The best feedback convo ever
I recently had one of the best feedback conversations I’ve ever had in my journey as a leader. It was so good that it was actually fun. Can you believe that?!
Before I tell you about it, let me set the stage:
I had the conversation with Cheyenne, our Chief of Operations, who I’ve been lucky enough to work with for more than seven years. She has graciously supported this blog post because we think it can really help people.
Cheyenne and I work really closely together day-to-day. She’s responsible for the logistics and details it takes to bring my speaking events to life and is the main point person for all of our clients. Because Cheyenne focuses on the operations of our speaking events, I can focus on the parts that I love most: developing content, speaking and teaching, and building relationships with our clients.
Over the last few months, we’ve been in the process of adopting a new software that is taking our internal processes to the next level. (Shoutout to Cheyenne for doing the research that led to us adopting it!) This new software has been a huge undertaking: It’s causing us to overhaul many of our current systems and giving us a chance to think differently about our processes and how we want to elevate them. It’s a big investment of time, money, and energy, but we know the benefits to our team and our clients will be even bigger.
As it usually happens when we’re in an “in-between” phase of changing processes, things get messy, and details slip through the cracks. In a few cases, missing those details has had a negative impact. I’ve missed some, Cheyenne has missed some, and we’ve both missed some together. Luckily, none of them have been major, but they’ve still been frustrating.
Last month, Cheyenne was getting ready to take some time off around the time I happened to notice some of these missing details. I wanted to talk to Cheyenne about my observations and how we could incorporate double-checks into our new system to ensure we had our bases covered.
I struggled with whether to have the conversation with Cheyenne before she left or after she returned. These weren’t big issues by any means, and I didn’t want Cheyenne to be thinking about them while she was away. At the same time, I also didn’t want to wait to have the conversation. I know that addressing feedback in a timely manner is what builds trust, and as a leader, I have made a commitment to our team to address things when I feel them.
Knowing the trust that I have with Cheyenne and the way our feedback conversations have always gone in the past, I knew that we could have this conversation before she left. She had one more working day before her trip, so I asked her if we could make time for a chat. As a remote team, we often send each other voice messages on WhatsApp, so I sent her one to prepare her for our conversation. I shared the details that I noticed we’d missed, asked her to think about why they happened and if she had any ideas for improving our new system, and told her that I would be thinking about these things, too.
Because of the WhatsApp exchange before our chat, both Cheyenne and I showed up prepared. Not only did we both know what the conversation was going to be about, but we were both ready to give and receive feedback. We were really honest with each other about our reflections on why we each thought we overlooked these details. Cheyenne took ownership of the areas that were hers to own, I took ownership of mine, and we both committed to taking steps that will help us minimize the risk of missing these details again.
All of that was wonderful, of course, but it’s not what made this feedback conversation with Cheyenne one of the best I’ve ever had. What I just described is the norm for our team and is typically how our feedback conversations go, no matter who the conversation is with. That’s because we’ve worked really hard over the years to build trust, and we’ve committed to a culture of candor, which to us means we are willing to give honest feedback, receive it, and take ownership of our part.
It was the best because of these two reasons:
First, in the course of the conversation, Cheyenne shared something with me that was very vulnerable and led to a mindset shift for me as a leader. She told me that sometimes, she feels that she can’t make mistakes because every detail she handles is so important. While she knows that she has permission to screw up, she also knows that making mistakes in her role often has a negative effect on me, on our clients, or both. I was so grateful that she shared that with me and let me into her innermost thoughts. The last thing I ever want is for Cheyenne to feel that she can’t make a mistake, and I totally understand why she feels that she can’t. I took that as a chance to center us on the fact that there are thousands of details that Cheyenne tracks on a yearly basis, and no matter how hard we try to get every single one right, we’re going to miss some because we’re human. And every time it happens, I promised her that we would take a moment to pause, explore why it happened, and create a plan together to minimize the risk of the same issue happening again. Doing so is going to help us learn and become better and better—but it doesn’t mean we’ll ever be perfect. We committed to learning and letting go of the idea of perfection.
Second, we unexpectedly uncovered a process that was really burdening and overwhelming Cheyenne. I didn’t know that it was burdening her, but neither did she. We only made our discovery because we took the time to get curious, go deep with this conversation, and ask “Why?” several times. The best part was that there was an easy solution. Together, we came up with the idea of bringing in someone else on our team who has strengths in this area and who can help us build a better system that will make things easier for Cheyenne. We would have never gotten there if we hadn't been willing to get curious.
This is the gift of feedback. At its best, feedback is a dialogue. It’s not something we just dump in someone’s lap or send off in an email and never hear about again. If we prepare for it; strive to be honest, vulnerable, and curious about it; and open ourselves up to different perspectives about it, we can have a really impactful conversation that can be an inflection point for an even better future.
So thank you, Cheyenne, not only for being such a good friend and teammate, but for a conversation I will reflect back on with a smile. I would have a feedback conversation with you any day!
How about you, my friend? Is there a conversation you need to have that you’ve been putting off? What would happen if you thought about it as a meaningful conversation? What would happen if you brought vulnerability and curiosity to your dialogue? Hit reply and tell us about it! My team and I would love for you to tell us more.
You’ve got this!
Big hugs,
