Cathy Hawley on Building Great Company Culture

Michael Koenig: Hello and welcome to Between Two COOs, where phenomenal chief operating officers come to share their knowledge, advice, and at the very end of the episode, their crazy stories. I'm your host, Michael Koenig, and I'm excited to welcome our guest, Kathy Hawley, co-founder of Bolster, an on-demand executive talent marketplace that helps accelerate companies' growth by connecting them with experienced, highly vetted executives for interim, fractional, advisory, project-based, or board roles. Prior to Bolster, Kathy served in a number of executive roles throughout her career, which includes an 11-year stint at Returnpath, where she was the chief people officer. Kathy also co-authored The Startup CXO, which famed venture capitalist Fred Wilson described as not being a book, but rather a field manual to building a management team and scaling a company. Kathy is the first Chief People Officer that we've had on. I asked her to join us to help pull back the curtain on what is a vital role within any company, that of making sure that everyone at the company can excel, find belonging, and enjoy their work. Welcome, Kathy. I'm excited you're here.

Cathy Hawley: Thanks, Michael. Great to be here.

Michael Koenig: Let's start off. What was your path to becoming Chief Product Officer and landing at Returnpath and now Bolster?

Cathy Hawley: See, I started my career, actually, I did an HR degree. I got my bachelor's degree in HR, mostly because it was— by the time I decided my major, it was the only thing I could finish on time with. I went into HR for about a year. Then I left the country, went to the UK for a few years, and could not find any work in my field. I was a counselor for victims of domestic violence. I mention that because I actually think that helped me change the path that I might have had in human resources. My first HR job out of college was— I was actually HR manager for a truck stop and basically like really helped you understand everything. I did workers' comp and payroll and benefits and every, you know, legal issues, EEO issues, everything. And that might have been the path I continued on if I had not veered off and moved to the UK for a few years. So, so then I think that shaped kind of the kind of HR leader I became. So moved back to the US and just started working in HR jobs. Over various different types of HR jobs, ended up at a company called DoubleClick, which was acquired by Google. Actually, some of our divisions were acquired by a bunch of different people, but that was kind of my first stint back into real HR for a tech company where we could really start being— I guess I could start being more of a true people leader versus an HR leader.

Michael Koenig: Chief People Officer, it's such a vital but misunderstood role, and Oftentimes people have kind of like that stodgy view of HR, right? Where they jokingly throw out the HR violation type of deal. And it's almost like the people officer role or HR role is like a police in the company. But that really isn't the case at all. Can you kind of walk us through the different parts of people operations? What goes into keeping an organization ticking?

Cathy Hawley: Yeah, your police officer comment resonates with me. You walk in a room and people will be, "Oh, HR's in the room." And I'm like, you should be having the same conversation whether I'm here or not. And I'm just a person. I'm not your HR police. But I think there's a real misperception. Well, there's a misperception about HR and expectation of HR. So we started off as like personnel, tried to move to human resources to make sure that people saw the human in it, and then started talking about it as people for that very reason. So people, I mean, language changes and we want to say, we want to change what you think about when you think about your people HR department. So change the language around it, but also some of the practices changed around it. And there's a lot of industry type thing that would explain a little more about why was the function the way it was originally and why did it need to shift? But the way I think about it for tech companies, which is what I've been involved with, is You have a responsibility for really building a great culture. And maybe it started because it was hard to retain people if you were just focused on personnel. All you're doing is getting people in and paying them. Or even if you're just focused on HR where you're a little bit more like, I'm responsible for the company risk. And I think that it could have started because we ended up needing to focus on people so that someone in the organization was really focused on that. It probably came out of a business need of people to— of companies companies to understand their people and be able to retain and attract the right talent. But it definitely is that in tech companies where I've been focused the last 15 or 20 years. If you have knowledge workers and you want to retain them, it's not enough just to say, hey, here's a job and you're going to get a paycheck and here's your benefits. You have to really treat people as people, understand what their goals are, what their motivations are, how to how to best provide everything they need in an environment, not just their payroll benefits.

Michael Koenig: And it really has changed relatively quickly if you think of how long HR has been around and then modern people operations that at least within tech we're used to seeing. Can you maybe speak a little bit to that? Why is it that we've seen so much change and so much development with in the people ops function really kind of accelerate over the last maybe, I don't know, 20 years? At least since I've been in the workforce, it's changed.

