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Four Leadership Lessons From A VC To First-Time Founders

By Navin Chaddha

October 19, 2018 –

When emerging founders imagine a group of successful entrepreneurs talking over dinner, they might expect a conversation about yachts and second homes. In reality, I’ve found that many accomplished entrepreneurs are so focused on building their companies that they tend to just ask one another advice. They can be paranoid and want to get feedback from as many great people as possible.

That was certainly the case last month when I hosted a dinner with a dozen successful serial entrepreneurs. At one point, I wondered aloud what they would tell their younger selves; in no time at all, the ideas were gushing forth like water from a firehose. While their thoughts covered nearly all aspects of starting a company, there was one area that everyone agreed was most important: personal growth.

This wasn’t a big surprise. Over the years, I’ve found that successful founders are often eager to talk about how they’ve evolved as executives. And, as an investor who has backed countless first-time founders, I know how steep the learning curve can be.

Early on, a founder needs to do everything. But as a company grows, the founder’s role changes. In my experience, the style of leadership that netted the company’s initial success often won’t help it reach its next milestones.

It’s not an easy transition. But I’ve found that the founders who are most successful learn how to do these four things.

1. Accept your new role.

As your company grows, you can likely no longer interview every employee, approve every new product feature, or sit in on every customer meeting. You probably don’t have enough time, and you’ll just slow the company down.

Instead, the founder’s job becomes articulating the company’s vision and evangelizing culture. Doing these two things well can help you onboard new hires and motivate employees that you may never personally know.

2. Learn to multiply yourself.

As a VC, I’ve noticed that founders who are used to working closely with early teams can start to feel a bit lost when a company starts adding layers of employees. They sometimes react by micromanaging, and they sometimes become distant and wall themselves off.

I believe scaling as a leader means resisting both urges and, instead, figuring out how to be more visible and approachable and interacting with large portions of the workforce while not getting bogged down by any one part. At startups, the founders are often the culture, and so being able to have meaningful, albeit brief, interactions with employees is one factor that can allow your culture to scale.

One of the CEOs I spoke to said his personal goal is to use Slack to “touch” at least 200 people out of several thousand in his company a day. A quick “nice work” note from the boss can let employees know that their hard work is noticed and appreciated.

3. Make yourself vulnerable.

Everyone makes mistakes, and success doesn’t come from being perfect. Instead, I believe it comes from surrounding yourself with world-class people — like employees, board members, executives and advisors — and then trusting them.

Too often, I’ve noticed founders think they need to impress their board members by only showing the positive aspects of their business. Meanwhile, in the background, they’re frantically trying to fix any number of problems.

Board members usually know that the path to a great company is filled with missed quarters, bad hires and many other wrong turns. In my experience, successful entrepreneurs understand this and know how to engage their board in a trusted relationship.

Similarly, I’ve noticed that employees don’t want perfection in a CEO — they want to see a real person that they can relate to, for better or for worse. People will tend to stay with you and give you their blood, sweat and tears if you show them who you truly are and engage them in your journey.

4. Be open to criticism and endorse candor.

I find that my best and most productive relationships are with founders who are able to receive and engage with critical feedback. We have these conversations with the shared goal of making the company better. And it usually ends up that way.

These founders tend to be confident enough in their own abilities to understand that feedback on, say, a new product idea isn’t criticism of their leadership or the company more broadly. Many founders, however, don’t have this level of confidence, and they sometimes allow critical feedback to feel bigger than intended. Confidence comes with time and success, but early-stage founders would do well to remember that the people who want to engage with them on this level — including VCs — are usually their biggest supporters.

The qualities I’ve mentioned here require introspection, which doesn’t come naturally to all people, especially when they’re busy trying to run a fast-growing company. But that’s part of what VCs can help with. After all, great CEOs aren’t born: They’re made.

Originally published on Forbes.


Four Leadership Lessons From A VC To First-Time Founders was originally published in Mayfield Viewpoints on Medium, where people are continuing the conversation by highlighting and responding to this story.

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Published on Oct 19, 2018

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