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For many leaders, firing workers may serve as an escape hatch. If someone underperforms, you can replace them, but you won't learn whether the failure was theirs or yours.
Greg Kunkel, Co-Founder of Next Jump — an e-commerce platform and HR software business — took firing off the table altogether. This meant the only way through a struggling employee was to make them better, forcing the company to master the one skill some organizations quietly avoid: developing people.
In this episode, Kunkel shares the playbook behind this decision and how he re-built his company around the belief: developing your people is the most powerful and underused way to build a high-performance team.
For HR and People leaders, it's the case for reclaiming development as your highest-leverage work, plus the honest-feedback culture that makes it actually happen.
In partnership with:
Greg Kunkel is the Co-Founder and Senior Partner at Next Jump, a technology company with two businesses including (1) an e-commerce platform called PerksatWork as well as (2) an HR software business.
Joining the company in 1998, Greg currently is head of Perks at Work and most recently has led the launching of two ecommerce mobile apps with over one million downloads, 5,500 App Store reviews and a 4.9-star rating, getting to top 30 in the App Store.
Greg is passionate about helping leaders navigate uncertainty. His work focuses on the practical skills increasingly needed in the AI era—including judgment, rapid experimentation, product thinking and building alongside AI. He regularly shares the routines and habits he has developed to help teams innovate faster and turn ideas into working products.
Greg lives outside Boston with his wife Jill and their two sons.
This transcript has been generated by AI and may contain slight discrepancies from the audio or video recording.
Greg Kunkel: We experimented with no firing. We're going to commit to you. We're going to develop you. We're going to coach you. You can leave whenever you want.
Narrator: That's Greg Kunkel, co-founder of Next Jump, a company so good at developing its own people, they built an invite-only academy to teach everybody else, training leaders from the military to the Fortune 500.
Anita Grantham: I've read that you have no lying, no hiding, no faking. How does it work?
Greg Kunkel: That term is almost a higher bar of transparency. There's a real cost to not being truthful with each other. It is crucial for high performance, especially when things are changing. It's hard work.
When we get in a stressful situation, one that's really hard, our worst can come out, and we'll say, "The situation was terrible." If you look at it a different way, that's who you really are. That's what showed up. That's my habit. Now that I've seen it, I can work on that.
Anita Grantham: Why do you think that corporate America hasn't adopted this like so many other organizations have?
Greg, it's so great to be with you here today. Thank you for making the time to speak with us.
Greg Kunkel: You're welcome. It's exciting to be here, Anita.
Anita Grantham: I've been following your journey and the Next Jump journey for so long, and I've been really inspired by all of the work that you all have done. I'm curious if you can take us back to the time when you were with the team in the co-founding process. How did you decide that you would not have a people or HR department?
Greg Kunkel: That was an evolution. When we started, there were four of us. We then brought on interns. We grew to 200 at one point, then went from 200 down to six, so we had an up-and-down journey.
Anita Grantham: Just to give everybody a timeline — how many years from zero to four to 200 to six?
Greg Kunkel: I joined in 1998, so we went through the dot-com era. We brought on investors, brought on business leaders, and barely survived. We learned a ton of lessons.
We took on an investor from Google, hired engineers, built an engineering culture, and really transformed our culture. We had an HR department — senior HR from investment banks, very professional — and one of the things about our culture was that it really fell on senior leadership. You have your job of running the business, and you have a job of running the people. A big part of our culture was around coaching. How do we develop people? That's been one of our core philosophies along the way.
Anita Grantham: Was there something that made you decide you were going to focus on that early on?
Greg Kunkel: It really came from one of our founders, Charlie Kim. He comes from a background where he just always did it. He would teach our interns — when we had no money — how to present better after work. It was part of his DNA, and it kind of transformed into the company.
One of the things we started to think about was a frustration on the senior leadership side around this culture piece. It was really falling on our shoulders, and we were working the hardest. We thought, what would it look like if we used the people side as practice ground to train everybody?
