I just spent the better part of three days cleaning up the small systems that had quietly accumulated around my life: subscriptions I no longer needed, automated reminders I had stopped noticing, newsletters I once opened faithfully and now deleted without reading, apps that had been useful for a particular season but remained on my phone long after that season had ended. None of these things were foolish when I started them. That was what made the cleanup strangely difficult. Each one had once answered a real need. The reminder existed because I genuinely needed to remember something. The subscription solved a problem. The app saved time. The newsletter helped me think.

What had changed was not necessarily the quality of the thing itself. In many cases, it still worked exactly as promised. What had changed was my life around it. The problem had disappeared, or my work had changed, or I had found a better way to do the same thing. Sometimes nothing dramatic had happened at all. The thing had simply remained in place because removing it required a decision while keeping it required none.

That is how clutter grows. Not usually through foolishness, but through continuity.

Organizations accumulate in much the same way. A program begins because someone sees a need and cares enough to respond. A committee forms because an issue deserves sustained attention. A report is created because a board wants better visibility into the work. An annual event gathers momentum because people enjoy it and, for a time at least, it accomplishes something valuable. A partnership begins because two organizations discover that they can do something together that neither could do alone.

Then the years pass, as they have a habit of doing. The organization changes, the people it serves change, and sometimes the problem itself changes. Yet the structures created in response to an earlier moment have a remarkable ability to survive the moment that gave birth to them. The program still has a director, the committee still meets on the third Thursday, and someone still spends half a day assembling a report whose original audience may no longer remember why they asked for it.

None of this requires anyone to decide that these things remain important. That is precisely the problem. Beginning something requires intention. Continuing it usually does not. Once an activity has found its way into the budget and onto the calendar, inertia begins doing the work that conviction once did.

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Over the past year, I’ve had some version of the same conversation with a growing number of nonprofit leaders.

“We’re using AI.”

Usually that means a handful of people have begun finding their own ways to use it. Someone is drafting grant proposals with ChatGPT. The communications team is using Claude. A development person has figured out how to research prospects faster. Someone else has built a custom GPT that knows a surprising amount about one corner of the organization.

Sometimes there is an AI policy. Sometimes there is a committee. Sometimes nobody is quite sure what anyone else is doing.

For a while, this works.

People experiment. Some of the experiments are genuinely useful. Work that used to take several hours takes twenty minutes. A staff member who has always struggled with the blank page suddenly has a good starting point. Someone finds a way to pull useful information out of a spreadsheet nobody has looked at closely in years.

This is the fun part.

It is also the easy part.

The harder questions arrive later.

Imagine that someone on your development team builds a very good AI workflow for donor research. It starts as something she uses herself. Then another person asks to use it. Soon the whole team is relying on it before donor meetings.

At some point, it stops being her clever experiment and becomes part of the way the organization works.

That is when different questions begin to matter.

Where is it getting its information? Who makes sure that information is accurate? What donor information should it be allowed to see? Does anyone besides the person who built it understand how it works? If she leaves, does the organization still have it?

That line between experiment and operating practice is surprisingly difficult to see while you are crossing it.

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Most organizations still think of AI as a category of software. Another set of tools to buy, approve, secure and teach people to use.

But once AI starts becoming part of the actual work, it presses on things that have very little to do with software. It presses on decision making, authority, institutional knowledge, workflow, ownership and trust.

What began as a question about AI becomes a question about how the organization actually operates.

I suspect this is the AI problem many nonprofits are about to discover.

AI exposes how work really happens

Every organization has the system on paper and the system people actually use.

The employee handbook says one thing. The experienced program director knows how things really get done.

The CRM contains some of the donor history. Susan remembers the rest.

There is an official process for approving something, but everyone knows who actually needs to be called when the situation gets complicated.

Organizations have always worked this way. Humans are remarkably good at filling gaps. We remember the exceptions, learn the shortcuts and know who to ask.

AI has a harder time with that.

Which means that trying to use AI seriously has an interesting side effect: it exposes the gaps.

You discover that an important workflow has never been documented. You discover that the policy and the practice are not quite the same thing. You discover how much institutional memory resides in a handful of people. You discover that two departments have different definitions of the same thing.

In that sense, AI can act almost like contrast dye in an MRI. It moves through the organization and makes the hidden structure easier to see.

