Individual Contributor vs. Leadership, Applying Stand-Up and Improv in Business, and Striking a Balance

Callan Harrington 00:00:
What Apple's done, and I'm sure countless other companies have done this as well, is if you're an individual contributor, and you've been in that role for some time, you can continue moving up the pay scale without having to go into management. So you still get the same compensation, perks, and benefits of rising within your career in the organization, but you don't have to go into leadership. You can stay a top individual contributor, which I thought was super interesting. I'm curious if a lot of companies have been shifting to a model like this. You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here.

Callan Harrington 00:35:
Welcome back, everybody. Back by better-than-average demand, we have Sullivan Finlay with us. That's kind of the bar I try to set in life in general—just somewhere between average and too good.

Sullivan Finlay 00:45:
You’re a “meet expectations” kind of guy, yes.

Callan Harrington 00:48:
So for today, we're going back to that conversational format. To kick this off, we're going to do the hot-off-the-press segment. Do you want to kick it off? Do you want to go first?

Sullivan Finlay 00:56:
Sure. I was reading a few different things this week related to AI, as we do. One article that I thought was really interesting offered a fresh perspective on AI. We’ve heard a lot about how AI might take our jobs or the negative sides of AI, but I read an article co-authored by Sam Altman, CEO and founder of OpenAI, and Arianna Huffington of Thrive Global. The two of them have co-founded a new venture called Thrive AI Health. The idea behind it is that as language models grow in size and sophistication, they also grow in their power of persuasion. There are plenty of ways that this could be used poorly or dangerously, but Thrive AI Health has been created to serve as a personal day-to-day assistant, helping in different aspects of health like sleep, food, movement, stress management, and social connection. It will send you notifications, like, “Hey, you should move,” or, “Here’s how you slept last night.” It’s similar to what an Apple Watch might do now, but I think it will grow in size and scope over time. They even gave an example in the article about a busy professional with diabetes who might not be keeping up with their blood sugar levels. Thrive AI Health could remind them to take their medication or give them meal ideas to get their levels where they need to be. It’s a cool idea that shows how AI can be used for good, especially in the area of health, where any of us could do better.

Callan Harrington 02:08:
Yeah, Apple is going down this path heavily as well. I like that there’s going to be competition between the two. Although OpenAI integrating with Apple is going to be interesting, or I should say, if it does. And then there's the Oura Ring, which I was just looking into. They have the Oura Advisor, which will start to give you proactive recommendations based on what they’re seeing in your data. They haven’t launched it yet, but I was messing around with it a little, and it looks pretty interesting.

Sullivan Finlay 02:33:
What's it like now with Oura? What are they sending you, versus what they’re saying they’re going to send once they deploy this?

Callan Harrington 02:38:
They created this Oura Labs, which is cool. You can opt into some of the different features within Oura. It’s looking at trends, like if your heart rate variability was at a certain level for a certain amount of time, and if they notice a pattern, like every Thursday or something like that, it might be interesting to see how they interpret that data.

Sullivan Finlay 02:56:
Yeah, I have to say, in general, I’ve really been leaning on ChatGPT recently. I’ll give you an example. We conduct customer interviews and gather insights, and now AI can handle a lot more than it could even just a year ago. I remember you couldn’t even put a full podcast transcript into it because it would be too much—you’d have to break it into pieces. But now, I can upload multiple transcripts into ChatGPT and get insights. It won’t just give you the answers outright, but it validates a lot of what I was wondering. I’ve been finding myself using it for that a lot—validating ideas, prodding for insights, things like that.

Callan Harrington 03:34:
Yeah, that’s part of why I like the Thrive AI Health use case. There are so many ways that AI can be used for productivity and efficiency, but it’s cool to see how it’s being applied to health, improving health spans and lifespans—things we don’t always associate with AI. There’s going to be a wave of this, especially with the VC money going into this space. It’s going to be huge.

Sullivan Finlay 03:57:
As I mentioned in the last episode, any VCs who are bored of funding AI and want to fund creative ventures instead—come on over. That’s my pitch.

Callan Harrington 04:06:
You sold them for sure. That was really well done—50 million bucks for five posts a week. Who says no, honestly? What about you, though? What have you been reading?

