Operator to leader is the shift that unlocks scale.

Twenty years ago, I was the executive director of a nonprofit that provided consulting and coaching to other nonprofit and government leaders. We became very busy. I was maxed out. So, I did what leaders are told to do—I wrote the grants, got the funding, and built out my team.

I quickly realized I had created more work for myself than I’d offloaded.

Or at least it felt that way. In fact, they were all hard workers and committed. But every day people would come to me with, “What do I do now?” or “I’m not sure what to do here” type questions. It was my first real operator to leader wake-up call.

I began to resent what felt like constant interruptions. Then I began to resent them. This was unfair.

A few months in, it finally dawned on me: I was the problem. Not them.

I had hired them to help, but hadn’t built a system that empowered them to be successful. I hadn’t clarified expectations, decision-making parameters, or how to recognize a successful decision—without me being there. I was also a perfectionist—afraid of failure or how I’d be seen. (It took me many more years to realize most people aren’t paying my work enough attention to notice the “errors” I was stressed about.)

Once I fixed that, I was able to shift from operator to leader. And everything changed.

• My stress dropped
• (More importantly) Theirs did too.
• The team carried much more weight, solved problems, and grew—because they had what they needed from me: Leadership.

Operator to leader: a practical checkpoint

The Trap

Most entrepreneurs stay in operator mode too long. They hit invisible ceilings—but can’t see that they’re the ones creating them. The operator to leader shift is often the one thing holding them back.

Maybe you take pride in doing it all. Maybe, like me, you’re a perfectionist. Or maybe having more people just feels like more problems. Maybe you feel intimidated about the switch from operating to leading.

There is no path to sustained growth (or maximizing your exit) without figuring this out. So, if you don’t want to—that’s fine. Just accept what it means.

The Shift

Upgrade Your Identity

You’re not the doer anymore. You’re the builder of the people who do—and the one who defines where they’re going. Making that identity change is the essence of moving from operator to leader.

The Solutions

Solution 1: Use Vision & Values as Tools

Most companies treat values and vision as branding—not as tools. Or worse, they farm them out to a marketing team and forget them entirely.

But real values are decision filters. And vision defines direction.

Together, they should shape who you hire, how you onboard, how you set goals, evaluate performance, and define success.

Values and vision aren’t deliverables. They aren’t intended to be on t-shirts or walls. They’re tools—like a tape measure and square in a builder’s hands. They are also the tools that allow an operator to leader transition to take root.

Solution 2: Build Structures That Make Trust Easy

Trust comes when your people know what to do and can self-manage. It also makes mentoring, correcting, and scaling dramatically easier. To do this:

• Use your values and vision: How your values are expressed in ops may be slightly different (but aligned) with how your sales team uses them or your controller. Define this for or with them. Vision is the same for everyone—but everyone’s contribution to the vision is unique. Define that.
• Clarify expectations: Who does what, by when, and how will success be measured? Create a cadence of accountability for progress – weekly or monthly meetings where progress is checked.
• Document “how”: Playbooks, policies, procedures, checklists. These are what transform day-to-day management into an operator to leader system.

Solution 3: Delegate Operator Functions

Most owners start by offloading finance and admin. I recommend outsourcing as much of this as possible up to $10–20M. Once you hit those revenue ranges, it can begin to make more sense to bring in a controller. At higher revenue ranges, often between $50–$100M, an in-house CFO will be helpful.

Don’t cheap out on getting clean, accurate and timely financial records or finding someone to build a simple but strong financial management system. Unless this is your area of expertise, this should be the first thing you give to a pro.

Then, depending on your strengths, hand off either sales or ops. If you’re a rainmaker, hold onto that—hand off ops. If you’re the engine of delivery for products or services, give someone else the sales pipeline.

But whichever one you keep—your new job is to decode your secret sauce and train others to outperform you. This is the kind of shift that cements your operator to leader growth.

You might stay in that role up until around the $20M mark. Usually somewhere around there, things get complicated enough that the team needs you to only:

• Oversee alignment
• Architect, promote, and protect culture
• Mentor skills and build leadership
• Prepare for strategic jumps
• Make big deals
• Navigate key challenges

The Payoff

Once you reach that point, you’re truly leading. This will likely free your company up to leap forward. The next step is building an executive team who also lead instead of operate.

Follow the same principles from above.

Once accomplished, you will have true freedom, you’ll have built enormous resilience into your company, and you’ve built a company that can scale—or one someone else actually wants to buy.

Take good care,

Christian