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I was 15 minutes into a call when a CFO prospect cut me off:

“Is this going to make me money or save me money?”

“Save you money,” I said.

He leaned back, paused, and replied:

“I’m not so sure. Prove it.”

He wasn’t being difficult.

He was showing me the pattern I’d see a hundred times.

Because in sales, you don’t just meet prospects - you meet characters.

And there are 5 you’ll see over and over again:

1. The Asshole

You know this one.

The person who gets mad at your for just doing your job - cold outreach, sales.

The VP who cuts you off mid-sentence.

The buyer who goes back on their word after you’ve already looped in your execs.

How to spot them: needs no explanation

What to do: don’t chase them. Protect your time. Cut ties and move on — they’re a sunk cost.

Lesson: They teach you patience. More importantly, they teach you the cost of chasing bad fits — and the power of saying no.

2. The Connector

Thankfully, not everyone drains you. Sometimes you meet the opposite.

They may never buy from you. But they know everyone.

And when they like you, they open doors you didn’t even know existed.

These are the people you always ask for the referral from.

How to spot them: they’re constantly saying, “You should talk to…” or name-dropping contacts.

What to do: Treat them like a customer anyway. Follow up, thank them, keep the relationship warm. Their goodwill compounds.

Lesson: They teach you that relationships outlast transactions. One Connector is worth more than a dozen cold calls.

3. The Champion

Of course, introductions alone don’t close deals. To get across the line, you need someone inside the walls fighting for you.

Every seller remembers their first true champion.
The mid-level manager who pulled strings, escalated your email, or vouched for you in meetings you weren’t even in.

How to spot them: They use words like “we” instead of “I.” They might even ask, “How do I sell this internally?”

What to do: Arm them. Give them the data, slides, or ROI proof they need to fight your battle inside the company. Coach them like a teammate.

Lesson: They teach you that trust is the real currency in sales. Make someone look good, and they’ll make sure you win.

4. The Skeptic

But not everyone is rooting for you. Some people exist to test if you really know your stuff. (like the CFO story at the start)

They challenge every claim, push back on every feature, and ask: “Why you? Why now?”

I much prefer a skeptic to someone who gives you green lights through the process then goes dark in the end.

How to spot them: They interrupt, take notes, and drill into ROI. They won’t let you coast on charm.

What to do: Drop the fluff. Lead with data, case studies, and conviction. If you win them over, they’ll be your strongest advocate.

Lesson: They teach you rigor. And they remind you that conviction is contagious.

5. The Visionary

And if you’re lucky, you’ll meet someone rare.

They don’t just see what your product does today - they see what it could do tomorrow.

They stretch you, challenge your roadmap, sometimes even change the way your company thinks about the future.

How to spot them: They talk more about the future than the present. They’re excited by “what if” scenarios.

What to do: Listen deeply. Take notes. Loop in product or leadership. Visionaries can turn into lighthouse customers if you respect their input.

Lesson: They teach you to sell not just what you have, but to sell the promise land.

The Bottom Line

Sales is full of scripts, sequences, and playbooks.

But in the end, it comes down to people.

And if you pay attention, every person you meet in sales is a teacher.

Even the asshole.

Recognize them early, adjust your game in real time — and you don’t just get better at deals.

You get better at the craft.

Until next Thursday,

TSG

P.S. I reply to all emails.