I give a talk at conferences called “12 Ways Founders Hold Their Business Back.”
The talk isn’t about strategy, market conditions, or competition. It’s about the specific ways founders quietly sabotage their own business. When you put a mirror in front of someone, they either lean in or look away.
Last time, a founder came up to me and said, “I hated every minute of that. Because you described exactly what I’m doing.”
Today, I want to unpack three of the twelve. These are the ones that consistently make founders uncomfortable. If one of them stings a little, pay attention. That’s usually where the leverage is.
THE BIG INSIGHT
The business you want to build is being blocked by the founder you currently are.
Way #1: You’re Keeping Underperformers Because “They Were Here From the Beginning”
This is the one that makes founders shift in their seats.
You have someone who was great in year one. The company grew. The role evolved. They didn’t.
But they were there when it was just you and a laptop, so you keep them. You call it loyalty. It’s usually guilt.
Here’s the part founders underestimate: Your top performers are watching. They see someone staying in a role because of history, not results. And they draw conclusions fast.
Don’t: Keep someone out of nostalgia or obligation. You’re not running a reunion tour. If the role has outgrown them, pretending otherwise hurts everyone.
Do: Ask one question: “Would I hire this person today for this role?” If the answer is no, the decision is already made. You’re just delaying it.
Way #2: You Promoted Your Best Individual Contributor Into Management
Your best salesperson. Your top engineer. Your highest-performing account manager.
They were crushing it. So you promoted them. Now they’re struggling. Their team is struggling. And you’re wondering what happened.
Being great at the work is not the same as being great at leading people who do the work. You didn’t promote a manager. You promoted potential and hoped it would sort itself out.
Don’t: Promote based on performance alone. You didn’t lose a great performer and gain a manager. You lost both.
Do: Start training before the promotion. Have them shadow one-on-ones. Let them run meetings with feedback. Teach them how to coach and hold standards. Management is a skill. Treat it like one.
Way #3: You Delegate the Task but Not the Outcome (or Authority)
This one is subtle, which is why it’s so common.
You tell someone, “You own this.”
Then you say, “Just run decisions by me first.”
That’s not delegation. That’s supervised execution. They don’t learn judgment. They learn how to guess what you want.
Don’t: Say “you own it” and approve every decision. If they need permission, they don’t own it.
Do: Delegate authority with boundaries. “You own this up to $10K. Above that, we talk. Otherwise, it’s yours.” Set outcomes. Let them choose the method. Different isn’t wrong.
QUESTIONS
Q: How do I fix this if I’ve already made these mistakes?
Name it. Own your part. Reset expectations. The best time to fix a problem is before it starts. The second best time is today! Rarely is it too late.
This week, pick one move:
Address the underperformer you’ve been avoiding.
Get real training for the manager you promoted too fast.
Give actual authority to someone you’ve only half-trusted.
The founder you need to become is on the other side of that decision.
Chad Todd
P.S. These were three of twelve. The other nine are just as uncomfortable. If you want the full talk for a conference or leadership team, you know where to find me.