How To Make Sure It’s Never Lonely At The Top

Occasionally I read a tweet or post about how hard it is to be a startup CEO, and how it can be very lonely at the top. I have a pretty visceral reaction to that because first, you are a CEO; nobody feels sorry for you. And second, if you’re doing your job well, it should never be lonely. Here’s how to make sure you’re surrounded by people who can help you make tough business decisions.

Hire The Right Executives

I learned early on the value of a strong executive team. At a company I used to work for, our executive team was stacked with high-profile leaders of some of the biggest companies in the world. I was lucky to be in that room — and, to be honest, I was just barely hanging in there. Our CEO’s goal was to get the best possible people in the room, and then get out of the way. It’s hard to imagine a decision where he didn’t have multiple people he could turn to for guidance. If you feel lonely as the CEO, you may have failed to surround yourself with the right execs.

Leverage Your Board

I have been the CEO of two companies and was lucky enough to have supportive boards and investors at both. When I joined my previous company, it was in a tough position, and we didn’t have a lot of time or money to turn it around. The list of fires burning was longer than we could possibly handle, so the turnaround was going to live or die by our ability to prioritize. I was coming in as the new CEO, and the board’s input was essential in setting the direction that ultimately helped us land the plane.

At my current company, our board members and investors are as invested personally as they are financially. I meet with them regularly to keep them up to date on our progress, bounce ideas off them and hear their ideas. 

Many founders and CEOs are too standoffish with their boards. I find the pattern recognition they bring to be invaluable. They see what dozens of other successful companies are doing right now, and have the benefit of decades of investing and operating experience. Granted there is a fine line — they are not there to run your company — but from my experience, they take great pride in helping you find the right path.

For those of you in the process of raising funds or finding outside board members, the value a board member can bring should be the single most important factor in your decision process. If you have less favorable terms from a stronger investor who would be a better advisor and partner, I would take that deal over a better term sheet from elsewhere.

Find Advisors Everywhere

Advisors are everywhere, and your relationships with them don’t need to be formal.

One rookie move I’ve seen frequently is when a founder starts signing up big-name advisors and handing out equity like it’s candy, with no real structure or expectations as to what the advisor’s role or responsibilities may be. If you want to sign up formal advisors and compensate them with equity, that’s great, but be sure to set (and document) very clear expectations of their time commitment and how they will engage with you and the company. The grant should vest over a period of two to four years, and they need to be actively advising for the vesting to continue.

While formal advisors can be helpful, I’ve personally found my informal advisors to be the most valuable: former colleagues, people I’ve met at conferences, friends from the neighborhood. My dad happens to be an executive coach, so that’s been amazingly helpful over the years. While formal relationships can be great, I get more value from lunch or a beer with someone whose opinion I trust.

Build A Network Of Peers

Recently, I’ve been meeting with a group of five CEOs from companies in NYC of a similar size but in noncompetitive businesses. We meet once a month for “CEO group therapy” hosted at one of our offices over breakfast. We do a quick around-the-room of what we’re working on, what’s going well and what’s not. Occasionally we’ll pick a deep-dive topic where one of us has the expertise to get more granular. While the businesses may be different, the similarities in the stage of growth and employee base translate to similar challenges. Even if none of you have a good answer to a problem, it’s hard to feel lonely when you have four other CEOs facing the same issue.

As a founder or CEO, it’s not your job to have all the answers or make all the decisions. The most important part of your job is to get the right mix of experience, talent and strengths in the room so you have the right people making the right decisions at the right time. If you are feeling lonely at the top, you may not realize the power of the network you have or how much more powerful it could be.

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    Occasionally I read a tweet or post about how hard it is to be a startup CEO, and how it can be very lonely at the top. I have a pretty visceral react
    [See the full post at: How To Make Sure It’s Never Lonely At The Top]

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