Hiring a business coach typically costs £700 to £1,500 monthly (£8,400 to £18,000 annually). That makes it one of the most significant investments you’ll make in your business this year. Yet most business owners spend more time researching software subscriptions than vetting coaches.
I’ve been on both sides. I’ve had coaches who changed my business trajectory, and one I walked away from after three months wondering where my money went. Now I coach agency owners myself, and the questions I get asked (and the ones I wish people would ask) tell me a lot about who’s ready to get value from coaching and who’s about to waste money.
Here are 15 questions to ask before you sign anything, with the green and red flag answers to listen for.
The Experience Questions
1. What businesses have you actually built?
This must come first. Before coaching philosophy, before methodology, before pricing. What have they built with their own hands?
Green flags: Specific revenue numbers, team sizes, timelines, and outcomes. “I built a creative agency to £2.2M over 13 years before exiting” tells you something real. They’ve made payroll, handled client crises, and navigated the exact problems you’re facing.
Red flags: Vague answers like “I’ve worked with hundreds of businesses” without specifics about their own. Certifications and qualifications without entrepreneurial experience. Someone who has read about business but never bled for one.
2. What’s your industry specialisation?
The challenges facing a creative agency are fundamentally different from those facing a manufacturing company or an ecommerce brand. Scope creep, creative talent management, project-based cash flow, the emotional attachment to the work: these are agency-specific problems.
Green flags: A clearly defined niche. “I work with creative and digital agencies doing £20k-200k monthly revenue.” They can name the specific challenges your type of business faces without being prompted.
Red flags: “I work with all types of businesses.” Universal expertise means no depth. If they can’t articulate the difference between your problems and a restaurant owner’s problems, they don’t understand either.
3. What’s the biggest business failure you’ve experienced?
This question catches people off guard. It should. You want someone who has failed, learned, and come out the other side. Theory without failure is just opinion.
Green flags: A specific, honest story with a clear lesson. Mine is spending years with zero recurring revenue, starting every month at zero. That taught me more about cash flow management than any textbook.
Red flags: “I haven’t really had any failures” or deflecting to minor inconveniences. Everyone who has built something real has failed spectacularly at some point. If they won’t share that, they’re performing, not coaching.
The Methodology Questions
4. What does your coaching process look like?
A good coach should be able to describe their methodology in clear terms. Not a rigid formula applied to everyone, but a structured approach to diagnosing problems and building solutions.
Green flags: A clear framework with distinct phases. Something like: “Month 1 is a diagnostic. We look at your numbers, operations, and team. Months 2-3 we fix the biggest leaks. Then we build systems for scale.” Specific phases, specific activities, specific outcomes.
Red flags: “We’ll see where the conversation takes us” or “every client is different so there’s no set process.” That’s not flexibility. That’s a lack of structure. You wouldn’t hire an architect who said “we’ll figure out the design as we build.”
5. How do you balance coaching and consulting?
Pure coaching (asking questions so you find your own answers) has value, but it’s slow. Pure consulting (telling you what to do) is fast but creates dependency. The best coaches blend both approaches.
Green flags: “The first few months are more directive because you need frameworks and systems. Over time, I shift to developing your capability to solve problems independently.” They understand the difference and deliberately manage the balance.
Red flags: Rigid adherence to one approach. A coach who only asks questions when you need a pricing framework is wasting your time. A consultant who never develops your skills is creating dependency.
6. What do the first 90 days look like?
If they cannot articulate what happens in the first quarter with specificity, they don’t have a structured approach.
Green flags: A concrete timeline. “Week 1-2: financial diagnostic. Week 3-4: operational audit. Month 2: fix pricing and scope management. Month 3: build pipeline systems.” They know what they’re doing and when.
Red flags: “It depends on what comes up.” Some flexibility is fine. Total ambiguity is not. You’re paying premium rates for structure, not improvisation.
The Results Questions
7. What specific results have your clients achieved?
Not testimonials. Numbers. Revenue growth, margin improvement, time saved, valuation increase. Specific, verifiable outcomes.
Green flags: “One client went from £35k to £55k monthly revenue in six months. Another increased their average project value from £3k to £8k by changing how they positioned and priced. A third improved team utilisation from 58% to 71%, which dropped straight to the bottom line.” Specific numbers with specific timeframes.
Red flags: Vague claims like “my clients see incredible transformations” or “everyone who works with me grows.” If they can’t provide numbers, they either don’t track results or don’t have good ones.
8. Can I speak to current or past clients?
This is non-negotiable. Anyone worth hiring will have clients willing to vouch for them.
Green flags: “Absolutely, I’ll connect you with two or three clients who were in a similar position to you.” Enthusiastic willingness and specific introductions.
Red flags: “I can’t share client details for confidentiality reasons” (this doesn’t hold up; they can ask clients for permission). Or only providing polished testimonials on a website. Written testimonials are marketing. Conversations are verification.