We started a journey where we slowly made everybody's job the people side. So we'd have engineers who worked on product, but they might also do the performance evaluation process, give feedback, or do recruiting. We slowly turned everybody into what eventually became known as an "everyone culture."
Anita Grantham: At that point, did you eliminate the HR positions, or were they there building the frameworks for everybody to operate inside of?
Greg Kunkel: We kept some HR folks for payroll and more of the tactical side. But in terms of what would traditionally be thought of as HR work — evaluations, recruiting, hiring — almost all of it was done as everybody's second job.
Anita Grantham: I hear operators and people professionals saying, "Well, how do they have time to do that?" Even in large engineering organizations, a lot of engineering leaders would say, "They don't have time to do all the people stuff. They have to write code." And we would play with the structure so they wouldn't have to do the people stuff, but then they still had to deliver the work. How did you work through those constraints?
Greg Kunkel: Taking a step back, when I think of culture, I think of it as the environment you set — a mix of expectations, habits, and rituals, senior leadership modeling their actions, and what you tolerate. A big part was shaping the environment so you'd be able to give people time, set expectations around it, and establish the why.
In some ways it was fun for some people, but it also brought on new challenges. We were very transparent when we hired people about what our culture was like and what the expectations were. It took a while, but it eventually became the norm.
Anita Grantham: If you were able to go back in time and talk to yourself then, with all that you know today, is there any advice you'd give?
Greg Kunkel: One of the things I've really learned — and I'm still learning it today — is to truly take a step back and think, "What do I want? What do I think is the right thing to do?" And then be able to expose that truth to others and have more difficult conversations.
It's easier to not admit, "I don't really know," or "I'm confused," or "This may not work. What are my fears?" It's easier to follow what other companies do or what you hear. I've had to learn, with a lot of work over time, to tap into what I authentically think, what I authentically want to do, and expose that and get feedback on it. That was something I had to learn.
Anita Grantham: It's so insightful, because I feel like we're inundated with information all the time. I used to say, "If I could have a dollar for every person that told me I should run my organization like Google, I wouldn't be working anymore." Everybody's like, "Be like so-and-so." Do you think there would have been a way you could have gotten to that authenticity faster?
Greg Kunkel: I think we've always been a company that tries to be authentic and do what we want to do, and I give my partners a lot of credit for that. There's an element around culture — around the idea of being like Google — where it can be very situational to your mission.
I've worked with entrepreneurs who are more VC-backed and trying to reach a point where they can sell the organization. That type of culture may have a different need than someone who is more invested long-term. We've had the fortune of working with leaders across nonprofits, sports, education, and the military, and different missions may need different kinds of culture. Trying to situationally build one that's authentic to your mission is often where people get into trouble by trying to build something they're not.
Anita Grantham: So if I break it down into a framework for people: first, understand what your founder wants. Are you building for VC? Are you building for sale? Are you building for the long term? Then, what is the mission that aligns with your product? And then build a culture that aligns to make that a reality.
Greg Kunkel: And I think the environment today has changed. There's so much more uncertainty, so much more pace of change, and so many tools that didn't exist five, 10, or 15 years ago that enable individuals and small teams to make the influence and impact they want.
But that comes with different human skills, and I would argue different environments needed for culture. Even for us, with a very strong culture, our organization today looks quite different than it did pre-COVID. While you learn lessons and build on them, if you're not reinventing yourself as a leader — your own awareness and abilities, and how that translates into the culture for the team — it may not be the right approach for the current situation.
Anita Grantham: Very true. How have you rebuilt yourself and the team through this evolution of change?
Greg Kunkel: A little bit of context: we had a very strong in-office culture. We had four different offices, did a ton of coaching and feedback, and had rituals built around that. We had gyms in the office. COVID really shifted that, and like everyone else, we had to debate what type of culture we wanted going forward.