Cathy Hawley: Yeah. I mean, I think that, again, I think it was a little bit to do with the type of employees you are. When I was working back when I worked with more manufacturing or people who were on the ground doing work with their hands, there was a little more, you just need to write the rules and rules and people need to follow the rules and they need to know what to expect when they come in. But I think as times, as more tech companies have come on, there's more creativity around that. So you have companies, bigger companies like Google who are kind of setting the bar for what's expected in the workplace. I think that that's probably some of the shift that has happened with that. And yeah, everyone has to follow along and make sure that they're thinking through it. People have choice about where they go. I'm sure there's a lot of factors like social media. People can rate their employers now and they can, if you work somewhere that's great, you can tell me that it's great. It's not just your circle of friends who knows. It's your circle and their circle. So, I think there's probably a lot of factors that go into people needing to be a great place to work. But probably the biggest factor that forces companies to change what they do is whether they can attract talent or not or whether they can keep talent and their kind of bottom line. I mean, I don't like to think like that because I don't think that's the only reason you build a great company, but I think a lot of companies do that. They realize that they need a competitive advantage and that competitive advantage is people, which means that you have to build the practices and processes and values around your people if you want to be successful.

Michael Koenig: And they continue to add on, right? There are new employee benefits. Or new, let's call them flexibilities that we've seen throughout, pretty soon, who knows, it could be really great to be an employee somewhere.

Cathy Hawley: Yeah, exactly.

Michael Koenig: When I think back to at least when I lived out in Colorado, I recall Return Path, just everyone spoke so highly of it. It was such a great place to work. And you all had really nailed the culture portion. And I mentioned in the beginning, how a lot of people operations is also around creating a sense of belonging. How did you all go about that and create that culture at Return Path?

Cathy Hawley: You know, I would say probably started from the very beginning of the company that that was one of the drivers of our CEO really wanting to start a company because he wanted— he felt like he'd been treated so badly in some of the other places he worked. He wanted that. Surely you can have a successful company and treat people well. So a lot of things we did, I mean, he hired the right people who who had good vision around building a good culture. But a lot of it goes around back to his values and how he prioritized things. And I really, I just can't understate the importance a CEO has on this. I've worked with CEOs who don't have that same value and it's really hard to convince them that you should do the right thing by people. So, I'd say that the culture started with Matt and he was very intentional about asking the questions. Like, he hired, He hired a really, really strong chief people officer initially, Angela Baldonero. That was his first chief people officer. And she was really a visionary people leader. And they were only about 150 people, at which time most companies would just still have one HR person or maybe two, and they might not have someone senior. And then she hired me and I, as a director of HR or director of people, and that, that's unusual at that size company. And, you know, I had direct conversations with Matt on a regular basis, even though I wasn't his direct report at the time. And he just was really focused on, you know, get to know everyone in the organization, what makes them tick, what do they care about? How do we make sure we're creating the environment that is, people can do their best work? So I feel like that was the, that's really, that's a really critical part. If you had a CEO who you have to convince that like, oh, invest here because it will be, it'll be good for the business. I never had to do that. We always had to, He was always front and center about it and realizing he was going to make those investments regardless. And we just needed to figure out how to best take the investments he was making and build the right practices and programs around people.

Michael Koenig: It's so interesting how you mention that even at 150 people, bringing in a director was abnormal. I recently had a conversation with a very early-stage multi-time founder, so not their first time through this, and they had brought on a head of people operations as the 5th hire. That early on. And I asked them why, like, why are you prioritizing that? You're a tech company. Why are you prioritizing that over, say, another engineer? And Their response was just, "If I don't, then what is the culture going to be and what am I going to build upon?" Just in a short period of time, that is rather remarkable, like a remarkable shift.

Cathy Hawley: Yeah, I agree. Even 5 years ago, I don't think you would have found— and we work at Bolster, we work with startups every day, and I'm so like pleasantly surprised when people are— yeah, they might need a fractional chief people officer, but they're prioritizing that along with a product officer or an operating officer or a technical officer, they really understand how important it is to build that in from day one, especially if they're an all-remote company.

Michael Koenig: Absolutely. Can you speak a little bit to that? Can you expand on it?

Cathy Hawley: Yeah. I mean, I think that when you're all remote, well, it's just harder to— you're not seeing someone and saying, hey, let me just chat with you, Michael. I mean, it's not a natural part of my day-to-day, right? So, you have to put in things that that put in practices that allow us to all connect. Because having that sense of connection and belonging at a company is really important, as you mentioned. And if you just have hired someone and they're sitting at home on

Michael Koenig: It is an interesting challenge, isn't it? Especially when you try not to be on

