How to Build Comfort with Ambiguity

By Hannah Baker

Dear Reader,

You're expected to lead even when you have no idea what the hell is going on.

(I know, you’ve heard the next part a million times. Bear with me.)

The world is moving faster than ever. Technologies shift overnight. Markets pivot on a dime. And somehow, you’re still just trying to get everyone to show up to the team meeting.

We all know this, we’re surrounded by it.

The speed, the volatility, the endless flood of decisions.

Honestly, if one more person says “we’re living in unprecedented times,” I might throw my laptop out the window.

But even though we’re numb to the language, the pressure is real. Chaos isn't theoretical, it's today.

And somehow, we’re still expected to move forward. To lead. To be the calm voice in the storm.

Why Comfort with Ambiguity Matters

This is where we have to develop a new kind of leadership, one that builds comfort with the scary, with the unknown, with the fog.

One that doesn’t wait for clarity before taking a step but learns to move even when the ground feels a little squishy.

Whether you're designing a new product experience or guiding a team through shifting priorities, comfort with ambiguity is crucial. It’s not about pretending the uncertainty isn’t there. It’s about working with it instead of letting it overwhelm you.

It can feel like you’re supposed to have all the answers, even if you logically know that’s impossible. The pressure still creeps in.

But the truth is, the most impactful people aren’t the ones who have it all figured out.

Comfort with ambiguity isn’t some soft, squishy "nice-to-have."

It's the thing that separates leaders who collapse under pressure from those who build teams that can bend, flex, and keep moving forward.

Recent research highlights just how critical this skill is: A longitudinal study by Peter J. O’Connor and colleagues found that project managers with higher tolerance for ambiguity showed better adaptive performance and project progress.

Likewise, a Deloitte report emphasizes that organizations with leaders skilled in navigating uncertainty are significantly more likely to be high-performing and resilient during disruption.

Staying in the Mess

The instinct, of course, is to reach for certainty. To tidy up the mess. To "fix it" fast.

But the real power move?

Sit in the mess. Invite others into it.

So what does it actually look like to lead through the fog, not just talk about it? Building comfort with ambiguity isn’t just a mindset shift; it’s a practice.

Ways to build comfort with ambiguity:

• Practice "both/and" thinking instead of "either/or." (Ex: "How can we move fast and stay aligned?")
• Normalize saying, "We don’t have the full picture yet."
• Resist the urge to wrap things quickly. Let better answers emerge.
• Imagine multiple futures, not just one "plan."
• Encourage your team to run small experiments.

The Ambiguity Inventory

Beyond general tips, one tool you can use, either on your own or with your team, is an Ambiguity Inventory.

It’s a simple, structured reflection that helps you:

• Spot where ambiguity shows up most
• Notice your default responses
• Reframe where you actually have influence

Start by asking:

Then fill out four columns:

1. Situation (strategy shifts, unclear feedback, vague goals)
2. My current reaction (stress, decision paralysis, overthinking)
3. What’s actually in my control?
4. How could I respond differently?

This exercise helps you map the emotional terrain of ambiguity. It surfaces patterns like avoiding decisions, defaulting to overwork, or trying to control the uncontrollable.

Once you see those patterns, you can challenge them. Maybe you notice you spiral into over-preparation whenever priorities shift. Could you instead create a short-term check-in plan with your team? Or communicate what is clear while acknowledging what’s not?

Here’s what an Ambiguity Inventory might look like:

Doing this kind of reflection zooms you out from knee-jerk reactions and helps you move from reactive to resourceful.

And when done with your team, it builds shared language and trust around navigating uncertainty together.

Comfort with ambiguity isn’t about surrendering to chaos; it’s about leading through it with curiosity, flexibility, and resilience.

The future will not reward those who cling to old certainties.

It will reward those who can navigate uncertainty with confidence and bring others with them.

If you're noticing ambiguity in your work, good.

That means you're doing something that matters. Something complex. Something human.

So don’t run from it. Don’t rush to solve it. Practice walking with it.

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For the first time, we’re offering one of our courses in both AM and PM time slots to better accommodate people across time zones.

This 3-part live series helps you grow essential (and often overlooked) leadership skills like active listening, comfort with ambiguity, and suspending judgment, the human side of leading teams.

It’s a small experiment with a big goal: making live learning more accessible, no matter where you are.

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Until next time!

Hannah Baker ​Facilitator & Co-Founder ​The Fountain Institute ​

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