Why Most Founders Are Terrible at Delegating (and How I Got Better)
Founders are usually terrible at delegating.
I know—because I was too.
When you’ve dragged a business off the ground with your own two hands, you get emotionally tied to every detail. It’s your idea, your ambition, your future life wrapped up in this fragile vessel called a startup.
So when you hand even a small part of it over to someone else? It feels uncomfortable. Risky. Sometimes impossible.
I know—because I was too.
When you’ve dragged a business off the ground with your own two hands, you get emotionally tied to every detail. It’s your idea, your ambition, your future life wrapped up in this fragile vessel called a startup.
So when you hand even a small part of it over to someone else? It feels uncomfortable. Risky. Sometimes impossible.
Why it’s so hard to let go
Part of it is control. You’ve got a clear vision in your head, and no amount of communication ever seems enough to make someone else see it exactly the way you do.
Part of it is money. In a startup, it’s not some giant corporate paying salaries—it’s you. Your hard-earned cash. And I’ve seen founders slip into micromanagement because of it: “I’m paying you, so I need to squeeze every pound out of you.” That mindset can get toxic fast.
And part of it is ego. Some founders see delegating as a weakness. If I can’t do everything myself, am I failing?
Part of it is money. In a startup, it’s not some giant corporate paying salaries—it’s you. Your hard-earned cash. And I’ve seen founders slip into micromanagement because of it: “I’m paying you, so I need to squeeze every pound out of you.” That mindset can get toxic fast.
And part of it is ego. Some founders see delegating as a weakness. If I can’t do everything myself, am I failing?
What I’ve learned
I’ve seen brilliant companies succeed because the founder had the humility to step aside—to hire better people, even to bring in a CEO when it made sense. Removing ego from the equation is what makes delegation powerful.
I also had to learn that delegation takes time. It’s not just handing something over—it’s explaining the objectives, checking progress, and being patient when the first attempt isn’t perfect. I fell into the trap of saying, “It’s quicker if I just do it myself.”
But here’s the truth: if you never take the time to train and trust people, you’ll always be the bottleneck.
And sometimes? The work comes back different—not worse, just different. Often better. Accepting that “different” isn’t “wrong” was a big shift for me.
I also had to learn that delegation takes time. It’s not just handing something over—it’s explaining the objectives, checking progress, and being patient when the first attempt isn’t perfect. I fell into the trap of saying, “It’s quicker if I just do it myself.”
But here’s the truth: if you never take the time to train and trust people, you’ll always be the bottleneck.
And sometimes? The work comes back different—not worse, just different. Often better. Accepting that “different” isn’t “wrong” was a big shift for me.
How I got better
- I stopped seeing delegation as a cost, and started seeing it as an investment.
- I learned to explain the why, not just the what.
- I gave people space to solve problems their way, even if it wasn’t how I’d have done it.
- And I reminded myself: the goal isn’t to do everything. It’s to build something that lasts.
If you’re struggling to let go, you’re not alone. Most founders do. But the moment you stop trying to be everywhere at once, your business finally has room to grow.
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