We ended up both experimenting and shifting to a model where we have a small core team in the office full-time — more coaching, more responsibility, more accountability — and a work-from-home setup with contractors and collaborators who have more flexibility. We didn't do the hybrid model, and while that works for other organizations, it wasn't for us.
It was a huge challenge to move from the culture we had before into a model with smaller teams that are very transparent, working on themselves, and carrying more responsibility. Now I have people all over the world on my team, including someone who works within one of our client offices. Those kinds of setups wouldn't have existed before, so they bring both opportunities and new challenges.
Anita Grantham: Are there things you've done to operationalize that so it can work effectively?
Greg Kunkel: We're a very transparent culture, and I think that's been one of the things we're known for. Part of that transparency is being open about what the challenges are, creating feedback loops, and recognizing the need to iterate.
That has helped us a lot, because when times are uncertain and changing, we want more certainty. The hard part is it's very easy to say, "Okay, here's the new system," before it's been tested or iterated on and gotten real feedback. I've learned a ton of lessons over the years about how many limits we set for ourselves, which are often related to our fears and our predictions of how things might turn out.
As humans, we're not the best predictors. Being able to try things while also allowing for the messiness, uncertainty, and difficulty that comes with that process — and trying to set an environment, both for yourself and for others, that embraces that rather than fears it — is really important.
Anita Grantham: Let's talk about transparency, because I feel like that's a loaded word. In a lot of surveys, everybody comes back and says, "Be more transparent." I've read that you have no lying, no hiding, no faking. How does it work in a way that instills confidence for the future and doesn't create fear through the uncertainty?
Greg Kunkel: One of the things we talk about a lot is that it's important to keep working toward where you want to go, and you can iterate on that. But it's maybe even more important to understand the truth of where you're at now — and that truth can be messy. It's uncertain. People have different points of view on it.
That term — no lying, hiding, faking — was coined by one of our co-CEOs, Megan Messenger, and it's almost a higher bar than transparency. With transparency, you could just not say anything, not share your doubts, not say what you're hiding. You're not saying something false, but it's a higher bar than just being transparent.
For high-performing teams — in sports, the military, education, or at work — there's a real cost to not being truthful and open with each other. That means people may say they want transparency, but there's an element of putting the structure in place to enable it: enabling hard conversations, patience, messiness, and the human side. It is crucial for high performance, especially when things are changing. But it's hard work.
Anita Grantham: Is that why you put in place the no-firing policy? And is that still in place? I always think, "How do I get more transparency?" And I think they're not going to give it to me because they're afraid of repercussions in all these coaching conversations. So if I take away the fear of losing your job, does that open up this line of "I'll say anything in the spirit of the mission"?
Greg Kunkel: We've had the fortune of working with different military groups, and one of the things I think they do well that corporate America sometimes doesn't is recognizing there are two levers. You can hire someone who's already pre-made for a job description, or you can really develop them.
For us, we experimented with that no-firing policy, and it was as much for us — to push the envelope of saying, "We're going to commit to you. We're going to develop you. We're going to coach you. You can leave whenever you want." But when you take that lever away, when you get really frustrated with somebody and yet can't fire them, you learn to be creative about other ways to coach, train, motivate, and have more honest conversations. At the time, it enabled us to really push the envelope.
Anita Grantham: That's incredible. You shared that you have some stories around feedback and how that's played out.
Greg Kunkel: To share one of those stories — this was back when we had an HR group. We had a program we called Top 10. It was initially designed so that everyone in the company could see everyone else and give a thumbs up in a given month, with a description. Whoever got the most thumbs up would be our top 10 employee for the month.
Anita Grantham: How would I get a thumbs up? Like, what would I do?
Greg Kunkel: It could be for helping somebody else, doing a quality job — we didn't put too many parameters around it.
Anita Grantham: Was it built around the idea of better you, better me, better us?
Greg Kunkel: To take a step back, we talk about our programs and investments in people in terms of better me — grow ourselves — better you, which could be customers, community, or colleagues, and then those equal better us.
