Top 10 Questions to Ask When Hiring a Business Coach
You’re about to invest $30,000+ annually in coaching.
At Building Great Businesses, we help Sydney business owners build businesses that work without them.
Most business owners interview coaches like they’re hiring an employee. Ask basic questions. Get impressive answers. Make decision on gut feel.
Then six months later realise they hired wrong.
The right questions separate genuine expertise from polished sales pitches.
Here are the 10 questions that matter. What to ask. What to listen for. What red flags look like.
Question 1: “What Businesses Have You Personally Built and Run?”
Why this matters:
Anyone can read business books and regurgitate frameworks.
Real operators know what it’s like. Payroll stress. Bad hires. Cash flow crunches. Team conflicts.
They’ve lived the problems you’re facing.
What to listen for:
- Specific businesses they’ve owned
- Revenue levels achieved
- Team size they managed
- What they built, not just consulted on
- Outcomes (sold, still operating, exited)
Good answer: “I built a professional services firm from zero to $3.2M over nine years. Team of 14. Sold it in 2019. Before that, ran operations for a $12M manufacturing company.”
Red flag answer: “I’ve coached 150 businesses…” (didn’t answer the question) or “I’ve always been a coach” (no operating experience).
Why it’s a red flag: Coaching without operating is theory without practice. Like swimming instructor who’s never been in water.
Question 2: “What Specific Results Have You Achieved with Clients Similar to Me?”
Why this matters:
Track record with businesses like yours is what matters. Not generic success stories.
You’re $800K service business in Sydney. Don’t care about their work with $20M tech startups.
What to listen for:
- Similar business size ($500K-$3M)
- Similar challenges (owner extraction, team building, profit improvement)
- Specific numbers (revenue grew X to Y, profit margin improved by Z points)
- Client names you can verify
- Recent results (not just from 10 years ago)
Good answer: “Last year worked with a $1.1M consulting firm in Melbourne. Owner was working 62 hours weekly. We implemented team systems and hiring process. 14 months later: revenue $1.6M, owner down to 38 hours, profit margin up 9 points. Can put you in touch with him.”
Red flag answer: “I’ve helped hundreds of businesses grow” (vague, no specifics) or “My clients typically see 10x growth” (over-promising).
Follow-up: “Can I speak with 2-3 of those clients?”
If they hesitate or make excuses, walk away.
Question 3: “What’s Your Process for Diagnosing My Business and Creating a Plan?”
Why this matters:
Good coaches have systematic approach. Assessment. Diagnosis. Custom plan.
Mediocre coaches wing it. Generic advice. One-size-fits-all.
What to listen for:
- Clear diagnostic process (data gathering, assessment, prioritisation)
- Customisation to your specific situation
- Framework or methodology they use
- How they identify priorities
- Timeline for assessment and planning
Good answer: “First 30 days we run full diagnostic using the Black Diamond System. Review your financials, assess team, analyse where your time goes. We identify top 3-5 high-leverage opportunities specific to your business. Then build 90-day implementation plan customised to your situation.”
Red flag answer: “We’ll figure it out as we go” (no system) or “Everyone does the same program” (no customisation).
Question 4: “How Do You Measure Success and Track Progress?”
Why this matters:
Coaching without metrics is faith-based.
You need to know if it’s working. Not just feel like it’s working.
What to listen for:
- Specific metrics they track (revenue, profit, owner hours, team performance)
- Regular review cadence (monthly, quarterly)
- How they demonstrate ROI
- What happens if results aren’t showing
- Process for course-correction
Good answer: “We set baseline metrics day one. Revenue, profit, hours you work, team accountability rating. Review quarterly. Track progress against goals. If you’re not seeing minimum 3x ROI after six months, we diagnose why and adjust approach.”
Red flag answer: “You’ll just feel the difference” (no metrics) or “Success means different things to different people” (avoiding the question).
Question 5: “Can I Speak with 2-3 Client References?”
Why this matters:
Not actually a question. A test.
Good coaches immediately provide references. Happy clients who’ll talk honestly about experience.
Bad coaches hesitate. Make excuses. Claim confidentiality.
What to listen for:
- Immediate willingness to provide contacts
- Recent clients (not just from 5 years ago)
- Clients in similar situation to yours
- Mix of current and former clients
Good answer: “Absolutely. I’ll send you three contacts today. Two current clients, one who finished program last year. All similar business size to yours. Ask them anything.”
Red flag answer:
- “All my clients are confidential” (excuse)
- “Let me check if anyone’s willing” (means no happy clients)
- Only provides testimonials, not actual contacts
- Delays or avoids providing references
Action: If coach won’t provide references, end the conversation. No exceptions.
