420: Design Thinking Without The Jargon with Ashley Jablow

Most nonprofit leaders I talk to are not actually afraid of change. They are stuck between two sizes of it.

On one side, a monster decision. Restructure the program. Leave the role. Overhaul the funding model. A move so big it feels reckless to say out loud.

On the other side, no change at all. Keep going. Ride it out another quarter. Wait for more information. Wait for the board. Wait for a better moment.

What nobody offers is the middle option. The small, cheap, fast, reversible move whose only job is to teach you something. That option is almost always the right one, and it is almost always missing from the conversation.

I've been turning this over for a while. I recently had a conversation about exactly this with Ashley Jablow, who works with leaders and teams in transition and has deep training in design thinking. It sharpened how I think about why change gets stuck inside nonprofits and what actually unsticks it.

The short version: the problem isn't that leaders lack courage. The problem is that the only option on the table is too expensive to say yes to.

Change is constantly happening. Seasons turn. Budgets shift. Staff come and go. A funder's priorities drift. A board member rolls off. None of that is catastrophic on its own. What makes change feel charged is the story we attach to it.

In the nonprofit sector, that story is usually some version of: change is dangerous, so we should avoid it.

That story hardens into a posture. The posture becomes the culture. The culture becomes the reason your organization cannot move.

In short:

• Change is constant and mostly neutral.

• What makes it feel dangerous is the interpretation the organization layers on top.

• Culture that treats change as risky will struggle to adapt even when adaptation is overdue.

If you want an organization that can respond to what the world is actually doing, you have to separate the event from the story.

Here is the belief I keep running into inside nonprofits: doing nothing is the safe option. Especially with money. Especially with programs that "have always worked." Especially when funders are watching.

The truth is, staying put is not neutral. It has a cost, and that cost is usually larger than the one people are trying to avoid.

If a program is slowly losing relevance and you do not adjust, the cost shows up later as a funding cliff. If a leader is quietly burning out and the system does not adapt, the cost shows up as a crisis hire. If a revenue model depends on one big grant and you do not diversify, the cost shows up when that grant does not renew.

In short:

• Inaction is not the absence of risk. It is a different kind of risk.

• The cost of standing still usually arrives later and bigger.

• Every "we'll deal with that next year" is a decision, not a non-decision.

When leaders only weigh the risk of moving, they miss half the math.

Two structural things push nonprofits toward inaction.

The first is the donor stewardship story. Somewhere along the way, "be a good steward of donor money" got translated into "never take risks with money." That is not what stewardship means. Stewardship means using resources wisely in service of the mission. Sometimes that means holding the line. Sometimes it means making a bet.

The second is harder to see, and it matters more. In most nonprofits, the people with the biggest formal role in risky decisions, the board, do not experience the consequences of those decisions. The staff does. The community does. The executive director does. The board votes and goes home.

So when a decision comes with risk, the board defaults to "let's not do that." To them, sitting still feels responsible. To the people running the organization every day, sitting still might be the thing burning the building down.

In short:

• Stewardship is not a synonym for risk avoidance.

• The people voting on risky decisions in nonprofits often do not bear the consequences.

• The people who bear the consequences are usually best positioned to lead the decision.

Decisions belong, as much as possible, with the people who will live inside their outcomes. That is not a revolutionary idea. It is just rarely the way nonprofit governance actually operates.

This is where the size of the decision matters.

When every change is framed as a cannon shot, people freeze. The stakes are too high, the ambiguity too wide, the board too uncomfortable. So nothing moves.

But there is another option. Jim Collins calls it firing bullets before cannons. Ashley Jablow frames it as a design thinking question. It is the same idea in different clothes.

Ask what is the smallest, fastest, cheapest thing I could do right now to learn the most?

That is a different size of decision. It does not require a board vote. It does not require a three year strategic plan. It does not require certainty. It only requires that you be willing to run a small experiment and read the results.

In short:

• The question to ask before any big change is: what's the smallest move I could make to learn the most?

• A bullet is cheap. A cannon is expensive. Fire bullets first.

• Experiments replace certainty with evidence.

One line from that conversation with Ashley has stayed with me:

"What is the smallest, fastest, cheapest thing that you could do or try right now in order to learn the most?"

What I appreciate about this framing is that it does not ask the leader to be brave. It asks them to be curious. It shrinks the change until it fits inside the capacity the organization actually has, and then it uses the result of that small move to decide the next one.

That is how sustainable change actually works. Not through heroic leaps. Through a chain of small moves that each teach you something.

There is a second thing small experiments do that nobody talks about, and it may be more important than the learning itself.

They build self-trust.

Every small move you make and see through teaches you that you are a person who follows through. Every small experiment that works teaches you that your instincts are worth listening to. Every small experiment that fails teaches you that failure is survivable and useful.

You cannot lead a big change if you do not trust yourself to make a small one. And most leaders who feel stuck are not missing strategy. They are missing the lived experience of their own follow-through.

In short:

• Small experiments are also self-trust training.

• Leaders who have never run a small move do not trust themselves with a big one.

• Evidence of your own follow-through is what makes confidence durable.

This is why the "do one small thing" advice is not soft advice. It is structural. It is how capacity gets built.

Another moment from the conversation sat with me here. Ashley named a question she said often hides under any change effort, whether leaders realize it or not: "Can I trust myself to actually accomplish this and follow through?"

Most leaders never say that question out loud. So the answer never gets built. Small experiments are how you build the answer.

When leaders stop sizing every change as either "do nothing" or "blow it up," the whole posture of the organization changes.

What shifts:

• Change stops being a crisis event and becomes a practice.

• Decisions get made closer to the people who live with the outcomes.

• Self-trust builds through reps, not through a pep talk.

• The organization starts learning instead of defending.

The work is not lighter. It is just better aimed.

This isn't about being braver.

It's about picking a smaller move.

Nonprofits can adapt without crisis. They can change without drama. They can build self-trust through evidence instead of hoping for it.

Not by betting the whole organization on one cannon shot, but by firing a lot of cheap, honest bullets and paying attention to where they land.

🎧 Listen to the full episode of Inspired Nonprofit Leadership to hear the conversation that informed this thinking.

📬 Subscribe to the Inspired Nonprofit Leadership Newsletter for weekly insights designed to help nonprofit leaders build clarity, capacity, and results, without burning themselves or their teams out.

Related reading: Reclaim Your Capacity, The Energy Factor, and A Lesson on Delegation.

Ashley Jablow (Jab-lo, pronouns: she/her) is the founder of Wayfinders Collective and creator of Life Design School, a creative studio for people in career and life transition.

A seasoned facilitator, speaker, coach, and design strategist, Ashley blends design thinking and innovation, emotional intelligence, and creative tools to spark clarity and action for teams and individuals navigating change. She's also the artist and author of 100 Days of Designing My Life, a guided journal series for reflection and reinvention. 

Connect with Ashley:
Websites: wayfinderscollective.com,
lifedesignschool.co,
@ashleyjablow

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