How to empower others without sacrificing the things you love to do
Let me tell you about a time when I thought I was empowering someone on my team, but I got it totally wrong.
First, some context: Cheyenne is our Chief of Operations. This June marks seven years since we started working together. Cheyenne’s and my roles are very intertwined: As our Chief of Operations, Cheyenne handles contracts, logistics, and all of the details that have to sync up in order for my speaking engagements to be successful. This allows me to stay focused on delivering content and meeting the goals our clients want to accomplish as a result of our work together.
One part of the business that we both touch is sales. We set up calls with potential clients and determine where our offerings and their needs align. We determine the best content depending on the goals of the session, the format of the engagement (virtual, in-person, keynote, workshop, etc.), the cost, and all the details we need finalized before we issue a contract.
I love this part of the sales process. It's one of the most exciting parts of my role because it’s very much in my sweet spot (where my strengths and motivations meet). But it’s also time-consuming. In the past, we talked a lot as a team about whether I should be involved in this part of the process. I travel a lot, and finding time to schedule these calls can be a bit complicated.
Recently, Cheyenne expressed an interest in growing in her sales acumen. We decided together that taking over the more sales-oriented parts of our client process would help with that. When I think back to that conversation now, I remember feeling a little bummed. I really wanted to empower Cheyenne and help her grow, but I knew it would mean giving up part of my role that I really loved.
Still, I wanted Cheyenne to have the experience. So I taught her how to take over those parts of my role. I shadowed her on a couple calls and gave her feedback, and as she grew more confident, the plan was for her to start taking on more calls and me to take on fewer.
But then, we had a team meeting with our branding partner. We were discussing the marketing plan that would come along with the launch of our new website, and in that conversation, we just so happened to talk about our sales process. And Chris—the amazing owner of our branding partner, Video Narrative—asked us to share the parts of our sales process that we are the most excited about. It was in that conversation that I learned that Cheyenne didn't love the parts of the process she had taken over from me as much as she thought she would. While she knows that growth often feels uncomfortable, this new part of her role was making her stretch too far. It felt like it was too far removed from her sweet spot.
That was the first time I’d heard her express those feelings. It then gave me the chance to speak up about how I felt about giving up parts of my role that I really enjoyed, and I shared that I would be really excited to take those parts back. We then took it a little bit further and realized that we both had given into a pressure that we hadn’t acknowledged was there under the surface. Cheyenne did want to grow in her role, but she also felt pressure to help me and take things off my plate. When I heard her express a desire to grow, I felt pressure to find ways to empower her, even if it meant sacrificing something I enjoyed.
This conversation was very freeing for both of us. I was excited to reincorporate these things into my role, and Cheyenne was excited to be able to focus on the things that she loves and does so well.
It’s possible that we would have eventually had this conversation and come to this conclusion on our own, but I think it would have taken us a lot longer. That’s why I’m so grateful that we got perspective from a third party who was able to help us identify this pain point. It's not that Cheyenne and I weren’t willing to be honest with each other; it's that we were both going into this arrangement with the intention of growing. Cheyenne was challenging herself to grow by learning a new part of her role, and I was challenging myself to grow by learning to let go and empower Cheyenne.
What this conversation reminded me is that sometimes, it doesn't make sense to push yourself so hard to grow. What matters so much more is that we are thriving in our authenticity. Growth is important, but it’s also important to strike a balance between growing and challenging ourselves and working in our sweet spots. And as leaders, when we’re delegating, it’s important to have regular check-ins to talk about how a person is feeling about what we've asked them to do. We also need to check in with ourselves and make sure we haven’t given up too much. Sometimes, it will be clear that it's working out for both of us. Sometimes, we might realize that we got it wrong, we learned a lot, and we need to try something else.
My biggest takeaway here is that we have to speak up when something feels off. No one can read our minds. I'm so grateful that in this conversation, Cheyenne and I could both be completely honest about how we felt because that's what allowed us to find our sweet spots again.
If you feel like you’ve fallen out of your sweet spot, I hope this inspires you to speak up to your team! You deserve to do work that you’re good at and that you’re inspired to do.
Big hugs,
