At the end of every week, my boss asks us to write down a lesson we learned. Mine are usually due to a slip up I made. Here’s how it goes: I make a mistake, apologize to the person, and end up saying something along the lines of: “I should have done x, lesson learned for next time.”

Because we work remotely, this apology is often over text. I did a quick search and found out I make a lot of mistakes learn a lot of lessons.

lesson learned

I don’t think we talk openly enough about the mistakes we make, especially as people in leadership positions. Maybe it’s because we are afraid to let people know we don’t actually have everything together or because being vulnerable feels not great. I just think it makes us more human. With that, I want to share a few of the mistakes I’ve made recently and the lessons that came out of them.

  1. I needed to make a big change that involved a number of people. I assumed one of the people involved was already aware but it turns out, they were not.
    Lesson: Talk to every party that is involved in the change. 
  2. One of my weekly one-on-one meeting with a direct report got canceled. I was going to bring something up that had the potential to get misinterpreted. I didn’t want to wait until a whole week so I decided to send it to them in a text format. It didn’t go well.
    Lesson: Have difficult conversations in person or on the phone. 
  3. I was working a three day week but didn’t adjust my to-do list accordingly. I ended up having to ask someone on my team to take over one of my bigger items without much notice.
    Lesson: Delegate early and often. 
  4. We had a team meeting that overlapped with a monthly company wide meeting. A couple people were excited to have our team meeting and wanted to watch the other one later (it was recorded). I decided to leave it up to everyone to decide what they wanted to do. This caused confusion, especially with new folks on the team.
    Lessons: Set expectations and communicate them clearly. Cancel team meetings ahead of time when they overlap with townhalls. 
  5. I came back from a three month sabbatical and felt extremely frustrated with myself that I wasn’t fully up and running by the second week back. I beat myself up for being so off my game and letting routine things fall through the cracks.
    Lesson: Transitions take time. Give yourself the time and space to make it happen. 

While sharing lessons I’ve learned is great, it really only tells half of the story. I’ve found that being open with people about the situation that lead to the lesson can be very freeing. Being so open also has the added benefit of creating a sense of trust, deeper relationships, and invites others to feel okay making and sharing mistakes of their own.

Published by Kelly Hoffman

Senior Design Director of commerce at Automattic.

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1 Comment

  1. Good stuff.
    Reminds me of the person that would start a conversation with
    “What has become clear to you since the last time we spoke”

    Like

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