You Promoted Your Best Attorney. Now What?

There is a version of this story that plays out in a lot of mission-driven organizations.

Someone is doing really good work. They know their cases, they know the program, people trust them, and they care deeply about the clients and communities the organization serves. When a supervisor or manager position opens up, they are often the natural choice.

And honestly, they may be exactly the right person for the job.

The problem is that being a great attorney and being a great manager are not the same thing. We don't always acknowledge how significant that transition actually is.

One day, you are responsible for your own cases and your own work. The next, you are responsible for helping other people do their work well. You are suddenly having conversations about performance, figuring out what to delegate, trying to support someone who is struggling, making decisions that affect an entire team, and sometimes telling someone something they really do not want to hear.

Meanwhile, you are probably still carrying some of your own caseload.

We have both seen how easy it is for new managers to feel like they are supposed to already know how to do all of this.

They don't.

Most people don't.

The promotion is not the problem.

We are not suggesting that organizations should stop promoting strong practitioners into leadership. Some of the best leaders we know started exactly this way.

What matters is what happens after the promotion.

Too often, an organization recognizes that someone is ready for more responsibility and gives them a new title, a larger workload, and maybe a management training somewhere along the way. Then everyone gets back to work.

Except the new manager's work has fundamentally changed.

They may be trying to supervise people who used to be their peers. They may be figuring out how much autonomy to give someone and when to step in. They may know exactly how they would handle a problem themselves, but are now learning that their job is not necessarily to solve it for the person in front of them.

And sometimes the hardest part is realizing that the thing that made them such a successful attorney can actually get in the way.

If you are used to being the person who knows the answer, it can be incredibly difficult to sit with someone who is struggling and let them work through the problem. If you are used to being dependable by taking on whatever needs to get done, delegation can feel like letting people down. If you have built your reputation on getting things right, giving someone else room to make a mistake can be uncomfortable.

None of that means you are a bad manager.

It means you are learning how to lead.

Organizations have a role in that transition too.

We sometimes talk about leadership development as though it is something an individual employee needs to take responsibility for. But managers don't operate in a vacuum.

If roles are unclear, no amount of management training is going to completely fix the problem.

If every decision still has to go through the executive director, new managers cannot actually learn to lead.

If a supervisor is carrying a full caseload while managing a team, it may not be a personal time-management problem. The role itself may need to be redesigned.

And if an organization has never really defined what it expects from its managers, it is difficult to know whether someone is succeeding.

That is why we think leadership development and organizational design are so connected.

Sometimes the person needs new skills. Sometimes the organization needs better structures.

Usually, it is some combination of both.

Give people room to become leaders.

Good managers do not appear fully formed when they receive a new title.

They become better through experience, reflection, feedback, and having people they can turn to when something gets complicated.

That might mean giving a new supervisor a place to talk through a difficult personnel issue before it becomes a crisis. It might mean helping them think about what they should continue doing themselves and what they need to let go of. It might mean being explicit about what decisions belong to them, what needs to be shared, and what should be escalated.

It also means accepting that leadership will look different from person to person.

We do not need every manager to lead the same way. We do need them to understand what their role is, what their team needs from them, and how their leadership fits into the larger organization.

The goal is not to take a great attorney and turn them into a completely different person.

It is to help that person grow into a different kind of responsibility without losing the qualities that made them valuable in the first place.

Because sometimes the best person to lead the next chapter really is the person who has been doing the work all along.

They just need the support, structure, and space to learn how to lead it.

That is a transition worth investing in.

Your Organization has Outgrown it’s Org Chart.

There is a strange moment that can happen when an organization grows.

You look at the org chart and, technically, everything still makes sense. Everyone has a title. Everyone has a supervisor. The boxes connect in a way that looks perfectly reasonable.

And yet, somehow, the organization feels harder to run than it used to.

People are asking the same questions over and over. Decisions take longer. A few people seem to be involved in everything. Staff are not always sure who can make a decision, so they ask several people just to be safe. Leaders are spending more and more time solving problems that they thought they had already delegated.

Sometimes that is when someone suggests that the organization needs a new org chart.

Maybe it does.

But the chart is rarely the whole problem.

We have both been in organizations where the structure made sense when it was created. Then the organization grew. Programs changed. Teams got bigger. New funding brought new responsibilities. People took on leadership roles because the organization needed them to.

The structure did not necessarily change along with everything else.

One of the places this becomes especially visible is with people who become player-coaches.

A person who has been a great attorney becomes a supervisor, but continues carrying a caseload. A program leader takes on responsibility for a growing team but is still expected to do much of the direct work that made them successful in the first place.

At first, this can work beautifully.

