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My Biggest Leadership Regrets
Leadership is not for the emotionally fragile. It can shatter you into a thousand pieces if not you’re careful. Leading has a way of revealing our biggest weaknesses. Many leaders didn’t realize how much it makes you confront your own personal failings. How much of leadership is having a mirror held up to your face. Even more challenging? That mirror and your reflection is in public. There’s no where to hide those uncomfortable truths about ourselves. We have to confront our mistakes, our humanness in front of the team. This is hard stuff.
Being responsible for the work and well-being of others is like being in an intense obstacle course that tests your endurance. It’s a constant juggling act managing responsibilities to the team, getting your own deliverables done while driving a larger strategy for key aspects of a company. As a leader, felt pulled in a million directions, stretched beyond all capacity. This made it much harder to do the deeper inner work required to learn from my mistakes. While I tried to carve out time to reflect every week, it fell off the list at times. It’s a shame too, that time was essential for introspection. When I made time for that reflection I caught my mistakes earlier.
Here are four mistakes I regret along with a bit of advice.
Used the wrong emoji
You may think I’m being hard on myself but leadership is built in the small moments as much as the big ones. A team member and I had been discussing their promotion. The decision wasn’t mine alone and they knew I had a meeting to discuss it. The news was good. I was so happy that I sent them a quick Slack message to let them know I had news. I put a smiley face at the end. I was proud of myself. Then they replied. The message was polite with a hint of fear underneath. I was confused. Why weren’t they more excited?
We jumped on call. I told them the good news right away. They responded with a surprised “Oh! I thought it was going to be bad news! This is great.” I realized there was a communication misfire. The cause? The wrong smiley face. Apparently I used the slightly smiling face instead of a broader grin. To them, that emoji indicated bad news. I was crestfallen. I’d been so excited to share the good news. Instead, I sent the wrong message. I made someone worry unnecessarily…
