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How to Develop Your Operations Manager
- Lindsay Sheldrake
- 5 days ago
- 8 min read
Welcome to Diary of a Leader: Real Stories, Leadership Lessons, and Personal Growth
Most founders know exactly who they want to grow.
They already have someone. The question of how to develop your operations manager is not a search for a new person. It is a search for what to do with the right one.
That person usually has a title. Operations Manager. Studio Manager. Director of Operations. General Manager. The title varies. What does not vary is the role they are already playing: the one holding how things get done while the founder holds where things are going.
The trust is real. The gap is real too.
And waiting for it to close on its own is the most common mistake founders make.
Welcome back to Diary of a Leader, where we explore what is actually happening beneath leadership, growth, and the structures that support both.
What Operations Manager Development Actually Means
Developing your operations manager means investing in their capacity to lead the operational structure of the business, not just manage within it.
A gap in operations manager development occurs when a founder delegates responsibility without transferring the context, authority, and structured learning the role requires at its current level. The operator is trusted with the work but not equipped for the scope.
This distinction matters because most founders confuse stretch assignments with development. Stretch builds experience. It does not always build the thinking.
You Might Be Here If
You might be here if:
You have someone who handles a significant amount of the business and you genuinely trust them, but decisions still travel to you more than they should
You have said some version of "I just need them to take more off my plate" more than once in the last six months
Your operations manager is doing the work but you are not sure they see the whole picture
You have pulled them into bigger conversations and then noticed they are not quite operating at that altitude yet
You have added more responsibility over time without a clear conversation about what the role actually requires now
They fill gaps constantly and quietly but the business still depends on you to hold the direction
You have thought, at least once, that if they could step up you could finally step back
You are not sure what their development even looks like because no one ever gave you a model for it
They care deeply about the business, more than the job, and you want to reward that with something real
These are structural signals. They are not a reflection of your operator's capability or your effectiveness as a leader. They are a sign that the development infrastructure has not caught up with the trust that already exists.
Why Founders Wait (and Why Waiting Makes It Worse)
The informal approach to developing an operations manager goes like this.
Give them more responsibility. Include them in bigger decisions. Let them run with things. See what happens.
This works at first. Until the complexity of what is being asked exceeds what experience alone can carry.
At some stage, the operator is sitting in rooms where the conversation is about organizational structure, financial sustainability, leadership change, and strategic direction. They are being asked to lead at an altitude that requires specific skills they have never been formally taught.
Not because they are not ready.
Because the business never stopped long enough to build the foundation underneath them.
The founder is waiting for the operator to grow into the role.
The operator is trying to lead a role they were never fully handed.
Both of them are absorbing the gap. And the business is paying for it in ways that are hard to see but easy to feel: slow decisions, fragmented execution, a founder who cannot leave for a week without their phone lighting up.
What Capable Operations Managers Are Usually Missing
TWhen founders ask how to develop their operations manager, they tend to look for tools. Better processes. Clearer handoffs. Access to more information.
Those things help.
But the operators who make the real leap into trusted operational leadership share something more foundational. They understand the system, not just their piece of it.
They understand how work moves through the business. How decisions should travel and where they stall. How information gets lost between teams. How capacity actually gets consumed. How the founder's attention has been doing the work that structure should be doing instead.
They have also developed the judgment to lead the founder relationship with the same intentionality they bring to the team. That is often the missing piece.
Most operational development programs treat operations managers as functional managers who need better processes. The operators inside founder-led businesses need something different. They need to understand the specific dynamics of a founder-led business and how to lead within them.
If you are thinking about what a structured program for this looks like, the Trusted Operator Academy is built specifically for operators in founder-led businesses. It runs as an 18-week cohort and covers governance, financial fluency, change leadership, and the founder-operator relationship in depth.
How to Develop Your Operations Manager: What Actually Moves the Needle
There is no shortcut. But there are approaches that accelerate development faster than waiting.
Give them the real context, not just the task.
Most operators receive responsibility without the full picture. They know what they are managing. They often do not know why the structure is the way it is, where the business is trying to go, or what the founder actually needs from the role at this stage. That context changes how they lead. Without it, they optimize for today's problem instead of the business's next stage.
Name the expectation explicitly.