Sullivan Finlay 04:16:
All right, so I don’t believe this is a recent thing, but I heard it talked about recently on a podcast, and I hadn’t heard this before. What Apple does is when you have someone in an individual contributor role, and they’ve been with the company for a long time, one of the most common issues is that individual contributors are capped if they don’t go into leadership. You feel forced into leadership, even if you don’t want to be in a leadership position, and you end up feeling stuck. So what Apple’s done, and I’m sure countless other companies have done this as well, is if you’re an individual contributor, and you’ve been in that role for some time, you can continue moving up the pay scale without having to go into management. You still get the same comp, perks, and benefits of rising within your career, but you don’t have to go into leadership. You can stay a top individual contributor, which I thought was super interesting. I’m curious if a lot of companies have been shifting to a model like this.

Callan Harrington 05:02:
Yeah, that is interesting. I’m just thinking about my time in corporate America. By trade, I’m an accountant and a pretty introverted one, as many of us are. There were things about moving up the ladder that were fun, like coming up into middle management or leadership and having teams. But at the same time, there were definitely days when I just wanted to grind on what I was working on and be an individual contributor, without being responsible for a team. It’s nice that this caters to a wide array of personalities. Some people are natural leaders from day one, but there are also people who might not be leaders, but they’re incredibly efficient or productive, or they can knock out tasks faster or better than anyone else. Allowing them to stay in their roles as individual contributors lets them continue to hone their skills, which is valuable to the organization.

Sullivan Finlay 06:02:
Yeah, no question. This is always a hot debate in sales because, in a sales role, you’re either an individual contributor or a sales leader. Maybe you go into a sales operations or RevOps role, but that’s fairly rare. The challenge is that sometimes people get pushed into leadership because they think there’s no other way to advance. Personally, I think whether you’re an individual contributor or in leadership, from a sales perspective, you’re equally important. The top sales rep in a company is one of the most important people in the company—no question. I went into leadership, and I love the leadership side. I knew pretty quickly that was where I wanted to be, but I think people feel like being an individual contributor in a sales role is a dead-end career, and I couldn’t disagree more. You’re going to make ten times more money and have ten times more freedom. The top sales rep can do whatever they want, whenever they want, and it doesn’t matter—no one is going to tell them otherwise.

Callan Harrington 07:05:
Is that true even with the hours? Because I don’t come from the sales world, so I’m curious. You hear a lot about the long hours, especially for high-performing sales reps who are continually winning work. For those top sales reps, do they have enough freedom and flexibility within the hours to do whatever they want?

Sullivan Finlay 07:26:
For the top sales reps, 100%. Where it gets tricky as a sales leader is with field sales reps—those who aren’t tied to the office or their computer but are out meeting with clients, whether nationally or regionally. It can be hard to keep tabs on what’s going on, but for the top sales reps, it doesn’t matter. They’re going to be highly self-motivated anyway. So yeah, if they cut out to play golf on a Friday, they’ve probably already put in significant work. And you know what? This might be a bit controversial, but even if they haven’t, if they’ve built really good relationships and can pull in significant revenue while working part-time, very few people will tell them they can’t do that. You earn the right to have that flexibility in that role because it’s so black and white. On the flip side, though, you’ll get fired super fast if you don’t hit your numbers. It’s a double-edged sword.

Callan Harrington 08:20:
That totally makes sense. It’s kind of like being an athlete at the top level of their game. Dennis Rodman could go and party in Vegas for a week, and Phil Jackson would let him because Rodman was an incredibly integral part of the 90s Bulls. It’s about knowing what works for each person and recognizing that the flexibility is earned.

Sullivan Finlay 08:47:
Yeah, the only caveat is if that person is a bad culture fit. In my eyes, you’ve got to make a tough decision and separate from them because you can’t scale off of that. It becomes really difficult. What’s commonly referred to as a “lone wolf” needs to be cut, in my opinion, which is a hard decision.

