Deals Don’t Die at the Close. They Rot in the CRM.

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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.

I was on a flight last week, we landed early. Smooth approach. No turbulence. Textbook flight.

And then we sat.

Five minutes passed… Then ten.

Finally, the pilot came on:

“We’re waiting on ground crew. Jetway’s not in position yet.”

Everything had gone right …until the moment it mattered.

That’s what broken follow-up looks like.
You execute the plan… but no one finishes the play.

The landing was smooth, but the jetway never showed up…

The Handoff Is Where It Breaks

That’s what we see in so many deal teams.

The issue isn’t strategy. It’s handoff.

• Proposals go out, but no clear owner for next steps
• Buyer questions go unanswered while teams “circle back”
• Threads die in the CRM, not from disinterest, but from inaction

It’s not that the deals aren’t hot.

It’s that the team doesn’t know whose move it is.

The biggest delays in your deal cycle?
They rarely come from the market.
They come from breakdowns at the moment of follow-up.

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Speed Is Great… If You Know Where You're Going

The teams moving the fastest right now aren’t the ones with the most tools.
They’re the ones with the clearest next step.

• They use AI to define action, not just generate content
• They preempt silence instead of waiting for it
• They build next steps into the system, not just Slack reminders

They’re not chasing every deal.
They’re building a rhythm that doesn’t drop the ball.

What Great Follow-Up Looks Like

The best firms we work with don’t rely on memory.

They engineer follow-up that:

• Triggers automatically based on where the deal is
• Adjusts based on buyer signals
• Stays human, even when the system is doing the heavy lifting

It’s not about sounding smart.

It’s about making sure momentum doesn’t stall when the jetway doesn’t show up.

Final Thought

If your deal flow depends on people remembering what to send and when to send it,
you’re not building momentum, you’re bleeding it.

Next week, I’ll show you what it looks like when the handoff actually works.

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Thank you!

David