Why Do So Many Good Nonprofit Leaders Think They're Failing?

One of the greatest privileges of my mahi is spending time with nonprofit leaders. Every week I sit alongside people doing extraordinary work in incredibly challenging circumstances.

They’re thoughtful, committed, and deeply connected to the communities they serve. They care about their staff, they care about their organisations, and they care about getting it right. They are exactly the sort of people you would hope are leading our sector.

Yet over time, I often hear the same conversation emerge. Not immediately. Usually after we’ve built some trust.

Then someone will quietly admit they’re wondering whether they’re actually good enough for the role. They’ll tell me they can’t seem to get on top of everything, that they feel like they’re constantly dropping balls, or that perhaps they just need to become better at managing their time. Sometimes they’ll even question whether they’re in the right job at all.

There was a period during my time as a CEO when I’d often wake up around 3am. I’d lie awake for an hour or two thinking through funding challenges, staffing issues, relationships, governance challenges and everything else that needed my attention.

At the time I thought the problem was me. I assumed I simply wasn’t coping well enough.

Looking back now, I see something different. My brain had simply found the only quiet time available to do the thinking I hadn’t had space for during the day.

What strikes me is that so many nonprofit leaders reach exactly the same conclusion. They assume the pressure they’re feeling says something about them rather than the context they’re leading in.

Most nonprofit leaders spend very little time talking honestly with other nonprofit leaders. They’re busy leading their own organisations. The leaders they do see are often from much larger charities with communications teams, polished marketing and infrastructure that looks nothing like their own. Or they’re seeing peers who are quietly carrying just as much but have become very good at looking like everything is under control.

We’re comparing our own lived experience with everyone else’s public image.

The funding environment adds another layer. Nonprofits are competing for the same limited resources, so showing vulnerability doesn’t always feel safe.

We celebrate resilience. We celebrate people who somehow keep making things work. We don’t often talk about the personal cost of holding everything together year after year.

The irony is that the leaders who most often question themselves are usually the ones I admire the most. They’re not looking for an easy life. They’re not avoiding responsibility.

If anything, they hold themselves to impossibly high standards because the mahi matters so much to them. They know the names and stories behind the funding applications, the contracts and the reports. When communities are hurting, they carry that with them too.

Over the past few months, as I’ve been writing about reimagining nonprofit leadership, more and more leaders have been reaching out. One emailed me after my last article and simply wrote, “Your latest article is my work life!!!” Another recently registered for my upcoming kōrerorero and said they were “currently wrestling with whether it’s my personality and working style, or the role itself why there is just so much to do.”

I don’t think those comments are unusual. I think they’re much more common than we realise.

Perhaps one of the kindest things we can do for one another as nonprofit leaders is create more spaces where we can stop pretending we’ve got it all figured out. Spaces where we can talk honestly about the realities of leadership without feeling like we’re somehow failing.

Because when we hear other leaders describe experiences that sound remarkably like our own, something shifts. We stop seeing our struggles as a personal weakness and start recognising that many of us are navigating remarkably similar challenges.

This is one of the reasons I’m so looking forward to our upcoming Reimagining Nonprofit Leadership kōrerorero. It’s not a webinar and I’m certainly not turning up with all the answers. My hope is simply to create a space where nonprofit leaders can connect, think together and have the conversations we don’t often get to have.

If you’ve ever quietly wondered whether it was just you, I’d love you to join us.

📅 Reimagining Nonprofit Leadership – A free online kōrerorero
Thursday 23 July | 11.00am–12.00pm (NZST)

We’ll explore the realities of leadership overload, sustainability and what leadership might look like as our sector continues to change.