Callan Harrington 09:10:
All right, shifting gears here a little bit and moving to the “Work in Progress” session. For our listeners, this is something that we're working on, learning, using, or applying just in general. I'll kick this one off. So I learned about this book—I haven’t read it yet, but I’ve heard it talked about. It was discussed on the Tim Ferriss and Kevin Rose show, and then I listened to the author on Kevin Rose’s show. The book is called Superconnectors by Charles Duhigg. He’s the author of The Power of Habit, which is a great book on habits, breaking down the science behind them. Atomic Habits by James Clear is excellent for action-based habit formation, but Duhigg’s book focuses on connecting with people quickly. It’s about how to get to a deep relationship with someone by asking questions about their beliefs, values, and experiences. He had a couple of very tactical ideas on this. One idea was that when you’re going to an event or even just a lunch with someone, say it’s a networking lunch, write down three topics that you can talk about. Write them down, put them in your pocket. The interesting thing they found was that people would never reference the questions, but the confidence built from knowing they had something to talk about in advance was enough to help them build momentum and avoid awkwardness.

Sullivan Finlay 10:24:
Wow, that’s really interesting. I’m going to need to read this because I can be pretty socially anxious or struggle with that question of what to talk about, especially when it’s with someone new or someone I know decently well but have run out of topics with. It’s kind of like when you’ve been on three dates with someone, and you feel like you’ve already run out of things to say. It’s not going super well, but it’s not going poorly enough to stop seeing them, you know?

Callan Harrington 10:48:
Yeah, I feel like in this work-from-home environment for the past few years, there are times when I feel like the opposite of a superconnector—a “disconnecter” maybe? You feel like your social skills are atrophying. I’m curious, though—does he give examples of what those topics of conversation can be? Are they surface-level, like talking about someone’s day or the weather, or do they go deeper, like beliefs, values, politics?

Sullivan Finlay 11:14:
Regarding the first part—when you run out of topics, what do you do? This isn’t an apples-to-apples example, but he talked about a scenario where you’re at a party and stuck talking to the same person the entire time. I think we’ve all been there. I’ve definitely been in that situation because I feel bad. The person is usually super invested, and at this point, I don’t want to say I’m checked out, but I feel like that person is usually me. If there’s not a dog to hang out with, I’ll identify one person and be like, “Alright, we’re going to converse.” And to be crystal clear, I’m not saying I haven’t been the one talking someone’s ear off. I’ve been there too. But the example he gave was that you handle this by saying, “I want to go talk with some other people here, people I haven’t connected with in a while, but I’m really interested in this conversation, and I have one more question for you.” Then you ask that question, so you show that you’re interested in what they have to say, but you’ve given yourself an out to go see other people at the party.

Callan Harrington 12:02:
Yeah, that’s smart because it gives you different avenues to explore. If that last question generates new conversation, you can delay moving on. But if it’s a dead end, you can go and talk to whoever else is in the room. That’s super practical. I don’t know if it would work in the dating example you gave, like, “Hey, look, I’ve got a number of other dates I need to get to, but I’m really interested, and I have one more question for you.”

Sullivan Finlay 12:27:
Yeah, like, “You’re my 7:30, and I actually have a 7:35, so if we could just stick to five-minute increments...”

Callan Harrington 12:34:
Well, I haven’t been on a date in a million years, but if they’re coming in five-minute increments now, things have changed a lot.

Sullivan Finlay 12:40:
It’s revolutionizing the industry of speed dating, which the market needs. I don’t know—I’m getting married in three weeks.

Callan Harrington 12:49:
Well, this is a perfect segue. What are you working on?

Sullivan Finlay 12:53:
One thing I’ve been thinking about, specifically as it relates to content—and I know we’ve talked about this a lot, even in writing together—is exploring different formats or things adjacent to what I do now that could work. I’m almost thinking of it like launching another product line. I have this format where my videos follow a checklist on the screen, and as each character says something, it gets checked off. The idea is that people will stick around to see things checked off, and those videos tend to do better in terms of watch time and overall performance. But I’ve been thinking, what other formats are similar enough to keep people engaged but different enough to grow off of and avoid feeling stuck in a rut? It’s been interesting to think about it as different products and where I can go with each.

Callan Harrington 13:36:
Do you have an example?

Sullivan Finlay 13:38:
Yeah, a couple of examples. One is a countdown clock, kind of like on ESPN’s Pardon the Interruption, where there’s a list of topics and a countdown clock for each one. Another idea is a monologue format, where a character just talks through something. For example, in a lot of my corporate meeting videos, it’s usually just the corporate manager saying nonsense. If you’re an individual contributor in that meeting, you’re probably not saying much other than, “Okay, thanks, bye” at the end. So I thought about creating a dialog where people could duet the video and play the individual contributor, only to realize a minute in that they have basically no lines. I think that would keep people in suspense, wondering when they get to talk. These are just ideas I’ve been doodling on. It’s been fun to explore.

