December 9, 2024
December 10, 2024
I first came across Erin DeCesare’s unique approach to leadership when I read about her use of improv exercises to fuel innovative thinking on her teams. My immediate thought was: “I want to hear more!”
Erin is the Chief Technology Officer of ezCater, a food tech platform for workplaces, where she merges creativity and emotional intelligence to lead the company’s engineering, technology, product and data analytics teams. In an industry that often shies away from, or downright shuns, emotions in the workplace, Erin uses them as a superpower to get teams to think outside the box and create equal opportunities to share ideas.
I had the pleasure of sitting down with Erin as part of Mission North’s Women Leaders Q&A Series. We talked about her approach to leadership, how she uses creative prompts to fuel engaging meetings, and how she’s getting her team comfortable with the lightning-speed pace of AI advancement. Below is an edited version of our conversation.
What factors have shaped your approach to leadership?
I was introduced to the concept of servant leadership early on in my career, when I was taking on a senior leadership role for the first time, and it really changed my trajectory. I learned that leadership is not about being the smartest person in the room or making all the decisions. It’s about creating an environment where you’re inspiring others to feel empowered and creative. That was a much more inviting philosophy for me and better matched my own personality.
Another transformative moment was working with Anese Cavanaugh while at Vistaprint and being exposed to The IEP Method, which stands for intentional energetic presence. The idea is to be aware of what energy you’re bringing into the environment as a leader and what impact you want to make. To this day, I start every meeting and every conversation by asking myself: ‘What am I hoping to get out of this meeting, and what needs to be true to achieve that outcome?’ ‘How do I need to show up and what do I need to believe about the people attending the meeting?’ It really helps me identify the emotional dynamics of a situation so I can show up with the right energy and make an impact.
<split-lines>"Leadership is not about being the smartest person in the room or making all the decisions. It’s about creating an environment where you’re inspiring others to feel empowered and creative."<split-lines>
What do you know now about being a leader that you wish you knew 10 years ago?
One lesson that has been life-changing as a leader is that you can’t solve everything for everyone. Servant leadership doesn’t mean you’re constantly taking people’s complaints and being the fixer. The real goal is helping others solve a problem themselves. Women leaders often end up in this problem-solving trap, and it’s something I’m still working on. When someone comes to me with a problem, I try to coach up and repeat it back to them: ‘This is the problem I’m hearing, what do you think about that?’ Then, I help them draw a conclusion and come up with their own recommendation.
How do you encourage women and other underrepresented teammates to have a voice during meetings?
It’s so easy to get stuck in that default mode of a meeting where the loudest person in the room or the first person to put forth an idea ends up dominating the conversation. I’m a big fan of creative prompting as an antidote to that. At the beginning of a meeting, I give everyone a creative prompt to help us explore a topic, like, ‘What’s one approach to solving this problem?’ Everyone in the room answers the prompt, we vote on the most interesting ideas, and then explore them further.
I do this type of meeting every Thursday with my leadership team. Those who couldn’t come up with an answer on the spot can contribute in Slack afterward if that mode of communication works better for them. This structure helps everyone have an equal voice. It’s typically the person you don’t hear from as often who makes the most interesting contribution. This approach has led to richer discussions, quicker problem solving and engagement from a more diverse group.
What advice would you give to other women who are navigating their path to leadership?
Don’t care about what other people think. Obviously, it’s easier said than done and I’m still trying to take that advice myself. I think what holds women back in particular is getting in our own heads and worrying about how we’ll be perceived. Are we being too assertive? Not assertive enough? We can end up losing our authentic self. The best advice I’ve ever received was when someone told me, ‘You’re at your best when you’re analog Erin.’ In other words, when I’m not overthinking things and simply saying what I think and how I feel. It can be difficult to tap into that.
<split-lines>"I think what holds women back in particular is getting in our own heads and worrying about how we’ll be perceived. Are we being too assertive? Not assertive enough? We can end up losing our authentic self."<split-lines>
What are you most excited about right now?
Experimenting with AI has been fascinating, especially over the past year. Things are changing so quickly. Teams are used to navigating big changes and new challenges once a quarter, but now with AI, it’s happening once a month. Our job as leaders is to get teams comfortable with this rapid pace of change. It feels like free-falling.
<split-lines>"Teams are used to navigating big changes and new challenges once a quarter, but now with AI, it’s happening once a month. Our job as leaders is to get teams comfortable with this rapid pace of change."<split-lines>
What I tell my teams is, what if we think of it like going down a roller coaster instead of falling off a cliff? What if this could be fun? My job as a leader is to help them go along for the ride and have some fun with the free fall.