Sometimes what it reveals is impressive. Sometimes it reveals a mess. Usually it reveals both.

This is why I think the next stage of AI adoption will be more demanding than the first.

The first stage was mostly about individual productivity. Can this help me write, research, summarize or save a few hours?

The next stage is organizational.

Now the questions become: How should this work move? What should the machine know? Where does human judgment remain essential? Who owns the system? How does knowledge gained in one part of the organization become available to another? How do we know whether any of this is actually making the organization better?

Those are not primarily technology questions.

They are leadership questions.

And nonprofits may feel them particularly sharply because so many nonprofit organizations already run on a kind of institutional heroism. Thin staffs. Large missions. Complicated stakeholder relationships. People carrying far more knowledge and responsibility than their job descriptions suggest.

That can work for a surprisingly long time.

Until you try to teach a machine how the organization works.

Then you discover that nobody has ever quite said.

The question beneath the AI question

None of this makes me pessimistic about AI.

Quite the opposite. I think the possibilities are enormous.

But I am becoming less interested in the question, “What AI tools should our organization be using?”

That question will keep changing anyway.

The more important question seems to be:

How do we want knowledge, work, judgment and responsibility to move through this organization now that useful intelligence has become cheap and widely available?

That is a much bigger question.

It asks us to think about where decisions belong, what knowledge ought to be shared, what should remain private, where human judgment matters most, and which processes are worth preserving.

It also requires some humility.

We are still early. There will be bad experiments and expensive tools nobody uses. We will write policies for problems that never materialize and overlook problems we did not know to anticipate.

That is part of learning.

The mistake would be assuming that AI adoption is finished when everyone has an account and knows how to write a prompt.

That may turn out to be where the real work begins.

I’m spending more time with organizations working through this exact transition, and I’m curious where you’re seeing it.

If your organization, or one you know well, is at the point where AI experiments are beginning to collide with real operations, hit reply and tell me what’s happening.

I’d genuinely like to compare notes.

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Perhaps it’s all those years on a school calendar, followed by decades in nonprofit work where September meant the beginning of everything. Volunteers returned. Programs launched. Calendars filled. Summer’s permission to move a little more slowly disappeared, and suddenly everyone was asking what we were going to accomplish this year.

January has never felt quite as convincing.

So, in the spirit of an early New Year’s, perhaps it’s time to clean out the closet.

Most of us know what happens when we try this at home. You discover the shirt you haven’t worn since 2019, three nearly identical extension cords, and some mysterious object you are certain must be important because otherwise why would you have kept it for twelve years?

Then comes the dangerous sentence:

“We might need this someday.”

This is how closets fill.

It is also how organizations do.

Nonprofits are particularly bad at throwing things away.

We start programs. We create events. We form partnerships. We establish committees. We add positions. Most begin for perfectly good reasons. Someone saw a need, gathered people around it, found the money, and made something happen.

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Then time passes.

The need changes. The people change. The organization changes.

But the thing remains.

There is still a line for it in the budget. Someone is still responsible for it. It still appears on the website. Once a year the board still receives a report about it.

And because no one can quite remember deciding that it should continue, it continues.

This is one of the peculiar problems of mission-driven organizations. Starting something feels like leadership. Ending something feels like failure.

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Every tool teaches.

That may be the first thing we need to remember as artificial intelligence moves deeper into ordinary life and work. A tool is never only a tool. It does not simply do what we ask and leave us unchanged. It creates a response. It rewards certain habits. It makes some actions easier and others less likely. Over time, it begins to build a small world around its own use.

A hammer teaches the hand to look for nails. A calendar teaches time to appear as blocks. A dashboard teaches leaders to treat certain measurements as reality. A feed teaches attention to expect novelty. A search engine teaches inquiry to begin with a query we already know how to phrase.

AI teaches too.

It teaches us how to ask, how to wait, how to revise, how to decide, how to trust, and how to stop thinking. It can teach patience or impatience. It can widen attention or narrow it. It can help us move into reality with better preparation, or it can create a more comfortable representation of reality and invite us to live there instead.

That is why the conversation about AI cannot be reduced to whether it is useful.

It is useful. That is already settled.

People use AI because it helps. It helps with the blank page, the messy notes, the long thread, the difficult draft, the strategy question, the customer research, the spreadsheet, the first prototype, the awkward email, the old document nobody wants to reread. It reduces friction. It gathers context. It makes certain kinds of work lighter.

