Leadership Is Dealing with Ambiguity

“Learn to deal with ambiguity.”

That’s what my manager told me when I got promoted to management.

I didn’t get it.

I had been a developer all my life. In software development, ambiguity usually means failure. If the spec is ambiguous or the output didn't match the spec, then there is only one conclusion: your program failed. I worked in a world of clarity—binary logic, exact results, deterministic behavior.

So when I heard that advice, I brushed it off. I thought it was one of those management platitudes. Vague words that sound wise but mean nothing.

I was wrong.

# Budgeting Without a Map

I’ve been in enough client budget discussions and they’ll ask, “We want to implement CRM next year. How much will it cost?”

Now, any developer will tell you that you could build a CRM for $10,000 or $1 million. Depends on scope. Features. Integration. Support.

But that’s not how budget meetings work. They’re not asking for precision. They are looking for an approximately correct estimate to prioritize projects. You throw out a number knowing it's a guess. And that’s okay.

# Sales Calls Are the Same

Sales calls are another area loaded with uncertainty.

Even though I prepare well, every sales conversation is full of curveballs. You have to think on your feet. Respond in real time. There’s no time to double-check. No undo button. It's a live performance, with consequences.

# COVID Was a Crash Course

Take COVID, for example.

We were a small company where everyone worked from the office when COVID hit us. Less than 1% had laptops. Overnight, we had to figure out how to get people to work from home. Did they have internet? If not, what do we do? How do we get desktops delivered? How do we protect client data?

There was no playbook. Just problems. And a whole lot of ambiguity.

# From Certainty to Chaos

Now, as a CTO, ambiguity is my default setting.

I’d say 80% of my daily work has no clear inputs. No fixed process. No guaranteed outputs. There’s no spec document. No checklist. Just judgment. Conversations. Decisions that can’t be undone with a Ctrl+Z.

# A Mindset Shift

Looking back, that one line—“learn to deal with ambiguity”—has probably shaped my career more than any other advice.

I didn’t understand it at first. But once I accepted that ambiguity is part of the job, it changed how I saw everything.

I stopped panicking when things were unclear. I built my own ways to navigate them. And I learned to be comfortable saying, “We don’t know yet—but we’ll figure it out.”