Great Tech. Bad Execution. No Exit.

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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.

On a recent flight into LaGuardia, we were on final approach when the pilot pulled up sharply and announced:

“We’re going around, traffic on the runway.”

Half the plane groaned.

We weren’t late because of the plane.
We were late because of congestion.

That’s what AI feels like in M&A right now.
The tech is ready. But the runway isn’t clear.

 The Plane Can Fly, But the Tower Isn’t Ready

The tools are here. And they’re powerful.

• AI can analyze 5 years of financials in seconds

• It can compare hundreds of targets across sectors

• It can surface anomalies, parse contracts, and suggest deal language

But in most shops, it’s still stuck at the gate.

Because the value isn’t just in the tool. It’s in how you prompt it.

Great prompting turns junior-level questions into C-level insight.
It moves you from “what happened?” to “what should we do?” faster.

The teams seeing the biggest lift aren’t just adopting AI.
They’re retraining how they think, write, and probe. They’re turning analysts into insight generators.

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The Market’s Talking, But Adoption Is Lagging

AI is everywhere in the headlines.
You’ve probably seen it:

“AI is transforming diligence.”
“AI is reshaping M&A workflows.”

And yet, most deal teams haven’t changed a thing.

According to Bain, nearly 80 percent of firms believe AI will be critical in the next three years.
But fewer than 15 percent have embedded it meaningfully into daily workflows.

Here’s what we’re seeing up close:

• Some use AI to summarize CIMs, but still write memos manually

• Others feed it deal docs, but never ask it to challenge assumptions

• Many use it to clean data, but not to generate insight

• Few have trained their teams to prompt well enough to unlock real value

In our own work, we’ve embedded AI into sourcing, outreach, diligence, and internal deal reviews.

It’s not perfect. But when used right, it closes the gap between raw data and boardroom decisions faster than any junior associate ever could.

AI Isn’t a Shortcut, It’s a Skillset

AI doesn’t do the work for you.
It gives you the first draft, the one you used to spend nights and weekends grinding through.

The better your prompt, the better the outcome.
The clearer your logic, the stronger the insight.

It doesn’t replace experience. It amplifies it.

And when your team knows how to use it, even your greenest analyst can deliver insights that sound like they came from the managing partner.

The Bottom Line

If you’re just using AI to summarize, you’re missing the point.

AI isn’t just faster. It’s smarter… when you are.

The firms pulling ahead aren’t using AI to write memos.
They’re using it to test theses, challenge blind spots, and accelerate decisions.

The plane can fly itself.
But if your tower isn’t ready, you’re just going to keep circling.

In the next issue, I’ll share a few CustomGPTs we’ve built to turn deal data into clarity and how they’re helping teams move from overwhelmed to out front.

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David