Callan Harrington 14:29:
When you’re thinking about making these major changes within content, one of the challenges I always had was that I would find a structure for a post that worked well, and I would double down on it, which is often what you should do. But sometimes it gets stale or boring. When you make these changes, do you worry about it impacting performance, or is it more about getting the stuff out there and seeing how it goes?

Sullivan Finlay 14:55:
I do worry about performance to an extent. I tend to go into new formats thinking, “This probably won’t do well because it’s not what people know me for.” So I don’t always have high expectations, and if it does well, I’m pleasantly surprised. But I do worry about performance, and if it hits, then I think, “Okay, now we have something new to work off of.” I’ve had shorter formats that have hit before, and then I’ll do a part two or something similar with a different character. That’s usually my trigger for doing it again—if it does well. If it doesn’t do well, I’ll analyze why. If it didn’t do well because people weren’t interested, I’ll move on to the next thing. But if it didn’t do well because my jokes weren’t that good, or I could improve, then I’ll try the format again to see if it resonates with people.

Callan Harrington 15:49:
Yeah, it feels like it’s similar to stand-up comedy, where you’re supposed to do the same joke three or four times before you change it because you don’t know. Sometimes it just may not click with the audience, or the way you said it didn’t land. Is it similar to that?

Sullivan Finlay 16:05:
Yeah, I would say so for sure. I think stand-up is a good comparison because it’s the same thing with the audience. In stand-up, if a joke doesn’t work in one room but kills in another, you start to see patterns. Online, it’s like if an algorithm pushes out your video to the wrong audience, it might not engage. But maybe if you tweak it a bit, it’ll reach the right audience. That’s where hashtags, descriptions, and other factors come into play. It’s definitely an apt comparison.

Callan Harrington 16:40:
Boy, did I learn that lesson the hard way. My first paid gig in stand-up, and you know the story—I had one set that I was doing over and over again, and it hit in the areas where I was performing because I knew the audience. Then I went into a group that was much older, much more conservative, and I didn’t change a single thing. It bombed so hard.

Sullivan Finlay 17:04:
We’ve all been there. It’s just something you have to sit in. But it makes you better for other situations where you’re public speaking because you think, “It can’t be as bad as that.” Or even if someone insults you, you think, “Whatever, this is nothing compared to bombing that hard.” I remember I’ve only done stand-up a handful of times, but I remember one time during peak COVID, right as the Delta variant was coming out. I don’t remember the entire joke, but the idea was that this girl showed up to my gym with a carry-on suitcase, and I was like, “What is she planning to do? Is this the airport for her? Did Delta just land next to this gym? Talk about Delta variant!” The entire audience was quiet, except for one guy who just went, “Ha!” And I was like, “Okay, maybe for that one guy, this worked, but this is a joke we probably cut.”

Callan Harrington 17:52:
Well, in an open mic, that’s all you really need because half the comics don’t even want to laugh, and the other half have heard what you’ve said 500 times. If you get one person to laugh, that’s good enough for me to test it out in a show. But I’ll tell you what, both stand-up and improv have helped me tremendously in business, and I recommend trying both to everyone. I think improv is probably more helpful because the skills you learn in improv—like listening, building off of each other—help so much in a leadership capacity. The ability to get thrown into an uncomfortable situation and be totally fine with it is invaluable. And from a stand-up perspective, the ability to be concise, take feedback, and make iterations, and more than anything, that grit or perseverance you develop when you’re up there, and a joke you think is funny doesn’t land—it’s a unique experience. You can’t help but build thick skin that prepares you for a lot of difficult times.

Sullivan Finlay 19:05:
Oh yeah, 100%. I think the improv piece is especially valuable. I’ve said to a lot of people that everyone should almost be required to take an improv class. It really trains you to be more chill, go with the flow, and in a business setting, that helps so much. Whether it’s a meeting running over and you’re late to another where you’re presenting, it’s a stressful situation, but you have to be present in it. Improv teaches you to be present in the moment. Each day or moment is like a scene where you get to make choices to either improve the scene or not. I highly recommend it.

