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Webinar Offers a Clinic on Tech Leadership

Earlier this week I did something I don’t do often enough. I joined a webinar that I wasn’t involved in as a host, moderator, or guest. I really wanted to hear what these particular panelists had to say.

The webinar, hosted by GGV Capital, was tied to a news event. The “pizza tech” company Slice had just raised $40 million from a variety of players that included longtime investor GGV. But the most intriguing new investors were former Twitter honchos Adam Bain and Dick Costolo. The two are now partners in their own venture firm, 01 Advisors.

GGV assembled the two Twitter vets and Slice founder Ilir Sela to talk about the deal. But then there was a wider discussion about the life of a founder and what defines successful leadership. It was well worth the time for anyone who loves this kind of content. The conversation was led by GGV Capital Managing Partner Jeff Richards.

We covered the newsy bits from the webinar earlier this week. Today, we’ll share some highlights from the deeper conversation about what it takes to run a tech company. The biggest and least surprising message from the conversation is that leading a company to scale is a tough battle with very few lulls in the action. Dick Costolo shared an anecdote that sums it up.

“I had a young YC founder come up to me in a coffee shop in San Francisco, pre-pandemic, and he asked me, ‘If you could give me one piece of advice, going into starting and running a company, what would it be?’ And I just said, ‘It’s always hard. Remember that and you’ll be fine.'”

Watch the Webinar Here

Leadership Lesson: Remember that You’re in the Forestry Management Business

Dick made the point that CEOs who spend all their time stomping out small fires risk missing the big existential threats. Not to mention the transformational opportunities.

“A CEO called me the other day and he said, ‘Hey you know now that we’re this size, and there are five things on fire and I don’t know which one to put out.’ I said ‘Yeah, because you’re not firefighting anymore. It’s forestry management.’ You have to live with the fact that there are always going to be new things that are on fire. And you have to put them in the back of your mind and say ‘I can’t go do that right now.'”

The most important thing for leaders is to be disciplined about how they spend their time. And they need to choose the activities that produce the greatest leverage. This means being a forest manager and leaving the actual firefighting to those with front-line responsibility.

Leadership Lesson: Watch the Road Ahead

Another lesson these leaders have learned the hard way is to not focus too heavily on the competition. Play your game instead, Adam said.

“We used to talk about competition like driving a car. When you’re driving a car you have your rearview mirror. And when you drive you’re looking at the road ahead. And every once in a while you glance at the rearview mirror to check in on what’s behind you. I think that’s a pretty good analogy for competition. It’s fine to glance at the rearview mirror every once in a while. But you can’t drive while looking in the rearview mirror the entire time or you’re going to hit the wall.”

Ilir said the most important thing is to remain laser-focused on the “why” of your business. That’s the core mission that drives everything you do.

“If that ‘why’ is powerful and clear and focused on the customer, then that becomes the team’s main focus and where the motivation and aspiration and goals come from. If your ‘why’ is ‘Hey, I want to be bigger than DoorDash’, then the focus is going to be on DoorDash. And that can’t be the case.”

Leadership Lesson: Keep Your Eyes (and Calendar) Open

Dick and Adam shared some leadership lessons they gleaned from spending time with special forces veterans. They didn’t mention if any tactical training was involved. But they clearly learned a lot about effective leadership, especially within small teams.

Adam shared some key lessons from those conversations. One was that the team leader cannot get bogged down with day-to-day tasks and lose sight of the big picture.

“Everybody has a job in that small team, except for one person. The only person that doesn’t explicitly have a job is the leader. And the reason why it is the leader should be looking where no one else is looking. And I thought that was a pretty interesting story about leadership. High-performing organizations should be set up in a way where that leader is looking where no one else is looking.”

Dick later cited similar logic when he made a point about CEOs avoiding the overscheduling trap.

“One of the things that maybe is counterintuitive is, as you grow and scale, it’s more important that you have lots of free time on your calendar. And you’re not in meetings back to back every half hour from 8 am till 7 pm. So having free time to be able to look at the things we’re not thinking about right now because they’re not important to the next quarter that everyone else is jamming on. We really need to be thinking about it but you don’t have free time to go do that, or talk to people in the organization about it and think and focus, you’re always going to be on the treadmill.”

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