There’s a particular kind of meeting that every founder knows. The one where someone on the team asks a direct question — “Should we go after this market?” or “Are we cutting this product line?” or “What’s the plan for Q3?” — and you realize, with a clarity that borders on nausea, that you have absolutely no idea.
You’re supposed to know. That’s the job. The team looks to you for direction, the board looks to you for strategy, the clients look to you for confidence. And most of the time, you can provide some version of all three, even when you’re less certain than you let on.
But occasionally — and these occasions are more frequent than any leader admits — you genuinely don’t know. The data is incomplete. The market is shifting. The right answer depends on variables you can’t control and can’t predict. And you’re standing in front of people who need you to say something.
What do you say?
The Temptation to Fake It
The easiest move is to fake certainty. Pick a direction, commit to it with conviction, and project the confidence that everyone wants to see.
I’ve done this. I’ve made decisions in meetings that I wasn’t remotely sure about, delivered them with the polished assurance of someone who has Done The Analysis, and walked out feeling like a fraud. Sometimes the decision turned out to be right. Sometimes it didn’t. But in both cases, the team acted on it as if it were a considered strategy when it was really an educated guess wrapped in presentation skills.
The problem with faking certainty isn’t that you’ll always be wrong. You won’t. Random chance alone means you’ll be right roughly half the time, and your intuition probably beats random.
The problem is what it does to the culture. When the leader always has the answer, the team stops looking for answers. They stop questioning. They stop bringing competing viewpoints. They wait for direction instead of generating it. And the organization becomes exactly as smart as one person, which is never smart enough.
I’ve seen this pattern in companies far bigger than mine. A charismatic CEO who always knows the way. A team that has learned, through years of reinforcement, that disagreement is unwelcome and uncertainty is weakness. The company moves fast and confidently — right up until the CEO’s intuition hits a wall, at which point nobody has the muscle to navigate without a map.
The First Honest Conversation
The first time I admitted genuine uncertainty to my team was about two years into PipelineRoad.
We were trying to decide whether to expand into a new vertical. The data was mixed. Some signals said yes — there was demand, we had a referral opportunity, the economics looked promising. Other signals said no — we’d be stretching our team thin, the sales cycle was longer than what we were used to, and we’d be competing against agencies with more vertical expertise.
In a previous version of myself, I would have picked the direction that felt slightly more right, pitched it as the obvious move, and moved on. Instead, something — maybe exhaustion, maybe maturity, maybe just the honest realization that I genuinely didn’t know — made me say the thing leaders aren’t supposed to say.
“I don’t know what the right call is here.”
The room went quiet. Not the productive quiet of people thinking. The uncomfortable quiet of people recalibrating their expectations of me.
And then something interesting happened. Bruno started talking. Then Alfredo. Then the whole team was debating, sharing data I hadn’t seen, raising concerns I hadn’t considered, proposing a test-and-learn approach that was better than anything I would have come up with alone.
The decision we reached was: run a 90-day pilot with one client in the new vertical, with clear success criteria, and revisit. It wasn’t decisive. It wasn’t bold. But it was the right framework for a situation where boldness would have been recklessness in disguise.
The Framework
Since that meeting, I’ve developed an informal framework for leading through ambiguity. It’s not complicated. It doesn’t require a whiteboard or a consultant. But it works.
Name the uncertainty. Say it out loud. “Here’s what we know, here’s what we don’t know, and here’s what we can’t know yet.” This single act of transparency changes the entire dynamic. The team stops trying to guess what you want to hear and starts trying to solve the actual problem.
Define the decision type. Not all ambiguous decisions are the same. Some are reversible — you can try something, and if it’s wrong, you can change course without catastrophic consequences. Some are irreversible — a hire, a large investment, a public commitment. For reversible decisions, move fast and learn. For irreversible decisions, slow down and gather more information. The mistake most leaders make is treating every decision as irreversible, which leads to paralysis, or treating every decision as reversible, which leads to chaos.
