Series B & C: How do you scale a good business that does good?

ON THIS EPISODE OF HIGH GROWTH MATTERS

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CAITLIN ALLEN: Today we speak with James Cleveland, an executive who specializes in scaling really fast growth organizations with social impact missions, particularly doing during that very crucial time in a company lifecycle where product market fit has been achieved or is about to be achieved, and then go to market fit needs to be figured out as soon as possible. And James has done many of these things as a founder, a COO, a chief talent officer, chief people officer, and more for several decades. So really excited to dig in together. James, thank you so much for being here.

JAMES CLEVELAND: I appreciate the opportunity to have this conversation with you. So thank you.

CAITLIN ALLEN: It's gonna be a good one. So let's, let's start off with your professional background. James, what what holes did I miss that that needs to be filled?

JAMES CLEVELAND: I think he did a pretty good job. I, I guess I would, I would say that, you know, I feel that I've had lots of opportunities to really develop as a business leader and General Manager. And so my, my experience and track record really has been in opportunities that have allowed me to build team and build infrastructure in organizations, both on the on the for profit side, but also on the nonprofit side, where the stage of maturity was really around as either a strategic pivot or the opportunity to grow. And so I like to think of myself as someone who really knows something about being in a high growth, high impact organization, enabling scale and impact at a crucial phase of maturity. And most of my years have been spent in early growth companies and nonprofit on the ad tech side. But more recently, I've been in the FinTech space. Two things that I do appreciate about those experiences that I've had, and you've mentioned several of them is one is that I've had an opportunity to lead a variety of teams, not just people in culture, you know, I've had the opportunity to lead operations functions, and also be in charge of things of groups, including finance, marketing, HR, technology, etc. And so, you know, there's a lot of different infrastructure needs that, that, that a company that is about to embark on scale, needs to grow and develop. And I've had the opportunity to lead lead at each of a variety of functions at that stage. And then the second thing that I appreciate about my experiences is that all of these opportunities have taught me about the value and importance of investing in people and culture, regardless of the type of team regardless of the stage. And regardless of like the strategy and goals like it really, I've learned both through positive experiences, but also just through mistakes. And you know, hard knocks that people in culture matter and every at every point, and so I really sort of carry that forward, as I think about my work today.

CAITLIN ALLEN: Really excited to dig into to number two together on how do people in culture influence company growth? And then what do you do to build that in a fast growth environment? But a really quick comment on a number one, before we get there, to me, what I think is really stand out about your experience is, you've been the customer, so to speak, of a people operations are a people team, right? Like that the role of a people leader is to serve the head of marketing, the head of sales ahead of engineering, all the the teams there, that CEO, so on. And we've been in many of those roles. So you know, I think one of the things I've appreciated about from my career was I've had to be in sales roles several times. And I can't say that I think it's a fabulous fit. But it has, it has given me a lot of empathy, and maybe more education as a marketing leader. So I really, really can identify with what you're saying,

JAMES CLEVELAND: I mean, that you hit the word run, and you identify the word that I was gonna say. And that's empathy. Like I feel that because I've been a customer receiving services from say, a people and culture team, because I've actually been in these these various roles. I do feel like I have enough empathy to understand where the pressures are coming from for leaders who have to make hard decisions to develop their own teams and build their own infrastructure to deliver on the business strategy or the goal that they've set forth. So I think in a lot of ways that has allowed me to develop the kind of trusting the kind of trusting partnership that is necessary to develop the talent capability that will allow a team to ultimately fulfill its fulfill its obligations or fulfill its goals.

CAITLIN ALLEN: Very much so very much. So, James, one of the things that we ask every guest to get to know them a bit outside of their professional role, before we really dive into the professional topic at hand is what something is that your coworkers don't normally know about you.

JAMES CLEVELAND: And this is a personal item or professional item. I mean, there's certainly a lot on the professional side that I could say,

CAITLIN ALLEN: you know, to get where you want to, I think that's a good question. But there's fine.

