bookkeeping service for coaches
• officehourswithmark.com — My coaching membership