A recent MIT’s report shows that 95% of generative AI pilots are failing. The truth is, most of these projects never had a shot. They’re built on teams that weren’t ready, guided by leaders who didn’t know what to look for in the first place. You can’t expect AI to deliver business results when curiosity and readiness aren’t modeled at the top.
Everyone is chasing “AI-ready hires.” This might be your biggest waste of time. If the founder isn’t AI-ready, the whole thing collapses. Curiosity at the top is the real multiplier.
Most businesses will not survive this AI wave. This might sound exaggerated, but it’s not. It’s actually closer to the truth than the way most people are talking about it. We’re at the beginning of a new 20-year business cycle powered by AI, and if you’re still optimizing the old playbook, you’re already falling behind. You can’t outsource transformation. You can’t delegate curiosity. If you hired someone to “manage AI,” you’ve already lost.
Now the flip side. When the founder models curiosity, the company designs for it. Curious founders ask better questions, which forces better thinking downstream. Everyone from product to sales starts optimizing for exploration over explanation.
What the CEO prioritizes matters.
The companies seeing real AI productivity gains all have one thing in common: a founder who sends a clear signal from the top. That signal shows up in what gets resourced, what gets reviewed, and what gets permission to move.
Smart CEOs invite experimentation. They allocate time to review what shipped. They make room for failure, iteration, and process re-design.
You don’t need a “big bang” AI roadmap. You need a le who asks their team every week: What changed? What did we automate? What improved?
Budgets are a signal.
The companies seeing traction don’t fund giant, abstract strategies. They fund learning. They make room for short-cycle projects, quick pivots, and testable outcomes. The real signal comes from where priorities show up, in the org, in the budget, and in how time gets spent.
Systems thinking becomes the norm.
Good orgs do not layer smart people on top of messy systems. They fix the system first, then staff for leverage.
Hiring shifts from volume to velocity. The answer isn’t manpower anymore. It’s a flight to quality. Job descriptions focus on outcomes, not tool lists. Interviews sound like this:
- “Show me the last thing you automated.”
- “Walk me through a seven-day experiment you shipped.”
- “Where did it fail, and what changed?”
Work samples are scoped to one week, with a clear before and after. Scorecards weight learning velocity, systems thinking, data hygiene, and the willingness to kill old work.
Metrics tell you if it’s real:
- Time to first shipped experiment (TTFSE)
- Percent of workflows with measurable automation
- Pilot-to-production ratio
These are not vanity metrics. They are operational pulse checks. If they are not trending up, it is not an AI strategy. It is a science fair.
Revenue per employee might be the strongest signal of all. In our last business, we tracked it from day one. We hit $380K per head, which is software-level efficiency within a services org. You can’t get there without a culture of experimentation and systems that reward it.
Investors notice. In diligence, the strongest signal is simple: Where does the founder’s curiosity show up in the calendar and the P&L?
Look for repeated small wins. Documented workflows. Legacy work retired on purpose. Documentation is not busywork; it’s the flywheel. Every de-scoped feature and deprecated tool becomes a lesson the next hire does not have to relearn. That is what makes a business buildable.
Red flags? Founders bragging about tools. No shipped changes. No willingness to de-scope. Or worse, a team that looks exactly like the last five decks you saw. The sea of sameness does not just stall AI. It sinks companies.
Curiosity is not a nice-to-have in this market. It is the operating system.
You do not need to hire an AI expert. You need a leader who’s fluent enough to build momentum and curious enough to never stop learning. That is what changes a company. If you want teams that think with AI, start with a founder who does.
Curiosity compounds. Credentials depreciate.
