Let your team work without you in the room
Derek had to get comfortable with a simple idea: clients were buying the company's process, expertise and results. They were not buying his presence in every meeting.
Read This Lesson →Leadership & Delegation
Derek Fredrickson on the trap of staying the operator in your own business, making time to think, and trusting your team to deliver without you in the room.
Key Lessons from This Episode
Derek Fredrickson built a company that helps founders step out of operations. Then he had to take his own advice. The hard part was letting his team do the work without him in the room.
Derek had to get comfortable with a simple idea: clients were buying the company's process, expertise and results. They were not buying his presence in every meeting.
Read This Lesson →I asked Derek about the guilt that comes with handing work to other people so you can think. If you're used to measuring a good day by how much you did, an open calendar can feel uncomfortable.
Read This Lesson →An operator can love the systems, follow-through and accountability that drain a founder. I had to learn that other people don't necessarily want my job. Some enjoy exactly the work I don't.
Read This Lesson →You have the CEO title. But look at your calendar. How much of it is actually CEO work?
That question kept coming up in my conversation with Derek Fredrickson, founder and CEO of The COO Solution. His company places fractional COOs with growing businesses. He knows operations. He spent years doing that work himself.
And even he got caught in the trap.
As his own company grew, Derek kept joining client meetings and strategy sessions. He had experienced people doing the work, some with backgrounds that were a better fit for those clients than his own. He still stayed involved.
Then he looked at his calendar with his COO. Client work kept filling the available space. Sales and team responsibilities still needed time. Something had to change.
Derek had to get comfortable with a simple idea: clients were buying the company's process, expertise and results. They were not buying his presence in every meeting.
That sounds obvious from the outside. It feels different when you've built the business, won the client and spent years being the person who knows how to solve the problem.
He realized that staying involved could prevent the COO assigned to a client from doing their best work. Leaving the room meant giving that person space to lead.
He was honest about still working on it. This wasn't a story about making one decision and never getting pulled back into operations. It was about noticing the pattern and continuing to change it.
There's a part of this I think a lot of us recognize. Being needed feels good. You save the day. You fix the proposal. Everybody knows you can handle it. But if the business needs that from you every week, what exactly are you building?
I asked Derek about the guilt that comes with handing work to other people so you can think. If you're used to measuring a good day by how much you did, an open calendar can feel uncomfortable.
His practical starting point is a founder dependency audit. Look at where the time actually goes and sort the commitments into necessary, nice to have or neither.
Don't just assume every meeting belongs there because it has always been there. Ask why you need to attend. Have you set clear expectations? Does the team have the authority to move forward? Are you still driving the agenda when somebody else could own it?
Derek described one client who began every Monday with a two-hour finance meeting. The owner disliked long meetings and spreadsheets, and that meeting drained his energy for the rest of the day.
Over a few weeks, they changed the timing and format. Eventually, it became a weekly 15-minute Loom video the owner could review and respond to. The numbers still mattered. The way they reviewed them changed.
That's a useful distinction. Getting your time back doesn't mean ignoring the business. It means finding a better way to stay informed and make the decisions that require you.
If your calendar doesn't show where your time goes, Derek suggests writing it down for three weeks. You need something real to work with before deciding what to change.
An operator can love the systems, follow-through and accountability that drain a founder. I had to learn that other people don't necessarily want my job. Some enjoy exactly the work I don't.
Derek's point is to use that difference. Freeing time gives the CEO room for the vision, relationships, culture and decisions that move the company forward. That time needs a purpose, too.
We also talked about AI. It's tempting to read about somebody replacing a team with agents and decide that's what your company needs. Derek starts with a different question: what problem are we trying to solve?
He uses AI to help pull business metrics together. But getting the numbers onto a dashboard and deciding what to do about them are different responsibilities. The information can improve the conversation. It doesn't remove the need to have it.
The same applies to delegation. Be clear about the outcome you need instead of just handing off a task you're tired of doing.
So here's a place to start this week. Pick one recurring commitment that depends on you. Ask why. Decide what needs to be true for somebody else to own it, and what you'll do with the time you get back.
Derek asks people what their version of Paris is, a reference to the life he has built there. It could be picking up the kids at 3:30 or having Friday free for golf. The point is to know what you want the business to make possible.
A bigger company that needs more of you every day may not be taking you there.
Meet the Guest
Derek Fredrickson is the founder and CEO of The COO Solution, which places fractional chief operating officers with growing businesses. After a corporate career on Wall Street and years working as an operator, Derek built a company of his own. He shares what it took to step out of client delivery, trust his team and make room for the work only he could do as CEO.
Meet the Host
Ben is the host of Untrapped Entrepreneur and founder of The Gents Place Franchise. His conversations explore how to build a business without losing sight of faith, family, values, and the people counting on you.