How one gets to be very powerful as a senior leader is that you've learned how to ask good questions and as you learn how to ask good questions, ultimately you learn how to nudge. But you don't learn that only by being really narrowly focused on one thing. You learn that by seeing adjacencies. And the higher up you go, those adjacencies are more and more important to one's capabilities.

In this episode

Mark Frein, COO of Oyster, discusses how he approaches his role as a multifunctional executive. He emphasizes the importance of focusing on the scope and responsibilities of the job, rather than the title. 

Transitioning from a single-function to a multifunctional executive, like a COO, requires a significant shift in how you operate. According to Mark Frein, whether it’s navigating a discussion on service metrics one moment and pivoting to product innovation the next, being able to adapt and change at a moment’s notice is vital.

Mark Frein is a seasoned leader and the Chief Operating Officer at Oyster. With decades of experience in the tech industry, including roles as Chief People Officer and a professor in academia, Mark has established himself as a dynamic force driving organizational growth and operational excellence.

In episode 3 of season 2, Mark offers valuable perspectives on effective goal setting, prioritization, and the power of hypothesis-oriented goals in driving success. He delves into prioritizing job scope and responsibilities over titles and shares insights on aligning people practices with business objectives. Mark explores the challenges of fostering cross-functional collaboration and highlights the importance of fostering a cohesive team environment. Drawing from his expertise as an executive coach, he discusses the role of HR in a business context and the significance of systems thinking and multidisciplinary approaches in leadership. Mark also addresses the evolving landscape of remote work in 2024, advocating for inclusivity and equal opportunities in distributed work environments.

Tune in to hear all about Mark’s leadership journey and the lessons learned along the way!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Context switching as a multifunctional executive


Shiny object syndrome


Creating cross-functional collaboration


Executive coaching in leadership


Systems thinking and multidisciplinary approaches


The state of remote work in 2024


The never-ending craft of being a manager

Resources mentioned in this episode:


Mark, welcome to the show. 

Mark Frein  02:43

Hi, nice to be here. And thank you for having me.

Aydin Mirzaee  02:46

Yeah, super excited to dig in. You’ve had a really interesting background leadership at a bunch of different companies Oyster, InVision, one of the things that I did notice about your background is at InVision, you were Chief People Officer. And today at Oyster, you’re the CEO. And I’m wondering about that jump in general, how did that happen? What are the differences between CEO and Chief People Officer? And how do you think about that stuff.

Mark Frein  03:17

If you roll back even further on the resume, I was CEO at one point in my career of a consultancy that was operating out of Vancouver, Canada. At our largest we were about a 70 person firm, so not not too small. So I’ve collected a lot of three letter acronym titles in my career. And I would say at a certain point in one’s life and career, they cease becoming meaningful in and of themselves. And what becomes very meaningful as is the scope and the things that one is responsible for. And so the way I think about like an executive job or a C suite job today in the job I have today at Oyster HR is what am I responsible for? And how can I help move those things forward. So the biggest difference here from InVision when I was Chief People Officer and I’ve been Chief People Officer more or less for the last decade at a number of different tech startups is I am now what you might call a multifunctional C suite executive, meaning beyond operating and organizing and booting up and running a people function. Here I’m responsible for a whole bunch of different organizations from our legal team, to our people team, to our service and operations groups to our product engineering groups. And so it’s a much broader remit, which just means that one has to be really thoughtful about where one puts one’s eyes and ears at any given time. So when you think about executives, you think about breadth and depth. And in terms of just sheer operational overview, it’s the broadest organization I’ve ever had under me, which has challenged me to figure out how I operate at that level of breadth with by literally just I’m gonna use a bad analogy like the eye of Sauron, but that implies it’s like bad luck. Like, once again that from using geeky metaphors already, and it’s only a couple of minutes in, but an executives attention that sometimes the most important thing that she, he, they can can put. And when you have a wide scope, you just have to travel that attention around wherever it’s needed at a given time. And I think the most important change from being a single function executive to being a multifunctional executive is your AI and how you adapt that AI at any given time has to be able to change on a dime. So I have to be capable of going from a conversation around our service metrics to around product innovation, on a half an hour switch. So that context switching just becomes the most important thing in some ways, and how one spends one’s attention, because that’s the most limited thing I have in the day is my attention and how I spend it, with whom I spend it is really important.

