You don’t know what you don’t know. It’s a riddle challenging every new leader. I wish I’d understood twenty or twenty-five years ago there were ten thousand things I didn’t even know I needed to know. If I’d understood that, I would’ve been a better leader from the beginning.

More than twenty-two years in nonprofit executive leadership, ten years before that in nonprofit middle and senior management, and a brief and unhappy stint in the for-profit world of health care have defined my legacy. So many moments. Spectacular, funny, embarrassing, scary, even horrifying moments, each informing the next. I have hundreds of stories for hundreds of memorable moments. Humbling stories about how in the same year I was recognized as best executive director in our field and told by a senior leader on our team that I don’t support people very well. Hard work stories including one year when we could barely make payroll and the next year ending well ahead of budget because of our teamwork. Stories of barely having the emotional fortitude to lead us through two devastating events in one summer and learning the value of external support, for me it was therapy. Stories of bad hires and “how did I get this lucky” hires. Stories of how my “passionate” (self-righteous) declarations have become more patient and considered communications and problem-solving. Stories of how life and work and people who have been there for me have given the gifts of maturity and wisdom.

I know now the moments, the stories, build on each other. It’s slow wisdom. Some days feel completely routine, I don’t even know I’m learning. Other days feel so uncomfortable, I’m thinking more about my car keys than the lesson being forged. Still, what I try to do now is to think deliberately about what I’m learning. What did I just learn from that achievement or disaster? Not like a big, formal aha moment but a quick review either in my head or out loud, “That was amazing! What did we learn? Let’s do it again!” or “That was a gnarly fail! How do we run from a repeat of that?!”

Had I realized in the beginning leadership is less about being correct all the time and more about growing wisdom through experience, I would’ve known to watch and listen more, speak less. I would’ve focused on learning. I thought I needed to hit the ground running to be a successful leader. I had an image in my head though of needing to project ultimate competence, like I knew just about everything. I thought I needed to at least project a “know everything” level of confidence. Did I come off as arrogant? Looking back, I didn’t have the I’m better than you, obnoxious kind of attitude, but I did have an “I’m pretty sure I know just about everything I need to know to do this job” attitude. It was enough arrogance to keep me from listening well. It was also enough to surely invite eye rolling behind my back on occasion. There were many things I did already know. And many more I didn’t.

I did know…

the buck stopped with me. I was responsible for the ongoing health and well being of the organization. Throughout the prior two years in another position, I watched my predecessor do many things well and some things less well. I learned some what-to-do and what-not-to-do lessons. I was also mid-career. I turned forty a few months after assuming the executive role. I knew I had solid experience. I had hundreds if not thousands of solid management decisions under my belt. I thought, for the most part, I was good to go. Maybe for the most part, I was. But I still didn’t know what I didn’t know.

I didn’t know…

the knowledge and skills I gained in other positions would be helpful but insufficient for the executive position. I didn’t know any new executive position would have its own learning curve but the first executive position would have a learning Kilimanjaro. The experience I brought to the position was like having purchased all the right mountain climbing equipment and done all the training climbs. Getting the title didn’t mean I’d magically planted my flag successfully at the top. It only meant I was ready for the climb.

image by crobi15 on pixabay

Three things:

If I had it to do over, I’d get a sherpa.

A coach or even an informal mentor would’ve steadied my climb up the learning curve. Actual coaching can be expensive, especially in the nonprofit world where salaries are less than in the private sector and budgets have skinnier bottom lines. I wish standard practice for boards was to include coaching in the first year’s budget of onboarding a new, or experienced but new to the field, CEO/Executive Director. There’s more accountability to the goals of the organization if the organization is paying for it.

If it were standard practice, it would also mitigate the problem of younger leaders like I was at the time. I think I might’ve been resistant to coaching, thinking it would telegraph “she’s not smart enough”. It also seemed too much out of the bookstore self-help section, full of 10 steps to perfect time management or 5 steps to accomplishing all my goals. It seemed a little indulgent as well. I was more a “get in there and figure it out” kind of person even if it meant reinventing the wheel. And let’s be clear, reinventing the wheel is foolish. It’s wearing the t-shirt that says “No, really, I’d rather do it the hard way” while the wise sherpa is wearing the t-shirt with the arrow pointing in your direction saying “she doesn’t know what she doesn’t know.”

If I had it to do over, I’d listen.

I’d listen to more experienced leaders. I’d listen to more experienced people. I’d listen better to my team. I’d ask questions. I’d write down the answers so I wouldn’t forget and could spend time thinking about the wisdom. I’d read a self help book or two about listening. I. would. listen.

If I had it to do over, I wouldn’t change anything for six months.

To be honest, I don’t remember how much I changed or didn’t change in the first six months of becoming executive director of the organization. What I do remember is feeling an urgency to establish myself as the new leader. I wanted to put my signature on us. The advice my now self would’ve given my then self would be to ask someone far more experienced to have lunch with me once a month, to talk about challenges, listen and learn. To listen to the team, everyone who worked for us as much as possible. To take care of things day to day, which I did already know how to do, and establish myself as someone who doesn’t know everything. Because I didn’t.

After all these years, it’s still true. I don’t know what I don’t know.

These years have taught me how normal and survivable it is to not know. I realize now, and wish I had then, not knowing isn’t a liability, it’s simply a place on the continuum. I’ve learned you never know what you don’t know, you just get better at seeing the oh-my-god-I-don’t-know-what-to-do coming. I’ve learned to build a network of wisdom in our team, friends and colleagues so I have people to run to for help when I need it. I used to think running for help looked weak, now I think it looks like wisdom in action.

Writer and metal smith/jewelry maker, Donna has lived happily as a mother, friend, creative, and nonprofit leader in Nashville, TN for more than 30 years. She is additionally committed to her cats, rock climbing, gardening and power tools. She believes that people are good, kindness is essential and artists should rule the world. Find her at
Writer and metal smith/jewelry maker, Donna has lived happily as a mother, friend, creative, and nonprofit leader in Nashville, TN for more than 30 years. She is additionally committed to her cats, rock climbing, gardening and power tools. She believes that people are good, kindness is essential and artists should rule the world. Find her at

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