There’s a stage almost every growing company hits where everything gets harder at once.
The early years were scrappy and fun. The founder did everything, knew every client, approved every invoice and could feel the business in their bones. It worked because the business was small enough to fit in one person’s head.
Then it got bigger. More people, more clients, more money moving around. And somewhere along the way the business stopped fitting.
That’s the awkward middle. Too big to run on instinct, not big enough yet for a real leadership team, real systems and real finance. Revenue’s growing and profit isn’t. Everybody’s busier than ever, and nobody can explain why it feels worse.
How you know you’re in it
The signs show up in conversations long before they show up in the numbers. The founder is still the approval for everything, from proposals to hires to the font on the holiday card. The best doers got promoted to managers, so you lost a great doer and gained a nervous manager. Senior people are doing junior work because nobody’s underneath them, while the junior people have time on their hands. Finance is a bookkeeper with a bigger title, doing their best in a job that outgrew them. Margin slides a little every year because overhead arrives before the revenue that’s supposed to pay for it. Nobody can tell you which clients make money. And growth stalls even though the team is slammed.
If most of that sounded familiar, welcome. Plenty of good companies are in the middle. The goal is to get through it, not to live there.
Why it happens
What got you here was the founder’s judgment and energy and relationships, applied directly to everything. That’s an incredible engine when you’re small. It just doesn’t scale, because there’s only one of you and you’ve been running at full capacity for years.
The middle is what happens when the business outgrows the way it’s run and nobody’s built the next version yet. It’s a renovation you’re doing while still living in the house. The kitchen’s torn out, the dog’s confused, and somebody still has to make dinner.
The order I’d fix it in
Order matters here. Fix the wrong thing first and you spend money without feeling any lighter.
Get yourself out of the approval path. Write down who can decide what, and how much each person can spend or commit without asking you. Then live with the decisions they make, including the ones you’d have made differently. If you overrule everything, you haven’t delegated. You’ve just added a step. This comes first because every other fix depends on getting your time back.
Turn your managers into managers. Most people promoted from doing the work were never taught how to manage it. Give them training, a clear description of the job, and a scorecard that measures their team instead of their own billable hours. And be honest about the ones who’d rather go back to doing the work. Not everyone should manage. Forcing a great practitioner into a management job they hate is a slow resignation with a bigger title.
Upgrade finance by one layer. You probably don’t need a full-time CFO yet. You probably do need someone who closes the books every month on a schedule, reconciles everything and gives you numbers you can trust. That’s usually a controller-level job. (I went through the layers in “Who Should Run Your Money?” if you want the full version.) You can’t make good decisions on numbers you don’t trust.
Find out which clients make money. Once the numbers are solid, look at profit by client. You’ll find a few carrying the business and a few eating it, and the ones eating it are often long-time, well-loved accounts where the scope drifted years ago and nobody wanted to bring it up. Now you can reprice, re-scope or let go based on data instead of feelings.
Plan with triggers instead of dates. Build next year’s plan so the big, hard-to-undo moves (hires, office space, big software commitments) happen when specific things are true. Hire the next account lead when you’ve signed enough work to keep one busy, not in March because it felt right in November.
A few things that feel like progress and aren’t
Hiring a big-name executive before the basics exist is the classic one. A senior leader with no systems, no data and no authority spends their first year doing the job of the layer below them, at senior rates. Buying software to fix a process problem is another. New software on a broken process just gives you the same broken process with a monthly subscription. And trying to grow your way out only makes a model that doesn’t work fail faster and more expensively.
Waiting for it to pass doesn’t work either. It doesn’t pass. It compounds.
Where to start
If you only do one thing this month, write down every decision that currently needs you and circle the ones somebody else could make. That list will tell you more about where you are in the middle than anything I could write here.
It’s a good problem to have. It’s still a problem. Fix it in order.
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Originally published on Substack.
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