A good coaching relationship can change the trajectory of a practice. A bad one costs you a year and a lot of money. The difference usually comes down to the questions you ask before you start — not the ones you ask after.
When advisors evaluate a coach, they tend to weigh two things: do I like this person, and can I afford it. Both matter. Neither predicts whether the engagement will actually move your practice. I've seen advisors hire someone they clicked with instantly and get nowhere, and I've seen productive relationships that started out cordial and businesslike. Chemistry is nice. It is not the variable that matters most.
Here's what I'd actually screen for.
1. Do they coach your specific situation?
"Business coaching" is a broad category. A coach who works with startups, real estate teams, and dentists is not the same as one who works specifically with financial advisors — because the constraints are different. Compliance, the referral dynamics, the way advisors get compensated, the plateau points at different levels of production — these are particular to this business. Ask directly: who do you work with, and what does a typical client's practice look like? If the answer is "everyone," keep looking.
2. Is there a framework, or just conversations?
There's a real difference between a coach who talks with you every couple of weeks and a coach who runs you through a structured process with a defined beginning, middle, and end. Conversations feel good and often change nothing. A framework produces a path: here's where you are, here's the gap, here's what we close first, here's how we know it worked.
Ask what the actual structure of the engagement is. If it's just "we'll meet and talk through what's on your mind," you're paying for a sounding board, not a coach. That may be what you want — but know which one you're buying.
3. Will they measure against a baseline?
A serious coaching engagement starts by establishing where you are — real numbers, real metrics — and ends by comparing where you finished to where you began. Without a baseline, "progress" is just a feeling, and feelings are easy to manufacture at the end of a program.
Ask: how will we know this worked? If the coach can answer in terms of your metrics rather than your mood, that's a good sign.
4. Are they willing to tell you the truth about fit?
The best signal I know of is whether a coach will tell you no. A coach who takes every advisor who can pay is optimizing for their revenue, not your result. A coach who reads your situation and says "this isn't the right time" or "you're not the right fit for what I do" is someone who cares whether the engagement actually works.
You want someone who will tell you the truth in the sales conversation, because that's the same person who will tell you the truth once you're working together — and the truth is the entire value of a coach.
5. Do they hold you accountable, or just encourage you?
Encouragement is cheap. Accountability is the product. The reason advisors hire a coach is usually that they set goals for themselves and quietly miss them, because no one is watching. A coach who only cheers you on isn't solving that problem. A coach who checks whether you did the work — and doesn't let it slide when you didn't — is.
Ask what happens when you don't follow through. The answer tells you a lot.
The one question underneath all the others
Strip everything else away and it comes down to this: will this person make me do the things I already know I should do?
Most advisors don't have a knowledge problem. They have a follow-through problem. The right coach isn't the one who teaches you the most — it's the one who closes the gap between what you know and what you actually do, week after week, until it becomes how you operate. Choose for that.