The Question That's Setting You Up to Fail

I've been watching CTOs nod along in C-suite meetings for years now. They look engaged. They take notes. They leave with "action items." And then they go build something that technically works—but somehow misses the mark entirely.

I used to think this was a communication problem. Now I know it's something more fundamental.

We don't actually know what we're building toward.

The Uncomfortable Discovery

When we launched the CTO Compass workshops, I thought we'd be helping CTOs track their initiatives better. Give more accurate updates. Stop being the tech person who only talks tech.

Instead, we hit a wall I didn't expect.

People raised their hands and said: "Sorry, I don't actually know how to articulate the business objective."

Not the technical goal. Not the sprint deliverables. The business objective—the thing all that work is supposed to serve.

And these aren't junior people. These are seasoned technology leaders running teams, managing budgets, sitting in C-suite meetings. They know their craft. What they don't know is whether their craft is pointed at the right target.

The Five Levers You're Not Thinking About

When your CEO says "we need to go from $5 million to $7 million," what do you hear?

Most CTOs hear: build more stuff faster.

What you should hear is a puzzle with exactly five pieces:

Acquire. How do we get new customers?
Retain. How do we keep the ones we have?
Expand. How do we sell more to existing customers?
Price. How do we capture more value from what we already offer?
Enter. How do we open new markets?

Every revenue conversation fits into one of these buckets. And as the person in the room with what I call a "logic machine" and a "complexity calculator" built into your brain, you should be the one asking: which lever are we actually pulling?

Because "increase revenue" isn't a strategy. It's a wish.

The Sleepy Syndrome

There's a phenomenon I keep seeing in leadership teams. I call it the sleepy, sleepy syndrome.

Certain phrases put the whole company to sleep. "Our product needs a refresh." "We need to reduce churn." "Let's improve NPS." The words get repeated so often that brains actually tune them out. You hear the sounds but stop processing the meaning.

And then something weird happens. In a quiet moment—maybe late at night, maybe mid-meeting when your focus drifts—you wake up and think: Wait. Why are we doing this again?

That rational moment? That's the most valuable thing you can bring to a C-suite meeting. The willingness to hear familiar words as if for the first time and ask: does this actually make sense?

I was in a meeting recently where I thought, "We don't have a churn problem—it's only 2%." But beneath that sleepy assumption? A wildfire of issues we'd been blanketing with comforting metrics.

The Statement That Changes Everything

Here's what a real business objective looks like. It's almost disappointingly simple:

Verb + Metric + From + To + By When

"Reduce churn from 8% to 4% by Q3."

"Increase average contract value by 25% by year-end."

"Launch three new product features by June."

Nothing airy-fairy. Nothing aspirational. Just a measurable commitment you can actually track.

The beautiful thing about this format? Spreadsheets love it. You can run projections. You can model good, better, best scenarios. You can see whether your technical initiatives actually connect to the outcome.

The terrifying thing? Most companies can't write these sentences for their most important goals.

The CTO's Unique Burden

You're not the visionary. That's the CEO's job—calling into being what doesn't exist, already mentally at the IPO while everyone else is figuring out next quarter.

You're not the cheerleader. That's Sales, getting fired up about enterprise deals and suite tickets at SoFi Stadium.

You're not the margin optimizer. That's Finance, reconciling accounts and watching every line item.

You carry the burden of evidence-based growth. Your feet are planted in reality while everyone else is running on energy and enthusiasm. You're the one who instantly knows how hard something will be—that complexity calculator firing before anyone finishes their sentence.

Use it.

When the C-suite throws out fuzzy ideas about growth or innovation or transformation, you're the one who can turn vague aspirations into concrete targets. Not because you're being difficult. Because without that translation, everyone's building toward something different.

What I Fear For You

I'm going to be direct: if you can't articulate your company's business objectives right now, I fear for you.

There's only disappointment, upset, and unhappiness at the other end of loosely-coupled initiatives. You'll deliver something technically excellent. It won't move the needle. Your presence will be questioned. Not to mention the sleep you lose and the stress you carry.

This is what happens when the CTO becomes "the tech person who delivers tech" instead of "the steward of technology-driven growth."

The Question to Sit With

Before you do anything else, ask yourself:

Do I know what my company's targets actually are?

And can you map those targets to the five levers? Acquire, retain, expand, price, enter?

If you can't, what exactly are you building toward this year?

If this landed with you, we're running CTO Compass workshops where we work through this live—connecting company targets to business objectives to technical actions. It's the pre-work most leadership teams skip, and it's setting up everyone (especially the CTO) to fail.

The next workshop is open for registration: https://luma.com/g5t8ptq0

Come wrestle through it with us.