CHALLENGES FOR A LEADER PROMOTED FROM WITHIN — HOW TO WEAR FEWER HATS?
In my leadership practice, I often work with founder-led companies. Some have been around for a long time, and even some of those are run by founder CEOs who — even after building out a great leadership team – – still struggle with letting go of some responsibilities, especially in areas where they are technically very adept.

I’ll give you an example from my own experience. When building a sales organization for a company that I have founded or co-founded, I’ve wanted to stay close to the sales process with an eye on the sales pipeline and an interest in working with the customers themselves. So, it could be difficult for me to let go and bring in others to lead that process. It was an area that I would drift to naturally.
I don’t think that maintaining this kind of involvement is a bad thing: I just think it prompts a balance question.
To the concern about how a founder steps into the CEO role with a team that he or she delegates to — that kind of letting go — that’s honestly the dream! To have a team that is better than you, smarter than you, more experienced and skilled than you in multiple areas — as opposed to you being pretty good or OK at all of them. I think of everything from sales and marketing, to engineering and operations, to finance, administration and legal.
Once, as company founder, I was doing invoicing and cutting checks on the weekends. I was so excited to find and hire a Director of Finance because it allowed me to let something go. I still had enough knowledge of the system to be able to ask questions and review reports, and so I didn’t let go totally — I didn’t abdicate that work. In fact, because of my knowledge and prior experience, I was able to better manage and guide that piece of the business. For other areas like the deep operations or delivery side of things, areas that weren’t necessarily my strength, I had always relied on other people who had that genius or that talent. The trick sometimes is to get more deeply involved or lean into some of those areas so you can gain some knowledge, and function as an effective sounding board and accountability partner.

Thinking about the issue of letting go another way, you have to remember the bigger “why.” Of course, all founders are different. Some want to abdicate — have someone else run the business so that they can go to the next thing. If that is your motivation, that’s OK.
The challenge for all of us is that when you want to grow and scale, and you have a great leadership team filled with top talent, are you getting in the way or showing them what to do when they know rather well what they are doing?
The dynamic presents a challenge: are you becoming the lid on leadership, and not allowing growth? That is what I think founder CEOs need to watch out for. If you’re in that situation, I think you’ve got to go back to your “why.”
Why are you growing this thing, scaling it, and what are you trying to achieve?
Your role as CEO is critical in making sure that the team can trust and rely on each other to adapt to changing circumstances, and to make the next big strategic decisions.
And you, having a very unique vantage point and history, are best equipped to guide them.
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