Learning to Lead and Say "I Don't Know" With Confidence
Updated: Nov 16
You don't have to know all the answers. You do have to ask all the questions.
This article was originally published on Inc.
Startup land is filled with bravado. Between Twitter threads about crushing morning routines to the endless rocket ship emojis, it's easy to feel like being a founder is uncomfortably close to being a hype man. This temptation to match the energy is especially strong as a first-time founder.
But, I just can't square the public bravado with the fact that I know there's so much I don't know.
Excessively confident leadership is certainly getting a second look with the incidents at WeWork, Theranos, and the like, but it still feels like the dominant paradigm. I've struggled with this because I, personally, think mostly in hypotheses, not absolutes. I don't know for certain that Ethena will become an enduring and iconic company that defines what it means to be a modern, ethical, inclusive workplace, but I do see the path, the problems we'll need to solve, and the exceptionally talented people we'll need to do it.
When I encounter a problem, say, "How do we make our sales process more predictable?" a key part of my decision-making process is seeking out smart people and asking them all of my "dumb" questions. Then, I triangulate based on their advice, our company's data, and my vision and I make a decision. While the time and resources this process takes originally felt like a weakness, especially early in my startup journey, I now see my intellectual humility as a strength.
Humility helps build trust with my incredible team. Instead of holding onto and hiding problems, I share them. Two magical things happen. First, I get help. My team now knows enough about the problem to help solve it. Second, I continue building trust because my team increasingly believes that my commitment to transparency doesn't just mean, "I'll share the good stuff."
But this humility is also really helpful in recruiting new leaders. Case in point: it convinced an experienced Chief Revenue Officer, Arnie Gullov-Singh, to join our Ethena team. We had raised a $15.5M Series A based on early traction, passionate customers, and an exceptional team. The next step in scaling was getting our sales motion more predictable and scalable.
In the early days, startup sales is about deeply understanding your customers' pain and then as quickly as possible iterating until the product solves their pain. We did the hard thing and got to product market fit, which means building something that customers really want. Our incredible customers, including Netflix, Zoom, Zendesk, Carta, and Notion were loving the product and the 40k+ employees on our platform were learning from our training.
But we needed an experienced revenue leader to scale it.
Arnie came highly recommended from trusted investors and advisors, so I brought him on as a consultant while we kicked off our search for a VP of Sales. He got to work identifying the primary ways we could unlock faster growth and even in our first few weeks, it was clear he was having an impact. At that point, I asked if he'd consider coming on as our full-time CRO and he gave a polite, "you're a bit early for me."
After a few months of everything shifting into high gear, I shot my shot again, asking Arnie if he wanted to reconsider and come on as our CRO. To my surprise, this time he was interested.
Obviously I had to know what changed so I asked him. Arnie had a few reasons having to do with the business, our growth, and seeing the larger vision, but it really came down to humility. "You were one of the first CEOs I've ever seen come to me asking for help," Arnie explained. "Usually, leaders resist asking for help because it means they need to acknowledge they don't know something."
He also saw how my humility allowed my team to be comfortable acknowledging their opportunities for growth, which started a virtuous loop - we were open to feedback, so we got more of it, we implemented it, and like any athlete, we got better with coaching.
While humility has helped me bring on experienced leaders, it's even more helpful once they join. Managing experienced leaders, especially as a first-time CEO, is intimidating. I've hired them precisely because of their experience but usually, the day after they sign their offer letters, I have a moment of acute imposter syndrome. The panic train goes something like, "Oh no, they're going to realize how little I know."
For example, Brandis Anderson joined us as General Counsel a few months ago. She'd already had a big win under her belt, having worked closely with the Plaid founders as their Product and Regulatory Counsel. And before that, she was an enforcement attorney with the Consumer Financial Protection Bureau. She's a deeply experienced attorney and I am not.
In her first weeks, I found it really freeing to say exactly that. I explained to her what I know and am good at and where I need help. I told her that I expect her to educate and guide me, and she can only do that if I'm honest about the limits of my knowledge.
We had a recent conversation about corporate governance where Brandis asked if I understood the particulars of a change she was proposing. I said, "Nope. Break it down to the basics." I had to add that I am a religious watcher of the show Succession, but I assumed that what I learned about governance from t.v. was not equivalent to her legal degree. She smiled, agreed, and educated me so I could make an informed decision.
Whether I'm trying to attract or work with incredible talent, humility has, perhaps counterintuitively, been an asset not a liability. My goal is to be honest about the limits of my knowledge while also showing the high conviction I have in what really matters - great people build enduring companies.