The Exchanges

Q Do you think in your experience, when a manager gives feedback like that about being more strategic, that there's a few things they're generally trying to communicate? Or is it truly like a long tail? It could be 60 different things that that manager is trying to communicate.

A It's probably a few things for the individual that they're giving that feedback to. So the problem is, if you're the operator hearing that, You're not sure what those things are. But for the manager saying it, yeah, I do think that it's a couple situations that have shown that manager that, hey, this person could be thinking more strategically. And so a couple examples of what it could be, you know, I see operators sometimes be too zoomed in to the project or the task in front of them without considering organizational context. So that could be an example of you're not really thinking Strategically, you're, you're focusing on the how of getting this exact thing done, but you're not thinking about how does this stack rank amongst other things that we're doing? How does this impact other things or how is it impacted by other things? So that's one way of, you know, what be strategic could mean. Another could be thinking more about what, like choosing what to do versus just the how. If you are used to something being fairly scoped and defined by the time it arrives at your desk, You're thinking about, well, how do I get this done? How do I bring this to fruition? Whereas the next level that your manager might be looking for is you doing the shaping. You saying we should do this, not that. And here's why. And here are the trade-offs. And here are the risks involved. And choosing wha…

AI assessment note: “It's probably a few things for the individual that they're giving that feedback to.”

Q So what, what did that look like for you when you think about your own arc of your career, and like the first couple things that you've done, and now the last couple things that you've done? Like, how has it become more aligned with sort of that set of ideas you were talking about?

A Yeah, so I'll give an example where I worked on this skill or on this weakness, I would say, until it was not a blocker for me, but then intentionally started choosing roles where this was not a core need. So I used to be pretty disorganized and bad about operational details. And early in my career, this was pretty prohibitive for me because I was in a brand management role. And had to manage multiple launches for multiple SKUs with different launch timelines, production timelines, et cetera. It's a physical product. And it was really overwhelming keeping track of all of it. I dropped a ton of balls and I realized that if I am to advance to the next level where, you know, as a manager, I might not have to manage all these details myself anymore. I'm never going to get there because I'm never going to get promoted if I'm so bad at managing all these different details. And so I put concerted effort into learning to become more organized, to become better at project management to a point where I could keep track of different projects and where they were and could communicate upwards and keep the appropriate parties aware of what was happening. But I knew that this was never going to be a strength of mine, that to this day, logistical details very much stress me out. I tried to outsource it as much as possible. I still dread doing things that require a lot of Logistical detail, esp…

AI assessment note: “I literally changed career paths after that role.”

Q What's the last thing that annoyed you that turned into something you put out on the world that was interesting?

A Everything, almost everything I write about, the root is something that annoys me, and then I turn it into something much more positive, because the frustration part isn't always, you know, isn't always the best angle, but one that is more literal is I did a newsletter article and then posted this on social as well about, no, I don't want to hop on a call, and so this was about how many of us default to live conversations when they don't need to be live conversations, and it actually wastes everyone's time, and how You know, if you're not sure how you want to write a message and you're not clear on your idea, I, as your colleague, do not want to be taxed listening to you talk, you know, meandering for 30 minutes as you figure something out in real time. Like, take five minutes, think about it, and then if you really can't come up with an answer, fine, let's hop on a call, but don't make that just your default. And there's obviously many good reasons to hop on a call. Brainstorming, you know, situations where showing your facial expressions or tone of voice matters, discussion, etc. In my experience, many of the day-to-day interactions we have aren't that. Like, it's a simple question or, you know, sharing information, and you can do that in writing in a much more scalable way that respects the other person's time. So that was an example of something where the beginning of that …

AI assessment note: “I did a newsletter article and then posted this on social as well”

Q So how does that manifest itself for you? What have you figured out about yourself and then how does it translate into all the things that you do in the way in which you behave?

A That is a big question. I'm gonna, I'm gonna scratch the surface of it here probably. I think in the past, I thought that leaders had to look and act a certain way. Namely, you know, much more serious, much more formal. And I think I'm a pretty professional person, but I don't think I'm the most formal person. And one thing I really liked about Maven and my co-founders at Maven were that we weren't overly obsessed with an air of Formality or, you know, being more, more serious for the sake of it, being more corporate for the sake of it, or acting like a bigger company than we really were. And I really liked that. I think it allowed us to be more of ourselves and care about the quality of the ideas that we were sharing. And a big part of our ethos in the company was everyone should speak up and we should be able to back up our ideas no matter who we are. So if you're a co-founder, you need to back up your ideas too. If you're the most junior person, You need to back up your ideas. And, uh, yeah, I think that that ethos was really pervasive. And in the past, I would have thought, you know, well, you know, we need to be serious. I need to be more buttoned up. And when I kind of relaxed that rule, realized it wasn't actually a rule that you can inspire people. You can be a leader that people want to follow without necessarily being super formal. I think that's, that's one example.

AI assessment note: “when I kind of relaxed that rule, realized it wasn't actually a rule”

Q Why do you think there often is so much lack of clarity and communication?

A I think as founders and as operators, there's so much going on on a daily and weekly basis. We are often back to back jumping from one meeting into the next and then answering Slack messages in between. I think that people just don't put enough thought into their communication. One big takeaway that students of my course have is even by spending a couple moments Literally, 15 to 30 seconds getting grounded on what am I really trying to say? What does this person need to know? What is my main point and what's potentially secondary? Spending a couple moments asking yourself these questions allows you to write a message that is much clearer and allows you to speak up on a call in a meeting in a way that gets your main point across much better. So I think that the, the biggest bottleneck to clear communication, to being concise, Is lack of preparation. And I don't mean that you have to prepare for hours for every call, for every meeting, for every Slack message you're writing. Even a couple of moments can make a really big difference because if you are not clear in your own mind about what you are trying to say, of course, when you say it out loud, it's going to be confusing. Of course, it's going to feel meandering because when you're there in real time speaking, you're actually asking your brain to do a bunch of different processes. You are taking in information, In that real tim…

AI assessment note: “the biggest bottleneck to clear communication, to being concise, Is lack of preparation.”

Q For those that aren't familiar with Seth, how would you sort of describe him? And what was it like? I mean, I, I followed him from a distance for a long time. Many, many years ago, he spoke at a big conference that we put together. He's such a, a unique human. What, what is it like actually working day to day on something with him?

A It's hard to describe Seth in a few words because he is, he is such a unique creature and it was such a privilege to get to work with him so closely for three years. I learned so much and I would say transformed as an operator, as a leader, as a builder, um, from working so closely with him. What's he like on a day to day? He's even sharper in person than he is online, which I think is impressive because, you know, sometimes I'll, I'll read people's writing or, you know, watch them in videos and stuff, and then, and then I'll meet them, and I'm like, okay, like, you know, you're pretty, you're pretty sharp, but like, right? Seth is like a 10 times funnier, faster thinker in person, like, he's just even better in person, I would say, which I find impressive. He also has really high standards. He thinks incredibly quickly, and so, you know, there were so many times where I had prepared an explanation to describe something, I don't know, maybe it would have taken three to four minutes, and he would get it in 30 seconds, you know, and I'd be like, oh, ok, you know, and I remember going home for the holidays one year, and then coming back to the office, and feeling like I had actually dulled in like the two weeks that I had taken off, because Coming back to the office, I'd forgotten just how fast he thinks and how fast I needed to be to keep up. It was like a culture shock, like rei…

AI assessment note: “What's he like on a day to day? He's even sharper in person”