Why Projects Derail When You Have Fewer Than 50 Employees

Here’s the thing:

Small teams get things done. They’re gritty, scrappy, and wear every hat from strategy to “who ordered the printer ink.” But somewhere along the way, around employee #12, (definitely by #30) things start to break down. Projects stall, communication gets messy, and no one’s really sure who’s doing what anymore.

This isn’t a sign your business is broken. It’s just what happens when the hustle outpaces the systems.

So if you’re sitting there wondering why everything feels harder than it should, here’s why your projects might be going off the rails.

1. No One Owns It—But Everyone Has Thoughts

In small teams, roles are blurry. One minute you're the founder, next minute you're reviewing social copy and also trying to set up payroll. So when a new project kicks off, people nod along… but no one actually takes the wheel.

Suddenly it’s three weeks later and nothing’s happened. Not because your team is lazy—but because no one knew they were driving.

Fix: Assign a project lead. Not someone who might follow up. Someone who will own the timeline, the tasks, and the inevitable "hey, where are we with this?"

2. Process? What Process?

A lot of founders skip over “process” because it sounds corporate. (Also: boring.)

But flying by the seat of your pants only works until you can’t remember which Google Doc has the right info, or why there are 14 versions of the same client deck floating around.

Fix: Create just enough process to keep things moving. A simple checklist. A kickoff doc. Literally anything that lets people stop guessing and start executing.

3. The Bottleneck Bottleneck

You know the person. The one who “has to review” everything, but never actually has the time. Or maybe… that person is you.

Either way, when everything flows through one person, the entire project timeline is at the mercy of their calendar—and mood.

Fix: Stop holding up progress. Empower your team to run with things. Or better yet, hand off the orchestration to someone who knows how to keep the trains running.

4. Slack Isn’t a Strategy

Just because you’re talking all day doesn’t mean anything’s actually being tracked. In fact, most teams under 50 people are so busy doing that they forget to zoom out and ask: “Is this working?”

By the time you realize a project is off track, it’s already three weeks behind and everyone’s burned out.

Fix: You need visibility. Not micromanagement, just clarity. Use a project tool. Track priorities. Know who’s doing what, and when.

5. You're Hustling Harder Instead of Smarter

At some point, your business will outgrow brute force. You can’t just “work harder” to get through broken systems and overloaded teams. That’s when burnout hits. That’s when clients feel it. That’s when your good people start quietly browsing job boards.

Fix: Structure isn’t the enemy. It’s your insurance policy.
And no: you don’t need a full-time project manager with a clipboard and a Gantt chart. You just need someone who knows how to bring order to your workflows.

Want to stop feeling like you’re duct-taping every project together?

That’s what I do. At Managed by Megan, I step in to organize the madness so you can go back to doing what you’re great at. (And sleep at night.)

Ready to make things easier? Schedule a quick intro call here.