The Top 10 was initially a way to recognize individuals who were "better you" — thinking about others besides themselves. Then we had the idea to experiment with adding a thumbs down, almost the reverse — you could give candid feedback. We had a very senior HR leader with a lot of experience who was almost on his knees begging us not to do it.
Anita Grantham: Yeah.
Greg Kunkel: He said you can't have people publicly receive critical feedback — people would leave, it would ruin our culture. One of the things I've found to work well is, when you experiment, try it three times. The first time, if it's new, you're not very good at it; you're still learning. Three tries isn't the biggest commitment, and if you don't have traction after three times, you can re-evaluate.
So we decided to try it for three months. It was fascinating. It opened up a whole line of conversation about what we call eggshells — things unspoken within the community that weren't being talked about. Yes, it hurt some people's feelings, but in other cases it actually led to a much closer organization.
It led us down a path, and one of the pieces I learned is how much fear we bring into our predictions during culture change. It's been an awareness for me: when I feel a high level of certainty about a negative outcome, that's often an indication that it's more my emotions and fear leading me than the evidence. That's a very normal part of being human. But some of our ability to innovate and push the envelope requires leaning into that and being open to the possibility that the fear may not be an accurate prediction.
Anita Grantham: It's true. I always say between two people, there's your perspective, my perspective, and somewhere in the middle is the truth — and everybody else will see it through their own lens.
Greg Kunkel: And often, when they've done studies on this, the people who consistently predict incorrectly are much more predictable in their errors than the people who predict correctly. It's very hard to predict how the future will play out. There are so many factors.
That's why I think organizations and individuals that put out what they want, experiment, innovate, iterate, and try things — learning what is actually going to happen — will be even more valuable going forward.
Anita Grantham: You were written up as one of the best companies, next to Ray Dalio's Bridgewater, through Harvard as a deliberately developmental organization. Can you share a little bit about what that is and why people watching would want to take on some of these practices in their own organization?
Greg Kunkel: Bob Kegan, a professor at Harvard in adult psychology, coined the term "deliberately developmental organization." He looked at firms all across the world and ended up finding a very small handful — it was Bridgewater, a financial services company, among them — asking this question about organizations that have at their core a deliberate commitment to developing the people within them.
They ended up hearing about us and we got to know them. I think there are lots of organizations — more in sports and high-performance areas — where this is more normal. You have to train people up and develop them. And there are so many opportunities, even on the question we talked about earlier of whether an engineer has time for HR work.
We built about 50 apps that were all done within what you'd call HR, so they were able to experiment with technology even on the people side. There are ways to blend training into all of us that we just don't often recognize as training.
Anita Grantham: It's interesting because I've always said, everybody's like, "You need to build a training program." And I'm like, "It's in the work. It's what we do every day. We just need to highlight that it is this." Why do you think corporate America still struggles with developing people? Engagement is plummeting. Tenure and retention are challenged. I feel like we turn out humans and now everybody's excited we can rebuild it with bots. Why do you think corporate America hasn't adopted this like so many other successful organizations have?
Greg Kunkel: It's a great question — and a complicated one. A few thoughts come to mind. The first is that there is a lot of urgency, and it depends on the organization's desire for long-term growth. Not all organizations are run with that in mind. Some are run with very short-term intentions, and in that case, development is an investment over time that may not be the primary motivation.
Anita Grantham: So, like, back to the original premise: if it's built to sell or turn quickly, it may not be in the best interest — which is important for leaders to recognize.
Greg Kunkel: And I would argue that there are a lot of studies showing that organizations that do invest in that tend to have culture that holds up over time in the hardest of times — not just in the good times. So investment in doing the right thing over time pays off over time.
With that said, one of the challenges around development is that at the core, individuals have to choose whether they want to develop themselves, grow, and keep learning. You can't force that. You can set an environment that has that as an expectation, provides coaching, and provides feedback — but ultimately, one of the lessons I learned early on is that I used to spend most of my time with the individuals who were struggling.
