A nonprofit thought leader’s resolutions for a new year: To follow and to fail

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Department of Sanitation workers sweep up confetti the morning after New Year's Eve celebrations in Times Square.

A nonprofit thought leader’s resolutions for a new year: To follow and to fail

The goal would be to become a more effective champion for New York City’s nonprofit sector.
January 7, 2022

Although the New Year came in without much fanfare, amidst the pandemic and uncertainty, I did make a few resolutions that will guide how I do my work and live my life this year. The two resolutions that I hope will make me a more effective champion of New York City’s nonprofit sector this year are to follow and to fail. 

Following:

All through high school and college, and during my 30 years in the non-profit sector, I have been trying to prove what a great leader I am. I have been looking for better ways to do my work, to stand out from the crowd, to innovate. As a line staff, manager, board member, and funder – my implicit and explicit goals have been to do better … better than what came before, better than what my peers are doing, better than people doing the same job in other places. 

But as I’ve gotten older, and a tiny bit wiser, it has become clear to me that a lot of other people are already pretty good at their jobs. Instead of trying to outdo them, I could try to learn from them, copy them, read what they write, listen to what they have to say, and seek their advice and guidance. And while it is true that sometimes program design, strategy, and operations can use updating and re-thinking, it is also true that it doesn’t always have to me that does that work. Most often there are other people who live closer to the problem, or have deeper experience, or have skills and intelligence that I do not, who are already thinking and doing. I suspect that my time would be better spent finding them, lifting up their work, and following them. 

I have come to think of leadership as the last option – if there is something that we really, really believe we have to do, and no-one else is doing it, then we should take the lead. Otherwise, let’s get in line and help an effort that is already in the works.

Failing:

The second of my resolutions is to fail. Admittedly, I have been failing all my life – but now I am going to fail out loud. In my historic attempts to be the best, to be the leader, I have been trying to cover up my failures, or at least not draw attention to them. But figuring out what doesn’t work is just as important as figuring out what does work – and it is almost never a conversation we feel free to have in our sector. When non-profit leaders are asking for funding, competing for resources, attracting staff, donors, or board members – they are highly discouraged from talking about failure. For all the conference sessions and journal articles I have read about ‘best practices’, I have never seen anyone talk about their ‘worst practices’, or even their ‘mediocre practices’. 

And – not to brag - I have gotten better at failing over time. I fail faster than I used to, or at least I recognize when I am failing faster than I used to. I’d like to share these failures with other people doing the same kind of work – and not in some fake humble-braggy way, but in a safe and generative manner, where we can dig in and figure out where I went wrong, and how I can change my practice. 

I hope next New Year’s will be a more peaceful and celebratory one – and that we can gather together over a glass of champagne, and talk about who we followed and how we failed in 2022.

Lisa Pilar Cowan
is the vice president of the Robert Sterling Clark Foundation and in this capacity she helps with strategy, development and oversight of foundation programs and grantmaking. Lisa has been working with community-based organizations for the last 25 years, first as a community health educator and program director at several youth-serving agencies, then as a senior consultant at Community Resource Exchange. Lisa was the co-founder of College Access: Research and Action, where she continues to act as an advisor. Most recently, Lisa was the principal consultant at Hummingbird Consulting from 2013-2016.
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