Aydin Mirzaee  05:57

Yeah, thank you for explaining that and kind of explain it to while you’ve been a CEO before. So you’ve run companies, you’ve run different functions. And it’s almost like what is the goal that I have? And can I help and you can call me whatever you want? What is the outcome that we’re trying to achieve here.

Mark Frein  06:13

And I have had the funny titles that I’ve for a while here I was chief workplace officer, which was a little bit even of unintentional bit of humor, because Oyster HR has no physical workplace. So I thought, well be nice to have Chief Workplace Officer considering it’s a little bit about the message, which is one couldn’t have a workplace and still be placeless, in this world of distributed work. I don’t want to say titles are overrated, because they’re important for career. But I’ve just tended to feel like at the end of the day, what do I over? What am I watching? And how am I helping those organizations move ahead, and I love this term, like a multifunctional Exec. So I mean, that sounds pretty hard. How do you know what to work on? When you wake up? Yeah, in any given day, the most straightforward answer is about where the organization is either experiencing the most blockage, so where there’s problems that my attention push, or energy can unblock. And also where there’s opportunity. So it’s a little bit of being able to just see where things are getting stuck in the organization’s velocity, and how my presence can move it along faster.

Aydin Mirzaee  07:18

So it’s almost about where can I provide the most leverage? And you’re always asking that. And so I can imagine that at a large organization like Oyster, you’re getting pulled into many directions, or it might be easy to go down many different rabbit holes. And so do you start quarter or whatever else and say, Here are the main leverage points that I’m trying to address? And if other things come my way, I’m like very actively saying no to them, are we directing them or trying to make sure I don’t get pulled into things that are not in that high leverage area?

Mark Frein  07:51

Absolutely. We have objective key results type framework here at Oyster. And, and while I’m not particular about the objective, or goaling framework one uses and you can use whatever helps you organize yourself, frankly, but you know, the OKRs is one that a lot of companies use. And that ideally just gives you the way I like to think about as a set of hypotheses about if I do x and y will happen. And those hypotheses, that set of hypotheses are hopefully the most important things that one might do to make a difference in the organization’s performance. So if you think about an organization a little bit like, you might think about an athlete, for example, metaphorically, if an athlete practices a certain kind of sprinting technique, they can shave off a couple seconds from their run. Or if an athlete practices certain kinds of weights, they can, you know, you just think of those same things for an organization and metaphorically, you can think of organization like a piece of performance work in that way. And your goal Ling or whatever priority system you use is a set of hypotheses. If we put attention and effort on x, then y good will happen. And over the course of a quarter or two quarters or a year, you just test those and then you revise them whenever you learn something about whether or not they’re working or not. And I mean, it’d be remiss to say that on any given day, I only wake up and look at my OKRs and figure out what I’m going to do. But I think a solid company knows what it’s trying to accomplish corporately. And then someone in a position like mine can link us to say any additional effort I put on anything, I can link it in the backdrop of whether or not it’s helping any of those things. A trap I think a lot of executives fall in sometimes is what people talk about is the shiny object syndrome, like something interesting and new comes along well, in startups, at least, which is where I’ve spent most of my last at least 15 years of my career. There’s times and shiny objects sort of practically shiny because they’re really valuable. The examples funny because you know, a diamond might be worth going and grabbing out of the rough because startups have to move fast. But you still have to have that against the backdrop of a set of assumptions about how the company is going to progress. So at least that helps me on a given day. Oh, we’re trucking along, focusing on things and all sudden a really interesting partnership emerges that we didn’t expect we would have, well, how do we understand partnerships strategically in 2020, for our partnership, something that we value and want to work to foster. And in case in point Oyster this year has, uh, one of its strategic priorities for the year is enhancing partnerships. So that means that that shiny object or that diamond that I that glints out there, if it’s a partnership opportunity, it’s probably worth spending time on that at least keeps a framework in place for how I prioritize my day. The other thing I do, I think, on a day to day, week to week basis is think about who needs to help the most. I mean, it’s just teaching in a classroom or anything else, where you have a bunch of people, all of which who need you at some level, but you can’t necessarily be of service to all of them all the way the same time. And so there’s times when one of my direct reports needs help, because they’re struggling with a managerial issue underneath them, there’s times when one of them is particularly blocked, and recognizing what that is partly because we have a trusting relationship is important. So they, if I know they’re struggling with something I can help, I don’t know, they’re struggling with something I can’t. And so it’s building those pathways, those mutual relationship pathways are really important. I don’t have to go and work to get out of someone who’s my direct report that they’re struggling, they’re just telling me oh, I need help. I can divert myself.