JAMES CLEVELAND: Well tell you what, like, I'll just sort of say a lot of people don't know that. I grew up as an Air Force brat, and I spent a lot of time in the outdoors. And in fact, I became an Eagle Scouts because I was so enamored with the outdoors, I joined the Boy Scouts and learned what it takes to survive in the outdoors. Certainly, there's other things that people know about me, you know, I love sci fi, fantasy and the Star Wars, you can always see the Millennium Falcon behind me there. And then I'm really keyed in on technology. And in fact, oftentimes I am the go to in an organization that a small that doesn't have a technology team, and oftentimes to go to that teams will seek out when there's challenges there. But I do want to share one thing professionally, that I think a lot of folks are surprised about. I because of the work that I do in my approach, especially today, I do tend to have a strong brand among many of my colleagues for my ability to do effective team building development and management. And I have surprised many of my colleagues with the fact that my very first opportunity to be in a general management role, which was in my mid 20s. I was actually awful at it. In fact, I was so bad that my CEO informed me about to two months in that my people hated me. And anybody who knows me, is shocked by the idea that one I'm terrible at management or two that people might hate me in this way, because I was a terrible manager. And it's a great story that I'm happy to tell. But I think it's what's important to understand is that great managers are not always born. Right? It is a journey that requires intentional investment and personal growth. And I made a choice when my manager when my CEO told me this, it was I was so shocked that I made a choice to figure out why, and have since worked hard to invest making 100 mistakes along the way to try to develop my ability. And I feel like I'm still in that Learning Mode. But people are usually very shocked to know that I was terrible from terrible at the outset of my management career.

CAITLIN ALLEN: Well, the shock speaks to what I would assume is some growth. And I'm excited to I would love to hear how that is informed. Once we get into that part of our conversation, how that's informed how you approach manager trainings, I bet it's really, really shaped like basically giving the gift back of what you gave yourself.

JAMES CLEVELAND: Did Yeah, I'm happy to talk about that. I have some I have some strong beliefs based on experiences that I'm happy to share. Okay, great. Thank you.

CAITLIN ALLEN: Well, then transitioning into to more of the professional topics at hand. So bringing order to chaos, that's very typical in a fast growth, early stage environment. I guess let's start with the why what is it about that part of the company lifecycle that that you liked so much, it's attracted you to really specialize there?

JAMES CLEVELAND: Yeah, I think this is a great question. I think everybody is unique, that, you know, they thrive in different phases of a company's maturity. And I'm just not the guy that loves wrote, work in a sort of a bureaucratic setup. And that tends to be what you see in more mature or established traditional organizations, I get a kick, I really get a kick out of solving problems that are blocking individuals or teams from being effective or efficient. or problems that are really about raising the level of trust and engagement for individuals. For me this, it's really about creating leverage the most leverage possible with the limited resources that we have in front of us. And that's usually about time, people money, you know, when you're at that really grow stage, to deliver the highest impact possible. And the challenges are really unique, because you haven't faced them before. You're still kind of in that chaotic moment. And there's something about bringing some order to that chaos, that's just really gratifying for me. So that's, that's, that's one thing. So I just get a kick out of solving those kinds of problems. Because I know it's ultimately gonna allow us to be much more effective and more and more powerful as a team, which ultimately leads to stronger results from the business and you know, because I'm so mission minded, also the impact for the mission. The second way I would answer this is that I also just like partnering leaders, to help bring their good ideas into realities and visionary leaders have lots of ideas. Many of them are really good, some of them are great and a lot of them are really bad, but I just I love helping them parse through and sort of figure out which ideas should be brought into reality. And there's something about helping others around those leaders. Turn on the light bulb, right? Helping it click on. So they also understand what the idea is. And ultimately from from, from the standpoint of a vision for where we're going directionally why the plan matters, and what their part can be in helping us bring that forward, I really get a kick out of helping people really get excited about that. So So there's something about this phase, it's just really inspiring. And I feel like I have an ability to get people excited about it through the work that I do, but also helping them connect to the leader with their ideas.

CAITLIN ALLEN: Well, and I do think that process of prioritizing is one that is really difficult in the early stage environment, because there is so much that can be done, there's so many things that need to be done, there's so many problems that need to be addressed to figuring out which matter and what to prioritize. And then also creating a rallying a team around how their role ladders up to bringing it to life is really perhaps one of the the secret sauce items and the companies that you know, win and lose, so to speak.

JAMES CLEVELAND: 100% agree with that I oftentimes talk with leaders about the importance of connection. employees want to know how they are connected to the bigger plan. And so oftentimes that starts with you know, I've kind of like my personal passion is connected to the mission or the work that this organization is bringing, people want to be connected to their leaders, they want to know that they have a leader that they trust, that is making a leader that is making great decisions, and is invested in them. So that's that's a big part of that. They also want to know like, what the plan is, like, how are we going to win. And one of my part in contributing to this winning formula was winning strategy, the progress that we're making. And oftentimes that requires clarity around how we are allocating our resources again, and bringing up that resourcing and, and, and in order to do that, you have to be relentless about your prioritization. So that people understand what decisions are going to be made, are going to be made and why. And which basically informs like, here's why we will do this, and here's why we will not do these other things, right. And then being able to cascade out of that, here's what I'm going to do to contribute to the things that we are going to do. So that connection really is as crucial. I also talk about connection in terms of me feeling like I'm part of something bigger than myself. So again, that's partly mission, but also part of a team. So I'm connected to my teammates, and my manager, etc. But those are the things that I think about, when we talk about a person really feeling like they understand where things are going and how we're making our how we're prioritizing our work.