They stay close to the work. They understand what their staff are experiencing because they are experiencing some of it themselves. They bring practical knowledge into leadership decisions. And in organizations where resources are limited, it can feel like the most responsible way to structure a role.

But there is a point when being a player-coach stops being a bridge into leadership and starts becoming a barrier to it.

The person is expected to lead, but there is no real space for them to learn how.

Their calendar fills with supervision meetings, staff questions, program responsibilities, and organizational meetings, but the caseload is still there. The work still needs to get done. And when something urgent happens, the easiest thing is often for the leader to jump back in and do what they already know how to do.

That is the work they are good at.

It is the work that got them promoted in the first place.

So they keep doing it.

Meanwhile, the organization is waiting for them to become the leader it needs.

That can be an unfair expectation.

Leadership takes time. It takes practice. It takes enough distance from the day-to-day work to notice patterns, think ahead, and pay attention to what the team needs rather than only what needs to get done today.

If someone is spending nearly all of their time being the practitioner they used to be, it is very difficult to ask them to simultaneously become the leader the organization now needs.

And this is where organizational structure matters.

A restructuring is not always about adding another layer of management or moving people into different departments. Sometimes it is about recognizing that a role has changed and allowing the role to actually change.

That can be uncomfortable.

There is often a very real need for the work that person has been doing. In legal services, particularly, there are more clients who need help than there are people available to provide it. Taking an experienced attorney out of a caseload can feel like losing capacity at exactly the moment the organization needs more of it.

But leadership is capacity too.

If that person is responsible for developing a team, improving a program, or helping an organization navigate its next stage of growth, then creating the space for them to do that is not taking them away from the mission.

It is part of the mission.

The same thing happens in other parts of an organization. A role gets created to solve one problem, then gradually accumulates three more responsibilities. A manager becomes the person everyone goes to because they have been around the longest. A program expands but remains tucked inside a structure that was designed when it was much smaller. People develop informal ways of getting things done because the formal structure no longer quite fits the work.

Eventually, the organization can start feeling inefficient or disconnected.

But often, the people are not the problem.

The structure is simply asking them to work in ways that no longer match the organization they have become.

That is why we think restructuring should begin with the work, not the boxes.

What has actually changed? What is the organization asking people to do now that it was not asking them to do two years ago? Where are leaders spending their time? Where does work get stuck? What decisions are unclear? What has become dependent on one person simply because nobody has had the time or space to build something different?

Those questions tell you much more than an org chart alone can.

Sometimes the answer will be a new structure. Sometimes it will be a different distribution of responsibilities. Sometimes it will mean creating more leadership capacity. And sometimes it will mean letting someone stop doing work they are very good at so they can become good at the work they have been asked to lead.

That last one can be the hardest.

Growing organizations have to be willing to let people grow with them.

The structure that helped you get here may not be the structure that will help you get where you are going. That does not mean it was wrong.

It means the organization has changed.

And sometimes the first sign that your organization has outgrown its org chart is not that the boxes look wrong.

It is that the people inside them no longer have enough room to do the work those boxes are supposed to represent.

You Don’t Have a Staffing Problem. You have a Design Problem.

Sometimes an organization reaches a point where everyone is overwhelmed and the answer seems obvious - You need more people.

The demand has grown. The team is stretched. Everyone is working hard and there is still more work waiting. So you write a job description, find the funding, hire someone, and hope that the pressure eases.

Sometimes it does.

But sometimes, six months later, the new person is just as busy as everyone else.

We have seen this happen enough to know that hiring is not always the first question to ask.

Sometimes the problem is not that there are too few people. It is that the work has never been designed for the organization you have become.

That can be hard to see when everyone is already working at capacity. When people are exhausted, it feels almost absurd to suggest that the answer might be to stop and look at how the work is organized.

But that pause can matter.

Think about what happens in a growing organization. A program starts small, and the people closest to it figure things out as they go. Someone takes on an extra responsibility because they are capable of it. Another person becomes the one who knows how a particular process works. A supervisor keeps doing some of their old work because there is still so much of it to do.

None of those decisions are necessarily bad decisions.

In fact, they are often exactly what allows an organization to keep moving.

The problem comes later, when those temporary solutions quietly become the way the organization works.

A person is still doing something because they have always done it. A process exists because that is how it has always been done. A manager is spending hours on work that could probably be handled somewhere else, but no one has had the time to stop and figure out how.

Eventually, the organization starts hiring around those problems.

That is when more people may not actually create more capacity.

They may just create more people trying to navigate the same system.

This is particularly easy to miss in mission-driven organizations because the people doing the work are usually very good at compensating for what the organization lacks. They stay late. They pick things up. They remember what everyone else forgot. They figure out a workaround when the process breaks down.

The organization keeps functioning.

But it is functioning because good people are working incredibly hard to make it function.