Founders often carry an unstated hope: that their operator will grow into something closer to a true operational partner. Someone who sits at the altitude the business now requires. Someone who makes the founder feel less alone at the top.
Most operators do not know that is what is being asked.
When the expectation becomes explicit, development has something real to aim at.
Invest in structured development, not just stretch.
Stretch assignments build experience. They do not build the thinking that experienced leadership requires.
What operators at this level need is a structured way to develop the skills that founder-led businesses specifically require: governance and decision rights, financial fluency, change leadership, cross-functional influence, and how to hold the founder relationship in a way that serves both people and the business.
That kind of development does not happen through osmosis.
If you want to understand what the operational structure underneath your business looks like right now, the Operational Assessment is usually the right place to start. It surfaces where your operator is absorbing friction they should not have to carry and what structure would hold instead.
Create a real feedback loop.
Development requires signal. Your operator needs to know what is landing and what is not. Not through performance reviews. Through regular, honest conversations about how they are leading and what the role now requires.
Most founders avoid this because it feels uncomfortable. It is less uncomfortable than watching a capable person plateau and not understanding why.
What Happens When the Investment Is Made
Founders who invest in structured development for their operations manager describe a shift that is hard to put into words but impossible to miss.
The operator starts making decisions that used to travel upward.
Work moves without the founder having to push it.
The founder starts to feel, for the first time, like they are not completely alone at the top.
This is not a management outcome. It is a structural one.
The operator did not suddenly become more talented. The business gave them what the role always required. The development infrastructure caught up with the trust that was already there.
That is when things change.
What if My Operations Manager Is Not Ready for That Level of Development?
Worth asking honestly.
Sometimes the gap is not a development gap. Sometimes the fit has changed as the business has grown, and development cannot close a fit gap.
The signal is usually this: you have given them context, named the expectation, and created opportunity. And the ceiling has not moved.
That is a different conversation. And it is a real one.
But in most cases, the founders I work with have not yet given their operator what development actually requires. The question of readiness is almost always premature.
Start with the investment. Then assess from there.
The Question Worth Asking
Most founders ask:
Why isn't my operations manager stepping up the way I need them to?
The better question is:
Have I given them what stepping up actually requires? Not just the trust. The structure, the context, and the investment.
Those are two different problems with two different answers.
Reflection Questions
When did you last sit down with your operations manager and describe exactly what you hope they grow into?
What decisions are still traveling to you that should be living with them? What would need to be true for that to change?
If you named the full scope of what you need from this role, would they recognize it as what they signed up for?
What would it mean for the business if they left tomorrow? What would the business lose that no org chart would capture?
Wrapping Up: The Gap Is Not Talent
The operations managers I see struggling inside founder-led businesses are almost never struggling because they are not good enough.
They are struggling because the development the role requires was never structured.
The founder trusted them with the work.
What they needed was to be trusted with the investment.
When that happens, things shift. Not all at once. But in a direction that becomes unmistakable.
The founder starts to exhale. The operator starts to lead. And the business starts to carry its own weight in a way it never quite could before.
You Don't Need to Solve This All at Once
If this resonated, that is enough for now.
Awareness comes first.
Clarity follows.
Investment comes next.
When you are ready to have a real conversation about what your operator needs and what development could look like, reach out here.
Frequently Asked Questions
What does it mean to develop your operations manager?
Developing your operations manager means building their capacity to lead the operational structure of the business, not just manage tasks within it. It includes giving them the context they need, naming the expectation clearly, and providing structured development in governance, decision-making, financial fluency, and leading the founder relationship with intention.
How long does it take to develop an operations manager into a COO-level leader?
There is no fixed timeline, but founders who invest in structured development alongside real responsibility typically see a meaningful shift within six to twelve months. The pace depends on how clearly the expectation is named, how much relevant context the operator is given, and whether development is structured or left to experience alone.
What is the difference between an operations manager and a COO in a founder-led business?
An operations manager manages workflow and day-to-day execution. A COO-level operator holds the organizational structure, leads at a strategic altitude alongside the founder, and makes it safe for the founder to step back. The gap between the two is not talent. It is scope, context, and the specific development that founder-led businesses require.
Continue Reading
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Stay tuned for more real-world reflections on leadership, operational clarity, and purposeful growth in the next installment of Diary of a Leader.
