A CEO’s Strongest Support System May Be Found in Other CEOs

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The third entry in our founder wellness series explores advisors and CEO peer groups – informal communities where founders can be honest and get honest feedback.

Guiding a company through a pandemic and an uncertain economy is intense enough for any one of us. Yet oftentimes, CEOs have nobody to talk to about their leadership challenges and how they’re holding up, making it that much harder.

One of the reasons we launched this series on founder wellness is because we know how lonely it can be to be the CEO – and that was before isolation protocols and non-stop Zoom meetings. In our last blog, we acknowledged that as CEO, you cannot always open up to your employees. You may have a founding team to share the burden, but ultimately, the buck stops with you.

We also know that it can be hard to be vulnerable with your investors. While we partner with entrepreneurs as colleagues and counselors, we understand the dynamics are more complex. We want founders to be able to share their inspirations and frustrations with us. And yet, we know the relationship is not the same as talking with a peer.

That’s why we encourage peer support systems like CEO circles.

Building a Community Across Companies

Founder peers can be invaluable. So can co-founders, informal mentors, advisors, and friends, though no one can truly understand what it’s like to run a company unless they have undergone the journey themselves. Your fellow CEOs in the startup community are often going through many of the same challenges you are.

A few months into the pandemic, we worked with Reboot to launch two CEO Circles across our portfolio. Eight leaders commit to meeting once a month for a year. Within these small groups, CEOs can share ideas, as well as the joys and strains of leadership.

Founders in our portfolio have told us that these are the most meaningful new connections they made through the whole pandemic. “The ability to speak candidly with peers is very helpful in facing the challenges of our roles,” participants often say.

“Hearing other founders be vulnerable,” was another reason founders kept returning to their CEO Circle, even though the last thing they need is another 90-minute commitment. What makes CEO peer groups most helpful is just “listening to other’s experiences, knowing they are going through similar situations. Getting their feedback and advice on our own situation.”

It’s Important to Walk the Talk

Valuing that connection shaped Flourish’s CEO Retreat earlier this year. We wanted to give our CEOs space to reflect and focus on wellness, but most importantly to build authentic relationships across our portfolio.

At the retreat, we also made clear that as investors we value self-care. Sometimes, CEOs may feel reluctant to take vacation or time away from running the company to stay healthy. That’s why we promote CEO Circles, leadership coaching, retreats with co-founders, and tools like Modern Health.

Just as we make these resources available to CEOs, we encourage CEOs to make similar resources available to their employees. During the pandemic, many people found support through apps like Calm or BetterHelp and clinical care offered by their employers. It’s also important to bring employees together, to build relationships and team morale – similar to how investors bring like-minded founders together.

For CEOs, it can be difficult to spend money on these benefits and activities unless their investors clearly value it. Our hope is to model wellness for startup leaders so that they, in turn, will model wellness for their teams.

Finding People You Can Trust

Bringing your team together is affirming and motivating for a leader, but you probably still need a peer to work through the tough issues.

As we noted in our last blog, even leaders who encourage feedback may not get the unvarnished truth from employees. It’s not easy to critique the boss. And there are some problems – business as well as personal – that you can’t share with people who work for you.

You need somebody to confide in. Somebody who can be honest with you, and let you know if or when you need to make an adjustment in your leadership approach. If you went through a startup incubator or accelerator, the peers in your cohort would be a great place to start. Some entrepreneurs we admire have taken a very pioneering approach: reaching out to potential mentors and assembling their own informal, personal board of advisors.

Executive coaches and services like Reboot or Torch will do a 360 evaluation, talking with you and your team to get an objective viewpoint and advice that you can use and easily put into practice. Coaches can help you cultivate self-awareness and discover how you work best – especially when your company is growing fast.

Put on Your Own Mask First

We offer all these services to our portfolio companies, but ultimately, as a CEO you’ll need to find someone who can give you an honest reflection of how you’re doing. Mentors, advisors, and CEO peers are invaluable. They’ll keep you balanced when you’re overloaded and overwhelmed.

If your investors offer bonding opportunities with other CEOs, take advantage of them. Not just for “networking” or to participate in another workshop, but to build authentic relationships. That’s what it’s all about.

Then, give your employees the same opportunities and resources. As the airline crews alway tell us, “Put on your own oxygen mask first, before assisting others.” That’s good advice for CEOs too.

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