How to be a more effective startup CEO by getting out of your people’s way

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A good friend had been working for a startup for about six months. He was very excited about it initially. It involved robots, artificial intelligence, and some large-scale computing problems. It was right up his alley. We went out celebrating when he got the job, and he gushed about how cutting edge their technology was.

Now, he was six months in and things were starting to lose their initial luster. The company had amassed an impressive amount of venture capital and had poured it into developing their cutting-edge product. Yet, despite having what my friend described as “some of the smartest people I have ever worked with” on their team, they had yet to ship a single unit. They had a demo scheduled for their first customer in six weeks and they were way behind.

I was out in my yard on a Saturday, cleaning up some leaves, when I got my friend’s text. He’d planned to come by for lunch and a relaxing afternoon walk around the neighborhood. We rarely see each other, so it was special.

“The CEO wants us to come in every Saturday for the next six weeks to finish the product. Starting today. Sorry, I have to miss lunch,” he said.

I didn’t see my friend in the following six weeks. What I know was happening was that the previous round of funding was running out fast. The next round depended on getting this first customer onboard. Things were looking precarious, and so the CEO, having lead the team into this valley of despair, was putting all of the pressure and responsibility on the team to lead themselves out.

Some heroic but futile efforts followed to dead-lift an impossible product in an impossible timeframe for a CEO who was completely out of touch.

When I talked to my friend by phone on the final Saturday, he was at home. He was supposed to be at the office with the team. “Screw it,” he said. “I called in sick. On Monday, I am giving my notice.”

I don’t blame him one bit, and he was neither the first nor the last to quit during that six-week blitz. That was over a year ago. My friend is now happily self-employed as an independent technology consultant, and that startup company has since gone out of business.

Why are there so few good startup CEOs?

My friend’s story is hardly unique. A couple of times a week, I talk to someone who tells me “a startup CEO bad behavior story.” I have begun to collect these anecdotes so I can include them as anti-patterns in my public talks. Heck, maybe it’ll become a book.

Startup CEOs seem to come in two flavors. There are former employees of other companies who were usually either tech or salespeople. They are tired of working for someone else, so they strike out on their own. If they have any leadership skill at all, it’s usually because they held some management position in their last company. This doesn’t help them as a startup CEO at all.

And then, there are those with MBAs. Fresh out of business school, they come armed with marketing and finance knowledge. They can certainly run a P&L but are often horrible managers. (To my friends who have MBAs, I don’t mean you guys, of course!)

Neither of these two typical CEO flavors come equipped inherently with the capability to lead other humans. Leadership is a discrete skill. It must be sought out through coaches, mentors, and advisors. It’s not something that one just “knows” or was taught (at least not effectively) in business school. And it certainly doesn’t emanate organically from anyone’s middle management experience.

Talk less, listen more

For starters, leadership requires a great deal of empathy for your people. And to build empathy, you need to learn how to listen effectively. Nearly every CEO horror story I have encountered over the years has started with a CEO who doesn’t really know how to listen.

Empower your people to think, not just do

Compose your organization out of small autonomous units

Structures to support autonomy

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