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Commentary: ‘Crying CEO’ post provides leadership lessons on authentic vulnerability

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Prem Kumar.

Editor’s note: The following is a commentary written by Prem Kumar, co-founder and CEO of Seattle startup Humanly.

Braden Wallake, the CEO of HyperSocial, now known infamously as the “Crying CEO,” caused a social media storm last week by sharing a LinkedIn post that featured a close-up selfie of himself crying — taken right after executing a layoff at his company. 

Many went after him hard with mocking retorts and calling him out for narcissism while sharing in a collective cringe. 

While a social media pile-on is rarely productive, situations like this can be teaching moments.

As a founder/CEO, I reached out to several peers to discuss this gaffe and the broader context of public vulnerability as leaders after seeing this story unfold.

Why did this post cause such an intense stir, drawing in thousands of comments and opinion pieces in mainstream media? 

As a founder who has been in similar challenging situations, the problem with Braden’s post was not that he cried. It was that he made the post and the situation about himself and his emotions — while members of his team were impacted by job loss.

Braden is someone who, like myself, gets to come into work every day doing a job we created for ourselves. Being a founder/CEO is a choice. Being laid off is not. 

The attention should have been focused on the latter — at least in that specific moment. 

Being a founder or CEO is not without its many challenges; even on good days, we have a very complex job. And yes, sharing vulnerability about the many difficulties is not only OK, it is usually a healthy and emotionally intelligent thing to do, with benefits for not just ourselves but our teams.

But context, content, timing, and focus in sharing matter. In fact, there are few parts of the CEO job I find more challenging or important than mastering contextual awareness and response in any given situation.

Own contextual cues, and you can win the room. Don’t, and you may just end up all over the internet in a way you don’t want to be. 

“Own contextual cues, and you can win the room. Don’t, and you may just end up all over the internet in a way you don’t want to be.”

When the desire to be publicly vulnerable is self-serving, takes a space that could be filled with support for team members, is poorly timed and overshadows the needs of our team, we have to bear the cost of the pushback. 

“I have a hard time with the concept of public vulnerability because it seems that often the person being ‘vulnerable’ is not aiming to add value, but themselves asking for emotional support,” Pradnya Desh, CEO and founder of Advocat.ai, told me. “That’s not a fair ask to an employee who has been laid off or even to the world at large, but it is appropriate for a CEO (or anyone) to seek out the mental health support that they need through family, friends or professional services.”

Again, context matters. Public vulnerability can bring attention to issues that may otherwise go unnoticed. It can also be counterproductive, and in some cases, it can be contrived or even malicious.

Shannon Palus, in a post titled “Don’t Blame the Crying CEO” added her thoughts on what makes some of these public displays unsettling: “They claim to offer some kind of window of insight, some humanity —”CEOs are people, too!”— when what they really are is marketing. That’s why it’s so unsettling to see vulnerability show up on the feed — even if it may come from a genuine place, it is released into the world to serve a much different purpose than human connection.” 

As a CEO, I asked my peers if there is a right way to approach authentic vulnerability as a leader.

“Too often leaders see vulnerability as a strategy for managing their public presence, influencing peers, and being seen as ‘progressive’ leaders,” said Aparna Rae, CEO and founder of Moving Beyond. “Real vulnerability isn’t in public posts, it’s in the day-to-day of managing a team or running a company. It shows up as making room for emerging leaders, acknowledging when you don’t have answers, cultivating deep listening, and accepting the ways in which your personal life and stressors impact work.

“Ultimately, the true sign of vulnerability is being honest with the people we work with — about our challenges, goals, dreams, and limitations.” 

At the end of the day, we owe it to our teams to always think about them FIRST. And yes, that applies to LinkedIn posts and public commentary. 

Ask yourself: does it hurt our team? Does it help our team? Is this the appropriate timing for the post? Shall I sleep on it? 

We all make mistakes (I know I do), and to his credit, Braden Wallake is now trying to use this new attention to help others. 

That is good, especially as there are a lot of Braden’s out there. He and I are both examples of today’s average U.S. CEO/founder: men who are choosing this job out of desire — not need — and are drastically and unfairly overrepresented in VC investments and the U.S. startup ecosystem. I hope that changes soon and will work to see it happen, but until it does WE must do better in how we think about ourselves and our teams. And how we post on Linkedin. 

I, for one, will be asking myself the above questions a lot more frequently from now on.

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