A page from my leadership diary

©The Bees Knees Photo

©The Bees Knees Photo

When I’m struggling with something, I write about it. I write to get clear on my thoughts and feelings about the situation, and doing so usually helps me identify the best path forward. It also helps me reflect on what the experience is teaching me. 

Below is a glimpse of what I’ll call my “leadership diary,” a fancy name for the very personal word doc where I document my challenges and lessons learned. Last week, I journaled just before entering a difficult conversation with a member of my leadership team and again after the conversation was over. Some context for the situation: We had a meeting that didn’t go so hot, and I left feeling unsettled about it. We weren’t the best at listening to each other; we interrupted each other at times; and we lacked patience. And because of all that, we didn’t accomplish as much as we could have together. I knew I had to tell her how I felt even though I didn’t want to, especially because she’s not just someone I work with; I consider her to be one of my dearest friends. I wrote this piece just before giving her feedback.

This strategy of writing down how I feel before and after really helps me when I’m facing something hard. Hope it helps you too.

Happy reading!


September 24th, 2019 at 10:00am

I have that feeling in my stomach. The one I get right before I’m about to tell someone how I feel.

Why is this so hard? I’ve been leading people for 12 years. You’d think giving feedback would be easy by now. But it’s not. I still get nervous. I still get butterflies. It’s hard to tell people how you feel, especially when your words might hurt them.

I’ve thought about what I’m going to say today a million times. I also tried to convince myself that I don’t need to have the conversation at all. If I don’t say anything, maybe it will just breeze over and never happen again. But who am I kidding? Of course it will happen again. It always does. If I don’t address it now, next time it will be even harder.

I know I have to tell her how I feel. I made a promise to always be honest and transparent with my team, so this is what it means. Plus, I care about her. And if I care about her, I have to tell her the truth.

I’m making this a much bigger deal than it needs to be. As soon as we meet, we’ll both feel better and we’ll grow from it like we always do.



September 24th, 2019 at 8:30pm

Just like I thought...the conversation earlier today went SO WELL.

Turns out, she had some of the same feelings I did. Thank goodness I said something.

It’s funny to me that I always dread these conversations, yet they bring me so much closer to my team. We always grow. We always trust each other more. We always come up with solutions and better ways of doing things.

Here’s what I learned today:

  • I began the conversation with, “I have some thoughts about how our meeting went yesterday. I’d love to hear how you thought it went and I’ll share my feelings too.” That was a good way to intro. Do that again because it gives the person the chance to speak first.

  • Feedback is uncomfortable no matter how much experience I have. I need to stop thinking that one day it will be easy. It’s not, and that’s okay.

  • The toughest part is starting the conversation. Once you start it, it will flow from there. Just start.

  • I’m glad I had the conversation, but maybe I shouldn’t have waited until today to have it. I could have called her yesterday to talk about it instead of sitting on it for 24 hours. Next time I’ll have the conversation sooner.

  • Being uncomfortable = I care. And that’s a good thing.

Today was a good day.


I shared this with you to remind you that no matter where you are as a leader, we all have these thoughts, feelings, and moments. You never really “arrive” in leadership. We’re all learning and just trying to do the best we can. 

The next time you are challenged or struggling, write about it. Maybe it will help you as much as it helps me.

Big hugs,