CAITLIN ALLEN: Great. I like that a lot. And I think it's the importance of connection to your point, it's it's central to the Social Impact mission at some of the companies you've you've been at, and I think is, is also part of the part of what matters to every employee, whether or not there's a social impact component of the mission. It's why why someone shows up at their office or their desk every day. So it should really is something that's widely accessible. Let's, let's shift gears a bit and talk about planning. You've, you've shared previously with me how important it is in your roles, for you to work with the executive team to create not just a three to four year plan or something along that timeframe, but to equip the exec team to have a very vivid description of it. So we'd love to understand like why that is and how you approach that process.

JAMES CLEVELAND: Sure. Again, I'm gonna speak from experiences that I've had there, there, there are some individuals in the professional world that that are very comfortable with the abstract, and uncertainty, I find that to be the majority of professionals. Most individuals, even though they come to startups, or they come to early stage organizations still really need some level of certainty of where they're going. Now that can be very hard to create in an early stage organization. However, certainty can can come in many forms. And I have found that if you can help an individual visualize what success looks like, three to four years from now, that can create the certainty or the grounding that an individual needs to plan and work and push through the challenges that are inevitably going to show up. You know, so I've, I've taken this language of vivid description from some of my early readings of Jim Collins who talks about how great organizations have various components in place. That helped a culture thrive. And one of those components is a vivid description. If you think about the work or you think about the In, there's a lot of noise in the media now about like the Artemis mission going back to the moon, just remember back in the 50s and 60s, with with the race, the space race, and how Kennedy sort of articulated for a nation that we were going to put a man on the moon, put a man on the moon is a very vivid description, right? Of what we're going to do. That's that was 10 years out, right? So people couldn't fathom, like the idea of going to the moon, but actually putting a man on the moon and returning him home safely, vivid description, which then allow for individuals that NASA and other agencies to start planning out like, Okay, well, what are the different steps to actually get there the milestones that will allow us to achieve that, really through galvanized the nation and our resource, our limited resources to basically do something special. And I think Jim Collins really latched on to that idea for how companies can actually do the same thing. And so I have found in my experiences that when I get a team to sort of think about what success looks like, and how you really defining that success, like getting teams to participate in the exercise of defining successful vivid descriptions, right, like, what does it look like? What does it feel like? What does it sound like? What have we achieved, then the ability to prioritize resources and plan is much more effective and efficient. And people feel a lot more settled about, about what they can contribute to create success. When it's abstract. When it's not clearly defined, what I find is that individuals actually make up the make up the idea in their own minds. And oftentimes, what you have is a variety of different definitions and people moving in different directions. And so suddenly, you're not rowing in the same direction. And so that is the reason why that the description really matters. It creates a grounding spot and allows people to grow in the same direction.

CAITLIN ALLEN: So what put you on the spot here, I guess, but what are some examples of vivid descriptions that companies you've been on have had in the past?

JAMES CLEVELAND: Yeah, so I, you know, I'll think about her nonprofit when I was working as the CEO of jumpstart, and one of the vivid descriptions that we talked about was tripling the impact of students. And specifically, what that mean meant was that we were going to triple the number of students that we were working with without necessarily increasing the number of volunteers. And so that meant something related to how we were using our volunteers, in terms of like the number of students that you're working with, whether they're working with students one to one multiple times, or whether they were working with groups of students, groups of students in a way that they hadn't before. That was a that was an example of a vivid description for how we were going to increase our impact at a time when resources were being that this was happening during the recession. More recently, you know, I think about, you know, when I was at untangled, and we were being acquired by guild, I remember sitting down with our people team, and we were talking about the fact that we only had eight weeks to figure out how do we bring our two teams together. And we talked about what it would take to create a seamless transition experience for every entangled employee to join guild. And we went through an EQ before we started any planning, we went through an exercise, identifying what are the things that people need to experience and feel in order for that seamless word to be to be accurate. And so we talked about things like people have the ability to truly understand and appreciate the benefits. So the HR benefits, and can make a decision before and have a seamless transition into this business before the actual transition go date. We talked about you know, what payroll, the payroll is very different. And so we talked about how to create a seamless experience with that. But we also talked about like, what it would take to basically transition into a new team. So what are the experiences they need to have with their new manager? So by having this description, we were then able to prioritize by phase, like, what, what, what each, what each of the, the workstreams would be, and what the milestones for each of those work streams would be in order for us to achieve the result. So those are a couple of things, a lot of sense.

