Don't try to replace yourself

Most business books and executive coaches say you should try to replace yourself. Build the team that can run without you, get yourself out of the work, and free up your time for strategy.

For most founders and operators running businesses under 50 million in revenue, this is REALLY bad advice.

The thing that made the business work is usually the thing you're trying to outsource. The specific instincts, the judgment, the operator-level understanding of how to actually move the number. That's your magic sauce. Replace yourself, and you risk losing it.

The two failure modes

When the founder or key leaders try to replace themselves, it shows up two ways.

First, abdication. The founder who's the best marketer in the company hires a junior to "own marketing" so they can focus on strategy. The CEO who's the best at closing deals builds out a sales team and stops talking to customers directly. In both cases, outcomes generally get worse, because the work that was being done by the best person in the building is now being done by someone who isn't.

Second, cloning. The thinking goes: I'm great at X, so I'll hire people I can teach to be great at X too, and then I can step back. The problem is the person you hire usually doesn't become as good as you. You've added management overhead, the work is worse than it was, and you still don't have anyone doing the things you're actually bad at.

Both mindsets lead to the same outcome. The magic sauce that made the business work is now being handled by someone less qualified, and the founder is busy managing instead of doing.

What this actually looks like

The example that stuck with me happened last year. The founder came to me with a request: solve this thing. It was a problem I'd worked on directly for years and could have solved fairly quickly.

Instead, I delegated. I told the VP of Marketing. The VP of Marketing told the Director of Paid Media. The Director of Paid Media told the junior. The junior reached out to the agency. The agency did the work. The answer came back up the chain, layer by layer.

When it landed back my desk, it was a reasonable answer… not the best answer or the answer I would have given, though. It was the answer you get when the work passes through four people who each know less than the one before them.

That's what replace-yourself looks like in practice. It feels like freeing yourself up for strategy. What's actually happening is you're handing off mission critical activities, and the output of the business gets a little worse with every layer.

What to do instead

The better play is to stay close to the work that only you can do at the level the business needs. Get clear on the two or three things you do better than anyone else in the building, and stay close to those. Then build a small team around you to bolster your weaknesses. Leave the strengths alone.

That's a different shape of organization than the one business books push. It looks like a flat structure with a few decision makers. Not the deep org chart with people whose primary job is managing other people who manage the work.

For most brands at this scale, that's the shape that wins. Magic sauce intact, work getting done at the level it needs, and no organizational bloat.