Set a decision deadline. Ambiguity without a timeline becomes perpetual indecision. Pick a date. “We’re going to make this call by Friday, based on whatever information we have by then.” The deadline forces prioritization of the information-gathering. It also prevents the team from living in limbo indefinitely, which is more damaging than a wrong decision made on time.
Make the smallest possible bet. When you don’t know the answer, don’t bet the company. Find the smallest version of the decision that generates real learning. A pilot. A prototype. A conversation with five potential customers. A two-week sprint. The goal isn’t to eliminate uncertainty — that’s impossible — but to make the uncertainty smaller with each iteration.
Communicate the reasoning, not just the decision. When you do make the call, share the thinking behind it. “We’re doing X because of A and B, despite the risk of C, and we’ll revisit if D happens.” This transparency does two things: it gives the team the context they need to execute intelligently, and it makes it safe to raise a flag if the assumptions change.
What Travel Taught Me
I’ve written before about how travel shapes my thinking, and ambiguity is one of the places where the connection is most direct.
When you’re navigating a city where you don’t speak the language, don’t know the layout, and can’t read the signs, you develop a comfort with not knowing that’s hard to build any other way.
I think about a specific afternoon in Marrakech. I’d gotten lost in the medina — which is easy to do and slightly terrifying the first time, because the alleys are narrow, the turns are unmarked, and the GPS on your phone gives up after about three minutes.
I had two choices. Panic and try to retrace my steps — the equivalent of clinging to the last known position, the familiar ground. Or accept that I was lost, pick a direction that felt roughly right, and navigate by observation — the sounds of the main square, the direction of foot traffic, the occasional glimpse of a landmark above the rooftops.
I chose the second option. Not because I’m brave. Because retracing steps in the medina is hopeless, and standing still draws a crowd of people who will “help” you to their cousin’s rug shop.
I found my way back in about forty minutes. Not by following a plan, but by staying alert, making small directional bets, and adjusting as new information appeared.
That’s leading through ambiguity. Not having the map. Having the willingness to move without one.
The Emotional Part
The part of this that nobody writes about in management books is the emotional toll.
When you’re certain — or faking certainty — you sleep fine. The direction is clear. The team is moving. Whatever doubt you feel is manageable because you’ve committed and now it’s about execution.
When you’re genuinely sitting in uncertainty, the doubt is constant. You lie awake running scenarios. You second-guess the framework. You wonder if admitting uncertainty made you look weak. You compare yourself to the mythical founder who always knows the way and wonder what they have that you don’t.
What they have, usually, is a better poker face. Or a shorter memory. Or a team that’s afraid to tell them they’re wrong.
I’ve learned to sit with the discomfort instead of rushing to resolve it. Not comfortably — I don’t think you can be comfortable with uncertainty, and I’m suspicious of anyone who claims to be. But I can tolerate it now. I can hold the tension of “I don’t know” without it collapsing into “I need to decide right now just to make this feeling stop.”
That tolerance is a skill. Like any skill, it develops with practice. And like most important skills, nobody teaches it in school.
The Counterintuitive Truth
Here’s what I’ve learned after years of this: the moments of greatest ambiguity have produced PipelineRoad’s best decisions.
Not because ambiguity is some magical force. But because when nobody knows the answer, everyone has to think. The hierarchy flattens. The best idea wins regardless of who suggested it. The process becomes genuinely collaborative instead of performatively collaborative.
Our best client engagement started from a meeting where I said “I have no idea how to approach this account” and the team spent two hours figuring it out together. Our best internal process was designed during a period when we were genuinely unsure whether the business model was working.
Certainty is comfortable. But comfort is the enemy of the kind of thinking that produces breakthroughs.
So now, when someone on the team asks me a question I don’t know the answer to, I’ve learned to resist the reflexive reach for a confident response. Instead, I pause. I say what I know. I say what I don’t know. And I ask the room what they think.
It’s less impressive. It’s also more honest, more effective, and more respectful of the intelligence sitting around the table.
The best leaders I’ve met aren’t the ones who always know. They’re the ones who are comfortable enough to not know, and skilled enough to find the way anyway.