Everyone Needs Help

A fascinating part of VC is sitting on the board of directors of companies you invest in. You get a view almost never offered to public market investors.

I sit on the boards of a few of our portfolio companies. One thing that has stuck out to me: Everyone needs help.

Running a business is hard. Brent Beshore equates it to eating glass while being punched in the face. Being a CEO of a young company requires the ability to endure the frontline fatigue of a soldier with the leadership of a general.

The board is an interesting creature in that battle, because a CEO has to simultaneously be the Commander in Chief and answerable to the directors, while directors have to simultaneously be the CEO’s trusted advisor and their overseer. The balance is – and I say this very generally – a CEO who is in charge of everything and a board who has to figure out where they’re wrong and how both parties can strategize to do something about it.

What happens in this situation I find fascinating: Problems a CEO doesn’t notice or confront on a daily basis are often discovered in board meetings.

Why? I have a theory. And it applies to everyone, not just CEOs and boards.

There is a natural desire to appear competent in front of people who rely on your competence. Rallying your troops – employees, customers, suppliers – behind a defined strategy is critical to leadership, and the appearance of doubt when you’re in charge is good way to sink morale.

So day-to-day, doubt can be buried beneath a well-intentioned display of leadership. It’s not until you’re with a group that allows you to comfortably say, “Here’s our strategy, but we need help with it,” or, “I’m having trouble with this, how would you solve it?” that the most essential part of your thought process is given airtime. And boards effectively require those conversations, whether they come naturally or not. They reveal – even release – problems and questions that are silenced day-to-day. Not silenced by ego or deception; Just the natural desire to show your colleagues black or white in an overwhelmingly gray world.

I’ve realized that a key – though certainly not only – benefit of boards is giving a CEO one of the only outlets they have to ask for help on topics that most people would expect a CEO to solve on their own.

“What would you look for in a person to fill this role?”

“Are these projections realistic?”

“Are we getting ahead of ourselves?”

It’s not that the board is so smart that they can provide every answer. It’s that laying out a time, place, and structure where help can be asked for opens up minds and reveals that, in the real world, everyone basically needs help with everything.

The most important problems anyone faces are the ones that outwardly seem beneath your qualifications, because they’re the problems you’re likeliest to ignore.


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