Updated July 17, 20265 min read
Written by Malcolm Reid Sr
Founder, President & CEO of ProGlobal Business Advisors
TL;DR
Before hiring a business coach, ask what they'd examine in your business first, what they've personally operated, for references you can call, what's in and out of scope, and what happens if it isn't working. The good ones answer in specifics and welcome the questions; the weak ones deflect to mindset and their own results.
Why the questions matter more than the answers you expect
The point of these questions is not just the content of the reply — it is how the advisor handles being asked. A legitimate one expects due diligence and answers easily. Deflection, vagueness or irritation is itself the answer. Here are the five worth asking, and what a good response sounds like.
The five questions
- What would you examine in my business in the first 30 days? A real advisor talks about your numbers, your sales process and where things break when you step away. A weak one talks about mindset and momentum.
- What have you personally operated? You want evidence they have run a business and carried its risks, not only taught others to coach.
- Can you give me two references I can actually call? Real results produce clients willing to vouch. Reluctance here is a serious signal.
- What is in scope, and what is not? Clarity protects you from scope creep later. Anyone who says everything is included is selling.
- What happens if it isn't working? A confident advisor has a straight answer about how they handle a poor fit. Evasion means you'll be the one absorbing that risk.
Watch the reaction as closely as the answer. Confidence in your own work looks like welcoming the questions, not resenting them.
Two more if you want to go deeper
If the first five go well, two further questions sharpen the picture: 'What kind of business are you not a good fit for?' — an honest advisor can name one — and 'How do you measure whether this worked?' — the answer should be concrete numbers, not feelings.
What your own answers should be first
Before the call, do your own homework. Write down, in one sentence, what you want to be different in six months. That sentence is your brief; it filters advisors immediately and stops you being sold a generic package. If you cannot name the change you want, no advisor can price it fairly — and you are more likely to buy on charisma than fit.
What's the most important question to ask a business coach?
What they would examine in your business first. It reveals instantly whether they diagnose (numbers, process, dependencies) or pitch (mindset, momentum, their own success).
Should I ask a business coach about their failures?
Yes — it's a useful question. An experienced operator can talk honestly about what hasn't worked and what they learned. Someone who claims an unbroken record of success is either inexperienced or not being straight.
How many business coaches should I talk to before choosing?
At least two or three. Comparison sharpens your judgement, exposes who is diagnosing versus pitching, and makes it easier to walk away from high-pressure sales.
About the author
Malcolm Reid Sr
Founder, President & CEO of ProGlobal Business Advisors
Malcolm Reid Sr is the founder, President and CEO of ProGlobal Business Advisors. Before founding the firm he spent more than 25 years in operating leadership, and by his own account generated over $1 billion in sales across the companies he led. He advises business owners and trains the advisors who do this work.
- 25+ years in business and sales leadership
- $1B+ in sales generated across companies led (career total)
- Founder of ProGlobal Business Advisors, Columbia, Maryland
Key takeaways
- Ask what they'd examine first, what they've operated, for references, scope, and the exit plan.
- How they react to the questions matters as much as the answers.
- Write your own one-sentence brief before the call.
- Talk to two or three before choosing — comparison sharpens judgement.