Cathy Hawley: You know, I think that a lot of companies— I know I work in a couple, I have a couple professional development groups that I'm part of with a lot of HR people. And I think a lot of them had a hard time shifting at the beginning to saying they didn't acknowledge that they might be remote for a long time. It was more of a need, you know, okay, we have to do this, but let's just see how fast we can get back to the office. But the ones who like pretty immediately said, okay, So how do we embrace what we have and how do we make sure that we are setting people up for success? I think those companies did well and the ones who were constantly talking about what can we do differently? What can we do better? What's working? What's not working? So that agile mindset of how do I, how do we take what we have and make sure that it's working for everybody? Is it meeting our goals? Okay, let's do a retrospective on it and say, let's adjust that. I'm on calls with people sometimes and it's, we have a couple of VCs and we're with their portfolio companies and hear CEOs talking about that. Like, yeah, we've done it like this right now, but then I get feedback and I'm going to change it a little bit. And so even at a CEO level, they're really intentional about thinking about how does that, how do we create a remote experience that's really good and, you know, good for individuals and good for the company. So the ones I think have done really well are the ones who are creative like that and listen to their teams. Like at Bolster, we had a company offsite and we all agreed to get together last November, which was, you know, not everyone was doing that at that time, but, and we gave people options of it and we had some good protocols. But during that offsite, it was a really good time for us to say what isn't working. And one of the things we found is we didn't have enough social time. So we're now trying to figure out ways we have, you know, people in Colorado, we have people in Indianapolis, we have people in New York, and then a couple other remote. But we're meeting up in person where we can. We had a coworking day the other day, and sometimes people, they're like, we don't want it all the time, but maybe once a month. So it's kind of that adjustment of like, you know, you have 20 people, maybe 20 people want slightly different things, but how do you figure out what are the things you do that meet most people's needs?

Michael Koenig: And do you see remote as being another one of the perks that companies just have to offer in order to compete for talent and retain, or? Do you think that this is kind of something that may just be par for the course now?

Cathy Hawley: I mean, my, I have a bias on there. I've had a bias for a lot of years that we need to offer more flexibility to employees. I know it doesn't work for every type of role and every type of company. So I don't think it's 100% remote has to work for everyone. And not everyone wants that. I think that, I think companies have to offer some kind of flexibility though, in order to stay relevant and competitive because even if it's not 100% remote, offering some flexibility that people can manage their, their work, their personal life, um, because they blend together so much anymore. Um, I think that's going to be required. And I think the peop— the companies that don't have it will definitely have a harder time attracting and retaining people.

Michael Koenig: Getting back to what Return Path got right, you spoke about Matt's desire to create an amazing place to work. It was just part of who he was. And Matt Blumberg is known as a remarkable entrepreneur and a remarkable CEO. For some of the COOs and CEOs listening that maybe don't— aren't at the same place that Matt was, what sort of advice can you give them for how they should approach working with PeopleOps? What are some of the keys to collaborating with people officers successfully? How do we, how do we build our version of the return path culture?

Cathy Hawley: Yeah, that's a great question. I think that the CEOs I've known and worked with who are maybe, like you say, they don't have it in there, they don't know the exact thing they need to do next. They usually still have the idea that they know that they want to do like the right thing by people. And I would say the more you can partner with your chief people officer and be a you know, have a true partnership, the better, especially on a CEO level. I think the CEO and the Chief People Officer, like, to me, those are like real, real partners. I kind of laugh because in our book, Matt kind of says that like every role thinks that they're that person, like, oh, it has to be the CRO, it has to be the COO role. But I feel like a trusted advisor to Matt, like if he had something that he needed to talk about that was confidential or anything he could talk about, he could come to me first if he wanted to. I feel like that's a really important place to be. So, I think for both sides to really invest in the relationship so that you are, you can really trust each other and make sure that you're aligned on goals, on values. I think those are really important. And I think the same thing for the COO role. I think the COO and the Chief People Officer role are really like, there's such a really nice partnership there. Let's just say often I'll stereotype people, but often Chief People Officers are a little more on the people side, a little Chief Operating Officers more on the process side. Not to say both of them can't be cross those. And I've heard people on your show who talk on your podcast, you talk about the people side of it and they get that. And I hear HR people who talk about process side and get it. But if they can really say like, wow, if you partner together, you have real, real strength in both of those. But those are the kind of two things that really help the company be successful. Like building that, the operating system around people and process can be really, really powerful.

Michael Koenig: In terms of Bolster, can you tell us a little bit more about it? I mentioned it right at the beginning in, in your intro, and we have had Jenny Lawton on, your colleague and coworker. But I'd love to hear more from you about it because everything that Bolster's doing, I mean, it's almost an extension of part of the people functions.

