June 25, 2025
You’re not broken. You’re in the middle.
At some point, growth stops feeling exciting and starts feeling… confusing. The team has doubled. Maybe tripled. The founder isn’t in every meeting anymore. Nobody knows who owns what. People are doing two jobs—or none—and everything is urgent.
Welcome to the messy middle.
This is where momentum becomes chaos unless you lead differently.
At Polaris Pathways, we’ve supported teams right at this breaking point. Some made the shift and scaled with clarity—others didn’t get there immediately, but walked away with insights that reshaped how they lead.
1. Growth changes everything—including how you lead
In the early days, leadership was instinctual. You knew everyone. You made calls fast. Culture happened in conversations, not strategy decks.
But scale introduces friction. Suddenly:
You’re not doing anything wrong. But your leadership needs to level up with the company, not lag behind it.
As you scale, you realize, ‘Huh, I really need more of these.’ And the danger is getting too process-y instead of outlining the objectives so people understand, ‘Okay, we’re doing this for this reason.
–Elad Gil, High Growth Handbook
2. The illusion of alignment is one of the biggest risks
In the middle, it feels like everyone’s still aligned. After all, you’re still in the same meetings, still moving fast, still “scrappy.”
But alignment isn’t how fast you’re moving—it’s whether you’re moving in the same direction.
In misaligned companies, you see:
You can’t fix this with more standups. You fix it by saying clearly, “Here’s where we’re going. Here’s how we’ll get there.”
3. Decision debt compounds like technical debt
In the early days, skipping decisions didn’t seem to cost much. A little ambiguity was fine.
But as headcount grows, every unclear decision starts to carry weight on morale, on productivity, on trust.
Just like technical debt slows down product velocity, decision debt slows down people.
Cleaning up those decisions isn't busywork. It’s infrastructure repair.
A study on decision-making in complex systems found that as organizational complexity increases, leaders become slower and less effective—understandable in the messy middle, where rapid growth adds layers of ambiguity.
4. Your job now is building the engine, not being the engine
This is the hardest shift for founders and early execs. You build by doing. Now you lead by designing systems that other people can run.
If that sounds boring, you’re not seeing the full picture.
Your new job is:
The middle is where you build the actual company—not just the product.
5. The myth of “experienced hires will just figure it out”
Hiring senior talent feels like the answer - until they stall.
And it’s not because they’re unqualified. It’s because “figuring it out” without context, support, or access is a losing game.
Even the best hires need:
“Just let them run with it” often becomes “why aren’t they delivering?” Skip onboarding and you don’t get leverage - you get confusion.
Organizational life‑cycle theory shows that most companies pass through predictable phases—startup, growth, maturity, decline, and renewal—each bringing its own inflection point. The “messy middle” is exactly that stage where creative, informal structures fail and new systems become essential
6. The culture drift that happens in the middle
Culture used to be organic. It happened in daily interactions, unspoken rituals, and shared rooms.
But as teams grow, those touchpoints get replaced with Slack channels and calendars.
What used to be felt now has to be reinforced.
If the company feels “different,” it probably is—because the systems that carried your culture haven’t been upgraded.
Your job is to help your team keep naming it, showing it, and practicing it—before it starts being rewritten without you.
7. You don’t need more hustle. You need more clarity.
Leading through chaos isn’t about being tougher or faster. It’s about becoming a different kind of leader—one who builds clarity, sets boundaries, and lets go of control in order to scale it.
When you’re growing a startup, chaos is part of your day‑to‑day… But when you try to go from startup to scaleup, you need to eliminate as much chaos as possible so you can really enter the SCALE phase.
“When you’re growing a startup, chaos is part of your day‑to‑day… But when you try to go from startup to scale‑up, you need to eliminate as much chaos as possible so you can really enter the SCALE phase.”
— Lempire CEO, reflecting on navigating chaos
This isn’t the end of startup energy. It’s the start of organizational maturity.
— Michelle
Before you go, a few questions to sit with: