October 03, 2026 | Read online
I was out in San Francisco this week for Apollo's NEXT conference (which was awesome btw), and I stayed a few extra days to spend time with my mom, my sister, and my nephew.
I also got to catch up with two of my good friends, Roderick Jefferson and Richard Harris.
The three of us are all over 50, and we've been in the training and consulting game for a long time. What stuck with me was how much energy was at that table. Most of the conversation was about what we're building and testing with AI right now.
AI has given a lot of us a second wind. I think it's a Gen X thing. We were the latchkey kids who had to figure everything out on our own, and that's exactly what this moment asks for. I’ve even added a new tagline and t-shirt - "figure it out."
Then I talk to friends my age who are looking for work, and I hear a very different story. They're running into ageism in hiring, especially in tech.
I get it. Tech, SaaS, and sales have always been seen as a young person's game.
I went back and forth on writing this one, because nobody signed up for this newsletter to read a 50-something guy yelling at the clouds. So I went looking for data instead, and what I found surprised me.
WHAT THE NUMBERS SAY
The uncomfortable part first. AARP's 2026 survey found that 64% of workers 50+ have seen or experienced age discrimination at work. In 2018 it was 61% (for workers 45+). Eight years of talking about it, and the number hasn't moved.
The most common bias in that survey was people assuming you're less tech-savvy (33%).
That one stung a little, because some of us earned it. I've watched plenty of people my age dig in on "this is how we've always done it" while the world moved on around them. I've been guilty of it myself more than once.
Then I found the part that changed how I was thinking about all of this.
The Stanford Digital Economy Lab has been tracking ADP payroll data to see who AI is affecting. Their August update shows employment for 22 to 25 year olds in the most AI-exposed jobs is now about 19% below where it should be, up from 15% a year earlier.
Experienced workers in those same jobs show no gap at all. In roles that rely on tacit knowledge, the stuff you only learn by doing the work for years, their employment actually went UP.
CEOs are seeing it too. An Oliver Wyman survey from May found 40% of CEOs plan to cut junior roles in the next year or two and shift toward mid-level and senior people. Only 17% plan to add junior roles.
The market is starting to put a price on judgment. AI can write the email. It can't tell you whether this VP, in the middle of this acquisition, should get that email at all.
My guess is the hiring filters haven't caught up to what the work requires now. That's on the companies doing the hiring. It's also on those of us over 50 to prove the "not tech-savvy" label wrong.
THE PROBLEM NOBODY IS TALKING ABOUT
The more I sat with this, the more something else bothered me.
If companies stop hiring junior people and lean on experienced ones, where does the next generation of experienced people come from?
You don't learn judgment by watching AI write your emails. You learn it by blowing a discovery call, losing a deal you were sure you had, and having someone who's been there sit down with you afterward to walk through what happened.
Cut the junior roles, and you cut the reps. Ten years from now, we'll have a lot of AI and very few people who know when it's wrong.
Last week, I wrote about The Last 10%. I'd taught college students who grew up with AI and veteran reps with decades in the field, and both groups needed the same lesson for opposite reasons.
The students were comfortable letting AI do the work, but they didn't have the context to judge what it gave them. The veterans had all the context in the world and were slow to let AI into their process at all.
That last 10% is judgment, and judgment comes from experience. Each group has exactly what the other one is missing.
GO FIND A MENTEE
Back in June, I had Colleen Stanley on the podcast to talk about her book, Be the Mentor Who Mattered. She told a story that really resonated with me.
She was a regional manager at a fast-growing company when the national sales manager job opened up, and she didn't apply. The founder sat down next to her and asked why. She ran through a few excuses before she finally admitted, "I'm not ready."
His answer was, "We know. We'll help get you ready."
After she got the job, the CFO stayed at the office with her until 10 at night, more than once, teaching her how to read a P&L. He didn't hire her, and he didn't promote her. He showed up anyway.
None of that came from a formal program. It came from a culture where people helped each other.
Then she turned the usual advice around on people like me. In her 20s and 30s she didn't know she needed a mentor, and she didn't even know she was being mentored. So her charge to the rest of us is to stop waiting to be asked and "go find a mentee."
Nothing brings me more joy than mentoring young reps and sales leaders, and sharing the mistakes I made so they don't have to make as many of them. Most of my peers feel the same way. We're sitting on decades of lessons, and a lot of us are waiting for someone to ask.
It runs both ways, too. You don't need a big title to mentor someone. If you're really good at one thing, you can mentor on that thing. Some of the best AI workflows I use came from watching someone half my age build something in 20 minutes that would've taken me a week.
I said it on that episode, and I believe it even more now. Nobody is going to survive this world of AI by themselves, and the companies that keep sales, marketing, and everyone else in silos are going to fail hard.
RUN A WEEKLY SALES HACK-A-THON
That's why I keep pushing companies to run a sales hack-a-thon every week. It puts the right people in the same room on purpose and lets the mentorship happen on its own. Here's how it works:
- Pick one component of your GTM process that isn't working as well as it should. Lead routing, the SDR to AE handoff, follow-up after a no-show, whatever is bleeding pipeline right now.
- Build small teams with one person each from sales, marketing, ops, and engineering.
- Mix experience on purpose. Put the AI-native rep who can build an agent before lunch next to the veteran who knows why the last three versions of that idea failed.
- Leave with a fix you'll test that week.
You solve real problems and break down the walls between functions while you're doing it. Your org gets more agile because people get used to fixing things together every week. And I'd bet retention and employee satisfaction go up, because people stay where they're learning and where their experience counts.
Colleen told me about a CEO she knew who ran two national sales meetings a year, which are not cheap. When she asked him why, he said, "If I prevent three people from turning over at the company, I've just paid for this meeting." Run the same math on a weekly hack-a-thon.
If you want help setting one up for your team, that's exactly the kind of thing I do in my advisory work and team training.
I'm curious where you sit on this. Are you feeling the experience premium right now or the experience penalty? And if you're early in your career, who do you wish would take you under their wing? Reply and let me know.
The best thing my generation can do with everything we learned the hard way is go find someone who's going to run faster with it than we ever did.
#MakeItHappen
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