Cathy Hawley: Yeah, absolutely. Yeah, I think about it as we help CEOs scale themselves, their leadership teams, and their boards. So all at an executive level and mostly around talent, although we, we do have some assessments that help with development as well. And I think that, I think the founding story of it's kind of interesting too. It's related to this is we left Return Path, sold the company, and a group of us got together and said, we really wanna work together again, but we really, we really wanna work on something like we're really passionate about. Not to say email marketing isn't, you know, isn't sexy and exciting, but how do we, and we, what we thought was we really wanted to help CEOs be building great cultures. And, you know, kind of fast forward a little bit and getting the investment and getting some other ideas that, um, The idea for the Bolster Talent Marketplace actually came from a couple of our investors who put it together and then brought us in. But we really, like, it was a really interesting way. We have 8 co-founders and out of our team, many of us have worked together, even outside the co-founders, many of us have worked together before. But it was a really interesting experience in taking what we already had and saying, okay, how do we then take that and share it with other people? And then we also are a company that needs to have our own operating system and how do we build our operating system that's inclusive, that brings people who didn't work with us in the past, who still can help them be successful as well. But that was an interesting, interesting kind of people, Chief People Officer, Chief Operating Officer type of a challenge we had, but a really fun journey.

Michael Koenig: Well, that's really interesting and I wonder if you can expand on what you just said about building your own operating system to bring in people who you haven't worked with before so that you can kind of, I don't know, welcome into the group or the family. At some point in our career, we've worked with people that we've worked with before and you have that rapport that's already built. How have you all designed that to welcome people into that group?

Cathy Hawley: It's probably an agile way. The first two people we had who were non-return path folks, We, we helped, we brought them in and said, okay, well, like, here's the operating system we have now. And like, what's missing from to make you, and then they asked a bunch of questions to make us go, okay, that needs to be brought into onboarding. Next time we hire someone, you need to tell them, we need to make sure they, so then we built a kind of a lightweight onboarding that the next people who came in got a more lightweight onboarding with, okay, we talk about our philosophy, our values, our operating system. How do we do work? So we. We're still lightweight, we're still only less than 30 people, but we're more intentional about bringing people in and making sure they understand, hey, relationships are first for us because that's a really important thing. So, you actually are going to meet most of the people in the company in your first 2 weeks because you need to have a relationship in order to work with them in the future. So, it's not wasted time by spending time with each person and us spending time with each person who comes in. But, right now, we're small enough that that's a really important component. But we've also articulated our operating system and our values a lot more effectively than we did for the first couple of people who came in who we made a lot of assumptions because we'd worked together for so many years. Like, that's just how you do things. So, we probably did a lot of things by making some mistakes on the first couple, but they were very strong people who, and we knew that coming in, they wanted to be in a mostly self-managed organization. They were great people to test out our, our system.

Michael Koenig: So did you iterate on your values? Because I imagined you and Matt and Jenny and your other super experienced co-founders just saying like, all right everyone, first 5 minutes, let's just knock these out. We all have worked together, we all know what a great working environment is. And like knocking out those company values in like 5 minutes and, and them being perfect. And maybe, uh, it's, It's a folly on my part, but can you tell us a little bit about that? How—

Cathy Hawley: That's about literally how the conversation went. We were like, hey, what didn't work before? What do we want to take that did work? What else do we need to articulate? And we— and then we iterated on them. So we did that within the first week. Then we— and we also had some operating principles that we really wanted to stick to. And some of them were because we knew as a team we had some we had some things that we didn't do well and we needed to hold ourselves to. We probably all have a little bit of a tendency to make things more complicated than they are. So, one of ours is be simple. I think it was damn simple to start with, but it's probably changed now. But then when we had our offsite with everybody, the entire company was there in November except for maybe one person who couldn't make it and she participated a little bit remotely. But we revisited all of them and said, "Are we right still?" We didn't change any of the values, but we changed some of the wording around them. So that was a really, and that was just a great way for, I mean, it's so nice being so small where you can really, everyone gets a say in, in what we're doing. And, and we also articulated more of our philosophy. So we knew we were not hierarchical. We knew that we liked the self-management philosophy, but we hadn't really identified exactly what that was. So now we call it our MSMO. So we're a MSMO. We're a mostly self-managed organization. We made that up, but we had a lot of different, like, you know, terms over the course of the few days. And finally we're like, that's what we are. We're mostly self-managed. So we have a good operating system around, you know, how do you figure out what your work is for the quarter? How do we all figure it out together? How do we make sure we're on the same page? But yeah, we're mostly self-managed.

Michael Koenig: Mostly and not moderately.

Cathy Hawley: So maybe moderately, but I want to shift gears a bit.

