Why it was a great idea to rebuild a talk the night before presenting to 30+ intimidatingly successful founders
I had a pretty meta experience a couple weeks ago, giving a talk to the VC-backed founders in On Deck Scale. It started as a terrifying gauntlet being thrown down, and ended in an incredibly powerful conversation, with a whole lot of ambiguity and uncertainty in between.
It’s a fun story to tell, so I won’t spoil any more. Hope you enjoy.
“Life imitates Art far more than Art imitates Life." — Oscar Wilde
At 4:15pm the day before I was to give the talk, they asked me to redo the whole thing.
In all the rules of giving presentations, "don't change the whole thing the night before" is right up there with "practice," and “know your audience.” It's not something that you do, and I knew that. But I also had a hunch.
I told them I'd give it a shot.
My talk, called "The Dark Side of Crushing It," was about leadership. Using my own experiences as examples, the talk was about the way that many founders feel like they need to present themselves as 100% certain and confident about everything, and the issues that sustaining that type of persona can create in their business. The talk explores how trying to sustain a persona of success and certainty throughout the inherently uncertain process of building a business burned me out and nearly destroyed my business, and concludes with my hard-won learning that leadership is more about asking the right questions, rather than having all the answers.
My talk was about how leading through uncertainty requires leaning into that uncertainty, owning the fact that you don't always know what will happen, and instead asking the right questions to unlock your team's best performance. I’d given the talk to founders around the world to great reviews, and by this point had honed it to a fine point. Good thing, I had thought, because this time I was presenting to 30+ entrepreneurs who'd raised collectively close to half-a-billion dollars in VC. It was stupid to change everything the night before.
But they said they wanted it to be more interactive. They'd gotten feedback from the entrepreneurs after previous talks that they were looking to be more involved with the speakers, and so my invitation was to turn a talk — a talk-talk, as in the kind in which I stand on stage telling a story, with no audience participation until the Q&A at the end — into an interactive workshop. I had no idea how I would do it. But I had that hunch, and over the last year I'd learned to listen to those feelings.
I banged my head against the presentation for 90 minutes that afternoon before leaving it for the night, in precisely the same state as it was before my headache. I still had no idea what I'd do.
But I woke up the next morning and I knew. I knew what I needed to do because it was obvious, once I'd seen it. It was poetic. It was also a big risk, and I was very nervous.
I made the necessary changes, finishing the final tweak 16-minutes before showtime. I took a quick walk around the block to clear my head, but my heart was still pounding as I logged into Zoom. I had a sense that I was doing the right thing, but I had no idea how it would go.
Three personal stories made up the meat of the talk, each the kind that I used to be scared to share with people.
How I'd lead our company into a boneheaded strategic move because I was too blind to listen to our team (lesson: "crushing it" leads to bad strategic decisions).
How I'd boxed our team into the safe course of action by selling a very specific plan to our investors (lesson: "crushing it" stifles innovation).
How, to keep up appearances in the face of serious problems, I eventually strapped on a mask to go to work each day (lesson: "crushing it" leads to imposter syndrome, and burnout).
I'd told those stories to audiences of founders before, but each time it felt raw. Like I was sharing something that would cause the audience to think less of me. I knew intellectually that my story wasn't uncommon, but it was still agonizing to be the one taking that first step. I'd have to go first again this time, only this time, as I got to the point in the talk where I'd typically tell my story, if all went well I wouldn't be the one sharing. This time, the talk would be interactive. I hoped. Either that or the voice in my head was right, and sharing my stories really did make me look incompetent.
I explained the concept, how portraying an image of success and competence can lead to a leader making bad decisions because they don't listen to their team, instead focusing on being "right." I said this was the type of thing that happened to a lot of founders, and then instead of sharing my story, I asked what I hoped was the right question. "Has anyone experienced this? Anyone want to share a story about being so convinced they were right that they missed what their team already knew?"
And I waited.
Science says most humans can comfortably withstand four seconds of silence. After five seconds everyone was still just looking at me, or down at their hands, or off screen at what was hopefully a monitor of my talk and not their email. Everyone was not sharing a story like mine. I felt exposed.
I felt panic building in my chest. I was almost ready to give in, to get it over with by telling my story as I had before. But I knew if I did that the rest of the talk would be one way, and I'd be all alone. I almost did it anyway.
"I have a story like that," a founder said.
When later I asked for someone to share their experiences around stifling innovation, I only waited a second. And I had to choose between volunteers to share their story about wearing a mask to work. Each story they told was very different from mine, but each fit perfectly, as if it were my own.
During Q&A, a founder asked me if it was contextual. He said he felt like he'd become more successful as he stopped being open and instead intentionally curated an image of himself and his company as a rocketship. But that along the way he'd also begun to feel more isolated and lonely. He asked me, the speaker, what I thought. And I said "it's a good question. What do you guys think?" This amazing group of founders spent the next 20 minutes debating crushing it versus vulnerability, and I learned from their stories just how grey it all really is.
In his book Crossing the Unknown Sea, workplace poet laureate David Whyte says that leadership “can never be legislated or coerced. It is based on a courageous vulnerability that invites others by our example to a frontier conversation whose outcome is yet in doubt." Building a company is an outcome which is yet in doubt. Rearchitecting a presentation, banking its success on a hope that an audience of uber-successful founders will volunteer to be vulnerable in front of their peers, is an outcome that is yet in doubt. In the face of that doubt, I was scared. I wanted to play it safe.
But I was there to talk about leadership. The kind of leadership that doesn't have all the answers, but rather leads from a worthy question. So I asked the question, my reputation as a founder, coach and human being hanging in the balance (at least in my head). I asked the question and had no idea what answers would come.
And it turned into the best talk I've ever given.
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
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