Aydin Mirzaee  11:25

Yeah, the way you phrase the you know how to think about goals, and that I have a series of hypotheses that these things are doing these activities, you’re gonna move this numbers are really good way to think about it, actually. And it actually makes it more fun. It’s like we’re gonna play a game, we’re gonna re-hypothesize.

Mark Frein  11:42

I kind of like to think about, like, productizing goals. It’s a product mindset, or product design mindset with goals is very much a question of, of learning. And I think sometimes when goals simply as an input output equation, or put, there’s too much focus put on the input output, you sort of lose sight of the fact that the organization should be evolving as it’s performing, not in growing in its capability to perform more, not simply, a goal of that is simply a metric doesn’t really do much, because it doesn’t point you towards anything, you just ask the binary question, did we meet that number or not meet that number that’s important, but it isn’t organized, in and of itself was a dashboard item. 

Aydin Mirzaee  12:21

So it’s interesting. So you have a variety of different functions reporting into I think you mentioned product as part of that, too, right? A lot of people have difficulty with fitting product related goals into an OKR type structure. Do you do that at Oyster? Or is it? Is it easy to do that? Or do you really have to bend the way things work in order to fit product goals, and the same…

Mark Frein  12:46

Not generally, there’s always going to be build things, ship it has got to be fairly discreet and specific. But there’s also build things, ship it, and have it capture a certain amount of revenue. So you can’t you know, or if we ship it, then they will come and give us their certain amount of revenue. So even though one might argue that a product goal that has a revenue tie to it is dependent on say the go to market or sales organization to achieve that’s okay. That just means you’re saying that, you’re not simply going to build a thing and ship it out the door and hope something good happens you’re going to build into but out the door, because you think you’re solving a customer problem for which the customers will want it. And how do you measure that? Well, they buy it. And so there’s this ways, and again, it’s a hypothesis oriented goal. Like if we get this thing into the hands of customers, they’re going to appreciate it enough to put down money for it. That helps make them very concrete. At least in our case, there’s going to be very, very long term product discovery goals for organizations that don’t have a immediate dependence on revenue that might be a little bit different. But ours as a venture backed 500 some odd person software company that has moved fast, we’re gonna try to ship things and have them be monetized relatively quickly.

Aydin Mirzaee  13:56

Yeah. So being a multifunctional executive, one of the things that I assume you have team meetings where all the different functions get together. And one of the questions I have for you is, have you learned ways of really creating cross functional collaboration between the groups make it really feel like a team, even though their day to day might involve very specific things that maybe are not as interesting to the day to day of each and every one of them?