Michael Koenig: Because what we're seeing right now in the talent marketplace is just kind of abnormal. There's so many people changing jobs, right? It's being known as the Great Resignation. I don't think you can go on to LinkedIn and not see that posted at least once or twice. There are a lot of potential causes, but what are your thoughts on them? And at what point do you think it'll start to calm down?

Cathy Hawley: Yeah, it's a really interesting one. I think that people are— I mean, there's so many articles out there already about what's causing it, but I think people will start to really reflect on what do they want from work and what do they want from, you know, what do they want from their life and from work and what's most important to them and if there's a way they can put their passions alongside with how they're making money, they're going to do that. And I think the lesson for employers is to continue— it's really important to build a great culture and invest in people and figure out where do they want to go? How do you help them get there? You know, what if you want to go somewhere that's not a focus of the company? I think that if you're a really strong leader, you're going to help someone get there regardless of whether they're going to be at the company for 6 months. I'd rather have someone stay at the company for 6 months who's really good at what they what they do, but starting to develop skills to do something different rather than not support them in that and have them not achieve their goals. But I think that's what's going to happen. These companies have to get better about caring about what their people want in the office. Do you want autonomy? What do you need? What do you crave? And can we provide that for you?

Michael Koenig: Do you think that there is a shift in the power dynamic between employer and company, right? Where maybe pre-pandemic, let's just take remote for example, company said, hey, be here 9 to 5, right? And now it's shifted first out of necessity, but as we were talking about before, is remote, it's more acceptable, it's been normalized quite a bit. And it's potentially turning into another one of those perks, another one of those benefits that companies just have to offer, at least within the tech space, in order to be competitive. Would that be a fair assessment that there is this shift?

Cathy Hawley: Yeah, I think that, I think that's absolutely right, that there is a shift in it. And there's still going to be employers who can pay their employees a lot of money and you kind of have a little bit of golden handcuffs. Like, that's just going to happen, at least for a while, because there's some companies where you don't want to leave because you can't quite make that and your lifestyle is what it is and people are going to make a choice to stay at those companies. But there's going to be others that can't afford that, or that's not the, you know, their strongest value. But what you provide employees in the way of development and growth and autonomy and, you know, helping them master things like those are the things that I think are going to keep people excited about where they work. And absolutely, I think it's a shift in, shift in dynamic. And I mean, I've always had a philosophy that you should treat people like they're volunteers. Like they have a choice in whether they're going to stay with you or not. Don't treat them as like, oh, you work for me and I'm paying you, so I'm going to have you do this. Like, I feel like you should always treat people like that. And I think that when, if you have a little bit of a different mindset about the way you treat people, then people respond in, in that way. And when that's not working out, then you have a conversation about why that's not working out.

Michael Koenig: I love that. What goes into treat people like volunteers? What does that actually look like?

Cathy Hawley: I think it's a lot less of telling people what to do every day and a lot more of bringing people along for the ride, helping co-create what your environment is. So, I think of it as like you co-create what the goals of the company are and maybe there's a smaller group of people who co-create that because if you have a 500-person company, you're not all going to be in a room co-creating what the goals of the company are. But that you're co-creating at least part of what you do every day. And if you're co-creating that in a way that achieves the company's goals, or like, you know, I'm helping my team, I'm helping myself achieve my goals, my team achieve its goals, the team achieves, helps achieve the company's goals, co-creating that. But I have a sense of, you know, that I have a choice in what I do. So I want to show up every day, not that I have to show up and you're telling me what to do, but I want to show up and I want to do the things because I've helped co-create what that is. And maybe not all volunteers are treated like that, but I think that the ones— if you want to get me to come back and volunteer again, you'll treat me in a way that I'm like, I'm making an impact somewhere and I'm actually doing work that I find joy in and I'm making an impact. Because that's important to me. Maybe that's not as important to someone else, but you're figuring out what's important to me and you're making sure that I have the environment and the leadership to be able to achieve that.

Michael Koenig: That's interesting. Yeah. So it's, it's a change in environment, but it's almost a shift in mindset about gratitude. So not taking anyone for granted. You spoke previously about building a great culture. Now for some of us that are listening and saying, okay, culture's pretty good, or, uh-oh, I'm seeing a lot of attrition within my workforce, um, within my team. What advice would you have for them to kind of take a step back and be able to look at their culture and evaluate what's working and what isn't and what they need to do?

