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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.

Why Simplicity Wins in Software—and in Business

Early in my career, I thought complexity signaled sophistication.
Big words. Big diagrams. Fancy solutions.

But after building software for 30+ years and leading a consulting firm through market swings, tech revolutions, and team transitions, I’ve learned the opposite is true:

Simplicity wins. Every time.

In software:

The simple solution ships faster.
It’s easier to test, easier to maintain, and easier to explain.
Clients understand it. Developers trust it. Users prefer it.

Yes, some problems are inherently complex. But that’s all the more reason not to add layers just to look smart. Good software makes the complex feel simple—not the other way around.

In business:

A clear offer converts better.
A focused strategy beats a scattered one.
Teams move faster when they know exactly what matters.

We’ve said no to “opportunities” that didn’t fit our core business because we know what we’re great at—and more importantly, what we’re not. That clarity creates momentum.

The cost of complexity:

Confused customers
Overstretched teams
Projects that drag on
Decisions that never get made

Complexity creeps in when no one’s watching. It takes discipline to say, “This is enough.” Or even better: “This is too much.”

Simple isn’t easy. It’s a choice.
It requires thought, tradeoffs, and a bias for clarity over control.

But when you choose simplicity—whether in an architecture diagram, a process, or a product offering—you gain something far more valuable:

Focus. Velocity. Trust.

AI Is Great—But It Can’t Think for You

I use AI every day.
It drafts proposals, outlines blog posts, summarizes meetings, and even helps prep for client calls. It saves time, sharpens execution, and makes life easier.

But here’s the mistake I see too many people make:
They expect AI to do the thinking.

It won’t.

AI is fast, but it’s not wise
AI can generate five paragraphs in two seconds. But are they aligned with your strategy? Your client’s goals? Your voice? That still takes human judgment.

Speed without direction is just fast noise.

It doesn’t understand nuance
I’ve asked AI to write content before and thought, “Well… technically, this is fine. But it misses the point.”
Why? Because it doesn’t know what matters most. It doesn’t know your team’s dynamics, your client’s unspoken concerns, or how trust actually works in your industry.

It’s a tool, not a replacement
AI can help you do the work. It can’t decide what work is worth doing. That’s strategy. That’s context. That’s leadership.
It’s like hiring the fastest assistant on earth who still needs clear direction—every single time.

How to use AI the right way:

Use it to generate first drafts, not final decisions
Let it automate low-value tasks so you can focus on high-value thinking
Pair it with your judgment, not your abdication

The real risk isn’t that AI replaces us
The real risk is that we stop thinking, stop leading, and stop learning—because we assume AI will handle it.

It won’t.
It’s here to help. But it still needs you at the helm.

Why I Don’t Micromanage (And What I Watch Instead)

I used to think that being a good leader meant staying involved in every detail. Check-ins, reviews, updates, approvals—I was everywhere.

Eventually, I realized something:
Micromanagement doesn’t scale. Leadership does.

So I stopped hovering. I stopped inserting myself into every decision. And I started watching the right things instead.

Here’s what I’ve learned:

1. Results > activity
I don’t care how many hours someone worked. I care about whether they delivered what they said they would.
Micromanagers obsess over inputs. Leaders track outcomes.

2. Trends > snapshots
Anyone can have a bad week. But over time, patterns emerge—positive or not.
I look at trendlines in client satisfaction, quality of deliverables, and internal collaboration. One-off issues don’t rattle me. Repeated ones get attention.

3. Questions > instructions
Instead of giving answers, I ask questions:

“Are you the right person for this goal or task?”
“What will you do?”
“What are your challenges?”
This builds ownership, not dependency. People grow faster when they think, not just follow.

4. Accountability > control
Micromanagement feels like control. Leadership builds accountability.
We use daily huddles and short check-ins to stay aligned. People say what they’re doing—and then they do it. That rhythm replaces the need to chase people down.

5. Culture > compliance
If you need to micromanage, it’s often a hiring or culture issue.
The right people, in the right system, don’t need constant supervision. They thrive with trust and clarity.

I don’t micromanage because I don’t have to.
Our team runs on trust, visibility, and accountability—not control.
That’s more sustainable, more scalable, and—frankly—more enjoyable for everyone involved.

The Most Underrated Meeting on My Calendar

Most people dread meetings. I get it.
They’re often too long, poorly run, and end without anything getting done.

But there’s one meeting I’ve kept for over two decades—rain or shine, remote or in-person. It’s quick. It’s focused. And it’s the most underrated thing on my calendar:

Our daily huddle.

What it is (and isn’t):
It’s not a status meeting. It’s not a brainstorming session. And it definitely doesn’t involve PowerPoint.
Our huddle is 15 minutes, same time every day, built to keep everyone aligned, accountable, and connected.

Here’s how it works:
Each person quickly shares:

Big updates from last 24 hours
Stuck items where help is needed

That’s it. No tangents. No deep dives. If something needs more discussion, we take it offline. The goal is to keep things moving—and surface blockers fast.

Why it works:

It creates clarity. Everyone knows what’s happening and who’s doing what. No guessing.
It builds trust. When people show up and consistently do what they say, credibility grows.
It keeps teams connected. Especially in remote settings, that daily touchpoint is a glue.

What it’s replaced:
Longer, less frequent check-ins that often felt like overkill, or came too late.
With our huddle, we solve minor problems before they snowball or “slay monsters” while they are little. We stay nimble. And we never waste time wondering what’s going on.

Final thought:
Not every meeting is worth protecting. But this one is.
The daily huddle keeps our team focused, our projects on track, and our culture strong.

If you want more on how we run it (and how you can too), I break it down further on my website and in my book The 100: Building Blocks for Business Leadership.