Mark Frein  14:28

Yeah, that’s a great question. It’s particularly pronounced, for example, teams that report to CEOs, which I was myself a while ago. And then I did a bunch of executive coaching in my career for CEOs, in some cases, even at very large public companies. CEO teams are particularly notoriously difficult in this way, because they should be rather self organizing. And the functional leaders should, generally speaking, be capable of running their functions without the CEO doing anything. It poses a really interesting conundrum like what is a CEO team? If generally speaking, they don’t need to act like a team. So it’s not all that dissimilar from my particular direct reports who happen to spread across a large chunk of the organization. And I would be remiss to say, I know exactly the answer to that question. I’ve been thinking about this question for decades. And where I currently stand is that even if not everyone on my team has something that they need to work on together. So for example, our head of engineering, and our VP people, beyond the transactionality of her supporting engineering as a senior people leader, on his needs related hiring and business partnerships, etc. What projects might they work on together? Well, we don’t know. I mean, it may not be that many frankly. But that doesn’t mean as to humans on a team of nine, they can’t say things within to each other that are useful to the group. So what I focus on, generally is making the group even if it’s not a team, and the way you might think about a team of basketball players are a team of product and engine design people all working on making something very tightly together, right, even if it’s not a very interwoven team, it still means they can be team like and how they show up with each other, and the kinds of conversations they have, and the kinds of questions they ask. And so the very specific recent example is we do a few rounds of engagement, surveying every year. And we had our last engagement survey results midway through q1. And we had a conversation as a group about engagement results, not just reporting out what we did. But also what did people do in q1, or in the last couple of quarters that helped drive positive results for people in your organization? And what can you each learn from each other? So like, why can you crib and bring back to the organization? And what kinds of questions can you ask each other that helps you run your organization better, so it doesn’t matter if they don’t have a project to work on the project could be the company, and the company culture and the organizational health? To the extent that almost two thirds of it is comprised of my team members in terms of the sheer mass of the organization, that’s a lot of importance. And they can collaborate on being leaders, even if they can’t collaborate on peaceful work.

Aydin Mirzaee  17:13

That’s really interesting. Was that an activity where you said, Okay, each person, what questions can you ask other teams to? Okay, and then it was everybody went around. And yeah, that’s a pretty fun activity.

Mark Frein  17:26

And I asked people to come back and share it. Again, it depends on how your listeners may or may not have engagement surveys as part of their normal cadence in their organizations, but you get the data. And then what I asked my leaders is you get your data, I want you to ask a series of questions about it, I want you to talk with your own leaders about it. And I want you to come back with kind of your plan on what you might want to do to make it even better next time. And that doesn’t mean that we over problematize, any engagement survey, it just means that I want to constantly be challenging my leaders to make the organization as healthy as possible. And we have this round of questions. And one, one of my leaders in particular came back with this just fantastically prepared document that was a set of conclusions he and his own team had made about what they want to do in the next quarters activity. I said to him, I said his name is Andrea said Andrea shared with share it with everybody just as an example of what good looks like and he did. And we talked about that a little bit, you know, so it’s almost as if well, it is isn’t it almost as it is that I want each of them to collaborate on being the best executive possible by sharing executive practice. So we often think teams can only be teams, if they’re, they’re sitting in a room or virtual room working on a thing together. But that thing can be being great leaders, right? And that continual building process can be how can we help each other lead the best weekend? So that’s no matter what level of team that’s available to you like that’s available to you as an executive coach, leader, to work on leadership together. And so that’s back to your very, you know, your question, which is a great question. How do you foster that? Well, you make that a practice you make that something you you work on is collective leadership.

Aydin Mirzaee  19:07

Yeah, I think this is again, really important because to some extent, the more senior you get within the organization, your role becomes creating the best team that also works really well together. Actually getting people to work well together is also a skill. That is, it’s not an obvious thing, you can get better at it over the course of time and so that makes a lot of sense.

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Aydin Mirzaee  20:19

In passing, you mentioned that you were also a coach to other CEOs. As part of part of your career, did you find that the act of doing that made you a better leader? Is that something you would recommend? I know some leaders are thinking about this idea of like getting a coaching certificate or something like that. Is that helpful? Like would you recommend that to people in general.