Cathy Hawley: If you're a leader in a company, I mean, I look at like a COO and chief people officer role, this could be a great, great project for them. And I think I heard one of your guests talking about when she first came into a company, just interviewing people. Talking to people. So you can do, you know, surveys of them. You can do interviews, but find out what it is that people are experiencing. What is the culture actually like? Because what you want it to be and what it is may be two different things. So figuring out what it is right now, what are people experiencing when they come to work? How are they treating each other? What do they love about what they do? What do they not like about what they do? I think when you talk to people, you will find out what's working and what's not at your company. And then having the plan to fix some of the things that aren't working. So we used to do a survey every year at Return Path and the last survey results we had, I remember like looking at it going, okay, one of the things that's not driving engagement right now is we don't have a good framework for career development. Like we have some tools in place, but not everyone knows about. So that quarter, that was our team's, one of our team's top goals. How do we make sure we have the right tools, the right practices, the right leadership in place and people have the right tools to be able to focus on this and that I want to see those scores go up next quarter because people are understanding what we can do and getting the support they need to develop their career. For example, I think that if you, as long as you interview people and take action on it, I think you can really make progress on that. So, as a leader, when you start, if you take it and say, "Oh, my half my team's leaving," don't point the finger at them. Look at yourself and say, what do I need to do differently to make it so that people want to stay here? And what's the environment I create? I think I hear sometimes when people will say, oh, if I just give this person a 5% more raise, they'd stay. But why did it get to the point where they're wanting to go somewhere for 5% or whatever that number is? I literally heard that last week. Someone left and they told their company they want 5% raise. Is that what they're leaving for? Are they leaving because they don't love what they're doing? They don't feel seen and heard. They don't— they're not getting the leadership they need. What's the real reason they're leaving?

Michael Koenig: You certainly don't want to get to a point where an employer who's offering raises when someone has resigned.

Cathy Hawley: You'd hope you can do that proactively. Yeah.

Michael Koenig: You mentioned something interesting about career development. Career development, you have described the part about kind of the professional development side. Learning, being able to practice and grow yourself. But then there's also sort of the career trajectory side of it, which can include titles, right? It's a measurable way to evaluate how you're progressing and where you want to get to over the, the decades. At smaller companies where there's maybe less of an opportunity to move into different roles like that, different leadership roles, to move from an individual contributor to a manager, what advice would you have for those companies to be able to still create an environment in which their people can grow?

Cathy Hawley: Yeah, it's an interesting one. I would love to say we don't need to do titles. And I think that we are moving in general away from that. I see a lot more titles that are just kind of generic titles, not level titles. Um, but there is sometimes a need for somebody. We, at Return Path, we decided at one point to just go ahead and do levels. We didn't, we, we wanted to stay away from it for a while, but we decided that we were big enough and people were asking for it enough. So it's one of those things that like enough people are asking for it and you haven't convinced them that it's not needed. They need it for their LinkedIn. They want people to see what they've, you know, um, what they're doing. So, um, so we did put those in place.

Michael Koenig: Getting back to, um, talking about career development and, and some of the layering that you discussed. I recall at Automattic, we were, I think, 80 people before we introduced even teams and squads. So it really is, you do get to that point, that sort of critical mass where it's like, right, this is getting a little too chaotic. We do need to bring a little bit of that order and that discipline. What do you, what goes into the considerations, or rather, what are the considerations in designing those layers and what have you seen work and what You know, what have you, what do you think you should have revisited?

Cathy Hawley: So I think there's two things that go into, into leveling. One of them is your functional expertise and what skills do you have to actually do your job every day? And the other is your leadership expertise, not only expertise, but your behaviors. Are you a leader? Are you leading yourself, others? Like there's, there's two different things. Are you communicating effectively? All those things that go into leadership. So, it's the how you get things done and then what you get done. And I think you have to factor both of those in because if you promote someone who's really, really good in their technical skills but not very good to work with, not a good collaborator, but the company's a collaborative company, that kind of thing, then you're going to get mismatched. I think you have to have both those, both those factors in place. You have to articulate what's the difference between the different layers or levels. So, when I first started at Return Path, we did a project that we said, let's just do 4 levels for the leadership skills. What does it take? What do you expect from someone's entry level for them to how they behave? What do you expect if someone's a senior executive, how they behave, and then what's in between? And then on the technical side, again, you don't have to have it all like, I'm not have to promote you to director, but you have to know what it takes to be a director, individual contributor engineer. If you're right now, that's your next level. You have to know what skills you need to develop. That gives you a little bit of a goal to get there. So I think those are the couple. I think transparency is really important and not over-engineering is really important. The first big one we did at Return Path, we over-engineered the heck out of it and it was so complicated. And we had engineers working on it, which probably helped, right? Make it complicated. But it was, people were like, after like a year, they're like, we don't really have, we have a hard time. Like this takes hours to do every time we do it. And so the next iteration, we simplified it to a point where it was really clear and it was transparent. If you were going to get promoted, you, your peers would be able to say, yes, I see you demonstrating those things. And that it, but it's transparent. Not that everyone has to agree on every decision, but I have to be able to justify it because then if someone else comes and say, why didn't I get promoted? You can point to like, oh, here's 3 things that you have to do in order to get to that level. And maybe the company needs that level. Maybe you only need 2 directors of engineering out of the, that team. Well, you're not going to get that role. So I think that. You're not going to get that role unless there's a position open. So, I think being really transparent about when can you get promoted, what does that promotion look like, and what do you have to do to get there, I think are really critical.