CAITLIN ALLEN: It makes a lot of sense. And I'm now applying it to my world where it would like no more layoffs or pay disparity, like goes away or things along those lines are the things that are coming to mind. For for my role, so thank you for that guidance. Is there is there a piece of the three to four year plan where you work with leaders of departments to figure out the talent capabilities don't need in place or is that thinking too far ahead?

JAMES CLEVELAND: No, I answer is yes. I like to think about talent capabilities all the time. When I when I so one of one of the things that I tried to do is actually become an effective partner to a senior leader, right. And so me understanding their long term vision but also their strategic Your goals for the next three to four years really crucial for then beginning to help a leader evaluate what will it take to get there. So I'm gonna try to use a salient example. There. There, there was a, we'd recently hired a may be as landed as example, we hired a Chief Marketing Officer. And we were talking about the need for, for expanding our sales presence, particularly among enterprise level businesses, which were really the way that we reached our customer who were the employees of these businesses. And what we were recognizing is that our sales approach had been pretty effective, but it wasn't moving fast enough. And the sales cycle was taking too long. And we also weren't, we weren't landing some of the larger businesses in a way that would actually drive the kind of traffic kind of conversion rates that we were looking for. And so in talking with the new CMOS, as she was sort of getting onboarding and sort of creating her own vision, me sort of listening and understanding what she was thinking about for the next two to three years, allowed a conversation around, well, what are the capabilities that are going to be required for us to achieve this? And so she talked about? Well, we're going to, we're going to need enterprise level sales experience using these kinds of methods. So we talked about the challenge or method or other sales methods that would allow us to get into enterprise, you also talk explicitly about like, you know, that there's a different way or approach that we're going to need to use for small to medium sized businesses. And so in doing that, we start to understand the kinds of sales strategies that are going to be needed from the people who are in the sales function. And you start to think about well, okay, do we have these skills and expertise is already on the team? If so, great. How do we continue to foster and improve those skills over time? And if not, do we want to develop those on the team? Or do we need to acquire them? Or is it a combination of both? And part of part of making that decision is a little bit of like the amount of risk that we want to take in terms of growing people internally, and the belief and webinar we can grow the team based on their potential? But also in terms? It's also based on time? Like, what, what time? How much time do we have to actually develop these skill sets. So understanding long term plan that allows us to then sort of begin to develop a talent strategy over time with milestones that then allow us to make some critical decisions about the people we have on board, and the acquisition of of skill sets, whether that is building them internally, or bringing them from the outside. So that's an example of how I think about talent development, because we want to get to the point where like, we're not behind the trying to bring these skills on when it's too late. Like, we want to basically ramp into those skills. So so I'll use the term, we want to develop the bench and make sure that we can bring people off the bench at the right time over over the period of three to four years, so that we achieve success. That's that's how I think about it.

CAITLIN ALLEN: Okay, developing the bench got it. That makes sense. Circling back on this topic to what you were saying at the beginning, around the importance of people in culture, and it's reminded me of something you said in our prep call, which was something along the lines of how a superior product and lots of money doesn't necessarily replace mediocre people. But it's also super possible to do incredible things. If you have amazing people in place, which, you know, partly I would assume as a talent, our people leader like that rolls up to you for to a certain degree. And it also, it also really relies on your partnership and trust with leadership, as you've pointed out. So what is what is your secret? Or what are your guiding principles for pinpointing and built building trust with leaders who know how to recognize and nurture that top talent and in a way that's super crucial to business strategy?

JAMES CLEVELAND:I love this question. My answer is definitely not a secret. I think there are some guiding principles or things that I have learned that I noticed and leaders who do this really well. The first is leaders who I have noticed in leaders, they actively connect to their people in meaningful ways, I have worked with leaders who basically are so focused on revenue and product that are not around they're not present. And I think that's it's important that they are able to focus on the external component of their job, but they also have to make a connection to people internally. So hellos sorry, good. I'm gonna cough here. So we might have to have this turn.

