What If One Button Could Sharpen Every Decision You Make?

Hey, it’s David

Welcome back to M&A from the Plane where I share quick stories and insights drawn from the many miles I log in the air talking to business owners, founders, and dealmakers.

AI is everywhere right now but here’s the truth: most of the people reading this don’t care about AI.

They care about the stuff that keeps them up at night:

→ Wasting months on a deal that unravels during diligence
→ Making strategic decisions with incomplete data
→ Missing red flags that only show up after the close
→ Watching margins erode without a clear fix

That’s where AI can actually help not as some magic fix, but as a faster way to get sharper answers.

Like any tool or button, it’s only useful if you know what to do with it. And that starts by asking better questions.

…I Wonder How Many Times I Can Call the Flight Attendant

Last week, I was on a flight home delayed 9 hours, everyone tired and cranky. A few rows down, one guy kept hitting the call button: more water, another snack, blanket, seat issue…

But here’s the thing: every time he pressed the button, he asked something vague “Can you make me comfortable?”

The flight attendant had to guess. Pillow? Headphones? Adjust the seat?

Now imagine he said: “I’d like a window seat, a blanket, and a noise-canceling headset.”

That’s a request with direction. A clear mission. Something actionable.

And AI? Works the same way.

Why Most AI Use Is Just Guesswork in a Nicer Interface

I was talking to someone at a PE firm recently. They were excited about using AI to streamline due diligence.

But when I asked how, the response was:

“We just ask it to analyze companies for us.”

That’s like walking into the gym and saying, “Make me strong.”

Here’s what I suggested instead:

“You are an M&A analyst. Identify key financial and operational risks in a $20M ARR B2B SaaS acquisition. Focus on customer churn, CAC:LTV ratio, and integration challenges.”

Now AI has a role, a filter, a job to do. It’s not analyzing in a vacuum   it’s solving a real business problem.

The Strategic Prompt Ladder

Think of AI prompts like a ladder, each rung gets you closer to something useful:

🔴 BAD Prompt: “Help me analyze this company.”
🟡 BETTER Prompt: “Identify risks in this $20M ARR SaaS deal.”
🟢 BEST Prompt: “You are an M&A analyst. Assess the customer retention, CAC:LTV ratio, and post-merger integration risks for a $20M ARR SaaS acquisition.”

Better questions → better insight → better decisions.

Final Thoughts

If you treat AI like a search engine, it’ll act like one.

If you treat it like a junior analyst and give it context, constraints, and mission clarity… it becomes a true strategic co-pilot.

You don’t need to be technical to get value. You just need to think clearly about the question behind the question.

Want help shaping prompts that move the needle? Reach out, we’ve been building a system that turns vague strategy into usable insight.

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Thank you!

David