You promoted your strongest performer. Gave them a project. Stepped back to let them run. Three weeks later, it's a mess and you're back in the weeds fixing it.
The instinct is to question whether they were really that good. The reality is something simpler. You handed them tasks when you should have handed them an outcome.
Most founders confuse delegation with creating a better to-do list for someone else. Task delegation keeps you in the loop for every decision. Outcome delegation puts you on the hook for one conversation: what does success look like? After that, the how belongs to whoever owns the result.
Chaz Wolfe built multiple seven-figure businesses by refusing to manage tasks. One of them was a construction company in Kansas City, an industry he'd never worked in. He didn't learn to swing a hammer. He architected a machine. He identified what roles the business needed, hired people with the right profiles for those outcomes, and let them figure out execution. That's not delegation in the traditional sense. It's designing a business that works without you from day one.
The founders who struggle here often have their identity wrapped up in doing the work. Their credibility came from being the best at the thing. Stepping back feels like stepping down. But running a business isn't the same as doing the thing. Working in the business means heads-down, reactive, task-level execution. Working on the business means seeing which lever matters most, which bottleneck is forming next, and which hire changes the trajectory.
The practical move is simple. Write down everything you do for a week. Don't filter it. Then circle five to ten items that actually push the business forward. The rest becomes your delegation list. But delegation without support is just abdication with better marketing. Whoever takes ownership needs four things: the vision behind the work, a clear picture of what success looks like, the resources to get there, and a way to track progress against the goal.
Skip any of those, and you've set them up to fail. Then you'll tell yourself delegation doesn't work for you.
Watch the Full Episode on Delegation with expert Chaz Wolfe below:
Follow us to watch live on YouTube and LinkedIn or listen to episodes on Apple Podcasts and Spotify.