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I thought I knew what it meant to lead with vulnerability. Then I became CEO

Brené Brown makes it seem so easy. It’s not.

I thought I knew what it meant to lead with vulnerability. Then I became CEO
[Photo: Jeremy Yap/Unsplash]

Vulnerability is a hot topic right now, with leading voices like Brené Brown and Elizabeth Gilbert sharing research-driven reasons to let down your guard at work and make space for real understanding and empathy. It’s an easy concept to buy into. Wouldn’t we all like to live in a world where people were honest about their insecurities and needs, rather than projecting overconfidence and aggression, especially in business?

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Throughout my career, I’ve spent a lot of time thinking about how to approach my work with vulnerability. I’ve read books on the subject, watched TED talks, and practiced active listening and radical candor, all to try to improve my emotional quotient and ability to relate to my team. I take my relationships seriously, and I’ve seen the results of my efforts reap dividends.

But, after becoming CEO of my company, I discovered that leading with vulnerability is much more complicated than it seems—and it takes more than a few TED talks to get it right. Here’s what I’ve learned:

Vulnerability looks much different from the top

One year ago, I went from a senior executive role within my company to CEO. This wasn’t a sudden move. There had been a deliberate and lengthy transition period with my predecessor to made sure we got it right for our employees and customers. I knew my team, they knew me, and I had a strategy for where I wanted to take the company.

This wasn’t my first time leading a massive organization through a growth phase, but it was my first time as the captain of the entire ship. I felt confident knowing that my style of leading with vulnerability and authenticity had worked for me in the past. I wasn’t going to flash my credentials or walk around dictating orders to declare my authority. I was going to be a supportive leader, someone my team could come to any time with feedback or questions. In return, I’d be open about places I needed help and answers I didn’t have.

But looking back at my first few months as CEO, I was so focused on not being a dictator that I swung the pendulum too far in the other direction. In the effort to be a good listener rather than taking a more top-down approach, I ended up leading with a trail of breadcrumbs and left my senior team in a leadership vacuum. This insight didn’t happen all at once but was the culmination of lots of interactions and crossed wires.

Not only were they unsure of what I wanted, they didn’t feel like they had my support, and this was creating uncertainty—and, to be honest, tension. Only when I finally laid out exactly what was on my mind did we really start to move forward. The big lesson here is that vulnerability and clarity are not mutually exclusive. Being vulnerable isn’t keeping quiet so as not to rock the boat. In fact, it means just the opposite. You must be clear about your needs and expectations and listen to feedback in return.

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It’s okay to be frustrated and show emotion

Similarly, vulnerability doesn’t require you to suppress feelings of disappointment or frustration. As former Google exec Kim Scott writes in her book Radical Candor, being brutally honest with your team is a cornerstone of good leadership. But there’s one caveat: all that honesty has to come with an offer of help, support, and guidance. This last bit is crucial because it shows you care about the individual’s well-being and experience—not just the company’s performance.

It’s okay to take someone to task for not holding up their end of the bargain or missing targets, as long as you’re armed with resources to help them overcome their hurdles. And—this is the most important part—it’s key to communicate the value you place in the relationship at the same time. It’s not about chewing someone out for falling short; it’s about uncovering the root cause and hatching a collaborative plan to get back on track together.

You can walk a firm line without being a jerk

We recently doubled down on our goals to improve diversity and inclusion in our company. While I’m proud of our commitment on this front, there’s always room for improvement. That included holding an event for employees who identify as women to discuss their challenges working in the tech industry. But at a recent company-wide meeting, a question about the initiative surfaced: Did it make sense to promote “inclusion” with an exclusive event for just one group of people?

Being good allies sometimes means taking a step back and giving space to people who traditionally haven’t had the same visibility or privilege. Instead of backtracking or waffling about my decision to hold this event, I shared the thought process behind our stance, aiming for total transparency so everyone in the company understood why we were approaching this issue in this way. I knew not everyone would agree, but the takeaway was simple: Agreement isn’t necessarily the goal; understanding is.

Asking is your superpower

A few weeks into being CEO, I walked into the office and saw a drawing on my desk. It was the outline of a big black bird and underneath it the word “vulture” scrawled in all caps. My insecurities immediately went into hyperdrive. Was this a veiled critique of my leadership?

Self-awareness is definitely an important part of leading with vulnerability. But doubting your worth or getting lost in narratives is another thing. At the end of the day, a lot of grief can be spared simply by fact-checking against reality. As it turned out, the drawing came out of a team-building exercise, and one of the teams—which just happened to have a vulture as a mascot—thought I should be an honorary member.

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It’s far too easy to get lost in your own speculations. No matter how smart we are, we can’t know what anyone is truly thinking without asking. True vulnerability isn’t doubting yourself; it’s having the confidence to ask the hard questions and the humility to act on the answers.

Bring in referees—and reinforcements

It’s crucial to note I wasn’t in this process alone. From the moment my predecessor started thinking about handing me the reins, we had an executive coach to turn to. She’s still with us today, and her role is anything but superfluous or touchy-feely (a common misconception about executive coaches).

Contrary to the idea that CEOs should have all the answers, real leadership is knowing that you don’t and you won’t. Having an outside perspective has helped me be better at my job and gain deeper insight into vulnerability and empathy. She’s been enormously helpful in identifying sticking points and making us talk it out instead of brushing over conflict, enabling everyone to work through the issue together.

We’ve now got an aggressive multiyear growth plan in place. We’ve rolled out new features to make life better for our customers, and we’re expanding our team. We’ve even won recognition for our company culture and leadership. But this process is far from over. I’m not a model of vulnerability, and I’m not a model CEO . . . yet. But living into vulnerability as a leader has given me the tool kit to start to get better—to acknowledge failings before they become fatal flaws and to course correct sooner rather than later.


Chris Litster (@cmlitster) is CEO of Buildium, a platform to help property managers streamline their businesses.

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