Uncertainty is the default

Early in my time at Freshworks, I found myself repeating a line so often it became a hiring filter:

“To be successful here, you need a high tolerance for uncertainty.”

If someone was going to thrive, it had far less to do with their résumé and far more to do with how they operated when nothing was clearly defined.

I saw the pattern repeat itself.

Someone would arrive with the right background, the right pedigree, the right experience — and still get stuck. They’d run straight into the reality of incomplete or non-existent processes, limited guidance, unclear ownership, and no established measures for success. There was nothing solid to lean on.

But the people who flourished were different. They didn’t wait for clarity or structure. They didn’t need instructions. They stepped into gaps, took initiative, and operated — as I told them often — like the CEO of their own job.

Most early companies don’t have  swim lanes. 

Many don’t have a shared definition of “good”. 

In the space left unfilled, silence moves in. And silence breeds stories — usually the wrong ones.

Working in a modern startup often feels like reading a book as it’s being written: the plot shifts, the chapters rearrange themselves, and the ending hasn’t been drafted yet. You have to stay alert, flexible, imaginative and willing to act before the page is complete.

This isn’t a startup quirk.

That’s what most modern work looks like.

What Uncertainty Really Costs

Across every role I’ve had — developer, infrastructure operations, MSP, advisory, analyst relations — the pattern is consistent:

Conflict and frustration rarely comes from bad news.

It comes from not knowing.

You see this everywhere:

• Customers asking status updates ” because progress isn’t visible 

• Teams growing anxious when leadership  goes quiet

• Stakeholders mistaking silence for lack of movement

• Employees pausing  while they wait for someone to define the path

I once wrote that uncertainty is worse than inconvenience. People can absorb almost any setback — as long as they understand what’s happening and why.  It’s the absence of signal — the void — that derails people.

Uncertainty isn’t a feeling.
It’s an operating environment.

And in that environment, people change how they behave.

A Parallel from a Very Different World

I relearned this lesson in a completely different world from technology: the musical-theater college admissions process with my daughters.

If you’ve never lived it, imagine months of prescreens, applications, auditions, scheduling logistics, essays, and financial forms  — nearly all of it completed with little or no feedback. You rehearse, submit, hope, and wait. 

The questions never stop:

• How do I film that prescreen?

• What’s a good classical monologue?

• What do I write in that essay?

• What is that school looking for?

• How do I know if this is good enough?

It’s peak uncertainty masquerading as a procedure!

And yet, young performers adapt to it early. They come to understand that clarity is rare, direction is fluid, and ownership is non-negotiable. They don’t wait for instructions. They build their own structure.

Very different setting.
Same fundamental skill.

Two very different domains. 

Same underlying skill.

Because in both, uncertainty isn’t a mood — it’s a way of working.

What It Looks Like to Operate Without a Map

Navigating uncertainty is a behavior pattern.

You can usually spot folks who can navigate uncertainty well. You can usually spot them before the answers arrive. Their advantage isn’t expertise. It’s movement in the absence of maps.

1. They act like owners

Ownership fills the vacuum  when structure is missing.

It keeps work moving even when no one has formally defined the path.

2. They narrate what they  know (and what they don’t)

Silence invites speculation. .

Early communication, even incomplete, keeps uncertainty from turning into fear or rumor.

3. They set expectations

Clear expectations turn uncertainty into something navigable.

People can handle almost anything if they know what’s happening, how it affects them, and when they’ll hear more.

4. They stay adaptable

Few careers follow the plan they began with. Adaptability isn’t a bonus skill anymore. It’s foundational.

A little curiosity helps here. As I wrote in The Case for Curiosity, genuine curiosity is the starting point for growth — and it’s also what keeps you open when the future refuses to sit still.

5. They bring in sensemakers

No one navigates uncertainty alone.

Sensemakers pressure-test assumptions and translate noise into meaning.

As I wrote in Who Are Your Sensemakers?, these are  people who help you navigate complexity and make meaning  

These aren’t coping mechanisms.

They’re operating principles — habits of people who work well while answers are still unfolding.

Why This Matters Now

Careers evolve faster than the plans we make for them. Markets shift faster than the decks meant to explain them. And the skills we rely on seem to lose their edge more quickly than they used to. When the path you’re on didn’t exist when you started, treating a fixed playbook like a safety net becomes its own kind of risk.

In Fast Isn’t the Point, I wrote that “moving fast is easy — knowing where to move is the hard part.” That distinction is unavoidable in a world where uncertainty isn’t a detour but the operating environment itself. Uncertainty forces a separation of motion from direction. It demands that you choose the next step even when the map is still being drawn.

We’re in a moment when stories change mid-sentence. New technologies don’t just alter the rules; they redefine what feels possible. Entire categories appear and disappear within a single planning cycle. Uncertainty isn’t new — it’s simply become the default setting. 

In times like these, the people we trust aren’t the ones claiming to have the answers. They’re the ones who stay grounded and present while the next chapter forms — the ones who don’t flinch when the world refuses to sit still.

A Simple Way to Shrink the Void

There’s one question I’ve found consistently useful:  

How will we measure success?

Its deceptively simple, but it does a lot of quiet work. 

It gives ambiguity edges. 
It turns uncertainty from a fog into something navigable. 
It reminds teams there is a direction, even if the route isn’t obvious. 

Pair it with a small discipline: 

• State  what you know. 

• State  what comes next. 

• State when you’ll check in again.

These brief signals shrink the void.
Not eliminate it — but make it workable.

Berkson’s Bits…

I wrote this back in 2016 on LinkedIn: 

I underestimated how dangerous. In the current environment, it’s not just shortsighted — it’s existential.

What I’m Listening to…

Winter has settled into NYC. My annual listen to “December” by George Winston offers quiet minutes of calm. Perhaps it will do the same for you. 

Uncertainty isn’t the enemy. The void is — the silence that forces people to invent their own stories about what’s happening and what it means. You can’t eliminate uncertainty, but you can shrink the void. You shrink it by offering signal where most people offer nothing: communicating early, setting expectations, owning what you can, staying adaptable, and bringing in sensemakers when the picture blurs. 

Those small signals are what steady people. They keep teams aligned and prevent drift. And, over time, the ability to shrink the void becomes its own kind of advantage — because most people don’t bother. They wait for clarity. The ones who move while the void is still wide open are the ones others trust when things get uncertain.

That’s the real work.

Looking forward to continuing the conversation…

Alan