But the more useful a tool becomes, the more formative it becomes.

A useless tool does not shape much because nobody returns to it. A helpful tool becomes part of the rhythm of thought. We reach for it before we notice we are reaching. We begin to ask in the form it can answer. We begin to see in the categories it can organize. We begin to trust the kind of clarity it provides.

That is the deeper question. Not simply, “What can AI do for us?” but “What is AI doing to us while it helps?”

A tool creates a response. Repeated response becomes habit. Habit becomes environment. Environment becomes world.

This is where the danger begins.

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The Seasons of an Institution

There is a curious assumption that runs through much of our thinking about organizations.

We imagine that maturity looks like stability.

A healthy institution, we tell ourselves, should eventually find its stride. It should discover the right strategy, the right structure, the right leadership team, and then simply continue refining what already works.

The language we use reveals the assumption.

We speak of “best practices,” as though there were practices best for all times and all circumstances. We search for the ideal organizational chart, the optimal board composition, the perfect succession plan. If only we could discover the formula, we imagine, the institution could finally settle into a long season of predictable health.

Reality is rarely so accommodating.

Living things do not settle into permanence.

They move through seasons.

An oak tree is no less healthy in autumn than it was in spring. A vineyard is not failing because it looks different in February than it did in August. The work of the gardener changes because the life of the garden changes. To prune in June what should have been pruned in January is not merely inefficient. It is destructive.

We understand this instinctively when dealing with forests and farms.

We struggle to remember it when dealing with institutions.

Organizations age.

Not simply in years, but in character.

The questions that once consumed them quietly disappear, replaced by questions that could not even have existed in an earlier season.

• A young nonprofit worries whether anyone will support the mission.

• An established nonprofit worries whether the mission is still shaping the organization more than the organization is shaping the mission.

• A new business wonders whether anyone will buy the product.

• A mature business wonders whether yesterday’s product is blinding it to tomorrow’s opportunity.

• A church plant asks how to gather people.

• A century-old congregation asks how to remain faithful without becoming merely nostalgic.

These are not the same questions.

It would be strange to expect the same leadership instincts to answer all of them equally well.

And yet we often do exactly that.

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The Bury Garden

When I was in graduate school in Philadelphia, our family attended an old stone church tucked into one of the city’s older neighborhoods. Like many churches built before land became scarce, it sat in the middle of its own cemetery. Every Sunday we would pull into the parking lot, gather our three small children out of the car, and make the short walk to the sanctuary through what they affectionately called the “Bury Garden.”

Children have a way of stripping away the self-consciousness adults bring to places.

To them, the cemetery wasn’t eerie or solemn. It was simply part of going to church. They would stop to read names they couldn’t pronounce, trace weathered inscriptions with their fingers, and ask questions that adults rarely think to ask anymore.

“Who was Elizabeth?”

“Why did this man only live to be twenty-three?”

“Do you think these people knew each other?”

We never hurried them.

There was something fitting about entering worship by first passing through the company of those who had worshipped there before us.

Only years later did I realize that those walks had been quietly teaching me something about leadership.

Those stones marked people who had once occupied the very pews we now sat in. They had argued over budgets and building repairs. They had buried parents and baptized children. They had welcomed new pastors and mourned old ones. They had worried about the future of the church with the same urgency that every generation imagines is unique to itself.

Some of them had almost certainly believed that the future of the congregation depended on the decisions they were making.

Perhaps, for a time, it did.

And yet every Sunday their silent testimony remained the same.

The church was still here.

They were not.

That is not a depressing thought.

It is one of the most hopeful truths I know.

The measure of a healthy institution is not that it preserves its leaders. It is that it survives them.

That little church in Philadelphia had quietly outlived every anxiety buried beneath its lawn. Every crisis that once felt existential had eventually become a line carved into granite. Every indispensable leader had, in time, become a beloved memory. The life of the church continued not because those people had been unimportant, but because they had understood—whether consciously or not—that they were participating in something that neither began nor ended with them.

I have come to believe that this is one of the deepest differences between organizations that merely succeed and organizations that endure.

Successful organizations often revolve around remarkable people.

Enduring organizations eventually become remarkable because they are no longer required to.

