AI First? Not Without a Strategy First Jun 02, 2026

AI First may actually mean AI F*cked.

…if you don’t know what the f*ck you’re doing.

Here’s the problem:

Expecting technology, even the smartest technology we’ve ever built, to compensate for weak strategy and poor planning only amplifies weak strategy and poor planning.

AI is powerful. But it s...

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Stop Inventing Acronyms: One of the Easiest Ways to Reduce Friction as You Scale May 26, 2026

Every growing company eventually creates its own language.

And that’s usually when communication starts slowing down.

A simple way to keep your business moving at top speed as it scales is to invent as few acronyms as possible.

Yes, some acronyms are fine.

Use the industry-standard ones everyone...

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Buyers Don’t Buy Tools. They Buy Outcomes. May 19, 2026

“Buyers don’t buy tools. They buy outcomes.”

That line should be tattooed on every sales deck and SDR forehead.

Because most sales teams are still leading with features.

“We have AI.”
“We integrate with Salesforce.”
“We built a unified dashboard.”
Cool. So does everyone else.

Nobody wakes up wantin...

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We Almost Named the Book Something Else (And It Would’ve Been a Mistake) May 05, 2026

I like process. There I said it. 

There’s something very interesting about how good things get done. 

How you have to allow time and space to be a part of the evolution.

That involving others in your creation helps a tremendous amount. Nothing good is actually created in isolation or by just one ...

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Don’t Let AI Replies Die in Purgatory Apr 28, 2026

If you’re using an AI agent to send cold email, you need a human inserted at the right moment and a system to do it at speed.

The biggest failure I see in AI-driven outreach isn’t the email itself. It’s what happens after a prospect replies.

Replies fall into purgatory. Opportunities get missed.

...
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The Best Place to Practice Sales Skills Isn’t on Sales Calls Apr 22, 2026

Learning new skills takes practice. Practice in low-pressure situations. 

Trying to learn under pressure is a recipe for fear, panic, and sloppy execution. Then comes the wrong conclusion: the skill doesn’t work.

(Sorry, another sports analogy coming...)
Imagine never bunting before, then stepping ...

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How Sales Keeps Breaking Trust at First Touch Apr 09, 2026

I tried to write this as one article. It wasn’t working.

So this is two parts. Please read both.

The second shows how AI is accelerating a trend I’ve pushed against my entire career.

 

Part 1: Stop Lying to Get the First Touch

Sales has always had a habit of inventing shortcuts.

They’re rarely...

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Speed Broke the Thinking. Apr 02, 2026

An SDR team moved to AI-driven research. Companies found. Buyers identified.

Clean bullets pushed into HubSpot and on to the dialer.

Data popped up the second a prospect answered.

Looked perfect. I loved it.

Then conversation:meeting conversion dropped.

I was puzzled. So I talked to the reps.

...
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How a Long Drive Turned Into a Sales Book That Doesn’t Suck Apr 01, 2026

Flashback four years ago:

On a long drive together Peter said,
“Are you ever going to write a book?”

I said,
“I don’t know. If I do, it can’t be boring. I’ve read too many of those.”

We dropped it… and went back to laughing about outrageous sales stories.

A year later, another long drive:

Peter g...

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LinkedIn Is a Rep’s Network — Not Your Prospecting Spam Machine Mar 24, 2026

There’s a quiet little lie baked into a lot of sales orgs.

It’s the idea that a rep’s LinkedIn network somehow belongs to the company.

It doesn’t.
It never has.

And it’s embarrassing how aggressively some companies try to weaponize it for prospecting.

Let’s call out what’s really happening.

Lead...

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Don't Train Your Reps on Product First. Do This Instead. Mar 09, 2026

Most companies train reps on the product before they train on the problems.

That’s backward.

When you start with features, reps default to describing what the tool does.

When you start with buyer challenges, they learn how to focus on what's more relevant: problems, aspirations.

If your outbound...

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The Prospecting Playbook AI Actually Needs Mar 04, 2026

When Peter and I wrote this book, we talked about various differences in sales today.

One question we had:

Do fundamentals still matter in an AI world?

Quickly we realized: yes. More than ever.

Here’s what I see working with teams every day:

  1. Most teams don’t have the fundamentals nailed

  2. The ...
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