A gritty Brooklyn warehouse space edged by a stark black curtain was a fitting background for hearing one of the tech world's best-known CEOs admit he'd had moments of feeling over his head.
"Running a successful start-up is no walk in the park. You may have a hockey-stick looking growth chart, but there's always chaos in the middle of it," Crowley said. "The more I talk with other folks from start-ups, I learn we're all going through the same stuff."
Fear, Learning, and Doing "Stuff You're Not Good At"
Colonna started the panel asking for CEOs in the audience to raise their hands. "How many of you are scared shitless sometimes?"
Unsurprisingly, few kept their hands raised.
"Somehow, people sometimes think that admitting they don't have a clue will get them fired. I encourage people to own up to the fact that they're figuring it out, that you're inventing new things, and that sometimes you're going to get it wrong," Colonna said. "When you admit it, it makes it OK. No one has gone to school to be a CEO--you don't learn this except by getting in there and figuring it out."
He also noted that once you're the CEO, you're not doing the work anymore.
"You'll be measuring progress by meetings you attend and emails you send. It's a transition from doing to being. It can be very unsettling because you can't look into the corner and say, "I did that today."
Crowley agreed, stating, "I was a good rapid prototyper, but I didn't feel comfortable doing the business development or CEO stuff. But at some point you have to do the stuff you're not good at to push the company forward."
First Step: Admitting You Don't Know all the Answers
Crowley told the crowd: "When we were around the kitchen table building this product and looking for funding, we didn't know what investors want to hear at a pitch, and there was no shame asking for help. But somehow there's a stigma for asking for help at the current point in our organization."
Colonna added: "Do you have the guts to tell your team an investor-meeting went poorly? They can see it in your body or your face. But can you tell them and talk it out?"
Growing--and aging--and getting wiser as your company matures is a natural process. Crowley said that's how he sees his path these days.
"I can see myself maturing into the role. We had to have the discussion--your job isn't to code anymore, it's to lead the company and make sure everyone who comes in knows what they're supposed to be working on, and why the company exists," he said.
Leading Means Encouraging Open Dialog
"The best thing I can get from people at company is feedback in one on one meetings," said Crowley. "We have them weekly even if we don't have anything to cover and it's only 10 minutes. I say 'what is it that's preventing you from getting your job done?' They answer, and in the process, they tell me what I'm screwing up and what I can do to make their life easier.
Along the way, Crowley gets help from advisors, mentors, and his coach, and each has a particular role in giving advice.
"There's a difference between a mentor and an advisor," Crowley said. "An investor may be an advisor. We tell them our strategy, and they try to help us. I get emails all the time from people who want me to advise their company. But typically that person has skin in the game. On the other hand there are mentors or coaches like Jerry [Colonna, his business coach] who help me solve management or personal problems with my job. These are different discussions than the business model problems. I get different feedback from those types of people."