That sentence may sound counterintuitive in an age obsessed with founders and visionary leadership. We are surrounded by stories that celebrate extraordinary individuals who bend reality through force of personality. The mythology of modern leadership is almost always autobiographical. We want to know who the founder was, what inspired them, how they overcame impossible odds, and what habits allowed them to succeed.

We are less interested in the quieter story that follows.

• Who taught the second generation?

• Who translated instinct into practice?

• Who built the habits that allowed ordinary people—not just extraordinary ones—to carry the work forward?

• Who made the institution resilient enough that it no longer depended upon the genius of a single person?

Those are less glamorous questions.

They are also, I suspect, the more important ones.

History has always loved founders.

Civilization depends just as much on successors.

The irony is that founders often understand this better than their admirers do.

Read the letters of Benedict rather than the tourist brochures about Monte Cassino. Read George Washington’s farewell rather than only the stories of Valley Forge. Read the closing chapters of Moses’ life instead of the opening ones. Again and again, the truly great leaders seem to share an instinct that our culture struggles to recover.

They know they are temporary.

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We like to believe organizations make decisions by carefully weighing evidence. Sometimes they do. More often they absorb new ideas only after enough experience has accumulated that the old explanation no longer works.

This creates a peculiar problem for leaders.

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The official meeting ends. Laptops close. Coffee cups are gathered. People drift toward the door. Somebody makes a joke. Someone else glances at their watch. The meeting is over.

Except it isn’t.

Two people linger in the hallway. Three more gather near the elevator. A Slack message appears. A text gets sent. Someone pokes their head into a colleague’s office and says, “Can I ask you something?”

Then the real conversation begins.

I’ve spent enough years inside organizations to know that the meeting after the meeting is one of the most reliable indicators of organizational health. Not because it exists. It always exists. Human beings are social creatures. We process information together. We compare notes. We seek perspective.

The interesting question is what happens there.

In healthy organizations, the meeting after the meeting tends to revolve around understanding. People test ideas. They challenge assumptions. They continue conversations that began in the room. The second conversation enriches the first.

In unhealthy organizations, the meeting after the meeting serves a different purpose.

It becomes the place where people finally tell the truth.

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One of the mottos in our family is simple:

It sounds almost embarrassingly straightforward written down. The kind of advice you might find stitched onto a pillow or hanging on a piece of reclaimed barn wood in someone’s kitchen.

But I’ve come to appreciate how difficult that principle actually is. Especially inside organizations.

Over the years I’ve occasionally gotten myself into trouble by taking people at their word. Someone says they want honest feedback. An executive team asks for candor. An organization hires consultants to provide an unvarnished assessment.

Then the honesty arrives.

And that’s often when the trouble begins.

Not because the feedback is inaccurate. Because it violates rules that were never written down in the first place.

It took me years to understand what was happening.

Most organizations have two stories.

The first is the story they tell about themselves. You’ll find it on the website, in recruiting materials, annual reports, employee handbooks, strategic plans, and conference presentations. It consists of mission statements, values, leadership principles, and carefully chosen language about transparency, collaboration, innovation, accountability, and trust.

The second story is the one employees learn through experience.

That story is culture.

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Not the words on the wall. Not the values printed in the handbook. Not the carefully crafted language approved by the communications department. Culture is the collection of behaviors that are rewarded, tolerated, and punished. It is the answer employees eventually discover to questions nobody asks directly: What happens when someone disagrees with leadership? Who gets promoted? Who gets protected? Which mistakes are forgiven? Which ones are career-limiting?

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When my kids were younger, one of their favorite books was We’re Going on a Bear Hunt. If you’ve never read it, the story follows a family searching for a bear and repeatedly encountering obstacles along the way. Tall grass. Deep mud. A river. A snowstorm.

Each time they encounter a new challenge, the refrain remains the same:

For years I thought it was simply a children’s book. Then I spent enough time leading organizations to realize it might be one of the better leadership books I’ve ever encountered.

Most leadership challenges follow the same pattern. The problem is rarely that nobody knows what to do. More often, everyone knows exactly what needs to happen and nobody wants to do it.

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I once worked for an organization that joked it “ate its own.”

At first it sounded like dark institutional humor. Every large organization develops stories about itself, and people laughed because everyone understood the pattern being described.

But eventually the joke stopped being funny.

