What I’ve learned in 30+ years of walking families through the moments that make or break the business — and exactly what I’d check before hiring anyone.
Last updated: August 2026
| A family business coach is someone who helps you run the company and protect the family at the same time — because in a family business, you can’t fix one by sacrificing the other. |
Let me be straight with you. After more than 30 years of coaching family businesses, I can tell you the right coach isn’t the one with the slickest brochure or the fanciest framework. It’s the one who can protect your relationships and your bottom line at the same time. So before you hire anyone, ask them one thing: “Can you show me how you keep a family close while we make the hard business calls?” Everything else you need to know follows from how they answer.
What Most Families Get Wrong
When a business struggles to pass from one generation to the next, we love to blame the money — taxes, legal structure, the balance sheet. The data tells a very different story, and it’s the reason I do this work.
| The numbers I want you to rememberIn a study of more than 3,250 families, 60% of failed transitions came down to a breakdown of trust and communication, and another 25% to heirs who simply weren’t ready. Fewer than 5% failed because of professional or technical mistakes. On top of that, only about 30% of family businesses make it through the second generation, and just 3–5% reach the fourth. |
Read that again. The thing most likely to sink your business isn’t your accountant — it’s a conversation you keep avoiding. That’s the whole reason choosing the right coach matters so much. And it’s why I’d tell you to weight your choice toward the human side of the work, not just the technical side. That’s where nearly every family stumbles, and it’s where the right coach earns their keep.
The First Question I’d Ask
Q: What’s the single most important question to ask a family business coach first?
Ask them: “Can you show me how you keep our family relationships healthy while we make tough business decisions?” I put this first because it points straight at the place family businesses actually break — the spot where family and business collide. A coach who’s done the real work will answer with specifics: a handover they guided, how they separated an ownership decision from a personal one, how they helped a parent and a successor disagree without doing lasting damage. If all you get back is fuzzy talk about “communication” and “chemistry,” keep looking. That one answer tells you most of what you need to know.
The Six Things I’d Insist On
Once you’ve asked the first question, hold every candidate up against these six. Together they cover your family, your business, and the person you’re about to trust with both.
1. Two-systems thinking. They see your family, your ownership, and your business as one connected system — and can explain how a decision in one ripples into the others.
2. Proven, repeatable tools. They bring structured frameworks you can keep using long after they leave the room. Good conversation feels nice; tools create change that sticks.
3. Real transition experience. They’ve actually guided a business through succession — the hardest, highest-stakes moment your family will ever face together.
4. Relevant credentials. They’re trained in leadership, human behavior, human resources, or conflict resolution, and they’ve put in real years with real companies.
5. The nerve to challenge you kindly. They listen first, then push you on the hard calls without bruising the relationship. A coach who only agrees with you is just an expensive cheerleader.
6. Independent proof. Their reputation is backed by other people — testimonials, endorsements, media, published work — not just their own website.
The Family Business Coach Fit Scorecard
I built this simple scorecard so you don’t have to go on gut feeling. Score any coach you’re considering from 0 to 2 on each of the six criteria, then add it up.
| What to ask about your coach | Score it: 0 = no, 1 = partly, 2 = clearly yes | Score |
| 1. Two-systems thinking | Do they treat your family, your ownership, and your business as one connected system? | ___ / 2 |
| 2. Proven, repeatable tools | Do they bring real frameworks you can keep using — not just good conversation? | ___ / 2 |
| 3. Transition experience | Have they actually guided a business from one generation to the next? | ___ / 2 |
| 4. Relevant credentials | Are they trained in leadership, human behavior, HR, or conflict resolution? | ___ / 2 |
| 5. Challenges you kindly | Will they push you on hard calls without bruising the relationship? | ___ / 2 |
| 6. Independent proof | Do others vouch for them — testimonials, endorsements, media, published work? | ___ / 2 |
| Your total | Add up all six. Maximum score = 12. | ___ / 12 |
How to read your score:
• 10–12 — Strong fit. This is your person. They cover both the family and the business, and others can vouch for them. Move forward with confidence.
• 6–9 — Worth a closer look. Promising, but dig in. Ask them to walk you through the criteria where they lost points before you commit.
• 0–5 — Not yet. Keep looking. A low score here almost always shows up later as a stalled transition or a strained relationship.
Why This Is Personal for Me
I don’t ask you to hold a coach to these standards lightly — they’re the standards I hold myself to. I’ve spent more than 30 years in the room for these moments, helping leaders in privately held companies, family businesses, and nonprofits move from the “Now Generation to the Next Gen” without tearing the family apart in the process.
• The tools: My approach is simple and repeatable: build awareness, create real motivation to change, and put clear, actionable strategies to work — backed by 25+ years coaching leaders in the Entrepreneurial Operating System (EOS).
• The credentials: A master’s degree in Human Resource Management, SPHR and SHRM-SCP certifications, and two leadership books, Defeat Team Drama Now! and From People Problems to Productivity.
• The proof: Endorsed by EOS founder Gino Wickman, featured on NBC Nightly News, Fox 2 News and NPR, and published in Entrepreneur and Crain’s Business.
I’m not telling you I’m the only coach who can help you — I’m telling you to use this scorecard on anyone you consider, including me. If the fit is right, you’ll feel it, and the numbers will back it up.
Questions I Hear All the Time
Q: How is a family business coach different from a regular business consultant?
A: A consultant usually focuses on the company’s strategy or operations. As a family business coach, I also work with the relationships, the ownership questions, and the generational dynamics a consultant tends to leave alone — and those are exactly the issues that decide whether your business survives the handover.
Q: What credentials should a family business coach have?
A: Look for real training in leadership, human behavior, human resources, or conflict resolution, plus years of hands-on work inside privately held and family-owned companies. A recognized method like EOS and independent proof — endorsements, media, testimonials — should give you extra confidence.
Q: When is the right time to bring in a coach?
A: Sooner than you think. The best time is before a crisis — while a succession, ownership change, or leadership transition is still on the horizon. Coaching works far better as preparation than as damage control, though a good coach can absolutely help calm a conflict that’s already boiling.
Q: What should I expect from our first conversation?
A: Expect me to ask about your family, your business, and what you actually want — and to give you concrete examples of similar situations I’ve helped through. If a coach answers that all-important first question with specifics instead of generalities, that’s your green light.
The Bottom Line
Choose the coach who can prove they’ll protect your family and your business at the same time. Start with the first question, score every candidate on the six criteria, and insist on independent proof. Do that, and you won’t just get good advice — you’ll come out the other side with a healthier family and a stronger business that’s built to outlast the transition. That’s the whole point. That’s the work I love.