Michael Koenig: Let's switch gears. I mentioned at the beginning that you wrote quite the field guide. I mean, I'm holding it right now. This is at least 10 pounds. I want to say 600 pages, and it really is not so much a book as Fred Wilson described it, but more a field manual to building a management team and scaling a company. And I mean, his, his description is spot on. It's something that I pull off the shelf for reference, and it's quite an accomplishment. How did it come to be and what was it like to set out and capture it all?

Cathy Hawley: Oh yeah, it was— well, started because Matt wrote Startup CEO with Brad Feld a number of years ago. And, you know, you got that too. Good. And he's, you know, when we started thinking about it, I think it was probably Matt's brainchild. And there was a little bit of resistance on the team because we're starting a new company. We're, some of us new to this. Well, most of it, all of us were new to the online, like a talent marketplace. We'd never done a marketplace. We had to learn that. We had to learn the business. We had to start a business. But Matt really had a vision for saying like, look, if we're going to put this out there and we're going to help people. Build their cultures. Let's put out the manual of what we need to do. And we can leverage that data to help us populate all of our roles within Bolster. So, when we had those things twofold, it was a really fun process. Matt got myself and Jack, who's our CFO, to write the first couple chapters or first couple R sections. We did enough on the R sections that we could then say, okay, we can help other people figure out what's a good way to do it. And we had someone who helped us with some of the editing. It was just a really fun process and it really did capture— we kind of started with capturing on a spreadsheet what are the different skills it takes to be successful in each role. And then that helped us build both the book and the IP for our platform and some assessments that we do. So, like that, it was helpful to get people thinking like, "This isn't just going to be a book," because some people, again, didn't want to write a book right away. But it's also going to be these other things. And I think Matt had a good enough reputation that like Wiley really wanted to, really thought it would be a good, a useful book. I think it was supposed to be half the size it is. So we were really trying to like reduce it, and finally Matt just was like, just let's print it on thinner paper, and Wiley went for it. And they said, yeah, really, it's a field guide. We think about it as a field guide and not something you have to read from start to finish. And you go, hey, I really want to have an idea about this, and you go look it up. Then that's a great resource for people.

Michael Koenig: Let's talk about some of those, my favorite questions, right? The crazy stories. And I know that HR and People Ops folks have some of the craziest, not most likely have the craziest, you all have the craziest.

Cathy Hawley: And most of them are like, you can't repeat them.

Michael Koenig: You cannot share them. I know.

Cathy Hawley: I know.

Michael Koenig: So this is a difficult question, but is there a crazy story that, you know, one of those things where you thought, uh, well, never thought I'd see that. Is there one that you can share with us?

Cathy Hawley: I thought about this over the weekend, cause I've heard you ask a few people, uh, this question. So I was like, I know he's going to ask me that. Let me think about that. Um, so many of my stories are like individual people stories. And so I, mine probably is not going to be very exciting, but I'll, I'll do it in a more of a way that's like, It's a way for people, professionals, to think about how to do things differently. The traditional way of going into a layoff or something like that is to be— you probably still hear about people going, "OK, you're going to be— you're changing your job. I'm making the decision. You're not going to be here effective tomorrow. I'm just going to tell you that." A few years ago, I worked with an exec who really wanted to do things a different way, and we both did. We were doing a reorganization where probably 100 people were going to lose their jobs, but we're also shifting a lot of jobs to something else.. And we did it in a really inclusive, we told everyone what we're going to do. And we said, all these jobs are going to be different. They're going to be this, you know, as of this date. And we ran an interview process for a week where people could raise their hands and say, I want to be part of that. I don't want to be part of that. Here's what I want to do. And at the end of the week, we committed by Friday, we'd make all decisions and communicate everything. So, we would say, okay, Michael, I'm going to talk to you and you're going to tell me what job do you want? What's most important to you? Would you rather not be at the company if this is what it's going to be? And we were told by our board kind of that they don't really agree with this approach. And we ended up with retaining almost everyone who wanted to stay and be in that job, we ended up retaining, and almost everyone who wasn't going to be the right fit in the job ended up opting out. And I think everyone thought that we would be losing the best people, that, "Oh, that person we want to stay is going to—" leave. And well, that's gonna be okay. 'Cause if they don't wanna stay and in 3 months they leave, that's a failure anyway. So let's, anyway, that was an example for me. I've had a number of those where people wanna do it kind of a traditional way and you kind of influence and help them think about what's a way that could, that you could do this thing without negatively impacting, well, it's still gonna negatively impact people, right? But having the least negative impact on other people. So again, not super exciting story, but that's like, that's when I think about the difference between kind of people in HR. It's like, HR will go execute what you tell them to execute. And I think a people professional will be, okay, how do you do this in a way that is really bringing in the people who want to be in the most humane way possible, the best way to have the least negative impact on people.

