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How to tell stories that sell

person → problem → shift

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The Briefing

AI just got good enough to do your job, and most people haven't noticed yet. New models released this month can build entire apps without human help. AI is now helping build the next version of itself, accelerating the pace of innovation unlike ever before.

My Take: entry-level white-collar roles in law, finance, medicine, and customer service are on the hot seat. You know what wasn’t mentioned, sales. Order takers and SDRs will slowly get rolled up. But the actual selling, that stays human

Ex-Amazon VP Ethan Evans managed 800+ people over 15 years. His career advice boils down to one loop: do your job well, ask your manager what they need help with, do that well, then ask for work that also grows your skills. Repeat.

My take: Your manager isn't thinking about your promotion - they're thinking about their own problems. Solve those first and the title follows.

Stop Explaining. Start Selling

I was at a friend's birthday party at a little brewery downtown a few months ago. My wife and I were making the rounds, and I ended up talking to a guy I'd never met.

"So what do you do?"

"I'm in sales."

"Oh cool, what kind?"

"Software."

"What kind of software?"

"Accounting and finance stuff. Mostly helping companies with reporting"

And then he gave me the look - eyes glazed over… I lost him.

I don't blame the guy. I bored myself saying it. What’s even more embarrassing is that I sell things to people for a living. And I couldn't even make a stranger at a bar care for 30 seconds.

A few weeks later, I was on a coaching call with a sales leader. He had a technical background and was thrust into the role after the last VP of Sales walked. I asked him to explain what their product does - he proceeded to list off features, integrations and capabilities. I was lost 5 minutes in.

"Tell me about a customer."

He paused. Then he told me about a sales manager who tracked his entire pipeline in the Notes app. Color coded, with emojis (skull meant dead deal).

"That's your pitch."

He looked confused. "The pipeline emoji guy?”

Yeah. The pipeline emoji guy.

That story did more in 15 seconds than his feature list did in 5 minutes. And it's the same mistake I made at that brewery - leading with product over problems.

Person → Problem → Shift.

Here's what made his story work. He started with a real person. Not "companies" or "teams." A sales manager with skull emojis in his Notes app. The VP who couldn't sleep before board meetings. The rep who dreaded Mondays.

Then the problem — specific enough that someone can picture it. "He tracked his pipeline in the Notes app with emojis" is a problem you can see. "Companies struggle with pipeline visibility" is a sentence you forget mid-hearing.

Finally, the shift - not what your product did… what their life looks like today.

So if I could go back to that brewery I’d say:

'I work with CFOs who waste days pulling numbers from six different spreadsheets, manually reconciling them, praying their team didn't make a mistake. I help make sure they're never wrong and everything's done in less than a day.'"

Think about the last time you pitched someone -

A prospect. An investor. A stranger at a bar.

Did you tell them what you do? Or did you tell them who you help?

You know what to do next time.

The Best Thing I Heard This Week

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Until next week,

TG

P.S. I reply to all emails.

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