Callan Harrington 19:42:
I think the trouble a lot of people have with that is that they see what a level one improv class is, and it’s often filled with people who are overly positive and have drunk the Kool-Aid from minute one. It can be a little overwhelming. What I recommend is to take a couple of levels because once you get into level two and three, you’re learning more advanced skills that are even more powerful, like the ability to diffuse an argument. And that overly enthusiastic energy is usually ironed out by that point.

Sullivan Finlay 20:11:
Yeah, that improv energy at first can be a double-edged sword. I remember showing up to my first improv class, and I think Amy Poehler said something similar—it’s like, “Oh, here you are. These are the people I was supposed to be with this entire time.” But over time, you become more jaded and learn different things that you can do in improv versus what you’re taught in level one. It’s a mixed bag when you’re starting out, but I definitely recommend it.

Callan Harrington 20:41:
This isn’t a plug—we don’t do this work—but I highly recommend corporate improv classes. Bringing someone in to do a corporate improv class is great for team-building exercises.

Sullivan Finlay 20:52:
Totally.

Callan Harrington 20:54:
Okay, one win and one loss—let’s move to the next segment. Want to kick it off?

Sullivan Finlay 20:59:
Sure. I have a half-serious win and a serious win that’s also kind of a loss. So that’s the format we’re working with for this week. My win: this past weekend, I was on my bachelor party, and as I mentioned, I’m getting married in a few weeks. We were in St. Louis—I’m a big Cardinals fan, so we went to a Cubs-Cards game and did the Anheuser-Busch brewery tour. It was super fun. But we also had this total bachelor pad of an Airbnb—me and my eight groomsmen. This place had copper shot glasses, every arcade game, and a huge movie screen. It was so much fun. Early on, I decided that I was going to be the best at Pac-Man for the weekend because I get way too competitive.

Callan Harrington 21:49:
You decided this?

Sullivan Finlay 21:50:
Yeah, it was an active decision on my part. So my win of the weekend was that I set the high score on the Pac-Man machine. My other win, which is also kind of a loss, I’ll save for later. But I’m interested to hear your win for the week.

Callan Harrington 22:07:
Interesting. So you’re going to do what I did last week and bring up that your biggest flaw is that you work too hard. Spoiler alert—it’s going to be that I’m a perfectionist. No, I’m kidding.

Sullivan Finlay 22:18:
So my win is that I kicked off a new project a couple of weeks ago, and going off what I talked about in the previous episode about bringing on experienced people, I brought someone onto this account who has a ton of experience in both consulting and go-to-market leadership roles. It’s gone excellent. In consulting, one of the toughest things is that people are typically buying you, and it’s hard to get out of that in two ways. It’s hard to get out of it from the client’s perspective because they see you as the person with the experience. And then, for me, it was hard to let go of that because I knew a lot of people with experience, but the way I did things made it difficult for me to let go. But after our first call with the client, I told the person I brought on, “I cannot tell you how good it feels hearing you lead this. I’m learning from you as we go through this.” I found myself taking notes on some of the questions he asked, and I realized this can really help scale the business to the next level. So I’m super excited about that. It opened my eyes to a lot of things, and I’m excited to continue with this.

Sullivan Finlay 23:14:
It feels like a level up in terms of where the business can go and what it can become.

Callan Harrington 23:18:
100%. All right, what’s the loss?

Sullivan Finlay 23:22:
The win side of this, I’ll say first. Lately, because of the busyness of this season of life—getting married, moving, having a dog, and trying to launch this comedy thing that’s only a few months old—I’ve had to adopt a survival mindset, almost like an essentialist mindset. I’m quoting from Essentialism: The Disciplined Pursuit of Less by Greg McKeown, which is one of my favorite and most impactful books. The win has been that I’ve had to think in that mindset of asking, “What do I really need to do? What’s important now, between now and getting married and moving?” For me, that’s looked like focusing on doing content well and allowing myself enough time for that while pausing on doing shows or writing outside of content creation, at least for the next month or two. The win is that I’ve started thinking like that. The loss is that I don’t always feel great about the execution. It’s very easy to get distracted by things like moving into a new apartment, which I can do quickly, but it might not be what’s most important. It’s not what’s driving your economic engine, as Jim Collins would say. I’m trying to figure out how to choose those things well, even though I’ve defined them at a higher level. The loss is in the execution—feeling strapped for time and that kind of thing.

