Management Meetings: The $10 Million First Date

How to Run the Most Important Meeting of Your Life

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If you’re selling your business, the management meeting isn’t a formality.

It’s the make-or-break moment.

You’re not just selling financials.

You’re selling confidence.

You’re selling trust.

You’re selling you.

It won’t win the deal, but it can definitely lose it.

What’s a Management Meeting?

It’s the in-person (or Zoom) sit-down where serious buyers meet you and your team.

They’ve read the CIM, reviewed your numbers, and submitted a preliminary offer (LOI).

Now they want to get to know the people behind the business.

Think of it like a high-stakes first date.

Your job isn’t to impress. It’s to connect, listen, and leave them wanting more.

What Not to Do

Most sellers mess this up by doing one of the following:

🚫 Talk too much – You want to sell the vision, but oversharing can reveal risk.

🚫 Act defensive – Tough questions aren’t personal. Stay cool.

🚫 Oversell – Desperation shows. Buyers smell it a mile away.

🚫 Show frustration – Lowball offer? Bad question? Smile anyway.

🚫 Reveal need – Divorce, burnout, or looming bankruptcy? Keep it to yourself.

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What to Do Instead

✅ Be warm, curious, and welcoming

✅ Ask open-ended questions about them

✅ Take notes, it shows you’re serious

✅ Listen more than you talk

✅ Be emotionally detached

✅ Highlight your team, not just yourself

✅ Maintain the aura: “We have options”

Rule of thumb: You won’t get a better deal by being charming.

But you can kill the deal by being difficult.

Why It Matters

Buyers are evaluating more than your business.

They’re evaluating:

  • How you handle pressure

  • How your team communicates

  • How much post-close risk they’re inheriting

  • Whether they trust you

Even if you’re exiting completely, this meeting gives them confidence in what they’re buying, and who they’re buying it from.

Be the Guy Everyone Wants to Work With

In Paul Giannamore’s words:

“You won’t win the deal here, but you can definitely lose it.”

So take the meeting seriously.

Play it cool.

Be likable, but not needy.

Let the process and the numbers do most of the talking.

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