Breaking the Lonely Hero story of Leadership

This past weekend, I was coaching at a CEO summit organized by MiLA Capital as well as a couple other venture capital firms. A theme that showed up throughout the weekend was a story of leadership that was driving lonely CEOs to exhaustion, which is one of the reasons they so appreciated this chance to connect with other CEOs in a peaceful supportive setting.

The leadership story is recognizable – the founder CEO starts a company, and has to do everything at the start. They hire a team, but somehow they still end up doing everything from sales calls, to making product decisions, to giving employees pep talks. Despite desperately wanting their team to take ownership and get things done without them, the CEO somehow still ends up as the bottleneck for the company. And yet they don’t feel they can show their frustration with the situation for fear of demotivating their team, so they just work harder and put in longer hours to try to get everything done themselves to keep the company moving forward. They swoop in like a superhero to solve any problem at the company, but this also teaches the team that the CEO will save them, which increases the chances that the CEO will be relied on to solve the next problem, perpetuating the cycle.

This model is reinforced by the way Silicon Valley culture lionizes the grit of founders being willing to spend every waking moment working on their start-up and fixing every problem, while always staying optimistic that they are going to figure out how to create a billion dollar company. Any startup CEO that complains that they are working too hard is going to be mocked, because “everybody knows” that is what you sign up for as an entrepreneur. And yet does it have to be that way?

Part of what makes it so hard to change this model is that founders generally don’t talk about their experience. I was privileged to listen in on frank discussions of how lonely and exhausted these CEOs were feeling, and I was touched to see how relieved they were to find others felt the same way. They felt they had nobody to confide in, as they feared their team and their investors would freak out if they heard the CEO had doubts. It’s hard enough to be a startup entrepreneur, but having to do it alone with no support makes it even more difficult. They also fear that if they slow down for even a day, the company will fail and it will be their fault, so they do whatever it takes, even at the cost of their own well-being until they are literally at the point of breakdown.

So how do we shift this model? One idea shared at the summit was to increase transparency, so that people in the company have a better sense of the dependencies the CEO is managing. For instance, a CEO might tell the team “this feature has to ship on this date”, and yet the ship date slips. However, if the CEO shares a little more and says “this feature has to ship on this date, because this feature is required for us to sign this partnership, which will then allow us to hit our revenue milestone, so that we can raise our next round of financing on better terms, so that all of our stock is worth more”, that might motivate the team to stay a little later and work a little harder to make the ship date happen.

The risk that several of the CEOs feared was that transparency would lead to their team losing faith, and leaving to find another job with better prospects; when the next unicorn is literally around the corner in Silicon Valley, retention is challenging. So they instead “protect” their teams from the hard reality that if things slip too much, the survival of the company is at risk. And since the CEO is the only one that knows that, they take on all of the work, leading to the lonely nights and weekends as they try to do everything by themselves to keep the company alive.

One of the things that makes leadership difficult is that every decision depends on the specific context, so I don’t think there’s a “best practice” around transparency. My personal bias is towards sharing more; when I worked at a startup that eventually went bankrupt, we all knew something wasn’t right, and because our leadership didn’t tell us anything, we assumed the worst. Then again, I don’t know if transparency would have helped in that case, because us workers didn’t really believe in the company or the leadership team; by the time layoffs actually happened, many people already had other jobs lined up.

On the flip side, sharing more with the team allows for the possibility that if you give the team the context, they may come up with creative solutions that you never imagined. I believe that the collective can have more intelligence that one person, no matter how smart that one person is, but it depends on the collective having the relevant information. Also, if the team feels included in the vision and trusted with sensitive information, they may take more responsibility for finding solutions. But it’s scary because if there isn’t that trust, people can betray you.

Several CEOs also feared that if they share that they don’t have all the answers, their teams will lose respect for them as leaders. It feels like they are subject to a myth that ideal leaders are unemotional experts with a clear vision of how to handle every problem. This myth seems very difficult for any actual human leader to live up to, and yet it’s a persistent take on the way leaders “should” be, in part due to alien robots like Larry Page and Elon Musk. And yet, if nobody talks about their fears, then there’s no way to find the others who share that fear, and no way to break this myth. Vulnerability and sharing leads us to find that we are not alone, and that others are there to support us. But somebody has to go first, and it generally has to be the leader.

Hearing the stories at this CEO summit got me thinking about leadership, transparency and the loneliness that results from holding to a vision of leadership where one has to be the all-knowing and self-sufficient hero. How can we all support each other to start to break out of the confines of that myth?

4 thoughts on “Breaking the Lonely Hero story of Leadership

  1. I’m really glad you wrote this. I don’t know that there’s an easy answer to this, because there are parts of the job that are lonely. But also what you said about transparency is absolutely true, in my experience.

    Every single time I’ve chosen to tell people when things were challenging, the response has been that the team’s stepped up and done amazing things. Every time I’ve shown vulnerability or uncertainty, it’s been received by the team with empathy and support. Every time I thought I had some cross to bear, and chose to share it with the team, they have leapt at the chance to carry the burden.

    But I think in part, it’s because there are things that I *don’t* share with them, and there are things that I work to insulate them from, because while I think the “lone hero founder” myth is bullshit, I also do think that there are some things that rest on the founder alone. Sometimes you have to make a call. And you rightly bear responsibility for that call. You can make a lot of calls with the buy-in of the team, and you can do a lot of communication that involves people and ensures that directionally you’re all aligned.

    But some times, you have to make a call that no one else is equipped to make, and because of the position you’re in, those calls affect everyone. Because of that, you have to be aware of the imbalance of power in your relationships with literally everyone on the team. You aren’t a peer, and it’s unfair for you to treat others as if you are, or expect to be treated as so.

    So it’s lonely. And you should be as transparent and vulnerable as possible. Sometimes it helps. Sometimes it doesn’t.

    1. Thanks for your comment, Seppo. I agree there is no easy answer, as these decision of when to share and when to withhold information absolutely depends on the context. And context changes over time, so what “works” one time may not “work” the next. So an element of resilience and self-compassion is also valuable to navigate the ever changing waters of leadership.

      I should also note that I’ve never been the one in charge, as you have. It’s different to be the one in charge, as you well know. So this post was not meant as any sort of answer, but as a way to start the discussion for leaders to know they are not alone.

      1. Which I think is tremendously valuable. Not just that the burden can be shared with other lonely leaders, but also that a lot of that burden *can* be shared with the team.

        It’s also funny – I’ve definitely been struggling the last six months or so with how much context changes, even if a lot of things look & feel the same. Trying to do things that I “know work”, but don’t work because the context has changed = frustration. And it’s only really relatively recently that I’ve really understood the core of *why* things are different, which then of course informs how to deal with it. But sometimes I feel like a complete moron for how long this stuff takes. And then sometimes feel like a total genius for getting to any kind of understanding at all.

        Sometimes the emotional whiplash is a whole rollercoaster on its own. 😀

  2. The lone ‘cowboy’ CEO myth really is just that – a myth. Or, it should be. Really great leaders don’t think of their teams as errand boys and admins, but as collaborators who they can trust to understand the nuance of problems and also *who* owns decisions.

    There’s a management ‘rule’ floating around, attributed to Jeff Bezos, that says teams should have free and open discussion and argument on a topic, but then realize that one person owns the decision and that once that decision is made everyone has to line up behind that decision. This addresses Seppo’s point – some decisions may need to be made alone, but the leader doesn’t need to be lonely.

    The trick for the leader is knowing when and how often to use that fiat power (a past co-worker used to say he was “Driving his management Fiat around a bit”) so they can maintain the bilateral trust of their team.

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