Why leadership uncertainty in startups is a skill, not a flaw

You’ll be praised for vision. But tested by ambiguity. In the early stages of building, people don’t quit because of hard work. They quit because they can’t stand not knowing where things are headed.

I’ve seen it in Singapore, I’ve seen it in Riyadh: early-stage founders trying to project confidence while quietly falling apart inside because they don’t have the answers. The product isn’t working. The market’s unclear. A lead investor ghosts them mid-term sheet. And the worst part? There’s no playbook. It’s not a lack of drive that burns them out. It’s the emotional drag of ambiguity.

We often reward decisive action in leadership. But in early-stage startups, premature action is often the thing that breaks you. Building the wrong thing too fast. Hiring too soon. Locking into partnerships just to escape the discomfort of pause.

What separates sustainable founders from the rest isn’t clarity—it’s the ability to stay grounded when clarity disappears. The ones who last? They’ve trained themselves to sit in uncertainty without flinching.

I had a founder mentee in KL who built a logistics SaaS tool. Smart guy, talented team. But he kept jumping between features every two weeks. Why? Because sitting still and waiting for clean customer signals was too uncomfortable.

When I asked him why he kept pivoting, he said: “I just don’t want investors to think I’m indecisive.” But what came off as speed was actually avoidance. And eventually, it exhausted the team.

There’s a myth that great leaders always know what to do next. That couldn’t be further from the truth in uncertain markets. Especially if you’re building in Southeast Asia or the Gulf, where ecosystems are still maturing, and global playbooks don’t always fit. Sometimes the most strategic move is not to move. To observe. To resist the pressure to be definitive before the signal is strong enough.

When Grab paused expansion into new verticals during COVID and focused on core logistics, it wasn’t cowardice. It was restraint. And it paid off. Uncertainty doesn’t mean inaction. It means you’re collecting enough signal to justify your next real bet.

Here’s what sitting with uncertainty actually looks like:

• Delaying a hire because the role isn’t yet shaped by real need.
• Not forcing a roadmap when the core product still lacks user clarity.
• Pausing a raise because you’re not yet clear on your own burn priorities.
• Letting a cofounder leave instead of rescuing a relationship that’s already cracked.

It’s not indecision. It’s discipline.

If you were raised in a culture that values certainty—where good leaders are expected to have a plan—you’ll feel exposed when you admit: “I don’t know yet.” Especially in public. Especially to your team.

But let me tell you something I wish someone had told me earlier:

You don’t have to pretend you know. You just have to be steady while you don’t.

In fact, I’ve found that teams trust you more when you admit the ambiguity, but signal how you’ll hold space for it. “Here’s what we do know. Here’s what we’re watching. Here’s when we’ll decide.” That’s not weakness. That’s mature leadership.

I once worked with a founder in Jeddah who made every key hire based on immediate certainty. “This person feels right. Let’s lock it in.” It worked—until it didn’t. When the company hit friction, none of those hires were built for scale. They were built for short-term comfort. Avoiding the discomfort of uncertainty baked fragility into the organization. Sometimes sitting with the unknown is what protects you from bigger pain later.

Rushing to define things too early—whether it’s strategy, people, or product—can create an illusion of progress while actually compounding misalignment. If your team has a six-month roadmap based on guesses and gut feels, all you’re doing is locking in rigidity. The cost of course correction gets steeper the longer you deny ambiguity.

Clarity should be earned, not forced.

Here’s what I tell founders in accelerator sessions when they hit this wall:

• Don’t fill the silence too fast. Let tension sit. Let the team ask questions. Don’t rush to answer just to soothe the room.
• Time-box your ambiguity. Say: “We’ll revisit this in 3 weeks with more data.” That gives shape to the uncertainty.
• Find a witness, not a fixer. Talk to someone who can hold the space with you without pushing solutions. A mentor. A peer founder. Not always an investor.

Anyone can execute when the plan is clear. But few can guide a team through fog without pretending it’s sunshine. The more you can sit with not-knowing, the more your team will learn to do the same. And that’s when your company stops being reactive—and starts being resilient.

Founders often think they need to do more. Say more. Move faster. But what many teams actually need is a leader who can say: “We’re not sure yet—and that’s okay for now.” Because clarity doesn’t always come from motion. Sometimes, it comes from stillness.