15 Jun Leading Through the Messy Middle: Growth Feels Harder Before It Gets Better

There’s a phase in every company’s journey that doesn’t get nearly enough attention: the messy middle.

It’s that in-between stage where you’re no longer a scrappy startup—but not yet a fully scaled, mature company either. You’ve got traction, revenue, and a growing team. Instead of feeling like progress, growth suddenly starts to feel… harder.

If you’re a CEO or founder in this phase, it can feel frustrating, exhausting, and sometimes even like you’re doing something wrong.

Here’s the truth: The messy middle is not a failure—it’s a signal.

What the Messy Middle Looks Like

In the early days, everything moves fast. You build, launch, sell, iterate—on instinct, hustle, and tight feedback loops. Your team is small and scrappy. Communication is informal. Everyone wears multiple hats.

Then, growth hits. And with it comes new complexity. Suddenly, what used to work doesn’t.

• Processes start breaking under pressure
• Roles blur and accountability becomes unclear
• Decision-making slows down
• Leaders are stretched thin
• And the CEO? Still pulled into everything

Sound familiar?

This is where many businesses stall—not because they lack product-market fit, but because they haven’t yet built the structure to support their next stage of growth.

The Real Challenge Isn’t Growth—It’s Leadership Evolution

The messy middle isn’t just operational. It’s deeply leadership-driven. What this phase demands is clarity:

• Clarity of vision.
• Clarity of roles.
• Clarity of process.
• Clarity in how decisions get made, and who’s truly accountable.

And that requires a very different kind of leadership than the startup phase did. It’s no longer about “doing everything.” It’s about empowering others, building systems, and stepping out of the weeds.

What It Takes to Lead Through the Messy Middle

So, what does it look like to lead effectively through this transition? Here’s what I’ve seen make the difference time and again:

A Clear Operating Rhythm

Establishing consistent, intentional rhythms of communication and decision-making—weekly team syncs, quarterly planning, scorecard reviews—helps reduce chaos and bring focus.

Defined Roles and Ownership

The “everyone does everything” mentality has to evolve. Every person on your team should know exactly what they’re accountable for—and what success looks like.

Scalable Systems (Not Scrappy Workarounds)

That spreadsheet you hacked together last year? It’s not going to cut it anymore. You need systems that scale—tools, automations, and documented processes that remove friction.

Strategic Support—Often Starting with Fractional Leadership

This is often the moment where CEOs realize: I can’t do this alone anymore. But, hiring a full-time executive team might feel premature or risky. That’s where fractional leadership steps in.

As a fractional COO, I’ve helped CEOs in this exact phase bring structure to the chaos. I don’t just advise—I embed within the team to:

• Unblock operations
• Create scalable systems
• Build clarity around people and processes
• And free up the CEO to focus on high-impact leadership

It’s about helping the business mature—without sacrificing momentum or burning out the founder in the process.

You’re Not Alone in the Messy Middle

If it feels like growth is harder than it used to be, that’s because it is. The decisions are bigger. The stakes are higher. And the need for structure, clarity, and leadership has never been greater.

But you’re not broken. You’re evolving. With the right support, the messy middle can become the launchpad for the next stage of your business.

What was your biggest turning point in the messy middle? Let’s compare notes—and if you’re in it now, let’s talk about how to get to the other side. You can contact me here via my website or email me directly at michael@consultstraza.com.