November 7, 2026 | Read online
If you'd told 20-year-old me that I'd be teaching a class at Harvard someday, I would've laughed, cracked another beer, and gone back to figuring out which 8 a.m. class I could skip.
I'm a state school kid. University of Maryland, class of 1998, and I'll be the first to admit I drank my way through a good chunk of it. Harvard was a place I drove past my whole life, growing up around Boston. I never pictured myself inside one of its classrooms, let alone at the front of one.
This week, I walked into a Harvard classroom as a guest speaker.
They even gave me a name card that said "Guest Speaker" on it, in case anyone was wondering what the guy from Maryland was doing there. I made sure nobody asked to see my transcript.
Here's how I got there.
I met John Westman at HubSpot's Unbound conference this year, and we clicked right away. I didn't know him well, but it didn't take long to see we lined up on values and on how we think about sales.
John teaches a two-day sales management program through Harvard's Professional & Executive Development program. A little while after Unbound, he asked me to come in and talk to his class about AI. I was honored he thought of me and said yes before he finished asking.
On one of the first calls I had with him to prep for the session, before we talked about the agenda, he asked how I was doing, and he wanted a real answer.
So I gave him one. I told him I was in a bit of a reflective spot at 50 years old. Part of me wishes I'd set myself up so I didn't have to work this hard at this stage of life. The other part feels lucky that I still can.
He reminded me that I already have everything I need.
I have a healthy wife and daughter, a roof over my head, and more than the vast majority of people on this planet will ever have. I needed someone to say it out loud, and it came from a guy I'd met once.
Then I showed up to his class, and he took it up another level.
He welcomed me in and handed me a small box. Inside were beaded bracelets he makes with his granddaughter, each one spelling out one of my phrases. Make It Happen was in there. So was "Human Kind, Be Both."
That second one is printed on the shirt I was wearing the day we met at Unbound.
He remembered.
I've been handed a lot of things at a lot of events. Nobody has ever handed me something that personal, from someone who barely knew me. It was a reminder of how much the personal touch matters, and how rare it's become.
THE OLIVE GARDEN GIFT CARD
It reminded me of something I did when Guy Kawasaki came on Make It Happen Mondays.
While I was prepping, I found a line buried in an old interview where he mentioned he's written almost all of his books at the Olive Garden. People at Guy's level get invited on a hundred podcasts, and I really didn't want him to bail on me.
So I mailed him a welcome box before we recorded. A Make It Happen t-shirt, a book for his granddaughter, and a $100 Olive Garden gift card.
When we got on the show, he reached into his back pocket and pulled out the gift card before I could even ask about the box. He told me he speaks all over the world, and everyone hands him a plaque he has no idea what to do with when he gets home. He'd told his wife he wished people would give him Olive Garden gift cards instead.
Two weeks later, I got an email from him with the subject line "Thinking of you!" It was a picture of him at the Olive Garden, holding up the card.
THE GIVE-A-SHIT FACTOR
I've always hated the phrase "personalization at scale." You can't be personal at scale. That's the whole point of personal.
Now AI lets anyone, at any skill level, write a message that sounds personalized. "Loved your recent post on..." is in every inbox. Buyers can smell it from a mile away, and it's made the fake version worthless.
Here's what I keep coming back to. AI could have found the Olive Garden line. It probably would have found it faster than I did. That's the force multiplier part, and you should be using it.
What AI didn't do was decide that line mattered. It didn't buy the gift card, put it in a box, and care whether Guy showed up. And it definitely didn't make anybody a bracelet.
Humans are the last mile. The research is cheap now. The give-a-shit factor is the scarce part, which makes it the most valuable thing you bring to any relationship, in a deal or out of one.
GET IN THE ROOM
None of the John Westman story happens on Zoom.
I've met plenty of good people on video calls, and I couldn't tell you what a single one of them was wearing. John remembered my shirt because we were standing in the same room having a real conversation, and that one conversation turned into Harvard.
I use Zoom every day, and it's efficient. It has never once handed me a bracelet.
If you're skipping events, client visits, and dinners because a video call is easier, you're trading your best opportunities for convenience.
HOW TO PUT THIS TO WORK
You don't need a big budget for any of this. You need to pay attention.
- Before your next important meeting, give AI ten minutes to dig past the LinkedIn profile. Old interviews, podcasts, hobbies, the thing they mentioned once that nobody else picked up on. Then decide what you're going to do with it.
- After every first meeting, write down one small detail. What they were wearing, a kid's name, a trip coming up. Bring it back next time.
- Ask people how they're doing, then stop talking and listen to the answer.
- Send something physical that costs less than a nice lunch and proves you paid attention.
- Get in the room whenever you can.
This is how I teach prospecting now. AI handles the research in minutes, so reps can spend the time they save on the part buyers remember.
If you or your team are looking for training that addresses the give-a-shit factor with fundamentals augmented by AI in 2027 or are planning an SKO, you can DM me or schedule a call with me here.
AI can scale almost everything. Caring is still on you.
#MakeItHappen
Got value from this? Here’s how to say thanks.
I put a lot into this every week, and I’ll keep it free. If it’s helped you, here’s how you can help me keep growing it. Pick one.
- Forward this to one sales leader who’d get value from it. If someone forwarded this to you, subscribe here so you get it every week.
- Give back. Donate $10-$500 to the Future Founder Project and help a young entrepreneur get started.
- Refer me. SKO season is coming. If your team needs a kickoff speaker or training, reply to this email and let’s talk.
Thank you. It means more than you know.
|
| How did I do with this edition? |
|
|
|
|