CEO Shift

3 Mistakes I Made as A New CEO


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When you’re building a business, you’re going to make mistakes. It’s how you respond to them that determines whether or not you’ll still have a business five years later. Knowing which pitfalls to avoid is key. Listen as I share the three mistakes I made as a new CEO. 

First up, I definitely needed to have more of my contractors be client facing, sooner. When I started bringing on contractors, I was already on the brink of burnout. Then I had a team and instead of finding relief, I found more responsibility. Because they weren’t client facing, I was still taking on the bulk of my business while then having to relay information. 

It was a problem. Once my contractors started being the ones interacting directly with clients, that’s when the whole structure of my business started to shift. 

Next, I wish I’d learned to trust my gut a little bit sooner. Not just with clients but also with hiring team members. If I had, I would have acted more quickly when I realized some of my first contractors were not a good fit and I would have saved myself thousands of dollars and many, many hours of time. 

Last, I did not have any kind of contractor onboarding process when I started hiring. In fact, I told my first contractors that we were building this ship together. But if I had taken a moment before hiring them and asked myself, “What do they need to be successful in this role?” I would have had at least a basis for training and responsibilities put together for them. 

Obviously I go into more detail in the episode, so take a listen, but these are the three things that I would have done differently had I known better. I don’t believe in having regrets, every “failure” is a moment in which we can learn. But I do wish I’d had hindsight to help me with these things at the time. 

What do you wish you’d known sooner? 

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CEO ShiftBy Jenn Bays