The Exchanges

Q in. And Jack's tactical framework that other founders and leaders can pull into their own playbooks. Now my conversation with Jack. So I thought one place to start would be to talk about your own journey from founder to CEO over the last seven plus years at Lattice. And I'm curious, like, how would you describe the sort of different chapters and things that you've figured out along the way?

A So seven years is a long time. Uh, there's a lot of sub journeys and all of that. And I think this is one of the big things that a founder has to go through is that the change in yourself that you need, uh, is, uh, it's very frequent, it's very substantial and what's right. In behavior for me now, with that I said, 600 people would have been wrong at 60, and the way I operated then would have been wrong at six, and so part of the mental, ah, you know, place you have to get yourself to is understanding that the way you operate really has to change dramatically. I think something a lot of founders experience at the beginning is that they can really operate through their own force of will, and you can really put your hands on each part of the company, you can hero, sort of, Uh, mode your way through problems that you have. You can, uh, you can go talk to extra customers. You can jump into the Figma files if you need to design something. And then reasonably quickly, what ends up happening is now you need to lead a group. And so somewhere around 10, 15 people, you go from this early stage founder to, for the first time, becoming a manager and a leader. And, you know, something flips where now the way that you can affect the most change is by Uh, impacting more people a lower percent than just doing everything yourself. You know, like for example, I can push my way through something …

AI assessment note: “somewhere around 10, 15 people, you go from this early stage founder to”

Q of broader topic that we're exploring, which is sort of how you effectively grow as a founder and CEO. When you think about the things you've Figure it out the hard way, or you're like, ah, I wish I knew that nine months ago. It would have saved me so much pain. Are there one, two, three, five things in the journey thus far that sort of come to mind?

A One that I consistently have to relearn all the time is that an uncomfortable conversation today saves you so much pain. Uh, any uncomfortable conversation that you think you need to have That you're just gonna push off. You're almost always taking on debt to do that. And there can be moments where it's worthwhile to push off something uncomfortable, whether it's telling somebody that they can't have the role that they want, or maybe that they're even not the right long-term fit for the company, or that you're actually gonna defund, deprioritize an effort that they really care about, that you're gonna go a totally different direction on the strategy than the one that they've felt really adamant about. Um, there's a whole host of these kind of things. And it's really tempting to convince yourself to put these off. And, you know, you're tired, you're working hard, you got a million things going on at once. You've got 200 emails in your inbox. Like, it's really easy to convince yourself, particularly in the early days when you don't have a lot of infrastructure that, like, I'm just going to take on debt. And I continually learn that that's a bad trade much more often than we let ourselves make the trade.

AI assessment note: “One that I consistently have to relearn all the time is that an uncomfortable conversation”

Q think about. Like when they think about all the, they might think about their exec team and how are they managing performance, but like up and down the org, Are we doing an excellent job of creating an environment where people can do incredible work? And at the same time, if somebody's not a fit, where it's not lingering for years or months or sort of that type of thing.

A I cannot say I have a solved answer to this. I think this is incredibly difficult to try to Drive this type of management at scale. I think there are things you can do. Certainly there are in some orgs, there are programs that you can have where it becomes a much more clinical decision, um, based on metrics and things like that. And so you take some of the workload off managers, people will try things like manager training. Uh, you know, you can have really generous severance to make that an easier experience for managers. Um, you can filter for this in your hiring of managers, uh, and you, you know, I, I do often like to ask people, like, tell me about a time that you had to, like, let go of somebody that you hired, uh, you know, in a relatively short period of time and just, like, walk me through that whole experience. And that can, that, you know, there's questions like that that can teach you something. Many people will have zero examples of that. There's not an easy solve to this. It is, like, ongoing, difficult work. Uh, I, I don't have the answer.

AI assessment note: “you can have really generous severance to make that an easier experience for managers.”

Q Do you just think about that, or how do you develop that self-awareness?

A I think exposing yourself To things that help you realize how much you need to learn is one path. I think depending on your starting point, you're going to have a different, there'll be like different medicines for this, but one is exposure to CEOs who are so much better than you and so much more equipped than you are, who you learn to trust and who are willing to take the time to sort of mentor and guide and holding yourself up against that gives you this Guidepost of, oh wow, like I realize when running ideas by this person, that helps me ground myself in how much further I have to go. Uh, that could be one. I do think for a lot of people, the right sort of coach can really help getting to a place where you don't hold, uh, too much attachment to your own self image or worth based on where you think you are today. Uh, cause you need to have both of those things, but sort of keeping the, the deep confidence while not being so attached to this is exactly who I am today. That allows you to have both, I think. So I think that can be a source of it. Um, for some people though, a lot of it, you know, it could be, it could be meditation, it could be like reading, it could be learning about, you know, spiritual practices for different people, you know, like it's, it's all over, but it's, it is really a quest of learning about yourself and getting yourself there.

AI assessment note: “exposing yourself To things that help you realize how much you need to learn”

Q In those, in those hundred conversations, what, how do you structure those, or what would you be asking or talking about with customers?

A Well, if you're coming in truly knowing nothing, I would tell you to go try to be friends with 10 and go just talk to a hundred and just like learn about their lives, but I would actually tell you to go be friends with 10 and what being friends with 10 is going to do is it will get you past the sort of more corporate back and forths and niceties and the surface level things of, okay, I'm talking to Lattice, so I should tell them about XYZ and it will get you to the more real places of learning, uh, Forget Lattice, but heads of HR get really stressed out by their finance partners in XYZ ways, or they historically have really felt that they didn't have like a good seat at the table, and so they actually are coming with a little bit of their chip on their shoulder, and they really want to feel strategically empowered or whatever. And there's a whole bunch of these, but getting past the surface will help you better understand the true motivations of who you're serving. Just the same way that like getting to know somebody as a friend will help you like better support that person. I think that's something a lot of founders miss is they keep it really clinical. And I've always found that for me to make good business decisions, I need to know People that we serve as well as I know, you know, people that work at Lattice.

AI assessment note: “try to be friends with 10 and go just talk to a hundred and just like learn about their lives”

Q you're out of alignment in that middle area, you're, you're actually unintentionally or subconsciously doing things that get people to continue to behave in that way. And so I don't know if there are other ways you think about figuring out kind of where you are in that state of equilibrium. And if you're out of alignment, how do you start to nudge the company back in the right direction?

A Well, there are both macro and micro Ways that you'll know. One macro way you'll know, for example, is just we are a company that was growing quickly through this, you know, hyper growth period, and it is likely that we experienced the same forces as any other company, and so we should start from a default place of assuming that we have a decent amount of this, because we all know we've made contortions along these dimensions over the last few years. So that's one starting point is the self-awareness to know that you are likely not above A lot of this stuff. Uh, I certainly know that we have not always been, and of course never will be, in perfect compliance with this, just like any other company would be. There are going to also be micro smells that you need to look out for, and so like an example of this would be if you've got somebody who you feel is well-placed, if you feel high confidence that somebody is well-placed, and that they match their role, and you feel strongly that the company is getting just what they need from that person, But that person is repeatedly unhappy and unsatisfied with it, that's a smell to you. Same with the other way around. If a person is very, very satisfied in the role and they think everything's going great, you don't, that's another moment for like an honest look, but You can tell certainly when you're in one of the zones because one side of…

AI assessment note: “Well, there are both macro and micro Ways that you'll know.”