Why is picking a coach so hard to get right?
Picture this. It is 9pm, the kids are finally down, and you are on your fourth coaching website of the evening. Every one promises clarity, growth and freedom. Every one shows smiling strangers and a calendar link. You close the laptop none the wiser, because nothing on those pages tells you how the person behaves once you have paid.
That is the real problem. Coaching is not regulated like accounting or law, anyone can use the title, and the good and the weak look identical from the outside. So stop reading the marketing and start asking questions. These eight work for any coach, including me, and a decent coach will be glad you asked.
Has this coach run a real business, and who will actually coach you?
Question 1: What have you built, run or lost yourself? You want specifics: the industry, the size, what went wrong. My own answer is thirty-plus years in business, nine companies founded or co-founded, and 200-plus owners coached one-on-one since 2017. Ask for the equivalent from anyone you meet, and listen for scars as well as wins.
- Good sounds like: a plain account of a payroll scare, a lost client, a pivot that cost money.
- Weak sounds like: only job titles, a framework with a trademark, or a story where nothing ever went wrong.
Question 2: Who delivers the work? Some firms sell with a senior name and hand you to a junior. Ask who will be in the room every session, and what happens if they are sick or leave.
- Good sounds like: a named person, with a stated backup.
- Weak sounds like: "our team will match you."
What should be in writing, and how should a coach diagnose first?
Question 3: Can I see scope and terms in writing before I commit? You should receive the length of the engagement, session count, format, what is included, what is extra, and who owns any materials, all on paper before money moves.
- Good sounds like: a short agreement you can read in ten minutes.
- Weak sounds like: "let's get started and sort the paperwork later," or a rush because a deal ends tonight.
Question 4: How do you work out what is wrong before you tell me what to do? A coach who prescribes in the first call is selling a product, not diagnosing a business. Look for questions about your numbers, your customers, your team and your own hours.
- Good sounds like: "I'd want to see your last six months of sales and hear how a typical week runs."
- Weak sounds like: the same five-step plan for every owner.
How will progress be measured, and how do you leave if it isn't working?
Question 5: How will we know it is working? Agree two or three measures in the first month. Revenue, margin, hours you work, a hire made, a decision finally taken. Progress that cannot be seen by both of you is a feeling, not a result.
- Good sounds like: a baseline, a review date, and permission to say it is not moving.
- Weak sounds like: "it's a journey," with no checkpoint.
Question 6: What are the exit terms? Ask what happens if you want to stop after month two. Whatever the answer, you should hear it before you sign, not after you ask to leave.
- Good sounds like: a clear notice period and an easy handover.
- Weak sounds like: long lock-ins, vague cancellation wording, or annoyance at the question.
Can you call their references, and what won't they do?
Question 7: Can I speak to people you have coached? Ask for two or three owners in a business something like yours, and then actually call them. Ask what changed, what was uncomfortable, and what they would tell a friend to check first.
- Good sounds like: names offered readily, with permission already given.
- Weak sounds like: only written quotes on a web page, or a promise to "get back to you."
Question 8: What will you not do? This is the most revealing one. A grounded coach will say they won't build your website, run your ads, give legal or tax advice, or make decisions for you. If the answer is "anything you need," you are talking to someone who has not defined the job.
- Good sounds like: a short list of limits and a willingness to point you to a specialist.
- Weak sounds like: no limits at all.
What is a fair first-session test?
After one session, ask yourself four things. Did they ask more than they told? Did they repeat back your situation accurately enough that you felt heard? Did you leave with one specific thing to do this week, however small? And did they say something you did not want to hear, kindly and clearly?
If you can answer yes to three of the four, keep going. If you left feeling flattered but with nothing to do, that is a warning. A good coach is useful in the first hour, not only after month three.
When do you not need a coach yet?
Honestly, plenty of owners are not ready, and a coach who says so is worth trusting. Hold off if any of these sound like you:
- You need a task done, not a decision made. A bookkeeper, a developer or a designer will serve you better.
- You have no time to act. Coaching only pays when you do things between sessions. If the week is already overflowing, fix that first or choose something lighter.
- You have not found any customers. Talk to twenty potential buyers before paying anyone to guide you.
- You want to be told what to do. A coach asks and challenges. If you want instructions, a course or a consultant fits better.
- Money is genuinely tight this quarter. Free peer groups, local small business development centers and industry associations can carry you for a while.
None of this is a sales line. If the checklist says wait, wait. Come back when the question has changed from "should I?" to "I'm ready to start, with whom?"
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