INL Episode #390: Leadership, Capital, and the Long View with Elyse Cherry

There’s a pattern I see over and over again in nonprofits.

Smart people. Deeply committed. Working incredibly hard.
And still feeling like they’re one surprise away from everything breaking.

Not because they’re doing anything wrong.
But because the system they’re operating inside is unclear.

When systems are unclear, people compensate with effort. That works for a while. Then it doesn’t.

I’ve been thinking a lot about this lately. I recently had a conversation about exactly this with Elyse Cherry, a nonprofit leader who has spent decades building an institution designed to last.

That conversation didn’t just reinforce what I already see in my work—it sharpened it. It pushed me to think more deeply about what actually creates staying power in nonprofits over time.

What I want to explore here is what really makes nonprofits durable—not motivation, not hustle, not optimism—but structure, sequencing, and long-view leadership.

These are ideas shaped by years of coaching nonprofit leaders and by paying close attention to what works over decades, not just during growth spurts or crisis moments. When leaders can explain why something holds up over time—not just that it did—I listen.

Here’s what keeps rising to the surface.

Strong nonprofits don’t struggle because they lack passion.
They struggle because they confuse mission with method.

Mission should be stable. It’s the anchor.

Methods should evolve. They’re the tools.

When leaders lock those two things together, they create risk. They make it harder to adapt without feeling like they’re betraying their purpose.

This is predictable.

Community needs change. Funding environments change. Policy changes. Labor markets change. If the mission is clear, you can update how you pursue it without creating chaos.

If the mission is fuzzy, every change feels existential.

One of the biggest mistakes I see is organizations trying to “protect” mission by freezing methods in place. What that actually does is force staff to work around broken systems instead of fixing them.

Clarity beats control every time.

Culture is often treated like something soft. It’s not.

Culture is how decisions get made when there isn’t a policy.
It’s how risk shows up.

It’s how people decide what’s worth raising their hand about—and what’s not.

If leaders don’t actively shape culture, it doesn’t stay neutral. It drifts. And drift always has a cost.

Not because people are bad, but because the system is unclear.

When I see organizations with strong culture, it’s usually because leaders consistently reinforce a small set of decision filters:

• Is this aligned with mission?

• Is this fully built or partially built?

• Does this work financially over time?

• Who carries the risk if this fails?

Those questions don’t live in a strategic plan binder. They live in meetings. In hallway conversations. In what gets funded and what doesn’t.

More detail doesn’t equal more clarity.
... Better questions do.

Elyse said in our conversation “No Money, No Mission”. And I loved that she said it out loud!

Nonprofits are often uncomfortable naming this, but it’s true:

If the money doesn’t work, the mission won’t either.

That’s not cynical. It’s mechanical.

Programs don’t run on intention. They run on capacity: staff time, cash flow, systems, and margin for error.

When leaders avoid financial clarity, they don’t remove pressure—they push it downstream. Staff absorb it. Programs absorb it. Communities absorb it.

That framing adds risk.

I want nonprofits to stop treating sustainability like a philosophical debate and start treating it like an engineering problem.

Put dollars in. Get dollars out.
Understand return per dollar invested.
Know which machines compound over time and which ones drain capacity.

You don’t need to convince anyone.
Let the results do the talking.

One thing I wish more nonprofit leaders understood: dependence is a structural risk.

When too much of your organization rests on one funder, one revenue stream, or one relationship, you lose options. Decisions get quieter. Tradeoffs get harder to name.

This isn’t about being anti-funder or anti-partner. It’s about designing for flexibility.

Independence gives you room to say:

“That doesn’t fit.”

“That’s not wrong, it’s just too early.”

“That works for you, but not for us.”

That’s how nonprofits avoid becoming reactive.

Results beat convincing.

If the system works, you don’t have to defend it constantly.

A lot of nonprofits are overextended not because they lack opportunity, but because they lack sequencing.

Everything sounds important. Everything sounds urgent.

So leaders say yes—and then try to make it work with the same staff, the same systems, and the same money. That’s how broken machines get normalized.

Saying no isn’t about scarcity.

It’s about protecting the conditions that make yes possible later.

If you only take one thing away from this:

Every yes commits future capacity.

If the system can’t support that commitment, the cost shows up somewhere else.

This is predictable.

Annual planning doesn’t create clarity.

Daily decision-making does.

The nonprofits that operate most effectively aren’t constantly rewriting plans—they’re consistently asking the same questions at the right moments.

What’s the real problem here?

What does done look like?

Is this fully built or partially built?

Who owns the outcome?

Leaders who don’t protect thinking time lose the ability to see patterns. They stay busy, but they stop being directional.

That’s not a personal failure.

That’s a design flaw.

One of the most important roles of a nonprofit CEO is seeing what’s coming before it becomes urgent.

That doesn’t mean predicting the future. It means noticing signals early and reducing risk over time.

If leaders wait until something is unavoidable, they pay for it in disruption instead of design.

Operating at capacity is not a badge of honor.
... It’s a warning sign!

As organizations grow, leadership often gets quieter.

Fewer people can hear uncertainty without mistaking it for weakness. Fewer spaces allow for real testing of ideas.

That’s why peer relationships matter—not as networking, but as thinking partners.

You don’t need a big group.
You need a few trusted mirrors.

When nonprofits take the long view, a few things start to change:

• Decisions get cleaner

• Teams stop compensating for broken systems

• Money conversations get more grounded

• Leaders regain thinking space

• Burnout decreases—not through self-care, but through clarity

This isn’t about doing less work.
It’s about doing work that compounds.

Nonprofits can have enough money.
They can pay people well.
They can operate without constant urgency.

Not by pushing harder—but by building systems that work.