Question 6: “What’s Your Fee Structure and What’s Included?”
Why this matters:
Need complete picture of investment. Not just session fees.
Some coaches charge for everything separately. Sessions. Resources. Events. Email support.
What to listen for:
- Clear pricing (monthly or annual)
- What’s included beyond sessions (resources, community, email support, events)
- Additional costs (workshops, assessments, tools)
- Total annual investment estimate
- Payment terms
Good answer: “Elite is $1,600/month. Includes weekly group sessions, one-on-one sessions as needed, Skool community access, quarterly in-person events in Sydney, all resources and tools. No additional fees. Month-to-month, no locked contract.”
Red flag answer:
- Vague about pricing (“depends on what you need”)
- Constant upsells (“base package is $X but you’ll also want…”)
- Hidden fees
- Refuses to discuss price until you commit
Question 7: “What Happens If I’m Not Seeing Results or It’s Not a Good Fit?”
Why this matters:
Tests their confidence. And gives you exit flexibility.
Confident coaches don’t trap clients in 12-month contracts.
What to listen for:
- Fair exit terms
- Month-to-month or reasonable commitment (3 months max)
- Refund policy if applicable
- How they handle clients not getting results
Good answer: “Month-to-month commitment. If after 90 days it’s not working, we’ll have honest conversation. Either adjust approach or part ways professionally. I only want clients who are getting value.”
Red flag answer:
- Locked 12-month contract
- No exit clause
- “You have to commit or it won’t work” (pressure tactic)
- Complicated cancellation process
Question 8: “How Long Should I Expect to Work with You to Achieve My Goals?”
Why this matters:
Tests honesty and realistic expectations.
Real transformation takes 6-12 months minimum. Anyone promising 30-day transformation is lying.
What to listen for:
- Realistic timeline (6-12 months for significant change)
- Honest about what’s achievable when
- Acknowledges your implementation pace matters
- Doesn’t over-promise
Good answer: “Typical engagement is 12-18 months for full transformation. First 90 days building foundation. Months 4-6 seeing initial results. Months 7-12 systems maturing and compounding. Some quick wins early but real change takes time.”
Red flag answer:
- “30-day transformation”
- “You’ll see results immediately”
- Unrealistic promises
- Won’t give timeline estimate
Question 9: “What’s Included Beyond Our Coaching Sessions?”
Why this matters:
Coaching is more than just sessions. Resources. Community. Support between meetings.
What to listen for:
- Email/message support between sessions
- Resources (templates, frameworks, tools)
- Community or peer group access
- Events or workshops
- What level of access to coach
Good answer: “Beyond weekly sessions: Skool community for peer support, email access for quick questions, quarterly workshops, library of frameworks and templates, two annual full-day events with team building.”
Red flag answer:
- “Just the sessions” (no additional support)
- Everything costs extra
- No community or peer element
- Coach unavailable between sessions
Question 10: “Why Should I Choose You Over Other Coaches?”
Why this matters:
Forces them to articulate their unique value. How they’re different.
Also reveals whether they’re confident or defensive.
What to listen for:
- Specific differentiators
- Confidence without arrogance
- What they’re NOT good for (honest about limitations)
- Why their approach fits your situation
Good answer: “We specialise in $500K-$5M businesses stuck in owner-dependency. Our Black Diamond System is proven framework, not generic advice. Stephen and Andrew both built and exited businesses. We’re operators, not just coaches. Focus is team optimisation and owner extraction, not generic growth. That said, if you want marketing coaching or startup advice, we’re not your fit.”
Red flag answer:
- Can’t articulate difference
- Defensive (“I’m the best”)
- Generic (“we really care about clients”)
- Can’t explain who they’re NOT right for
Bonus Questions Worth Asking
”What’s Your Typical Client Success Rate?”
Good coaches know their numbers. “About 80% of clients achieve their primary goals within 12 months."
"How Do You Handle Clients Who Aren’t Implementing?”
Reveals accountability approach. “We have direct conversation about whether coaching is right fit. Sometimes client isn’t ready."
"What’s Your Coaching Philosophy?”
Shows their thinking. “I believe 70% of results come from client implementation, 30% from coach guidance. My job is asking right questions and holding accountability."
"What Makes a Good Client for You?”
Helps you self-assess fit. “Someone ready to do the work, not just talk. Open to being challenged. Committed to 12 months minimum.”
