Flying Blind: Why Every Family Business Needs a Contingency Checklist
A Wellington bomber. Blue skies. Nothing on the radar. And yet, two men sat inside the cockpit rehearsing disaster. One of them was my father-in-law. A quiet man who knew that preparation is not pessimism — it’s wisdom.
Later, when the plane was hit by shrapnel and began to fall, they didn’t panic. They worked through their list. Step by step. And by item six, they were steady again.
Your family business is not a bomber, but it carries something just as precious your future. And it needs the same thing those pilots needed: a checklist made while the sun is still shining.
Seven Lessons From the Sky for Grounding Your Business
1. A Contingency Plan Is Your Checklist
What happens if your top client disappears? Or your supplier goes bust? Or your youngest team member — the one who understands the tech — walks out?
Most family businesses don’t ask until it’s too late.
✳ A checklist forces the question before the storm arrives.
✳ It removes panic from the room.
✳ And it gives your family a place to begin when everything feels like it’s ending.
2. Know Your Numbers (or Fly Blind)
A pilot doesn’t guess their altitude. Neither should you.
🔹 Revenue, costs, margin, retention: these are your instruments.
🔹 If you don’t check them weekly, you’re in the air without a dashboard.
🔹 That’s not brave — that’s reckless.
Start simple. Three core numbers. One meeting a week. No surprises.
3. Preparation Isn’t Paranoia — It’s Respect
The day they wrote that checklist, the skies were clear. But experience had taught them: blue skies change fast.
💡 Don’t wait until things go wrong to figure out what to do.
💡 Write down scenarios. Discuss responses. Allocate roles.
💡 Then get back to work, quietly confident you’re ready.
4. Learn From Those Who’ve Been Through It
That list wasn’t made up. It was passed down — by those who’d been hit before.
🧭 In your business, that might be a retired founder, an old friend, or a mentor who’s made mistakes and lived to tell the tale.
Ask the question: “What did you wish you’d prepared for?”
Write down the answer. Add it to your list.
5. Use Calm Periods to Strengthen Weak Links
Stress exposes what’s fragile. Don’t wait for turbulence to check the bolts.
☑ Is your communication clear?
☑ Are your roles defined?
☑ Do you know who owns what in a crisis?
In a family business, assumptions are dangerous. Clarity protects everyone.
6. Train the Mindset Rather Than Just the Mechanics
When the bomber dropped, panic wasn’t useful. Calm was.
In your team, mindset matters just as much as money.
🔹 Scarcity mindset leads to finger-pointing and hoarding.
🔹 Abundance mindset says: “We’ve planned for this. Let’s move.”
Model that mindset every day. In calm and in crisis.
7. Enjoy the Calm — But Plan for the Storm
It’s easy to be relaxed when everything’s working.
But the ones who last are the ones who prepare during peace.
A family business is not just about today. It’s about 30 years from now.
✳ Plan succession.
✳ Map your cashflow.
✳ Build resilience rather than routine.
Frequently Asked Questions
Q: Isn’t planning for disaster a bit negative?
No, it’s respectful. To your team, your customers, and your future. You don’t wear a seatbelt because you expect to crash. You wear it because you value staying safe.
Q: What goes into a good contingency plan?
Scenarios, roles, triggers, and actions. Think: if X happens, who leads, who supports, and what’s the first step?
Q: Isn’t this more important for bigger businesses?
Actually, smaller and family-run firms are more exposed. You don’t have departments to fall back on. Which is exactly why you need a plan.
Q: What’s the first step?
Start with three “what if” scenarios. Work through each. Then talk it through with someone wise. Simple is best.
Sit down. Write the list. One hour today might save your legacy tomorrow.
👉 Create your first checklist this week:
– What would we do if sales halved tomorrow?
– Who takes charge if the founder gets ill?
– What if our key supplier shuts down?
You may never need the answers.
But if you do you’ll be ready.
Because fortune doesn’t favour the bold. It favours the prepared.
Stephen Bray works with business owners who’ve had enough of the noise. Less spin, more truth. You’ll find him behind the mirror here.
© 2025 Stephen Bray. Patterns in life and business, simply told.