The Shift to Managing Managers
From managing work to managing context
The Shift to Managing Managers
One of the most abrupt transitions in a leadership career is the moment you stop managing a team and start managing managers.
It rarely happens gradually. One day, you lead a small group and their output. The next, you oversee an organization whose work you can’t directly touch. You can study, prepare, and talk to experienced peers, but most learning comes the hard way.
What makes this transition particularly tricky is that the behaviors that got you here often stop working once you arrive.
When you manage a team, being close to the work is an asset. When you manage managers, that same instinct quietly becomes a liability.
The real tension: leverage versus comfort
People often frame this as a choice between autonomy and control. That’s partly true, but not the core issue.
The deeper tension is leverage versus comfort.
Staying close to execution feels safe. You know what’s happening. You can catch issues early. You feel accountable in a very tangible way. When something goes wrong, you can point to where you were involved and how you tried to prevent it.
The problem is that this sense of responsibility doesn’t scale.
As your organization grows, your job requires a different orientation. You need to look outward and sideways, not just downward. You need to understand the business direction, align with peers, and identify organizational risks before they become visible problems. None of that happens if your attention is consumed by team-level decisions.
Managing managers isn’t really about getting closer to the work. It’s about being clearer about what the work actually is.
How over-involvement erodes ownership
When leaders stay too focused on the layer below them, the effects show up quickly.
The managers reporting to you lose ownership because you’re implicitly taking it away from them. If you’re paying more attention to their teams than to them, they stop behaving like leaders and start behaving like intermediaries. They wait. They escalate. They defer.
At the same time, you become a decision-making bottleneck. The fastest way to ensure decisions align with your thinking is to require approval. That works in the short term, and it feels responsible. But it trains the organization to route everything through you.
Once that happens, your leverage disappears.
You’re always busy, but the organization actually slows down because decisions wait for you instead of being made by those with the information.
Worse, your own growth stalls. You can’t take on a broader scope because you’re too essential to the current one.
Why context matters more than answers
Early in my management career, I was rewarded for being deeply involved. I worked hard to be a good manager, to support my team, and to fix problems directly. That approach produced results.
When I began managing larger groups, I kept using that approach, expecting it to work.
It didn’t.
My intent didn’t change, but the effect did. All the context lived with me: the business constraints, political realities, and broader trade-offs. My managers lacked that context. I failed to transfer my understanding.
Decisions slowed down. Some were simply wrong. And the surprises I got were coming from the wrong direction. Instead of hearing early warnings from teams, I was learning from peers that work had been duplicated, priorities had shifted, or entire initiatives had moved without us.
Managers don’t usually need more direction. They need better framing.
When people understand what their work means in the larger system, they make better decisions on their own. They know who to talk to. They know what to ignore. They don’t need you as a relay for every conversation.
If your managers need you for every decision, you don’t actually have a management team. You’ve built a relay where everything passes through you.
There is one relay role that is appropriate: translating senior leadership’s context into something your organization can act on. Being the relay for your own teams, or peer organizations, is not.
The shift in where your attention belongs
There are two directions mid-organization leaders can focus.
Looking down is about coaching, quality, consistency, and execution. You’re responsible for results, but no longer do the work. Your job is to ensure that your managers are capable and focused on the right things.
Looking around is about strategy, alignment, organizational dynamics, and external signals. This is where managers of managers add unique value. And this scope only increases as you move up.
At some point, your role shifts from decision-maker to context-setter, standard-setter, and sense-maker.
Autonomy doesn’t grow because someone has “earned it.” It grows because shared understanding exists.
Delegating decisions instead of tasks
One of the most common mistakes leaders make at this level is delegating tasks rather than decisions.
Task delegation keeps control with you. Decision delegation transfers ownership.
If managers bring you work to approve, you haven’t delegated. You’ve added a step. Permission makes you a bottleneck; reasoning makes you a coach.
A simple change helps: ask “why did you choose this?” instead of “what do you want to do?”
That question is neutral, non-confrontational, and incredibly revealing. It tells you how someone thinks, what information they used, and what trade-offs they considered. If their reasoning is weak, that’s a coaching moment. If it’s strong, you learn something.
Warning signs you’re overmanaging
Overmanagement has predictable symptoms.
Managers escalate decisions that clearly belong to them. You’re deeply involved in hiring, performance management, or prioritization well beyond what your role should require. People ask, “What should I do?” instead of “Here’s my thought.”
Work slows when you’re unavailable. Vacations create anxiety. Your calendar fills with internal reviews and status meetings. Teams schedule their work around your presence. When everything flows through you, things might work, but they only work while you’re there.
Feeling indispensable is not a success metric. It’s a warning sign.
If the system only works while you’re holding it together, you’ve capped both your organization’s growth and your own.
Resetting decision boundaries
If you recognize these patterns, the first step is acknowledging them. To yourself first, then explicitly with your managers.
Staying too close to execution limits their growth. It also quietly limits yours.
One tool I’ve found useful is making decision boundaries explicit. With each manager, define:
Decisions they should make without telling you.
Decisions they should make and inform you about.
Decisions they should consult you on before acting.
Decisions you will make together.
The specifics will vary by person and role. The important part is that expectations are clear at the decision level, not just the role level.
Over time, decisions should move steadily toward greater autonomy. That movement marks growth, builds trust, and reduces dependency.
Expect friction during the transition.
Stepping back doesn’t immediately make things better. It usually makes them messier first.
Decisions will be uneven. Managers will test boundaries. Two people will make different calls in similar situations. That inconsistency is uncomfortable, but it’s part of the calibration process.
Use one-on-ones to learn how decisions were made, not approve them. Ask about data, risks, and expected outcomes.
Sometimes you’ll realize they missed something important. Other times, you’ll realize they saw things you didn’t. Both outcomes are valuable.
Replace control with calibration.
What you’re actually building
Managers operate under pressure from their teams while lacking full information about the organization. New managers optimize for approval when leaders are hands-on. Experienced managers read close oversight as a lack of trust.
When context isn’t shared, people invent explanations for what they are seeing in the organization. Alignment drifts. Culture debt accumulates.
Prevent this by making the invisible visible. Share what you hear, explain trade-offs, talk about constraints, and show how decisions connect.
If you do this well, work won’t pause when you step away. Decisions will improve because they’re made closer to the work with better context than you could ever have alone.
Scaling leadership means building teams that make informed, independent decisions and create lasting impact beyond your presence. Transitioning from managing work to managing context is essential for real organizational growth.
To hear an extended discussion of this topic, please listen to my most recent podcast episode: The Shift to Managing Managers.
Some helpful references and tools related to Managing Managers:
“Using Agile Techniques to Build a More Inclusive Team” - In this talk, I explain an exercise I use with the managers who report to me to help establish a mutually agreed-upon framework for who makes what decisions.
This article discusses the problems that arise when managers on your team make conflicting decisions.
“Turn the Ship Around!: A True Story of Building Leaders by Breaking the Rules” by L. David Marquet. A good book on moving from controlling to delegating in management: https://amzn.to/49XH2Ty
Delegation Poker from Jurgen Appelo. Similar to the tool I describe in my talk above, but with more options: https://medium.com/@jurgenappelo/unclear-team-responsibilities-use-delegation-levels-985537dbea38
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