Mark Frein  20:39

I guess I’ve never thought about that. Having experience being an executive coach certainly doesn’t substitute for experience being a manager, like meaning I wouldn’t say in order to be a great executive go from being an IC, to getting a coaching certificate, and then you’ll suddenly become a great executive manager. So this certainly doesn’t take the place of that. I was learning to coach executives at the same time, I was running a company, about developing executives. And so I was able to think about my own evolution as an executive while helping others, I would say that my executive coaching experience certainly taught me a lot about the range of options. For being an executive, I don’t think there’s a single way to be a great CEO or Executive, there’s a way to manifest what one has is one’s abilities in the best way possible. And that’s going to be highly dependent on your personality, your value system, etc. And in many cases, where I thought I did some really good coaching work, or did some work with other coaches who are working on it, it was just about helping someone be the best version of themselves as intentionally as they could possibly be. So that have a positive impact on my own evolution as a leader, I’m sure it did. But you’re doing a very different thing. If I’m, if I’m coaching someone, if all I’m doing is coaching them, and I’m not also supervising them, I can stay in the realm of asking questions forever. So some coaches only ask questions is their practice, I don’t myself believe that that’s the only way to coach but if I’m managing someone, I can’t stay in the realm of questions forever, because I have to give them direction. At some point, knowing how to cross between asking questions and giving direction is a nuanced line. So having spent a lot of time as an executive coach certainly helped me ask questions and listen, which is a good part of how to be a good manager, too. But it’s not the only part.

Aydin Mirzaee  22:27

Yeah, I think one of the important things that you said is that it’s true that leaders should also be coaches, but this shouldn’t be exclusively coaches, it’s a fine balance. And you have to know when to use coaching, when to use mentoring, when to use delegating.

Mark Frein  22:44

I think great supervisors in general, have good coaching skills. But that doesn’t mean they need to be an executive coach to get better at it just means they have to practice their ability to ask good questions, and to listen, and to attend all the good coaching practices, right.

Aydin Mirzaee  23:01

So one of the things that’s interesting, just getting on this topic of getting people to be interested in being good team members for each other, we were kind of scouring your LinkedIn in advance, and you’ve gotten a lot of positive reviews from people who have worked with you in the past. There’s two specific things that I wanted to kind of dig in on. One was this idea of when you were Chief People Officer at InVision, it seems that you did well, you know, amongst the things that were called out were that you, you really helped the HR team, be really interested in the business of the company, like the actual business of it. And so my question is, was there a particular type of storytelling? Or like, how did you get that team super interested about the business of the company? Like were there things that you did, or ways that you explained it that really got them interested and engaged?

Mark Frein  23:52

So HR groups or people, people operations groups are sometimes I think, largely unfairly, but sometimes accused or criticized as being disconnected from the business. And it’s an unfortunate legacy, I think, for a lot of people, executives, even when those executives are very busy themselves. And in some ways, it’s often a critique or a view from the outside, not of actually what’s happening in an HR department. But it’s an assumption, and again, often erroneous, but in any place where there’s some assumptions, there’s some link to reality. And I think the link reality for HR executives goes back many years decades, where HR was a personnel department and the rule enforcement arm of kind of the policy wing of the organization. So great HR people have been working for years to move away from that particular characterization and, and increasingly, I think they are and they’re pulling it off with great aplomb and success, but I’ve done this basically, wherever I’ve gone in as a people executive is one of the first things I try to do is help the people to understand the demands of the business context and how those demands can shape and inform how we think about people matters. Because if you compare it, for example, to a finance department, and most finance departments would never be critiqued as being disconnected from the business. So, you know, they might be critiqued for other reasons, but they will never be critiqued for that. All you need to do for people team to say, look, this business has particular kind of shape, it has certain objectives, it has certain values baked within it, it has a certain kind of, say, assumption about how the business is going to impact culture. And so as people leaders is as humans responsible for advancing the people side of the business, we just have to understand how we use all those pieces and parts to create great policies and practices that advance people in the cause. And I’ll give a very specific example with InVision. So InVision, as some of the listeners may know, very, very prominent and key design platform company, particularly about seven, eight years ago, and also one of the most important all distributed companies kind of at the time, it was born, one of the most important parts of how we approached the design and development of the HR systems was thinking about it with a design framework, because the entire company was devoted to helping equip UX designers and others with a great design framework. So design, and a thinking about design and a philosophy of design was baked into the company fabric. So we thought, we thought, well, let’s bake it into the development of our people practices. So our people practices can have design, emphasis and design flair. So we spent time as a people team learning about design. And I don’t mean just learning about the design of benefits. I mean, learning about design so that we could design benefits. So it was helping people think from the basic understanding of user feedback, customer service, how to think like someone who’s going to create a service for someone else, and how to approach that in a product and design iteration fashion. So we really helped we did some fantastic work. And that’s replicable, not just in, that’s replicable not just in a company that happens to be a design focused company. But it’s replicable anywhere. So I would say anyone who is responsible for people programs, you think about how to connect those to where the company is going. If I was brought in to boot up people function at a AI company, for example, it’d be well, how do we use AI in the development of our practices, because we’re an AI company. So we have to build that into how we think about helping people grow, to help be alive, but at a bare minimum.

