Lessons Learned on the “Founder” to “Executive” Transition

For the past 7 years, I’ve identified myself as a start-up co-founder. Alex Cyriac & I started Lively, Inc. in 2016 and so much of what has defined us are the things we were willing to do in those early days to push the boulder up hill. I am almost positive that every other founder can empathize with us.?

However, one thing I’ve come to appreciate and understand is that the things that enabled us to get to where we are today can’t be the things that get us to where we’re going. While Lively has been on its journey, I’ve found myself on a different one - one that requires me to move from a Founder to an Executive.?

This all started a few years back when we began with our initial 360 review process. Until you see how others see you in writing, you are really blind to different perspectives. My feedback was a tough pill to swallow but one that got me to actively work on some of the constructive points. I was too in the weeds and detail-oriented, I had formed a conclusion even before hearing various perspectives, people came to me/Alex for decisions vs. making them on their own, etc. If I am being honest, at the time, I was proud of a handful of those things. My perspective was that I wasn’t going to be a disconnected founder, but one that could always know what is happening and be ready to roll up my sleeve and get into the nitty gritty alongside our team.?

What I didn’t realize about that perspective was that it was a bad use of my time and strengths. Despite my best intentions, my involvement in certain places actually prevented empowerment of others to make decisions. I unintentionally became a crutch without even knowing it. What Lively required of me was more than what I was giving to it.?

I concocted a story in my mind that I needed to be the expert in everything that I oversaw. But that simply wasn’t true. My job wasn’t to somehow magically get decades of experiences across multiple functions but rather find those experts that fit our culture, convince them to join the org, and then fight like hell to remove roadblocks so we could be successful.?

I began shifting my approach in subtle ways:

1. When a meeting invite came, if it didn’t have a description for what we were going to discuss or an agenda, I would decline it. I had to protect my time and make it clear that every minute spent working in the business is a minute I couldn’t spend working on the business.
2. I created a system for asynchronous monitoring so I didn’t need to have as many live conversations to understand what was going on.
3. I focused on communicating the most important things that I could think of to help move the teams forward. And then said it again. And again. And again.
4. We leaned into specialized outside recruiters to find senior level talent to bring into the org. A very important lesson I learned was sometimes you have to spend money to save money. Let that sink in.?

As a founder, you oftentimes get the benefit of the doubt on a whole host of topics. When you make a mistake, it seems that more people have empathy for you than if you were simply just an executive. I don’t know why that is and don’t believe it is fair. But it is what it is. Feedback typically doesn’t come your way. You have to go look for it. The easy thing to do is sit back and pretend everything is going as you expect but without asking hard questions and pushing yourself to be the best version of yourself, you will be operating with blinders on.?

It very much feels like I am in the first quarter of this journey. We continue to do 360 reviews each year and to me, trust is the single thing that helps create the bridge for this transition. You need to have trust in yourself that as a founder you did what you could to instill the values you want in the business. You need to trust in the systems you put in place so that it helps others make meaningful decisions. You need to trust the people you bring in to elevate the business to the next level in ways you could have never done without them.?

My journey isn’t over. But I hope these insights help others along the way.?