8 Mistakes from an Executive Director

The hardest and loneliest place to sit in any organization is at the top. We all struggle to climb the ladder and aspire to be the head honcho, the big queso, but nobody knows what you’re going through except for other leaders who are struggling with the same.Here are the mistakes I made as a leader and what I’ve learned from them.

Fake it till you make it…not

I was an Executive Director for the first time and leading a team that was not much younger than me. In some cases, I was managing people who were older than me. So, what’s an inexperienced ED to do? Pretend like I knew what I was doing. I was so afraid that people would think I was incompetent or a fraud that I was like a duck: calm-ish on the surface and paddling furiously underneath. I think I would have gone a lot farther if I had admitted earlier on that I didn’t know what I was doing all the time and asked for more input and help from my team. Of course, nobody likes a leader who doesn’t know ANYTHING, but I could have been more truthful and vulnerable at various points in my career.

Shooting the messenger

Oh, this is hard. I’ve shot the messenger more times than I would care to admit. Sometimes the message would be so explosive or so upsetting that I would dig into the messenger. I would like to pretend that I was the very picture of calm and grace all of the time. That would be a lie. So, I’m now going on the record to apologize to those who were simply message carriers for news I didn’t want to hear. I’m very sorry.

Regulating myself

I’m a fairly excitable person and I have had a hard time regulating my reactions both good and bad. I would like to be the sort of Zen, yoda-on-a-mountaintop person who accepts good and bad news with equal equanimity but that’s just not how I’m wired. I like to think that I got better about this as I got older, but it’s always a struggle for me to telegraph exactly what I’m feeling on my face. Big new grant! YAY! Party-time, jump around! Losing a grant: sagging shoulders and stormy face.I’m a terrible poker player, but an excellent charades player.

Shut the hell up

I’m a talker. It’s how I’m built. Over the years, though, I’ve learned the power of shutting the hell up and listening to other people. A 20 year practice of yoga has helped me to focus my naturally hyperactive monkey mind, but it’s still hard. I realized that I was so busy talking that I wasn’t listening to my people–their struggles, their fears, their triumphs and therefore I was out of touch with what was happening on the ground.

The cues I was giving that I didn’t realize I was giving

There were times that I was accused of having “favorites” and that I spoke more frequently to some staff over other staff. As I thought about it, it turns out that the staff I spoke to more happened to sit in cubicles that were on my way to my office. Everything that you do it interpreted whether you intend for it to be or not. Your staff is watching you all the time so be aware of the little things. Walk around to say hello to everyone, make sure to ask different people out for coffee or whatever…which leads me to my next mistake…

Playing favorites

Now, I didn’t know that I was intentionally playing favorites but there were certain staff members that I knew better than others. For example, I worked more closely with fundraising than with program and as result, I was able to speak about their successes with more depth and frequency. Also, I thought I was being publicly encouraging of folks–turns out that it was interpreted as “playing favorites.” Again, your staff will be hypersensitive to any signs of unfairness, even when you are not.

Waiting too long to give feedback

When you are not trained to give feedback or trained to take it, it can be a very messy process. Especially in the nonprofit world, we lead with our heart so fully that any constructive feedback feels personal. Because the work is personal. Which is great, but giving constructive feedback should not be taken as a personal attack. Because I was so scared of people freaking out, I often didn’t give immediate critical feedback until it became a really big problem. Think about how to create a framework for people to understand, accept and give feedback.

And, when all else fails, try again tomorrow

I’ve made a ton of mistakes and there are things I really wish I could go back and do over, but I also try not to rake myself over the coals too much. The work of leadership is a lifelong venture and, even after more than a decade as an executive, I still feel like there’s so much to learn. Maybe the lesson is in the journey and not the destination

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