Aydin Mirzaee  27:31

It’s so nice to be able to hear you describe that, because a lot of the leaders function is around storytelling. And, and this is, what a great way to do that in order to get people to understand that they can be designers of people related tools, and, and you know, incorporate that so that they can think in that way. And when they think like a designer, maybe they can get better at hiring designers or like understand the needs that designers might almost like customer service or an extent and building that across the board.

Mark Frein  28:00

And empathy and customer empathy was a very, very, very crucial value for InVision from the CEO downward. But it’s also just an absolute fundamental for good design is empathy. So yeah.

Aydin Mirzaee  28:11

The other thing I wanted to talk about was one of the other things that people called out about working with you was your ability to think in terms of patterns and scalable systems. So it sounds like Systems Thinking is one of the things that you tend to do. Are there examples or approaches that you take in order to think about the problems that you’re tackling in that more system viewpoint or like something that we can learn from the way that you think?

Mark Frein  28:42

By the way, I think LinkedIn is very happy that you’re showing evidence, read LinkedIn recommendations.

Aydin Mirzaee  28:48

Yeah, exactly.

Mark Frein  28:49

Half the time I don’t know if anybody ever reads those things. I’m not sure LinkedIn is having them work exactly as they intended. But it’s wonderful to have somebody who has actually read those, let’s just say that. I mean, this is one of those situations where it’s hard to know how to describe what may or may not be someone’s own talents. And so I’m slightly at a loss for words, because that other people have found me to be that way is wonderful and makes me feel good. And I don’t think is an accurate, but how did I get that way? Partly, probably is born with it. But partly, I think there’s things I’ve emphasized over the years. And I was lucky enough, I suppose to be trained formally as a philosopher and as a social philosopher, before I really was trained to do anything else. And one might say, what does it mean to be trained as a philosopher and what? How do you go get training as philosopher because it’s like one of the least practical things one could possibly do with one’s life? Well, you know, interestingly enough, everything comes around and there’s a number of interesting stories right now about how there’s all these philosophers and liberal arts students being picked up to do AI prompts scripting, because they’re just really thoughtful about language. I find that wonderful. Because it shows there’s still some value, I guess, in in thinking about language carefully. And so from the time I was in undergraduate through graduate school, language and how people say things, and how those things are meaningful or not meaningful, how they’re confusing or clear, really important to me, you know, I wrote 250 pages in a dissertation almost about this exact subject. We as human beings, we think in language, and we act in language. And we make things happen in language. And so where people probably have noticed things about patterns or being able to abstract patterns from things, it’s partly about, I think, being broadly informed, caring a lot about different things. They say, if you read the Steve Jobs biography, or you read a little bit about him, I mean, by the way, I am in no way comparing myself. So more the point about what’s interesting about Jobs and his background, is that he was a multidisciplinary thinker. And he was interested during his school in, in design in history, in fine art in a whole wide range of things. And that breadth of interest and education, helped him see patterns in places that people didn’t expect, being, I guess, liberally and philosophically educated myself, I think maybe I picked up a little bit of that same interdisciplinary thinking, which has certainly helped me.

Aydin Mirzaee  29:00

Yeah, there’s also this great book, titled Range.

Mark Frein  29:50

I love that one. Yeah.

Aydin Mirzaee  29:55

Exactly, yeah, it’s really a great book, I struggle to remember the name of the author right now. But incredible book that basically talks about the difference between being very deep in one function versus actually having multidisciplinary experience or trying different things. And, and sometimes when you’re super experienced in one area, maybe you start to advance, and it looks like you’re ahead of everybody else. But it turns out that multidisciplinary folks come back really fast and are able to actually achieve a lot more over the distance. 