JAMES CLEVELAND: So I was saying that like, it's really leaders who are able to connect to people in small but meaningful ways. So that means like hellos to everyone, not just their loan leaders, but to everyone in the organization. Every now and then having lunch or hosting a conversation, to explore ideas, conducting skip level conversations, to learn how one of their direct reports is doing, I think is a really great way to connect with people in small meaningful ways. And also being present during meetings like you know, not always being on the phone showing up to meetings, particularly like a group events, sharing stories of themselves sharing a little bit about themselves. That's That's one. That's that's the big thing. So like actively connected. The second is that they are actively engaged in their direct reports, not only about them as growing professionals, but they're also asking about their people. Remember, I talked a little bit before about like developing a bench, they are curious. And they want to know who are the up and comers, where's the potential who are the high performers, etc. So they're actively asking about this on a regular basis. Now, this could mean on a weekly or monthly or quarterly basis, but they are curious, they are showing that. Third thing that I noticed is that they will oftentimes randomly provide stretch opportunities for individuals, in least in unexpected ways. Oftentimes, especially when you're in an organization that is, maybe still figuring things out, or maybe has a product that is, or a service that is pretty good, but could be better. They are eager to explore innovative ideas, or to test out new strategies. And they want to, they want a unique perspective. So they'll, they'll ask somebody to basically come on board, and maybe take, take a project or take an idea and run with it for a little bit. Those kinds of stretch opportunities are one a way to identify new talent, and test the potential of an individual, but to again, create that connection. So they're basically demonstrating curiosity, again, through the stretch opportunities. The fourth thing that I noticed is that they're always involved in recruiting. And I've worked with leaders who basically divest themselves from recruiting, they basically say, hey, we need this person. And they basically farm it out to somebody, whether it's an external agency or the internal recruiting team, and then they will come in at the last step. Most of the leaders that I've worked with who cares a lot about people and culture are involved in recruiting in small meaningful ways. They're constantly on LinkedIn saying hello to people who they think might be great for the organization, or might have a network that would be beneficial to the organization. So they are contributing to the font that started the pipeline development. In that way. They are meeting people at conferences and talking to them about possibilities of the organization. They are participating in interviews, particularly their direct hires, but they're curious about key hires across the organization, asking questions and may even participate. I have found that in early stages, that a CEO or a leader who spends anywhere between 30 to 50% of their time in recruiting mode actually tends to have the strongest teams and I know that number sounds incredulous, but I'm talking about these small collectivities. You know, like they're on LinkedIn, they're saying hello to people, they're there. And they're asking about key hires, etc. Like, this is not about them actively recruiting all the time, but they might they might be, but the point is, is that they are invested in recruiting and who's coming into the organization. The last thing that I'll say and I kind of hinted at this in the in the first bullet is that they are a participant in the cultural norms, and rituals, they are not above them, they are a part of them. And as much as any other leader or employee may be participating in these rituals, they are part of it as well, when those so those are some examples. I'm sure I could come up with more. But those are some examples of how I know a leader is really invested in the people and talent and frankly, the culture of the organization.

CAITLIN ALLEN: Love it. I really like how practical those are, too. So thank you for that. As it as it relates to maybe what you learned when you found out you weren't a good manager and then learned how to become one as you think about training the bench for that future state of what the business will need from its talent. How do you how do you approach training existing employees in you know, in factoring in both where they want to go into careers and also what the business needs from them?

JAMES CLEVELAND: Yeah, I I think there's a there's a few strategies that are worth it. Exploring, I don't have a best practice per se, because I actually think it's very bespoke to individuals and oftentimes very bespoke to companies. Things that I think about. So hopefully it's a food for thought for the audience. One is, is that every company has a unique set of requirements are capabilities that are necessary for delivering their product or service and sort of that are unique to their culture. And so I really encourage, and I think about this a lot, I encourage the identification of the core competencies and behaviors of management that make our organization work well, right. And so some of those are going to overlap. Some of this can be very, very familiar and similar in organizations, but there might be two or three things that are very unique to your or our organization. So that's one thing that I think about. Because once you do that, then you can start to think about like the kinds of activities and trainings or opportunities that will allow a person to develop the skill, and ultimately, the behaviors that need to be shown in order to deliver on those competencies and behaviors. And second thing is that

CAITLIN ALLEN: I'm sorry, I might say interrupt interrupted you. Do you think that changes as well, like in a remote environment, we've actually been talking about this so much yes, in our executive team have, you know, specifically for especially for folks that are earlier in their careers, they maybe don't have much time and as much time in seats in the office environment or in a remote environment? So what are the special characteristics that kind of highlight or earmark those top performers in a remote setting? It's sometimes very different than it has been, you know, in previous roles that were in office.

JAMES CLEVELAND: Totally, totally agree with that. I absolutely agree with that. I think revisiting this on a regular basis, especially if conditions change, I think is really critical for ensuring success. Yeah, the second thing, I think,

CAITLIN ALLEN: oh, sorry. No, I was gonna ask you for.

