What This Is
Most family business leaders know a conversation they need to have. They’ve known for months — sometimes years. What they don’t have is the preparation to have it well. This challenge closes that gap.
Over five days you’ll face what’s been stopping you, understand the landscape of conversations transition requires, map your vulnerabilities, and prepare for your specific listener. By Day 5, you won’t just be ready — you’ll have a date on the calendar.
How It Works
01
Day 1 — Face It
Name the one conversation you can’t keep avoiding. That’s your starting point.
02
Days 2–4 — Build Context
Map your vulnerabilities, surface your family’s assumptions, and triage which conversations matter most.
03
Day 5 — Prepare
Clarify your message, assess your readiness, understand your listener, and set the date.
04
After Day 5
You go back in — with a question worth asking and the preparation to hold your ground.
What You’ll Walk Away With
✓The one conversation you need to have — named and written down
✓A clear picture of where your business is vulnerable without you
✓Your family’s assumptions surfaced and mapped
✓Your core message clarified and your opening line ready
✓A deep understanding of what makes your specific listener difficult
✓A date on the calendar — and the preparation to back it up
Time commitment
20–30 minutes per day · 5 days · Work at your own pace
🎬
Videos Coming Soon
Each day will include short videos from family business leaders sharing their experience around the conversations they wanted to have — but hadn’t.
Begin Day 1 ›
You can move through the days at your own pace. Your progress is saved as you go.
“Families assume everything and discuss nothing.”
— Michael O’Malley Jr., Family Business Life
When You’re Done
Tell Us What You Think
This program only gets better because of people who take the time to use it honestly — and say so. Whether you finished all five days or stopped somewhere in the middle, your feedback shapes what gets built next.
Share your feedback — 12 questions, about 3 minutes →