Mark Frein  31:54

Well and both things are valuable. Yeah, I mean, I would never discredit when I think about professional grade concert level musicians, I mean, they are exceptionally deep at a single thing, you know, their instrument, and we wouldn’t have amazing symphonic productions without them. And I don’t in any way trivialize I don’t think I have it in me to be that good at anything, frankly, which is, you know, a limitation. I just don’t know if I could be that good at anything. But there’s a nice complement to depth, which is just maybe the forgotten emphasis of the ability to carry on a conversation about a bunch of different topics with a bunch of different people, which in a funny way, is kind of the world of multifunctional business. Can you be curious and interested in a wide range of things and learn in a wide range of contexts? And again, it doesn’t matter if you went to school for this or not. But can you develop a what sometimes it’s called, like a childlike mind about new things and be interested in curious and non presumptive and be I don’t know anything about blank, but I’m here to learn. And as I learn, I’ll ask questions. And as those questions become more refined, maybe I can make recommendations. And that’s how one gets to be very powerful as a senior leader is that you’ve learned how to ask good questions. And as you learn how to ask good questions, ultimately, you learn how to nudge. But you don’t learn that only by being really narrowly focused on one thing, you’ll learn that by being by seeing adjacencies and the higher up you go. I think those those adjacencies are more and more important to one’s capabilities.

Aydin Mirzaee  33:24

Yeah, that makes a lot of sense. And very well put my having you on the show, obviously, given your work at Oyster, and the mission of just making it possible for people to have fully distributed teams everywhere and, and making work democratized, so anywhere you are, you can have great employment, I would be remiss not to ask you about your state of remote work and 2024. So yeah, I wanted to just check in with you, what are you seeing in remote work in 2024? Are there new insights or things that you’ve been thinking about or observed? And, yeah, just want to wanted to hear the latest from Oyster on that.

Mark Frein  34:04

We’re both interested in making sure that the distributed work is successful. And we’re also interested in ensuring global opportunities are there because ultimately, we believe that, that there’s great people all over the world to contribute to this technology sector, and we just want to make sure that they have availability, and they have they have a road in because not every great developer is in the Bay Area, obviously, and not every great customer service person is in New York or you know, etc. These are traditional bastions of talent. But more and more to Mike’s perspective and our perspective, good talent for these kinds of jobs are being seen all over the world. So we just want the world to be here. No pun intended one’s oyster on this kind of thing. The trends I think are really interesting and that COVID was like a wave accelerator in a sense, the wave was already moving. There are already lots of companies exploring distributed work and COVID dispersed everyone whether or not they liked it or not to give it a go. I think we’re almost at the tail end of what is kind of like the ebb out of the water after a wave of crashes in that you saw over the last year, kind of retrenchment of some people who probably never really wanted to be remote in the first place arguing about whether or not it was effective or return to work mandates to get people back into offices. I am one of these distributed proponents who doesn’t believe that it’s the beyond end all of everything I like working in person too. I like seeing my team members in person. I think that there’s room for companies that have all sorts of different ways of working from always distributed to hybridize to in office. I’m not precious about any of that. But I do think it’s the conversation has become binary as a lot of conversations these days do with proponents and and antagonists, and then there’s yelling at each other. Fundamentally, more and more companies over I think the next decades, are going to have a wide range of people who are plugging in to what the organization is doing, not physically proximate, like not walking into an office, and we’re going to have to continue to get really good at having that be a cultural boon, not a problem. Having it be technologically easy, having leaders be really comfortable, literally jacking in people for different circumstances in different ways. Literally having the systems and processes and communication flows, that companies be great at being inclusive. No matter where you happen to be. In timezones, it doesn’t take a lot of the science fiction brain to imagine work in 100 years, with even more digital enhancements to our day to day life. Where if somebody can play civilization with a chip on their head, what’s going to happen, it wouldn’t be true in the following decades gonna be even more crazy in terms of how people interface digitally. So we’re only going to see more of this, the thing that I I’m most, I guess, interested in is how doing so distributes opportunity more. And so here at Oyster, we’re all about that. Let’s just call it the distribution aspect. And we’re a B Corp for a reason. We think it’s a mission, not just not something that disconnected from something about values. And it would be easy for some of the most prominent tech sectors in the world tech hubs in the world, to only be the people advantaged by this. And there’s some good critique out there right now in some aspects of distributed work that it’s advantaging people who are already advantaged by their privilege as a tech worker. So how can we we make the world of distributed work as inclusive as possible, with as many people participating from many different countries around the world? That’s what we care about.