Michael Koenig: Yeah, absolutely. No, it's so helpful because it's hard to remember unless you yourself have been let go from a role before, it's hard to put yourself in someone's shoes, right? This is a horrible moment in their life. And so anything that you can do to inject that humanity and that empathy, I think is very valuable. Well, I know I said that was the last question, but maybe we have time for one more. And that is, because there are so many people changing jobs right now, what would your advice be to them when they go into a new company, whether you're exec, whether you're an individual contributor, how should they go in eyes wide open?

Cathy Hawley: I mean, first thing, I think, as you're making the decision to go and you look at the leadership team, are you happy with their values and what they do? And do their actions meet what they— their stated values on the page? Which is, can't always tell, but the more you can understand that, the better. You do have a little bit of an upper hand when you're When you're negotiating, just making sure that you understand the company you're getting into. Then I think once you're in and you're all in, figuring out who you develop those relationships with is really important. I really like the book, The First 90 Days. I think it's a really good reminder of just like what the first 90 days are so important in what you do. Hopefully, your company also has kind of an onboarding program that you can fit into, but really thinking about what do you want to achieve in that first 30, 60, 90 days? What is it gonna take to achieve that? And achieving it could be, I know the names of 40 of my coworkers and I know a little bit about them and I could, I could tell you what they do. I mean, that, that kind of achievement could be enough. But if you're a leader in a company, you know, how do you want to get to know the people who are there and how do you want them to get to know you? And, and then yeah, what do you wanna achieve in your first 30, 60, 90 days? I think it's really good to be intentional about that.

Michael Koenig: Okay. Last one. One more for. People ops folks that are heading into a new company, um, how should they think about the company operating system and maybe how to evaluate what they should kind of pursue and what they shouldn't? How should they prioritize? Because I'm sure you bring a lot of your own ideals, you bring a lot of the practices that you've seen before, but How do you prioritize those when you're heading into a new company in a people operations role?

Cathy Hawley: Yeah, I mean, I think ideally, if it's an ideal situation, you go in and pay attention for 30, 60 days and watch things. Usually things are more fluid than that, right? You come in and there's some emergencies that need happening, but the more you understand about what's in place now, why is it in place, then before you make changes and you, and hopefully you have a team you can co-create changes with, you're not coming in unilaterally making changes and you're bringing people along for the ride. I think that's a really critical one. But, again, if you're really partnering, say you're the chief people officer, you're partnering with the CEO, you come in, you do your kind of evaluation for the first however long you have to do it, 30, 60 days. What do people say? What do the data tell you? What are the company priorities? What seems to be working well? What doesn't seem to be working well? And then, obviously, fix the very broken things. But I think the more you can look holistically and say, you know, our priorities for the next year, have to be these 3 things. Co-create that with your CEO. That's the most important one. And then you have— then you're not trying to cover everything at once. You're not peanut buttering your time across the entire company, but you're focusing on the highest priority things and communicating what those are. Telling your team members like, "This is what I'm focused on. Is that good for everybody? Because that's what I'm going to skip this other stuff. It's important, but not critical right now." Did you just say peanut butter?

Michael Koenig: That's fantastic.

Cathy Hawley: And we always use that in compensation. Like, you can peanut butter the— like, you can take a dollar and spread it and a penny for each person, or you can take a dollar and give 50 cents to one person and, you know, 10 to each of 5 and nothing to the other. You know, like, that's the term we use in compensation often. Don't peanut butter things around.

Michael Koenig: Peanut butter things around. Well, we don't give titles to episodes, but if we did, I think it would be Don't Peanut Butter Things Around. That's fantastic. Well, Cathy, Thanks so much for coming on the podcast. Where can people go to keep up with you and also learn more about Bolster and the Startup CXO?

Cathy Hawley: Yeah, my LinkedIn is Kathy Hawley, but Bolster, Kathy@bolster is my email address, and go to bolster.com and we have a bunch of stuff on the website there. Be happy to talk to people if they're thinking about being a consultant or they need one.