2026-08-28 · Friday Report Team
I try not to make predictions about technology anymore. Not because I don't have opinions, because the pattern I keep noticing is that the best insights usually come from staying curious longer than everyone else. So take this less as a forecast and more as something I've been turning over in my head.
A few months ago, a CIO told me his company had just walked away from a platform they'd spent four years building their processes around. It wasn’t broke. A leaner, AI-native alternative did the same job for a fraction of the cost, set up in weeks instead of quarters. He actually said something pretty cool: "We were maintaining a museum."
I keep thinking about that sentence, because I think it's about to apply to a lot more of us than we'd like to admit.
Nobody knows what's coming, and the honest people say so
I've been reading through this year's forecasts from people who genuinely study this for a living, and something jumps out. The confident predictions don't agree with each other.
Some think we're headed toward software that builds itself on the fly, a different interface for every person, generated in the moment instead of designed once and shipped to everyone. Others are betting on something stranger: AI agents that stop acting like tools and start showing up more like coworkers, with their own place on the team.
What I find oddly reassuring is that the people making these predictions keep admitting how much is still unsettled. One recent CIO survey found AI adoption climbing by an almost unbelievable margin, and in the very same breath, found that a large share of leaders are still hesitant to hand over real autonomy, because trust in the underlying data remains the thing nobody's fully solved.
I don't think that hesitation is fear of change. I think it's something more useful: an industry collectively noticing that the technology is outrunning our confidence in it.
Maybe the interesting question isn't what the software will do. It's who we'll still believe when it tells us something. |
The one prediction I keep seeing that I actually believe
Buried in almost every one of these reports is a version of the same quiet admission. As the tools get more capable, the human skills around them are getting more valuable. Judgment. Adaptability. The ability to read a room, or read a client, or know when a number everyone trusts is actually wrong. One workforce researcher put it plainly, as machines absorb the mundane parts of the job, the uniquely human ones become harder to find and more in demand.
I notice this in my own conversations constantly. People don't ask me what the platform does anymore within the first five minutes. They ask who they'll be talking to when something breaks. That question didn't used to be the first one. I think it's becoming the only one that matters.
A guess….
So here's my honest, hold-it-loosely guess about where this goes. I think the software itself is going to keep changing shape faster than any of us can plan around, new interfaces, new agents, new categories that don't have names yet. I think a lot of platforms we consider essential today will look, in five years, the way that CIO described his old ERP system: a museum, kept running out of habit rather than need.
But I don't think the appetite for genuine relationships changes at the same speed. If anything, the less certain the technology feels, the more people seem to want a real person who understands their business, picks up the phone, and stays around long enough to actually know them. That part of this industry feels, to me, stubbornly human, and I say that as someone whose company is built on AI.
Maybe in five years I'll hand this essay to an AI and ask, gently, how wrong I was — and it will answer, as they always do now, with impeccable manners and a faint, unplaceable condescension. Or maybe I'll hand it to you instead, over coffee, and you'll tell me the truth. I know which conversation I'd rather have. So consider this less a conclusion than an invitation, and it's the bet I'm making with how we build, and more importantly, with how we show up for the people who trust us with their work.