Aydin Mirzaee  37:42

It’s almost like democratizing opportunities across the globe. And so yeah, and that’s really interesting. I didn’t know that you all were also a B Corp. And so yeah, that makes sense. So Mark, as we get close to the end here, we talked about so many different things. We talked about evolution from Chief People Officer to COO, to being CEO, the differences being a multifunctional exec, we talked about how to think about OKRs as hypotheses of doing X will lead to y, how to create teams that actually work well together, the idea of being a coach, and so much more. So lots of great insights. What we’d like to do in this part of the conversation is just ask you a bunch of rapid fire questions.

Mark Frein  38:22

I hate these, but go ahead.

Aydin Mirzaee  38:24

Yeah, so if you feel compelled to answer, I’ll do my best. Yeah. And then if you don’t have anything for one, you could say, let’s get that no problem there. So what is something that you wish leaders would stop doing?

Mark Frein  38:37

Thinking It’s their job to know the answers.

Aydin Mirzaee  38:39

All right, that’s good answer and something you wish more leaders would start doing?

Mark Frein  38:45

Seeing it as their primary job to teach the people and help the people that report to them, then there’s a whole bunch of jobs, but seeing that as the most important aspects.

Aydin Mirzaee  38:54

Love it. For all the managers and leaders constantly looking to get better at their craft are any final tips, tricks or words of wisdom that you would leave them with?

Mark Frein  39:04

Being a manager is a trade or profession or a craft or an art that, like a lot of things in life, like is never ending. Metaphorically, it’s, it’s like a yoga practice or playing a musical instrument. And those people who have practices like that, know that you don’t do a 30 minute “How to supervise” video and then I’m gonna learn piano, I’m going to take a 30 minute course on learning, I’m doing piano and I’m going to be a pianist. Well, obviously, no. So why would we imagine that that is what happens with managers. And I think I know this is not a quick answer. So my apologies, but but I wanted to get on this. This one is important to me. We’ve done a disservice ourselves to managerial practice by making it as if there is like, we’re going to give you the toolbox or we’re going to give you the half day course and then you’ve gotten the shot, like the inoculation and you’re certified. We do that. Like we, we even people practitioners do that. And that’s not helpful. Fundamentally, if you’re going to be a manager, the best analog, I can think in addition to the arts, like a parent, for those of kids, like, I’m going to struggle being a decent parent the rest of my life, because I have three kids and, and there’s times where I’m gonna get it right. And there’s kind of times we’re gonna get horribly wrong. And it’s going to flux every week, every day, every month. And the best I can do is care. If I care about my kids, or if I care about my, my guitarist and musician, like if I care about my guitar work, if I care about these things, at least, I’m never going to lose sight of the point. And so similarly, as a manager, if I care about being above that trade that craft, I’ll get better. I think some people actually don’t care. That’s the biggest problem is they don’t care about being a good manager. And if they don’t care about being manager, they’re never going to really be a good manager.

Aydin Mirzaee  40:52

So start by caring, everyone, start by caring. Mark, this was amazing. Thank you so much for for doing this.

Mark Frein  40:59

Likewise, thank you really appreciate it. I hope this is engaging for your audience.

Aydin Mirzaee  41:04

And that’s it for today. Thank you so much for tuning in to this episode of the Supermanagers podcast. You can find the show notes and transcript at If you liked the content, be sure to rate, review, and subscribe so you can get notified when we post the next episode. And please tell your friends and fellow managers about it. It’d be awesome if you can help us spread the word about the show. See you next time.

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