Over time I watched a long line of employees become quietly isolated, blamed, emotionally exhausted, and eventually removed. Each departure was explained individually. One person supposedly lacked alignment. Another was too negative. Another could not handle the pressure. The organization always had a reason.

Eventually I realized the pattern itself was the story.

And then I became part of it too.

Most employees do not suddenly stop respecting leaders. Respect usually erodes slowly through repeated experiences that quietly teach people what leadership actually values.

Employees notice when difficult conversations are endlessly postponed while dysfunction spreads through the organization. They notice when priorities constantly change but accountability somehow never reaches leadership itself. They notice when meetings generate more confusion than clarity and when emotional exhaustion becomes normalized as professionalism.

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I have heard some version of “kids these days just don’t want to work” for most of my life. As a member of Gen X this was a critique I commonly heard.

Every generation seems convinced the next generation lacks grit, discipline, resilience, or work ethic. The complaints change slightly with the decade, but the underlying message stays remarkably consistent: younger workers are supposedly softer, less loyal, and less willing to sacrifice.

What gets discussed far less often is how dramatically organizations themselves changed during the same period.

Many workplaces quietly became extraction machines.

Staffing was cut to the bone. Loyalty became conditional. The boundary between work and life eroded and was replaced by a 24/7/365 asynchronous demand platform ironically called Slack. Economic insecurity was reframed as flexibility and renamed the gig economy. Employees became permanently reachable while institutional trust steadily eroded. Every year organizations demanded greater efficiency, greater responsiveness, greater emotional labor, and greater adaptability from increasingly depleted human beings.

And I am not only talking about corporate America.

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Employees now have tools that provide structure, insight, and momentum many managers were supposed to provide themselves. The result is a growing divide between leaders who create clarity, trust, and growth—and those who have been hiding behind ambiguity for years.

Many say they are worried AI will make employees less thoughtful. That is not the real fear. The deeper fear is that employees now have access to tools that provide some of the clarity, structure, insight, and momentum leadership was supposed to provide.

For years, weak management survived because organizational confusion was expensive to escape. Employees depended on managers to interpret priorities, summarize information, clarify direction, structure work, and help them think through problems. Now a twenty-dollar-a-month AI tool can often do parts of that faster than a 90 minute meeting.

That should make some leaders deeply uncomfortable.

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• You revisit a decision after it’s already been made.

• You replay a conversation that didn’t quite land.

• You keep coming back to the same question: what should I have done differently?

At first, that can look like care. You’re paying attention. You’re trying to get it right. But if it keeps going, something changes. You’re no longer just reflecting on what happened. You’re starting to take on more responsibility than what was actually yours.

That shift is easy to miss. It doesn’t announce itself. It builds quietly, in the way you stay with things longer than you used to. You carry them forward. Into the next meeting. Into the next decision. Not because you’re trying to take on more. Because there isn’t a clear place to set it down.

Over time, things that are shared start to feel personal. A team issue starts to read as something about your leadership. A constraint starts to feel like something you should have anticipated. Even the things that were always going to be difficult start to trace back to you.

Nothing about the work has fundamentally changed.
But the way it lands on you has.

You start to lose your sense of what’s yours. What you can influence and what you can’t begins to blur. So everything starts to sit in the same place. With you.

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Most nonprofits are still building their strategy around donors in their 60s and 70s.

At the exact moment the largest wealth transfer in history

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You review the latest updates.

Progress is real, but uneven.
Some things are working.
Some aren’t.

You pause.

“How do we frame this?”

You tighten the story.

You lead with wins.
You smooth the edges.
You resolve the tension.

The call goes well.

They’re encouraged.
They stay engaged.

Nothing went wrong.

But something just got reinforced.

The assumption most organizations carry:

Donors shape the organization.

Their expectations.
Their preferences.
Their questions.

This is true.

But incomplete.

Because donors are also being shaped.

Quietly. Repeatedly. Structurally.

By you.

How formation actually works

Every update teaches your donors something.

What matters.
What success looks like.
What is normal to expect.

If you consistently present:

• clean progress

• clear outcomes

• resolved stories

Your donors learn:

this work is predictable
this work is measurable
this work is under control

Even when it isn’t.

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The mission statement is clear. The language is careful. The stories are compelling.

But there is a quieter truth that shapes the work over time:

You …

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