JAMES CLEVELAND: Yeah, so the second thing I think about, I do think that, especially for new managers, and this was my issue, you're fumbling around, and trying to figure things out, and you oftentimes, especially when you're under stress, you know, you're being, you have a lot of pressure for your manager to deliver results, they tend to default to what you know, which is basically how you were managed, right. And sometimes you have a good model, and sometimes you don't, right, or you maybe you have experience managing a different type of individual. So in my case, I was very used to managing teenagers, 1314 15 year olds, who needed to be told what to do. And that was my mantra model, if I told everybody what to do, and that included, smart, thoughtful college, graduate professionals, told them what to do. And you can imagine why people might hate that if they are capable of thinking and figuring problems out on their own. And so I actually believe that a way to break that is to one introduce a newer manager to a framework that challenges their the models that maybe their, their, their, their using, or had been exposed to. And oftentimes those frameworks will help an individual recognize that the people that they are working with, have a range of skills, and have a range of ways of communicating and receiving information and actually approaching work that need to be considered. I call this, you know, the, it's sort of an adaptive, recognizing that everyone needs a range, a range of management behaviors, it's sort of an adaptive management strategy. So one side or one size does not fit all different strokes for different folks. That's how I kind of think about management. And there are a lot of books out there that talk about the fact that everybody's different, and therefore, as a manager, you need to figure out what are their capabilities? And how are you going to approach so that you maximize their potential. And so and that requires sometimes a person to sort of sit down and think about what are all the ways that they have been successfully managed, that brought out the best in them, so they can second think about how they, how they might do that for others. And it does require sitting down and being reflective about your people and recognizing this is what this person brings to the table versus what this person brings to the table. And sometimes it changes depending on the situation or the project or the kinds of activities that we're engaged in. And so recognizing that recognizing that sometimes takes the introduction to a framework or a set of frameworks that allow you to sort of think and begin to approach your, your your style, with a little bit of care and intention, versus just kind of diving into what you know Yes. And then the third thing. Yeah. And then the third thing that I will offer is, and so I do believe that like, you know, sending someone to training or sending somebody to like to like to read a book or whatever can be very helpful provided that they recognize that they're going to have to invest a little time to figure out their own stop, I have yet to see a company, however, just sort of say, Hey, we're going to use this approach, everybody uses the exact same approach, like I've yet to see that work. But I have seen it, force a person to think critically about who they are as a manager, and how they need to how they need to connect with their people. The last thing I'll offer is that I do think I'm a fan of, of the range of strength and personality tests that exists in the professional market, not because they give you all the answers, but because they force a manager to recognize that everyone is different. And it actually helps the employee recognize what they need from their manager. And so I love these tests, because it opens a dialogue, it can create a two way conversation, and it actually puts part of the burden on the employee management is not a one way street, it is a two way conversation. And so and so so I tend to sort of think about performance and growth being the burden of both the manager, but also the employee. And so the employee cannot just sort of wait for a manager to come to their aid or to basically provide what they need, they have to be a great advocate for what they need in order to be successful as well. And so sometimes these, these, having that expectation, and then using the framework for a manager, and these, these tests for employees that help them understand their strengths, and gives them a language to have a conversation can be really powerful.

CAITLIN ALLEN: I love that I really, really enjoy that. And it's so true. It's there's a, there's a bi directional, like management relationship. And so being able to educate your manager about what you need, and then also being able to give your manager what he or she needs. And then same in the reverse, it becomes a very fluid, organic exchange that can really drive high performance.

JAMES CLEVELAND: I think a lot of employees are actually surprised when I tell them, It's your response, your 50% of this relationship is your responsibility. And if I'm not hearing from you, as much as you're hearing from me, then this is a one way street, it's not gonna work, right. And so, particularly newer employees don't understand that. But they start to appreciate the importance of that overtime. And so I, I think some of the best employees are those who actually take the Driver, take the driver's seat and continue to anticipate what their managers can expect of them, or the kinds of questions their manager is going to ask them and know how to leverage their manager to basically drive their own growth. I love I love it when employees are able to to recognize it, and they're able to do that.

CAITLIN ALLEN: Yeah, that's a really big skill. Rounding out the conversation, James, maybe bringing the the lens a little bit narrower to the people teams that you've built. How do you think about personally assembling a people team yourself from the early stages of a company?

