Ep 5. The Ick of Process

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Episode 5 focuses on something that every scaling business eventually runs into — the ick of process. You know that feeling. The one that creeps in when things start to feel… corporate.

But here’s the thing: as we scale, structure and process aren’t just inevitable — they’re necessary. They’re what keep things running smoothly when there are suddenly too many people, too many moving parts, and too many priorities to keep track of by sheer willpower alone.

So how do we navigate that discomfort — that icky feeling of “losing our startup magic” — while building the structure we need to grow?

The Shift From Scrappy to Structured

When you’re small and scrappy, everything runs on instinct and osmosis. Everyone just knows what to do. You wear ten hats. You move fast. You make things up as you go.

But as you grow, that stops working.

You suddenly have six people doing the same job in six different ways, talking to customers in six different tones, and making six different promises. Chaos.

At that point, you need structure. You need to start writing down how things work — your tone of voice, your handoff steps, your processes.

And that’s where the panic usually sets in. We swing the pendulum too far. After so much chaos, we think the only solution is to clamp down and create rules for everything. Step-by-step procedures. No wiggle room. No magic.

But that doesn’t work either.

Don’t Write the Rule Book. Draw the Playing Field.

Instead of building a fortress of rules, draw the playing field. Define the boundaries — the space within which people can think, act, and make decisions.

Rules stifle creativity. Boundaries create safety, and preserve the space for 'magic'. When people have space to play, experiment, and think within clear boundaries, you keep the magic and gain the consistency you need to scale.

Process Isn’t the Enemy — Rigidity Is

Support functions are a perfect example. They’re usually the last to scale, even as the business grows around them. So they get overwhelmed — endless requests, shifting priorities, moving goalposts.

They need processes to cope. But if that process becomes rigid, they can’t respond to change. It’s not about process or flexibility — it’s about both.

We love things to be black and white: “We do it this way” or “We don’t.”

But in reality, there’s a lot of grey. And we have to be okay with that. Sometimes, following the process step by step isn’t what’s best for the customer or the business.

So, pause. Revisit why the process exists. If the higher principle is “serve the customer faster and better,” then that should guide you — not blind loyalty to the process.

Bring People on the Journey

One of the biggest mistakes leaders make when introducing structure is assuming everyone else sees what they see. You live in the details. You know why a CRM is critical or why a new approval flow matters. But others don’t.

So, explain it.

Record a short video. Present at an all-hands. Talk to people one-on-one if you need to. Help them see the “why.”

They might not love it, but they’ll at least understand it. And that’s enough to get them to disagree and commit.

Beware the Curse of Knowledge - what’s obvious to you isn’t obvious to them.

Unlearning and Relearning

When you add structure to a scaling business, you’re not just changing the way people work — you’re asking them to unlearn old habits and relearn new ones.

And that’s hard. It’s uncomfortable. It’s where the ick comes from. But that doesn’t mean you’re “becoming corporate.” It means you’re growing — and growing up.

Just like people, businesses need to mature. You can’t keep operating like a toddler and expect to thrive as an adult.

Structure Creates Freedom

Here’s the truth: process doesn’t kill flexibility — it creates it.

When the basics run smoothly, you free up mental space for thinking, experimenting, and innovating.

Without structure, you’re too busy firefighting to think strategically. You’re sprinting through mud. So, instead of seeing process as handcuffs, see it as scaffolding — the thing that holds everything together while you build something bigger.

Your Action Item...

Take a fresh look at the structures in your world.

Are you writing rule books — or drawing playing fields?

Because in the chaos of scaling, structure isn’t the enemy. It’s what keeps you flexible, creative, and sustainable for the long haul.

Remember: business growth is messy — but the human side doesn’t have to be.

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