Kenneth Berger: evaluation

Transcript context

…I gave a talk about this sort of right after it happened, but I was fired from Slack three different times, which I feel like has to be some kind of startup record. I don't know who would be the record-keeping body for this. But now 10 years on, I have different perspective, of course. And so this was almost exactly 10 years ago, spring of 2014 and I just gotten the job as the first PM at Slack. It was already the hottest thing out there. It was only a couple dozen employees. I came in excited, but also a little insecure because I had just come off my breakup with my co-founder. I just wanted to put my head down and do a good job. I was engaged at the time, so Slack already knew I was going to be going away on a bachelor or backpacking trip. I have a wedding and honeymoon in the fall. And so I came in naive and overconfident of, "I've been a founder. I've worked on iconic products. I know how to do this. I'm a pro. I'm just going to go in and do the work." So instead of getting really clear on what does success look like here or what's your culture or what are your expectations of me, I just went in and made my best guess and went for it. And lo and behold, turns out what I came in with, that supreme overconfidence was not what they wanted at all. They'd kind of been in the trenches reinventing from the game to Slack. They'd been through layoffs, really hard times together. So they wanted someone to come in humble and to earn their trust of this kind of core team that had been together for years. I just didn't get any of that. I wasn't hearing that feedback. I wasn't hearing those nos, and I wasn't articulating what I wanted. What I wanted was really very basic. I just wanted to figure out how to do a good job, and I wanted to have a good relationship with the CEO because I was working for him. And you need to have a good relationship with your boss. But the problem was in the first firing anyway was I had not articulated those goals. And so I shouldn't have been surprised when six weeks into my tenure at Slack, I came back from my backpacking trip with my bachelor buddies, and I had an email in my inbox saying, "Hey, you're fired. It seems like it's not working out. Let me know how you want to wrap it up." So as you can imagine, I freaked out. I loved this job, I love this company, so I profusely apologized. I said, "I'll do whatever it takes. I'm so sorry. I'm going to be committed to turn this around." And so early stage startup turns out firing doesn't always stick. Monday morning, I had my job back. But obviously things were not the same as they'd been before because in the second era, what I wanted was sort of better articulated more clear, but all of a sudden that fear that had been under the surface, that insecurity was now very, very present every day because I was terrified of was I going to get fired? Was I going to not make the most of this opportunity? And so I went fully into people pleaser mode. insecurity was now very, very present every day because I was terrified of was I going to get fired? Was I going to not make the most of this opportunity? And so I went fully into people pleaser mode. And so that meant that even though what I desperately wanted was to have this good relationship was to be successful, build a great product. I had a year of one-on-ones with the CEO. I never, never ever asked for what I wanted. I never said it out loud because I was scared. I was scared of what the consequences were. I knew there were a hundred PMs standing behind me ready to take my job if the CEO is ever a moment unhappy with me. I said, "No, I'm not going to take the risk. I'm too scared of what the consequences might be." And so I held all that fear and all those desires of, "I just want to do a great job. I want us to be awesome partners and build this amazing industry changing product." I never said any of that stuff out loud. I just put my head down and I tried to obey. And so as you can imagine, this didn't work very well. I was feeling horrible day to day. I was terrified of this guy I was working for. And so again, I shouldn't have been surprised, but I was, when I got fired for the second time. It wasn't quite firing. But this time I'd come back from my honeymoon and I had a phone call on Monday that said, "Seems like product management is not working out for Slack. We're actually just going to get rid of product. You're going to be user research. It's going to be fine." And for me, I love user research, but that was the beginning of my career. I was not interested in going back to that. What was fascinating was at that point, I was actually able to articulate what I wanted there and was willing to say it out loud. Because what I wanted was, "No, let's keep me in product. I've got an idea for how we can run it." So I wrote a proposal, I sent it around to the management team. Turns out, when you actually ask for what you want out loud, you're much more likely to get it. And so within a week, this new plan had traction with the management team team and I had my old job back again. Everything was fine except of course it wasn't fine because now I was scared, but the stakes seemed really high, and this is where that deep imposter syndrome sit in. I was like, "Am I even any good at this? Should I even be in product management? Am I ever going to work in this industry again? Is this going to be my dark secret that I take to the grave that Stewart Butterfield fired me three times? " I think what I couldn't be with in that moment was the no's, because I was getting no after no after no after no from Stewart and the rest of the management team saying, "What you're doing is not working for us, right? Your ask are not landing. You're not being effective in the way that you want to be effective." And because I wasn't able to hear those no's again, because to that emotional regulation standpoint, I couldn't handle the feelings of like, "Ugh, maybe what I'm doing is not good enough." So instead of pointing the finger at myself, I pointed the finger at him. I said, "You know what? Actually this guy, he's not such a great manager. ike, "Ugh, maybe what I'm doing is not good enough." So instead of pointing the finger at myself, I pointed the finger at him. I said, "You know what? Actually this guy, he's not such a great manager. He's not so good at product. I'm the one who was on the ground with the users. I know what's right." Against all evidence to the contrary, by the way, is this product luminary, visionary, famous person. So clearly not based on any facts, but it was an emotional issue of I couldn't deal with the reality of what I was doing was not working. And so again, because I was not articulating what I wanted, I was not asking for it and I certainly was not listening to the no's. I shouldn't have been surprised when finally the third time it came down, and this time it was serious because we had HR. So it turns out once you hire HR, the firings are final. And so I only made it to a year at Slack and it was a year of just utter torture because I spent that year being fully out of integrity with myself. Never saying what I really wanted, how I really felt because it didn't feel safe. I was too scared. I kept it all inside. And it took me six months or a year even after that to really feel safe and okay again. It was a serious decompression time. My wife and I had a baby during that time. I was on zero sleep. It was a rough, rough period. But the irony is that when I actually came out of that experience, the reality of it was extremely simple. I hadn't articulated what I wanted. I hadn't asked for what I wanted. I had not listened to the no's in response to my non-ask. And so of course I was unhappy with the result. Why would I have expected anything different? I wasn't the victim. Stewart wasn't the villain. It was just ineffective asking. And so to me, especially because I was already on that path towards coaching, that lesson hit really hard in terms of how do we make this work more sustainable? We stay in integrity with ourselves even when it's hard, even when it's scary, even when we don't know exactly what the outcome is going to be. And so that's really the story of how I became a coach, of seeing exactly how much I'd screwed up at Slack and seeing how much I had suffered and how much a lot of people suffer in these similar circumstances. All you have to do to turn it around is ask for what you want. So this is why I'm so passionate about this stuff because it can sound so fluffy to say, "Oh, focus on integrity. Honor your desires. No, it's real life stuff of a year of suffering, of pain, of fear." I don't want other people to be going through that and that's why I'm so passionate about this stuff.…

Stored transcript either side of the excerpt. The highlighted words are the published quote; the surrounding text is unedited source, never generated.