JAMES CLEVELAND: Yeah, so I, in every case, when I come into an organization, I usually it's a situation where it's a founder or another leader who's wearing multiple hats, who is basically own aspects of the people function. And maybe there's another utility player, someone who has another job in the organization, but also doing some administrative support, to help out with some people operations functions. The thing that I have seen is that there's always a range of things that are in place, whether it's on the people operation side, or the culture, side, etc. And so I spent the first three months, maybe maybe 60 days, really learning what's in place. But maybe the more important thing that I do is actually go out and I learn what is the experience that everybody's having in the organization? So I actually go and talk to employees? Tell me, what was your experience, like when you were going through the recruiting process? And what was it like when you were doing your onboarding experience? And what's it like to be an employee here? What do you tell your friends and your family when you talk about being in this company? What keeps you here? What? What are the things that drive you absolutely crazy or prevent you from being your best self or prevent you from being productive? If you had a magic wand? Or if you were in charge, what would you change? By asking those questions, I can come up with themes that will ultimately determine what the people team needs to focus on next. And so essentially, the organization the employees are determining my priorities. And I use those priorities to determine where we focus next. And by doing that, I'm able to determine not only the roadmap for where we're going, so I actually think about remember I talked about a three to four year plan. I think about the three to four year plan with the people that might be part of the people team already, will then go through an exercise to develop our mission and create a vivid description of where we're going. We then set milestones together and we talk Talk about what we're going to accomplish over the next year. And then by doing that, we're able then to talk about, well, what are the capabilities that are going to be needed to achieve this. And in doing that, that helps me understand the kind of talent that we are in need to either develop within the team. And oftentimes, it's, there's not a team or it's just one person. But it allows me to understand how I can best position that person and create the greatest leverage out of their skills and insight and frankly, interests, right. But also the kinds of people that I need to bring into the organization. The other thing that I so that's that's basically how I determine like the kind of expertise that I need to bring onto the team based on it's based on the priorities that the organization helps me. So then, when I start to think about people to hire, I certainly look for expertise. So if I need if I need act with any talent acquisition, certainly I will look for recruiters, you know, if I need that people operations person, certainly I'll go look for people who are interested in this work. But I tend to find, I tend to go after people who have done other jobs. First, I already told you my background, my background, I've been in a lot of different roles, doing lots of different things. And it gives me an empathy to understand how best to serve the range of positions in our organization, because I've actually been in many of those roles. I actually go and look for individuals who have similar backgrounds, maybe they don't have as many years. But I want to know that they've done some other things first, before they move into a people role or recruiting role. And so for recruiters, I go and look to see, you know, have you been in an operations role? Have you been in a sales role? Or have you been, were you a former engineer, I want to know that you understand the challenge of being in these types of jobs, before you start to serve and fill those types of roles. I especially pay attention to this, when it comes to people operations people, I tend not to hire people who just went right into HR. I do that purposely, mostly because I need people who recognize that we are in an entrepreneurial situation, and it requires creative problem solving. And you have to be comfortable with a lot of gray in order to be successful in a role like this. And if we are coming in and creating black and white lines, we're going to actually create challenges for the organization. And so I purposely look for individuals who have have other types of experiences in their background, who have been pivoted in, into people in culture, because they recognized as much like I do, how important that is, and how much passion they have for in order for us to create a successful team. So those are my strategies.

CAITLIN ALLEN: I love it. It's we're all triathletes, so to speak, when we're in early stage companies, so it's having that elite, you know, mentality is is so important. And I really can understand how that that need for empathy is it I think it's important in every role, but particularly in a people leader role, because you were leaving people. That's so true. It makes so much sense.

JAMES CLEVELAND: And your your point about the triathlete, like at times, you know, there may be a call for us to actually cross lanes, like we may actually have to do work outside of our core lane, especially at this stage of organization. So I need people who are comfortable with that, who are have some comfort, pivoting strategy, midstream, changing priorities midstream. So they need to be comfortable with that. So I look for individuals who have that have those have those in their profile?

CAITLIN ALLEN: How do you think about transforming yourself as a people leader, James, like there are some pretty, fairly substantial transitions and initiatives that are very complex and both short term and long term that we've talked about today? So what is what is looking in the mirror look like for you both in the day that you're in as well as the future you want to be in?