That is not the same thing as having a sustainable system.

And there is a real tension here. We work in fields where the need is enormous and the resources are limited. There are people waiting for services right now. There are grants with deadlines attached to them. There are opportunities that could make a meaningful difference in the community.

It can feel irresponsible to slow down and redesign anything when there is so much work to do.

But sometimes slowing down is what allows you to do more of the right work later.

Before adding another person, it can be worth looking at what is actually happening to the people you already have. Where is their time going? What work has accumulated over the years? What requires their particular expertise and what does not? Where are they waiting on someone else? Where are they solving the same problem in slightly different ways?

You may still decide to hire.

In fact, you may discover that you need to hire more than you originally thought. But you will have a much better idea of what those people are there to do and how their work fits into everything else.

Sometimes the answer is a new position. Sometimes it is a different position. Sometimes it is changing a process that has become unnecessarily complicated. Sometimes it is taking work away from a leader so they can actually lead. Sometimes it is finally admitting that a program has become something different from what it was when it started.

And sometimes it means deciding that there is work the organization simply cannot keep doing.

That last one can be the hardest conversation of all.

But capacity is not just about how much work an organization can take on. It is also about whether the organization can do that work well without asking its people to continually stretch beyond what is reasonable.

The organizations we admire most are not the ones where everyone is somehow able to do more.

They are the ones that have gotten better at deciding how the work should be done in the first place.

That is what good design can do.

It gives good people a better chance of doing good work without having to spend all of their energy compensating for the way the organization is built.

Collaboration Sounds Great. So Why is Everyone Frustrated?

Most people like the idea of collaboration.

It is hard to argue with the idea that organizations doing similar or complementary work should find ways to work together. There are needs that are simply too large for one organization to address alone, and there are times when sharing knowledge, resources, relationships, or infrastructure can make everyone better at what they do.

But anyone who has actually been part of a collaboration knows that the idea is usually much easier than the reality.

At first, everyone is excited.

There is a shared problem. There are good people around the table. Everyone can see the possibility.

Then the meetings start.

Someone has a different idea about how the work should happen. Another organization does not have the same resources. One partner has more staff and another has deeper relationships in the community. Someone is moving quickly while someone else needs more time.

Suddenly, something that was supposed to make the work easier is taking a surprising amount of work just to keep going.

That does not necessarily mean the collaboration is failing.

It may mean the collaboration has reached the point where good intentions are no longer enough.

We have both been part of collaborative work where the hardest part was not agreeing that the problem mattered. It was figuring out what it actually meant to work together.

Organizations have their own histories. They have their own cultures and ways of making decisions. They have different levels of funding and different amounts of staff capacity. Even when they serve the same communities, they may experience the work very differently.

Those differences do not disappear because everyone has agreed to collaborate.

They become part of the collaboration.

That is where things can get uncomfortable.

What feels like a reasonable expectation to one organization may be a significant burden to another. A decision that seems simple to one partner may require a conversation with a board, a funder, or an entire team at another. One organization may have the capacity to take on something immediately while another simply does not.

If those differences are not talked about, they do not go away.

They usually show up later as frustration.

We have learned that one of the most useful questions in collaborative work is also one of the simplest:

Why are we doing this together?

Not because collaboration is good.

Not because funders like partnerships.

Not because everyone involved is doing important work.

What becomes possible because these organizations are working together that would be difficult or impossible for them to do separately?

Sometimes the answer is compelling. A group of organizations can reach more people, bring different expertise together, or build something that none of them could reasonably create alone.

When that happens, the extra work of collaboration can be worth it.

But sometimes the answer is less clear.

Sometimes organizations are meeting because they have always met. They are sharing information, but not really sharing work. They have created a new layer of coordination without changing what is possible for the people they serve.

That is when collaboration starts to feel like another obligation.

The answer is not always to walk away.

Sometimes the collaboration needs a clearer purpose. Sometimes the organizations need to be more honest about what each can realistically contribute. Sometimes the structure needs to change. And sometimes the people around the table need permission to say that something is not working.

That last part matters more than it might seem.

A collaboration built on the idea that everyone has to agree all the time is probably not going to survive very much disagreement.

The strongest partnerships we have seen are not necessarily the ones where everyone thinks alike. They are the ones where people can disagree without losing sight of why they came together in the first place.

That takes trust.

It also takes structure.

You need enough clarity that people know what they are responsible for and enough flexibility to account for the fact that organizations are not interchangeable.

Good collaboration does not require everyone to work the same way.

It requires enough shared understanding that different organizations can work alongside one another without constantly fighting the structure itself.

That is harder than putting people around a table.

It is also where the real value of collaboration begins.

Because the goal was never to have more organizations working together.

The goal was to make something better possible because they did.