They're All a Mess

For my nonprofit management course at Columbia (SIPA), I have recorded interviews with nonprofit leaders for the past few years. Students watch three of the many interviews and then write a leadership reflection essay.

I ask these leaders how they assessed their organizations when they arrived, how they manage change, and how they build a productive culture.

I love this assignment — from interviewing leaders I respect tremendously to reading students’ aha moments as they see their career goals in an expanded or entirely new way.  

And there are lots of aha moments and good reminders for me too.

During one of the interviews, I asked an executive director about figuring out where she should focus her attention when she arrived. She answered by telling me a story (so executive director of her) about a call from a colleague who had been approached about an executive director role at another organization. He was interested but hesitant. He’d heard the place was “a mess.”

Her response to him came quickly and emphatically. “They’re all a mess!”

We laughed (I needed to edit out a few seconds of our extended tittering).

She went on to explain that no leader ever finishes everything they hope to finish, that nothing ever runs exactly the way we want it to, and that every organization has a few scars from the constraints every leader faces that lead to diversions from strategy and less-than-ideal tradeoffs in how we operate.

Leadership, she said, requires grace for the predecessor who left us an organization with some issues they never got to fix – because someday we hope our successor will offer us grace for the things we never finished.

That conversation stuck with me, because it names something I think many leaders could raise their awareness about: messiness is not an exception in organizations. It is the norm.

And yet, we still treat “this place is a mess” as a warning – like something is way off – rather than a day-to-day reality of organizational life.

The mess often isn’t evidence of something being direly wrong (people are getting paid, right?).

I did a bit of digging and, of course, organizational research backs my colleague up.

For decades, scholars have pointed out that organizations are built and run by people with limited time, attention, and information. And in nonprofits, they are trying to pursue multiple, often competing goals because their many stakeholders have opposing views on issues. Decisions are made under pressure, with incomplete data, and very limited resources.

What ensues is a game of whack-a-mole, where we deal with urgent and competing priorities that pop up while trying to make space for strategic thinking and intentional action. And when we do set a “clear” direction, something changes in the outside world – donor interest, a new administration with outrageous policies, an AI revolution – that knocks us off course. 

Facing all of this, “good enough for now” is sometimes the best we can hope for. And there’s a lot of “not right now, but sometime soon” thrown in for good measure.

No leader gets to everything they mean to and, although it could be seen as a flaw in their management capacity, there is a greater chance that “life got in the way.”

Yet when a new leader walks in, unfinished work often gets read as evidence of incompetence or neglect. We forget that what we’re seeing is the residue of choices – many of them reasonable at the time, given the context.

A mess doesn’t mean no one cared or that they didn’t know how to fix the issue, necessarily. Often it means they had to prioritize which of the many issues they cared about would get their attention – which might be different issues than the current leader would choose.

Different isn’t wrong.

It reminds me of what happened when I left home for a summer trip to Germany during high school and then college a year later.

I confronted a new reality. Other people didn’t live the way I was raised (this was pre-social media times when you had to look for information, not have it thrown at you relentlessly every waking minute). They made their beds, cooked, and did the laundry differently than I was raised to do. It seemed odd to my younger brain, and my knee-jerk reaction was to assume that they were odd. Of course, with time, I saw that what and how they ate, washed the dishes, and interacted was different – but it all worked quite well. If I slowed down and observed with curiosity, not judgment, I might pick up a new way of doing something.

My way wasn’t the only way, and their way wasn’t wrong (by any stretch).

“Different” does not equal “broken.” It just means not your way.

New leaders can walk into organizations with the same misdirected curiosity. Processes seem clunky, overwrought, or non-existent. Files are strewn about the server, willy-nilly. Things get done, sure, but not in the way a sane and rational person (like them!) would do them.

Organizational theorists write about this. They describe most workplaces as loosely coupled systems – places where different areas of the business develop norms and workarounds that work for them. From the outside, it reads as inconsistency or confusion. From the inside, the adaptations become “the way we do things around here” or important differences in the type of work different areas of the business operate. It takes someone from outside the system to know that a different, more unified system or process might serve everyone better.

Add today’s volume of information and constant interruption, and leaders are almost forced to simplify what they see. If it doesn’t look like what you know, then it must be wrong.

But sometimes, it’s just different. Not everything that makes you twitch is a problem to solve.

As we start to organize the mess and separate the urgent from the important, I’ve found it helpful to distinguish among three types of mess that new leaders encounter and all leaders participate in creating:

• Unfinished Work. Decisions that were consciously postponed because something else mattered more at the time.

•  Stylistic Differences. Choices you wouldn’t have made, but that worked well enough for someone else.

•  Real Problems.  Issues of misalignment, risk, or mission drift that need more immediate attention.

If we don’t triage the issues, we risk missing the issues that truly matter.

There’s another piece we rarely acknowledge. Leaders are always trading off.

Once again, the research is clear. Organizations constantly balance exploration (adapting and innovating) and exploitation (refining and systematizing). Resources spent on one are time not spent on the other.

If a predecessor pushed hard on growth, partnerships, or new programs, systems and processes may have not kept up. If they focused on stability and infrastructure, innovation and a culture open to change may have fallen behind.

There is no version of leadership where everything moves forward at once.

Unfinished work isn’t a sign that someone failed. It’s evidence only that someone made a choice that seemed best at the time (just like you will).

And someday your successor will be sorting through the results of your choices, too.        

Grace goes two ways. You also need to practice it toward yourself. You will leave things undone. You will mean to circle back and not quite get there. You will make tradeoffs that look imperfect or tragic in hindsight. That doesn’t make you incapable. It makes you human in a role and industry with challenges built into the design. Leadership isn’t a solo performance, and no one hands off everything tied up with a bow (no matter what they say).

This is where the leader I interviewed landed and where I think the work of leadership lies.

She understood that the way we talk about our predecessors is practice for how our successors will talk about us. We can’t control the narrative, but we do put into the universe the approach we believe in. Hopefully, that will come back to you someday.

Every leader leaves loose ends. Every leader runs out of time, energy, or simply doesn’t know the best direction in every moment. Every leader makes bets that lose or pay off.

Grace isn’t about excusing poor leadership or ignoring real problems. It’s about recognizing the humanity embedded in every organization, including the one you’re shaping right now.

Leadership isn’t about inheriting something clean.

It’s about walking into something unfinished and deciding – repeatedly – what deserves attention now, what can wait, and what might simply be done differently without being wrong.

So, the next time you hear that an organization is “a mess,” it may be worth asking a few questions:

• What kind of mess is this?

•  What choices produced it?

•  And what grace will I hope for when someone else inherits mine?

Then, take the interview.

Want to sift through your mess with someone who’s walked this path? Email me at gary@garybagley.com or connect with me on LinkedIn.