Insights

Why your best people keep becoming your bottleneck (and so do you)

Every time you fix someone else’s work for them, you become their crutch.

Leo Judkins, Founder, The iGaming Leader  ·  September 2026

I’ve been the bottleneck in my own business. At one point I was doing twenty to thirty hours a week of work that should never have been mine to do, and the quality of everything dropped because of it. The fix wasn’t a productivity hack. It was hiring people and forcing myself to actually let go of the work, which turned out to be a lot harder than it sounds.

One of our members went through a sharper version of the same thing recently, after a piece of blunt feedback from his own boss left him genuinely rattled. The read on that feedback was simple: he wasn’t doing his job. Not in terms of effort, he’d put in more hours and more emotional energy into the business than almost anyone, but in terms of working hard on the wrong things.

The pattern underneath the pattern

When we dug into what had actually gone wrong, it wasn’t a strategy problem. It was that he’d been having the same conversation, with different people, over and over, about who actually owned what. A product manager assumed the development team owned the roadmap. The development team assumed the product manager owned it. Neither did, not really, because in practice he did, because he kept stepping in whenever something wasn’t moving fast enough or wasn’t good enough.

Here’s the part that matters: every time you fix someone else’s work for them because you’re frustrated or in a hurry, you become their crutch. And once you’re the crutch, they stop trying as hard, not because they’re lazy, but because they’ve learned, correctly, that it doesn’t actually matter what standard they deliver to. You’ll fix it anyway. So why make the extra effort?

It’s a completely natural response to pressure. When results are poor and everything already feels precarious, doing the thing you’re already good at, and doing more of it yourself, feels safer than delegating something you’re less confident about into someone else’s hands. But it’s exactly backwards. The busier and more under-pressure you are, the more this pattern costs you, because you end up more in the weeds, not less.

The real fix isn’t “delegate more”

Most advice on delegation stops at “give people more responsibility,” which is true but useless on its own. The actual mechanism is narrower and harder to practise: stop telling people what to do, and start asking them questions instead.

Concretely: when someone hands you work that isn’t good enough, the instinct is to fix it, or to tell them exactly what’s wrong and how to correct it. Both of those keep you in control and keep them dependent. The alternative is simpler and much more uncomfortable: “that’s not good enough, when can you have it done properly?” Not “I need it by Friday.” Ask them. Then, if the timeline they give you doesn’t hold up to scrutiny, ask again. “What’s more important than this in the next two days?” If the honest answer is nothing, then the timeline moves. You never told them what to do. You asked, and they decided.

There’s a second layer to this: delegate the why, the what and the when. Never the how. The moment you start dictating how a task should be done, you’ve taken it back, even if you’ve technically still handed it to someone else. The best people you manage should only need the why and the what from you. The more junior the person, or the higher the risk of the task, the more guidance they need, but even then the goal is to move them up that ladder, not park them on it permanently.

Catching yourself in the moment

The tell is a very specific kind of frustration: you asked for something, it came back not good enough or too slow, and your first instinct was to just do it yourself, quietly, without making a big thing of it. That instinct is the whole problem in miniature. It feels efficient in the moment and it is corrosive over months, because it teaches your best people that your standards, not theirs, are the ones that count, and that trying harder doesn’t change the outcome.

The practical version of catching yourself: before you fix anything, stop and ask a question instead of making a statement. If you can only say things, practise a rule for a while: you’re only allowed to ask.

Where this changes

Nobody inside your business is going to tell you that you’ve become the bottleneck. They’re the ones handing you the work. It takes people outside it, who have been the crutch themselves, to ask the question you’re not asking yourself.

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Questions this usually raises

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