When you do speak to references, ask specifically: “What did you disagree with? What didn’t work? What would you change about the engagement?” The honest answers are in the negatives, not the positives.
9. What results should I realistically expect in 12 months?
This question tests honesty. Anyone who promises transformation in 30 days is selling you something.
Green flags: Honest timelines with specific milestones. “At 3 months: improved pricing and profitability. At 6 months: better systems and team performance. At 12 months: significant revenue growth and reduced owner dependency. Typically 20-50% revenue growth depending on your starting point.”
Red flags: “You’ll double your revenue in 90 days” or any guarantee of specific outcomes. There are too many variables in business for guarantees. The honest answer involves ranges, conditions, and your own effort level.
The Accountability Questions
10. How do you measure progress?
Meaningful development goes beyond motivational feelings after sessions. You need concrete metrics tracked consistently.
Green flags: “We track revenue, profitability, utilisation rate, pipeline value, and owner hours every month. We review against targets quarterly and adjust the plan based on data.” A specific tracking framework with regular review cadence.
Red flags: “You’ll just feel the difference” or vague mentions of “accountability.” If there are no numbers, there are no results. Feelings are not metrics.
11. What’s the time commitment between sessions?
Coaching without implementation is just conversation. A good coach sets expectations for work between sessions.
Green flags: “Expect 3-5 hours of implementation work between sessions. I’ll give you specific tasks with deadlines. If you’re not doing the work, we’ll address why.” Clear expectations and willingness to have uncomfortable conversations when you’re not following through.
Red flags: “Just attend the sessions and you’ll see results.” If they’re not demanding effort from you, they’re not creating change. Real coaching requires work on both sides.
12. What happens when a client isn’t making progress?
This reveals their approach to difficult situations. A coach who avoids confrontation won’t help you grow.
Green flags: “I’ll be direct about it. If you’re not implementing, we need to understand why. Sometimes it’s a capacity issue, sometimes it’s a fear issue, sometimes the approach needs changing. But we don’t ignore it.” Direct, honest, problem-solving orientation.
Red flags: “That doesn’t usually happen” or uncomfortable deflection. Every coach has clients who struggle. The ones who refuse to acknowledge this are either lying or not challenging their clients enough.
The Commercial Questions
13. What are your fees and what’s included?
Full transparency should be immediate and straightforward.
Green flags: Clear pricing shared upfront. A specific list of what’s included: number of sessions, messaging access, resources, review meetings. No hidden upsells.
Red flags: “Let’s discuss pricing on a call” when you’ve specifically asked in writing. Pressure to book a “strategy session” before sharing fees. Tiered pricing designed to make you feel the cheapest option isn’t enough. These are sales tactics, not coaching signals.
14. What’s the minimum commitment and exit terms?
Understand what you’re signing up for.
Green flags: “I recommend a 12-month commitment because real results take time, but you can leave with 30 days’ notice at any point. I’d rather have clients who want to be here than ones who are trapped.” Confidence in their value with reasonable exit terms.
Red flags: 12-month lock-in contracts with no exit clause. Large upfront payments with no refund policy. These protect the coach, not the client.
15. What do you expect from me?
A coach who doesn’t set expectations for your behaviour isn’t going to hold you accountable.
Green flags: “I expect you to show up prepared, implement what we agree, track your numbers honestly, and be open to uncomfortable feedback. If you’re not willing to do that, this isn’t the right fit.” Clear standards from the start.
Red flags: “Nothing, just turn up and I’ll handle the rest.” Coaching without client commitment is entertainment, not development.
The Red Flags Summary
Beyond individual answers, watch for these patterns:
Guaranteed results. Business has too many variables for guarantees. Honest coaches acknowledge this.
No real business experience. Weekend certifications do not substitute for building something with your own hands, your own money, and your own sleepless nights.
Identical approach for every client. Each business is different. Coaches applying the same framework regardless of context are not providing genuine support.
Hidden pricing. If they won’t share fees until a sales call, the price is designed to shock you after they’ve built emotional investment.
More followers than clients. A large social media presence does not equal coaching ability. Ask about client results, not audience size.
Making the Decision
Quality coaching combines relevant entrepreneurial experience, a proven methodology, and genuine understanding of your specific sector. The right partnership justifies the investment many times over. The wrong one wastes money, time, and (worst of all) delays the growth you need.
Ask these 15 questions. Demand specific answers. Verify references. Anyone worth hiring will respect comprehensive vetting. If they’re uncomfortable with scrutiny, that tells you everything.
Ready to Vet a Coach?
If you’re considering coaching for your creative agency, I welcome every question on this list. I’ve built and sold a multi-million pound agency. I work exclusively with creative, digital, and design agency owners doing £20k-200k monthly.
Book a discovery call and bring these questions with you. Or take the free Agency Valuation first to understand where your agency stands before you start looking for support. Read the full guide on business coach vs mentor vs consultant to understand which type of support fits your situation.