Opinion: Why nonprofit leaders should discuss past mistakes as 2023 gets underway

New year, new notebook, blank page. I’ve already blown Dryuary, but I have been keeping to my most important New Year’s resolution – Make More Mistakes. More precisely, I already make plenty of mistakes – but this year I want to talk about them more, sooner, and louder. I think this is an underplayed strategy to learn and improve our critical mission work in the non-profit sector (and everywhere else, for that matter).

When I try to pick out a single mistake to talk about, there are many options. One is a mistake I made back when I was running a school-based health clinic in a large public high school in Massachusetts. I wanted students to feel welcome and comfortable in the clinic – and so I decided that hiring a student to serve as a receptionist would help to make the clinic more student-friendly. I hired a high school junior who I thought was great – she was interested in the health professions, she was friendly and popular – and once she started, a few of her friends started coming in for services and support, and just to hang out. But our numbers did not go up, other students did not come, and I could not understand why – until one day, I was in a bathroom stall and heard several girls talking about what a gossip our receptionist was – saying that they would never come to the clinic now!

I never told anyone about that conversation I had overheard. I didn’t want to fire the receptionist, I didn’t want my boss to know that my idea had backfired, and I didn’t want my co-workers to feel like I had failed them. I didn’t even tell the person who took my job after I left, and I have always hoped she figured it out. It was an understandable miscalculation on my part – but one that had real consequences for students who did not access the services available for them. I really should have talked about it in order to do my job right.

We are so often in settings where we promote our successes: we give speeches about our best practices, tell donors why they should give to us, invite people to work for and with us, tell government why they should enact our preferred policies, and instruct young people on how to become good citizens. And most of what we say is right and true – and yet not the full story. The things we don’t really talk about are just as important, if not more so: What are our worst practices? When have we spent our money badly? What is hard about working for our organizations? Where have policies fallen short? Where are we failing our young people? 

When I lie in bed at night, reviewing my day – it is not the things that went just fine that I think about – it is the places I went wrong. But when I get to work the next morning, I am hesitant to talk about those places – for fear that people will think I am dumb or misguided. And so I don’t warn people about things I have done wrong which they should avoid, I don’t take full accountability for what went wrong – and I don’t ask about how I should do things differently next time. 

Last month, I had the chance to talk about ‘The Gift of Failure’ with a group of colleagues at the NonProfit New York annual conference. Those of us on the panel agreed to share our mistakes with the audience, but we had to practice them over and over before we got up there. Even with our intention to do so, it was hard to get our mouths around the words admitting the mistakes we made. After we shared our mistakes, and the ways we had learned and changed because of them – we asked the audience to turn to the people next to them and share a mistake of their own. Many enjoyed the exchange, but some people thought that was a little squishy – and hard to apply. They wondered what talking about mistakes has to do with non-profit leadership. In my shifting understanding I have come to believe that creating an environment where people can ask questions and talk freely about both successes and failures has everything to do with creating organizations where we can learn and grow and most importantly - succeed in our mission work.

New Year’s resolutions can be hard, and uncomfortable – and can require practice. I have tried and failed many times over the years to lose 10 pounds or floss every day. But I think I am going to succeed at this years’ resolution – because I think that we will all find that there is a tremendous relief that comes with talking about our mistakes – that we can stop pretending all the time, and be more ourselves, and learn how to fix some of our old mistakes even as we continue to make new ones. So happy new year…now go screw something up and then talk about it!