How to Use These Questions
During discovery call:
- Don’t ask all 10 in interrogation style
- Weave them into natural conversation
- Listen more than talk
- Note which questions they avoid
- Watch for red flags
After call:
- Review notes
- Check which questions got solid answers
- Note any hesitation or evasion
- Compare across multiple coaches
- Trust patterns, not single answers
What Good Answers Look Like Overall
Specificity: Concrete examples, names, numbers. Not vague generalities.
Honesty: Acknowledges limitations. Realistic timelines. Doesn’t over-promise.
Confidence: Willing to provide references immediately. Clear about process and pricing.
Customisation: Talks about your specific situation, not generic coaching.
Track record: Recent, verifiable results with businesses similar to yours.
Red Flags Summary
Walk away if you see these:
- ❌ No operating experience (only coaching background)
- ❌ Won’t provide client references
- ❌ Vague about pricing or hidden fees
- ❌ Locked long-term contracts with no exit
- ❌ Over-promising (“10x in 90 days”)
- ❌ No clear methodology or process
- ❌ Can’t explain how they measure success
- ❌ Defensive or can’t articulate differentiators
- ❌ Pushy sales tactics
- ❌ No specific results with similar businesses
Even one of these is concerning. Multiple red flags? Run.
The Reference Check (Non-Negotiable)
After interview, before deciding:
Call 2-3 client references. Ask:
- What results did you achieve working with [coach]?
- How did your business change?
- What’s their coaching style like?
- How do they handle non-implementation?
- Would you hire them again?
- Any downsides I should know?
- Who is this coach NOT right for?
Listen for specific results. Generic “they’re great” is useless. “$200K profit improvement and 18 hours reclaimed weekly” is useful.
Frequently Asked Questions: Questions to Ask When Hiring a Business Coach
What are the most important questions to ask when hiring a business coach?
The 10 critical questions are: (1) What businesses have you built? (2) What results have you achieved with clients like me? (3) What’s your diagnostic process? (4) How do you measure success? (5) Can I speak with references? (6) What’s the full fee structure? (7) What if it’s not working? (8) How long will this take? (9) What’s included beyond sessions? (10) Why choose you over others? These questions separate good coaches from expensive mistakes.
Why should I ask about a coach’s business experience?
Ask about business experience because coaches who’ve actually built businesses understand real challenges—payroll stress, team problems, profit gaps, owner dependency. Coaches who’ve only ever been coaches can only offer theoretical advice. Real business experience means they’ve solved the problems you’re facing and can provide proven solutions, not just generic advice.
Should I check references when hiring a business coach?
Yes, always check references. Ask for 2-3 current clients similar to your business size and stage. Contact them directly and ask: (1) What specific results have you achieved? (2) How has your business changed? (3) What’s the coach’s biggest strength? (4) Would you hire them again? Good coaches provide references immediately; bad coaches avoid or delay.
What questions should I ask about coaching fees?
Ask: (1) What’s the total monthly investment? (2) Are there setup fees or hidden costs? (3) What’s the contract structure? (4) Can I cancel if it’s not working? (5) What’s included beyond sessions? (6) Are there additional costs for materials or assessments? Full transparency on fees shows integrity. Avoid coaches who won’t discuss pricing upfront or pressure you to sign immediately.
How do I know if a coach’s answers are genuine vs sales talk?
Genuine coaches provide specific examples, concrete results, and evidence. They answer confidently with details and welcome tough questions. Sales talk includes: vague promises, evasive answers, pressure tactics, claims without proof, or inability to provide references. Ask follow-up questions. If answers stay vague or defensive, that’s a red flag. Good coaches are transparent and confident in their answers.
Bottom Line
10 questions that matter:
- What businesses have you built?
- What results with clients like me?
- What’s your diagnostic process?
- How do you measure success?
- Can I speak with references?
- What’s the full fee structure?
- What if it’s not working?
- How long will this take?
- What’s included beyond sessions?
- Why choose you over others?
Ask these. Listen carefully. Check references.
Good coaches answer confidently with specifics.
Bad coaches evade, over-promise, or can’t provide evidence.
This is $30K+ investment. Treat hiring decision seriously.
Related Reading
- How to Choose a Business Coach in Sydney (Without Getting Burned)
- How to Find a Business Coach in Sydney (Step-by-Step Guide)
- What Makes a Good Business Coach? 7 Essential Qualities
Ready to Ask These Questions?
Book a Quick Fit Call with BGB. We welcome these questions.
We’ll answer honestly. Provide references immediately. Show you our process.
No pressure. No pushy sales. Just straight conversation about fit.
Book Quick Fit Call or learn about our approach.
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