What I’ve Learned from Working with Hundreds of CIOs

Over the years, I’ve had the chance to work with hundreds of CIOs—from Fortune 500s to fast-growing mid-market companies. Different industries. Different styles. But if there’s one thing I’ve learned, it’s this:

CIOs don’t want more tech. They want better outcomes.

They’re not looking to chase trends—they’re trying to solve real business problems. Quickly. Clearly. Without drama.

Here are a few lessons I’ve learned working alongside them:

1. Simplicity beats cleverness
CIOs don’t need consultants to show off. They need partners who simplify, prioritize, and deliver. If you can explain the solution in plain English and connect it to a business objective, you’ll go far.

2. Speed matters—but predictability matters more
Yes, CIOs want fast results. But they’ll take a steady, low-risk rollout over a “hero” team that burns out mid-project. On-time and drama-free often wins the renewal.

3. Trust builds over time—and disappears fast
One missed deadline or dropped ball, and you’re back to square one. But if you consistently deliver (even small wins), you become part of their inner circle. That’s where real partnership lives.

4. Every CIO has a top 3 list
It might not be printed on their whiteboard, but they’re always carrying three priorities—revenue, risk, or roadmap related. If your solution doesn’t map to one of those three? It’s noise.

5. They’re under more pressure than you think
CIOs today are expected to be technologists, strategists, diplomats, and firefighters—all at once. The best thing we can do is make their life easier, not harder.

Bottom line?
CIOs don’t care how brilliant your code is or how advanced your architecture looks. They care about outcomes. Alignment. And trust.

You win with CIOs by listening well, thinking clearly, and delivering consistently.

That’s been true for over 30 years. It’s still true now.