The Problem: Scaling is Just Puberty for Your Business (And It’s Just as Uncomfortable)
Scaling isn’t smooth—it’s awkward as hell. One day, you’re a scrappy startup where decisions happen over Slack and everyone wears 12 hats. The next, you’re a 50-person company, and suddenly nothing feels as easy as it used to.
I’ve worked inside companies at this exact moment—where the founder suddenly realizes that what worked before isn’t working anymore.
The team is confused, priorities shift every five minutes, and execution starts to slow down instead of speed up. But no one can quite pinpoint why.
The truth? Scaling is like puberty for your business.
Things are growing at an alarming rate, and you have no idea if it’s in the right places.
Some departments are maturing faster than others, leading to total imbalance.
Everyone feels slightly uncomfortable, but no one wants to admit they don’t know what they’re doing.
And just like actual puberty, what got you through childhood (aka early-stage scrappiness) won’t get you through this next stage of growth.
This is where I step in as a Fractional Chief of Staff—helping founders turn this awkward growth phase into something structured, scalable, and actually manageable.
How Scaling Goes Wrong (And Why No One Talks About It)
You’re Stuck Between Being a Startup & a “Real” Company
There’s a sweet spot between too much structure and not enough. Too little, and things fall apart. Too much, and you kill what made you special in the first place.Your Leadership Team is Out of Sync
I once worked with a company where half the leadership team wanted to go all-in on digital expansion, while the other half wanted to double down on community engagement. No one wanted to make the call, so they stalled for months—missing huge market opportunities.Decisions Take Forever (or Never Get Made at All)
At small startups, decisions are made fast and scrappy. But once you scale? Suddenly, everything is a debate, and nothing actually gets executed.
3 Steps to Align Leadership & Move Forward Faster
Run a “How Might We” Strategy Workshop
A How Might We (HMW) workshop is one of my go-to strategy sessions for breaking through analysis paralysis. Instead of debating the same question for months, I take teams through structured exercises that force clarity.
What do we actually want to be known for?
What creates the most value for our customers?
What’s the fastest path to revenue growth?
Instead of endless "what ifs," we get clear, fast.
Use a “Good Strategy vs. Bad Strategy” Framework
A lot of companies mistake having a lot of ideas for having a strategy. They’re not the same thing.
I use Richard Rumelt’s “Good Strategy, Bad Strategy” approach to break through this:
Good strategy = Focused, clear, and makes tough trade-offs.
Bad strategy = Everything is a priority, nothing is actually a priority.
I’ve worked with leadership teams who thought they were being bold by setting 10 objectives—but really, they were just avoiding making hard decisions.
Execution into OKRs & Strategic Rhythms
Once we have a direction, we lock it into OKRs & execution rhythms. Because picking a path isn’t enough—you need a system that keeps teams accountable and in motion.
At one company, the shift from random goal-setting to structured OKRs resulted in:
✔ Faster execution across leadership teams
✔ A 15% EBITDA increase
✔ A decision-making structure that stopped leadership infighting
Actionable Takeaway: The Puberty Check-In
What Needs to Grow Up? What Needs to Stay Scrappy?
Step 1: Split a whiteboard into two sections:
🍼 What worked when we were smaller that’s now holding us back?
⚡ What scrappy processes still serve us and shouldn’t get over-complicated?
Step 2: Categorise everything into these groups:
🔹 Needs to be formalised (e.g., decision-making, hiring process, financial planning)
🔹 Needs to stay agile (e.g., rapid experimentation, direct customer feedback loops)
🔹 Needs to evolve but not get rigid (e.g., leadership structure, OKRs, performance reviews)
Step 3: Assign ownership & timelines
Decide who’s responsible for evolving each of these areas, and set a 3-month roadmap to test new approaches. ONLY PICK 3 TOP ISSUES.
Scaling isn’t about forcing structure onto everything—it’s about knowing what to let grow up and what to keep flexible. Prioritise your top 3 and return to the others when you're done. Are they still relevant?
Reflective Questions:
What’s one process in your company that’s still running like a 10-person startup—and where is that starting to break?
What’s the biggest decision your company is avoiding right now—and how much time are you losing because of it?