04/18/2026
I read Abbie Lundberg's editor's letter in MIT Sloan Management Review this week. "AI Won't Fix This." She's right. I want to add one thing.
I started writing software at 15. I'm 55 now. Over 40 years in this industry and most of that time I've been on the inside of organizations trying to change, watching good people hit the same walls over and over. Committees. Process debt. Decisions that got made thirty years ago that nobody remembers making but everybody still defends. Rooms where the actual work would take a week and the approval to do the work takes six months. Anybody who's been in this long enough has been in those rooms.
Lundberg's numbers are brutal. 48% of digital initiatives hit their targets. 60% of technology investments deliver little material value. Her answer, from Linda Hill's work at Harvard: build a digitally dexterous workforce. People willing and able to use new technology.
That's a real part of the answer. I think there's more to it.
The people aren't the problem. The walls are.
You can't cut a new window into a load-bearing wall that's been there sixty years and expect the house to breathe differently. Teaching people to work around the wall helps, but the wall is still there. I've watched this pattern four times now. Client-server was going to change things. The web was going to change things. Mobile. Cloud. Every wave got absorbed by the wall and turned into another line item.
The leaders I see actually getting somewhere aren't fighting the wall. They're asking a different question alongside the transformation work. What would we build if we were starting today?
And then, carefully, they're building pieces of that answer.
That's the harder, quieter work. It's the work I want to be part of.
Lundberg is right. Technology won't fix this by itself.
But the right question, asked by the right people, just might.