JAMES CLEVELAND:I will say that I think there's been a couple of pivotal moments in my career, that have helped me learn how to be more self reflective. So I think there has been a journey. Early in my career, I was always very eager to demonstrate my importance, my value, my ability to grow and perform. And so there's sort of a natural eagerness there that sort of informed my my growth, a desire to do new things, right. So I was willing to go to class and you know, take the courses necessary to learn something I was willing to try the new projects I talked about the leaders who basically unexpectedly would drop a stretch opportunity on me, I was eager to do that kind of those kinds of things. As I moved into senior level roles, you know, I was the person that had to basically mentor others and there is a certain level of ego there were You're basically I know, I know a lot more than a lot of folks here. And I think it took a couple of things that sort of couple of moments in my career that forced me to be a little bit more self reflective, and to sort of lower that ego a little bit become a little bit more demonstrate humility, in other words, one is, is that my grandfather's death, really opened my eyes to the fact that life is short. And there's so much to gain from this world. And you got to have open eyes in order to do that. That's what allowed me to step down from from the CEO role at jumpstart where I was giving a lot of my life and energy to, and I just really thought like, this was the thing that I was supposed to do. And I started to realize that like I was really, that it was really not in the role that best suited the strengths that I brought to the table. But it was my ego, keeping me in that in that role. So that self reflection has really helped me. It took that that traumatic moment in my life to sort of get there. The second moment came about five or six years later, and for some reason, I had gone through several roles as a CEO and for leaders, and for a variety of reasons, those roles either worked, or they didn't work. But I started to realize that like, I was really positioning myself as a partner to CEOs with a lot of what I thought was knowledge that they could use, but it wasn't paying attention to what they really needed. Right. And it took, it took a trip, a transition that was happening between two companies, it took a lunch with a colleague, who basically, and this is after like spending a lot of time with a lot of other folks who were telling me, these are the kinds of things that you should be doing, here's what you should do next, etc. And this was the person that basically said, once you stop, can you tell that you're like to keep jumping on into these opportunities, and you think you know what you're doing, but it ends up not being a perfect fit. And maybe you just need to do a little bit self reflection, she called me out. She was the only person that told me not to look for another job, and to actually stop and do a little bit of self reflection. And I remember I spent, I was shocked in that moment. But I remember I spent that summer because of that he was the only voice that I heard, I spent that summer swimming and doing yoga. And doing a lot of self reflection. A lot of journaling was first time I started journaling in my life. And I basically reflected on every single job I had held up to that point from the job I had at the at the theater, to being a waiter in a restaurant to every single job that I've ever had let me title that I held. And I had to reflect on everything that I worked on, you know, why was Why was this successful? What are my accomplishments were all my failure. So it was a lot of reflection on failures and challenges, and what my values were in those moments, and it really helped me recognize that my focus was in the wrong areas, right, that I really should be focused, that's where I got the greatest joy happened to be on people and culture. And then I was actually trying to exert influence in areas that didn't really didn't really matter for me. And that I was not being self reflective enough and learning from my mistakes that I was repeating the same mistakes over and over again. And that that that reflective moment clued me into the fact that like, I actually can be a much more effective coach for myself. And I can be a much more effective coach for the leaders around me. And it was the reason why we decided to fully go into people in culture, because I knew I wanted to be a strategic business partner, to leaders, particularly entrepreneurs, to help them make bring their their vision to reality. And I started using this learning approach where I basically come in and don't presume that I know everything, but I want to learn what have you built? What makes this place special? What are your strengths? What are your hopes and desires? And where do you see the challenges? And where can I be most helpful ask that question, Where can I bring the most value to you. And in doing that, it has allowed me to grow as a leader, and be far more effective in my work in building the kind of not only team teams that actually are focused on people and culture and organization, but help leaders understand the capabilities that are needed over time to be successful. So I really feel that those two moments have allowed me to grow. So I'm in a very different place than I was even five years ago. And I'm constantly reflecting on my past as a way to hopefully improve who I am as a professional and also as a person.

CAITLIN ALLEN: Thank you for sharing that. I think the the it takes a lot of courage to share what you what you've shared it also to do what you've done, and I think we can all learn from from some of what you've said. So I appreciate you cluing us into to some of those things. James, we've had talked about a lot of wonderful things today. And the last question I'd love to close with is just a really simple one around. If, if our listeners took action on one of the things you have said today, and you got to choose what it was, what would that be?

JAMES CLEVELAND: I think I would know, I know, I would say this connection matters. People want to feel connected, that's inclusive of you, as a leader, right? You connection matters. Like you need to feel connected to purpose, that you believe in the organization and what it stands for what it's trying to accomplish, that you are connected to your leader, that you understand the plan, and you're part of that plan, and that you will feel like you belong, you're connected to those around you. And if you can think about that for yourself, you can understand and empathize like what that mean with why that is important for your employees. So if, if you hold that one sort of phrase, from everything that I've talked about, during this last 45 minutes when our connection matters, I think you're going to be able to create some powerful impacts for for the people in your organization.

CAITLIN ALLEN: Really well said, Thank you so much, James, thank you so much for that, and for your time today for taking us through your amazing career. And I hope that 2023 is a wonderful year for you.

JAMES CLEVELAND: Hey, I wish the best for all your listeners as well for 2023 and I appreciate the opportunity to be here.

CAITLIN ALLEN: Thank you. Alright, everyone, have a wonderful day. Thanks for tuning in. We'll catch you next time.