Callan Harrington 24:48:
I can empathize with that completely. That book was also a big eye-opener for me. The challenge I had was taking too many meetings that weren’t focused on what really mattered, and it was hard for me to cut those out. But now it just evolves and changes into different things that I need to cut out and focus on. Actually, that segues into my loss. You and I have talked about this—I’ve been looking to hire an assistant and wanted to test the virtual assistant route. I’ve heard a lot of people having success with this. If you’re not familiar, this typically involves hiring someone overseas, whether in the Philippines or Latin America. I’ve never done this before. I looked at a lot of agencies, and I might still go that route, but I figured I’d try hiring on my own first through online jobs.ph or Upwork, or one of those platforms. I posted the job, got a ton of responses, and I was told to message back and forth a little, see how I connect with people. But I didn’t follow my standard interview process. My standard process uses the WHO method, which I’ve used for years for every position I hire. It involves a basic 15-minute phone screen, followed by an hour-long in-depth interview where you ask the same series of questions to go through someone’s resume and identify patterns. I’ve never hired anyone internationally before, so for some reason, I didn’t follow my typical process. I just went straight to a 60-minute interview with the top candidates. Three really stood out. I held all those interviews, found someone I liked, and shot them a job offer—after we had already discussed a lot of the specifics on the call—and they totally ghosted me.

Sullivan Finlay 26:19:
Wow.

Callan Harrington 26:20:
So I’m trying to get a lot of these things off my plate that won’t move the needle, but I need help with them. When I say they won’t move the needle, I mean they’re not what I’m uniquely good at doing. They’re things other people are better at than I am. So yeah, I got ghosted. Now it’s back to the drawing board, and I really need this position filled.

Sullivan Finlay 26:42:
First of all, consider this segment a job posting from Callan. So anyone out there looking to be a virtual assistant, come on over. Will you go with a new batch of interviewees, or will you consider the other two you interviewed? And with that, are you thinking of going back to the WHO method or changing it up again?

Callan Harrington 27:01:
All good questions. Thanks. I’m actually interviewing you for my VA position now. All good questions, all things I should have answers for. Here’s what I’m thinking. I liked the other candidates. One really stood out. So I think I’m going to start scheduling those 15-minute phone screens. Will I do the full WHO interview? I’ll probably test it. I’d like to test it, and if it works similarly to how I’ve always done it, great, then I’ll go with that. But I haven’t hired for this position before, and it shouldn’t matter because the WHO method is a very universal approach. Sequoia Capital gives it to all their founders when they first start because it’s such a good interview process for finding really good people. So I’ll at least test it, and if it doesn’t work for whatever reason, I’ll drop it and go back to the questions I asked. But yeah, either way, I’ve got to move on this quickly because I can feel things slipping through the cracks. I’m not there yet, but it’s close. The only reason I’m not there yet is because I’m working ten times more than I want to. I do want to try to get some more free time because, as we talked about last time, I can feel the stress building, and that’s okay, but it’s going to impact my health. I’m positive of it.

Sullivan Finlay 28:08:
Yeah, no, it always does. I remember last October, I was really starting to think about what it would look like to move on from corporate America, and I was in the early stages of planning for that. I was also about to propose to my then-girlfriend and was stressed about that, traveling, and all that. I remember at the end of the month thinking, “I definitely lost some hair this month.” The stress had aged me. So I can definitely empathize with that.

Callan Harrington 28:47:
Yeah, I’m trying to avoid that more, but it’s not easy to do—at least not for me.

Sullivan Finlay 28:51:
No, I’m with you. All right, that’s a show. As always, we really want your feedback on the episode. What did you like, what didn’t you like, and what needs to be removed immediately? Sullivan, thanks for coming on, man.

Callan Harrington 29:01:
Of course. No, it felt good to have some segments. I’m curious to hear from you all listening what you think.

Sullivan Finlay 29:07:
Yeah, 100%. If you liked this episode, you can find me on LinkedIn to let me know, and if you really want to support the show, a review on Apple Podcasts or Spotify is very much appreciated. Thanks for listening, everybody, and I'll see you next week.