Over the years, I have mentored a number of startup CEOs, and I’ve been one myself for over 30 years. I’ve made numerous mistakes over those 30+ years and have seen others in the same position making the same mistakes. In my mentoring role, I’ve been able to help CEOs and executive teams struggling with issues that seem to follow the role no matter what the company does. There’s a remarkable similarity in what I had to go through and learn as a CEO and what I am now helping others deal with.
As I look back on my experiences, I wish I had this article to read 30 years ago. I want to talk about what’s important, what your priorities should be, what your team is looking for from you – and maybe a little of what not to do in your role as a startup CEO.
The Role of a Startup CEO
Be Willing to Do Anything
First, be willing to do anything that needs doing. You aren’t the king with loyal subjects to do your bidding. A startup has an endless list of stuff that just needs to get done, and there aren’t always enough, or any, people to do it. Whether it’s writing code, being a tester, putting new ink in the printer or emptying the trash, establish the mindset that if it needs doing, do it. Your team isn’t going to think less of you, in fact, it’s quite the opposite.
You Don’t Have to Do Everything
While it may sound like I’m contradicting myself, stop believing that you have to do, or be able to do, everything. The difference is that there are things that must be done (just do them) and stuff that you are better off letting your team do (like their jobs, for example). This is part of not having to be the smartest person in the room, and instead learning how to trust your team and delegate tasks effectively.
I fell into this trap very early in my career. I was CEO of a software consulting firm that employed about 15 developers doing systems-level coding for Windows and NT. The belief I had was that, as the CEO of a startup focused on software consulting, I needed to be the best programmer in the company (I wasn’t) and had to have answers to every question that came up, technical or otherwise (I didn’t). In short, I felt I had to be the smartest person in the room, because I was the CEO. Not only was I definitely not the smartest person in the room, the fact that I believed I had to be created an undercurrent of tension and a bit of resentment.
A Startup CEO Should Believe in and Trust Their Expertise
The more you believe in your team and rely on them to do what you hired them to do, the more they are going to believe in your leadership abilities. I used to think that if I wasn’t the ‘best at everything’ in the company my team would wonder why I was in charge. I have discovered since then that the opposite is true. They aren’t following you because you are such an expert in everything, they are following you because they believe in your idea and that you can lead them to success. Being a startup CEO is a unique skill, focus on becoming great at that and not being the overall expert.
Learn to Delegate Effectively and Listen
I decided a long time ago that the goal of the perfect CEO should be to have nothing to do. In reality this is, of course, an unrealistic and unreachable goal, but it speaks to the need to be a great delegator as CEO. You have an executive team there because you believe they know what they are doing. Let them do it.
Ask Questions, Lots of Questions
Many times it is better to not vocalize an opinion, and instead focus on asking all the right questions. When I was running my first VC-backed startup back in the early 90’s, I would run my business meetings and always have an opinion about whatever we were talking about (smartest person and all that…). Sometimes I would cut the conversation short with ‘I think we should…’ without hearing the entire conversation or making sure everyone was heard from.
I think I did this for several reasons. Primarily, I really thought I was the smartest person in the room (this was a real problem back then), or at least had to create that impression with my team. I was fortunate to have someone on my team that was willing to be honest with me. He told me, “When you gave your opinion in that meeting, it was like putting it on the front of an 18-wheel truck and driving it through the room.” Effectively, he was telling me that moment when I had vocalized an opinion, the conversation was over. Nobody was willing to argue; I hadn’t developed that level of honesty in communication with my team.
Whatever I had come up with, no matter how wrong or bone-headed, was interpreted as the law. I once ended up with a telemarketing team that made no sense at all, just because I wondered out loud in a meeting whether we should have one. Now some of this is also based on the maturity and experience of the executive team, but if you are a new CEO, it’s likely that your executive team is also pretty new at this.
Sharing your own opinion too often can discourage your executive team from sharing opposing thoughts without fear of criticism. On the other hand, asking questions allows your executive team to feel you value their opinions (which you should) and encourages them to share those opinions without the inherent fear of speaking out against your own.