Structure Problem or People Problem? How Nonprofit Leaders Can Navigate the Messy Middle

Every growing nonprofit hits a point where things that used to work stop working.

Programs expand. Funding grows. Expectations rise. But internally, the organization is still running the same way it did when the team was half the size. Decisions pile up. Roles blur. People are working harder than ever and somehow moving slower.

Dee Benno calls this the messy middle. As VP of People and Operations at the Air Conditioning Contractors of America, and as a consultant to nonprofits and associations, she has seen it many times. Her definition is simple: it’s the moment when the mission grows faster than the structure.

The most important thing she wants leaders to understand is that this friction isn’t a sign people have failed. It’s a sign the structure needs to evolve.

The Early Signs Your Nonprofit Has Outgrown Its Structure

The messy middle rarely shows up as one dramatic event. It builds slowly, and then it can feel like it all went wrong overnight.

According to Dee, the early signals are consistent:

Decision-making slows down, and bottlenecks form at the CEO or within one department.
People feel unclear about priorities, not because they’re disengaged, but because there’s no shared map.
Roles become fuzzy. Everyone does a little of everything, but no one fully owns anything.
Communication turns reactive, and “I thought you were doing that” becomes a regular phrase.

There’s also a quieter signal that leaders tend to miss: emotional fatigue. It isn’t burnout yet. People still believe in the mission, but the constant lack of clarity slowly drains their confidence.

Dee offers a test every nonprofit CEO should keep in mind: if your smartest people seem confused, you likely have a structure problem, not a people problem.

Why Culture Problems Are Usually Something Else

When things feel off, many nonprofit leaders reach for the culture explanation. Morale is low. People aren’t collaborating. Something about the team feels broken.

Dee sees it differently. Culture issues are almost always symptoms of an underlying structural issue. If people don’t know what matters most, who owns what, or how decisions get made, the culture will feel strained no matter how strong your values are.

This matters because the fix for a culture problem looks very different from the fix for a structure problem. A culture initiative won’t solve unclear decision rights. A team retreat won’t untangle overlapping job responsibilities.

Getting the diagnosis right is half the work.

The Hidden Cost of Adding More People

At The Charity CFO, we see this pattern constantly in nonprofit financial management. A team feels overwhelmed, and the conclusion is that there’s a capacity problem. The solution is to add another part-time role.

Sometimes that’s right. Often it isn’t.

One organization we started working with had one full-time employee and four part-time staff sharing fundraising, accounting, and financial management tasks. An accounting staff member was sending donor acknowledgment letters. The office manager was paying bills. None of it was strategic. Each role had been added to relieve a short-term pain point, and nobody ever went back to restructure it in a way that could scale.

The result wasn’t a lack of people. It was too many people with unclear roles, which made accountability nearly impossible.

Dee describes the same dynamic from the HR side. Mission-driven organizations move fast, and leaders rightly focus on serving their communities first. Behind the scenes, though, the organization starts relying on workarounds, and those workarounds eventually become the culture.

It works, until it doesn’t.

A Five-Part Approach to Moving From Chaos to Clarity

When leaders call Dee, they often can’t name the problem. They say things like “We’re working hard, but we’re not moving forward,” or “Everyone seems frustrated, but no one can say why.”

Her approach is built on one belief: most organizations aren’t stuck because people don’t care. They’re stuck because people aren’t sure. Reduce the uncertainty, and confidence and momentum follow.

She works through five steps.

See what others overlook. Look for patterns in turnover, places where decisions consistently stall, and leaders who are unintentionally working around each other. Often the real issue is the thing no one is naming.

Bring structure. Clarify who owns which decisions, define leadership roles and expectations, and create simple operating rhythms so teams aren’t constantly reacting. The goal isn’t bureaucracy. It’s giving people enough structure to stop guessing.

Support leaders through change. Good decisions fall apart without support during implementation. That can mean coaching leaders through tough conversations or deliberately slowing down to prevent disengagement.

Strengthen through consistency. This is where clarity turns into capability. Strength comes from repeatable habits that reinforce accountability, not from pushing harder.

Steward what works. Document it, build it into leadership practices, and make sure the organization doesn’t depend on one person to hold everything together.

The Mistakes That Make the Messy Middle Worse

One of the most useful reframes from the conversation is that the messy middle isn’t a crisis. It’s a predictable stage of growth. The key is to evolve your structure before the strain turns into burnout.

The most common mistake is treating a clarity problem like a motivation problem. When things feel stuck, leaders add meetings and urgency. That usually makes things worse, because now people are busy and confused.

Another mistake is the CEO becoming the hub for every decision. It feels responsible. In practice, it creates bottlenecks and keeps the rest of the leadership team from building capacity.

How to Communicate When You Can’t Talk to Everyone

For CEOs leading larger or distributed teams, the question becomes practical. How do you create certainty when you’re not in weekly one-on-ones with everyone?

Dee’s advice starts with restraint. Stop trying to fix everything at once. Instead of launching a big reorganization, ask where decisions are getting stuck, where accountability is unclear, and where leadership energy is being drained. Pick one of those areas and bring real clarity to it.

When people see clarity in one place, anxiety tends to drop everywhere else.

Below the CEO level, Dee recommends that people leaders hold weekly or biweekly one-on-ones with some structure to them. Those conversations should go beyond project status to cover wins, challenges, and bottlenecks. Some teams also use tools like CliftonStrengths or DISC to shape how they communicate and collaborate.

At The Charity CFO, we’ve grown from zero to 65 employees in ten years. For a stretch, we re-engineered the business every six months. One practice that held up through that growth is a quarterly in-person meeting where we share goals and make it clear who owns each objective. Collaboration matters, but ultimately one person owns each goal. Not every nonprofit needs that exact rhythm. Every nonprofit does need an intentional one.

Where to Start Next Week

If you’re in the messy middle right now, Dee’s advice is refreshingly doable. Block a couple of hours and answer three questions:

What are our top three priorities for the next 30 days?
Who owns the decisions in each of those areas?
What are we pausing, and how will we communicate that?

That last question is the one most leaders skip. Pausing isn’t failing. Sometimes stepping back to focus on a few concrete items is what creates the relief your team needs and the clarity you need to move forward.

The Structure Needs to Catch Up to the Mission

Many nonprofits are doing important work with a structure that was built for an earlier stage. That isn’t a failure of leadership or of the people doing the work. It’s a natural result of growth.

The organizations that come out stronger are the ones that stop asking “who’s the problem?” and start asking “what isn’t working anymore?”

Connect with Dee Benno on LinkedIn for insights on nonprofit leadership, organizational structure, and people strategy.

💼 LinkedIn: https://www.linkedin.com/in/dee-benno-esq/