Using an A, B, C framework for the people on your team, I would spend most of my time with the Cs. I was known for being good at getting more out of them. Today, I'm 180 degrees on that — taking your best people and, instead of leaving them alone, finding ways to help them grow, help them teach, and put them in positions where they're genuinely challenged again.
As humans, we face a challenge, succeed at it, and then it's natural to want that to become the new norm. It's hard to get back on your version of the next bicycle and re-challenge yourself. As leaders, we have to ask ourselves first: if we're not growing and learning, what can we talk about in terms of lessons learned in the last six months or three months? What is our current thing we're working on? If you can't ask yourself those questions and answer and share and teach them, it's hard to expect that from others.
Anita Grantham: Give us those questions again — they're really good.
Greg Kunkel: What I was saying is that often when I'm at my worst in coaching, I'm sharing things from five, 10, or 15 years ago versus what's happening right now. What are the things I'm learning now? What am I struggling with?
There are times I have to put myself in the mirror first and ask: am I sharing something more recent, where I'm less comfortable explaining it and it's harder to find the words — or am I going back to my old story, which might not be situationally relevant right now?
Anita Grantham: But it's an easier script to run.
Greg Kunkel: It's 100% easier. And one of the things I've learned just in the last year that was eye-opening for me is how often my own expectations shape my reactions. I'm more of an optimist, so I get excited about a new idea and want to try it. Invariably, new ideas will be harder than I initially hoped. That leads me to get frustrated — with people, with the situation, with myself.
Then I got some coaching of my own, which used a video game analogy of normal mode versus hard mode. I was mislabeling what should be hard mode as normal mode. In my head, I was thinking, "This should be easier," but it wasn't. And I was doing that to myself.
If I go in knowing it's going to be hard mode — that it will need iteration, challenges, and setbacks, and that I need to be more resilient — my energy and the way I handle feedback as it comes in changes. I had a tendency to take really good ideas, hit two or three setbacks, and move on to the next new idea. That was an aha for me: my own expectations were dictating my future behavior.
Anita Grantham: It's really insightful. How much of what you're doing is backed through neuroscience? I felt so relieved when my coach and I went deep into how my brain was hardwired. I forget the exact number, but I think your brain serves up millions of thoughts every minute — and knowing that I don't have to attach to those thoughts, and should pick the ones that most perpetuate what I want to create. Do you bring neuroscience into your coaching and the frameworks you're building?
Greg Kunkel: We've been fortunate to meet leaders who are experts in that space, and I think they have words and frameworks that have been helpful to incorporate.
I've been careful in my own approach to really focus on hard challenges in the work itself, truly being challenged in ways that make you uncomfortable, because that exposes where you're really at. One of the things I've always loved is turning on its head the idea that when we get into a stressful situation — one that's really hard — our worst comes out. We'll say, "That's not really me. The situation was terrible."
There's an element of truth to that. But if you look at it differently: that's who you really are — not in a bad or judgmental way, but in the sense that that's what showed up. That's my habit. That's what I've built up to this point. Now that I've seen it, I can work on that, so in the next stressful situation a better version will show up.
It gives more ownership in terms of our ability to endlessly upgrade ourselves. But often we'll excuse it: "I'm not really like that. I have more patience. I'm a better listener when the situation is good." I would argue the real litmus test is in the challenge.
On the neuroscience question, I probably come at it from a slightly different angle, but it's very related. We're endlessly understanding how our brain works, how our emotions are connected to it. There are some fascinating experts on emotions and where that connects. They're all valuable in terms of bringing a deeper level of awareness and understanding — and bringing those conversations into the workplace, rather than saying, "That's not for here."
Anita Grantham: It's so fascinating, because if you look at all the things we deal with in life, I don't know how we wouldn't bring them into the workplace. So how do you look at all of this and still see how it drives performance at Next Jump? How do you bring all those things together and still keep people focused on delivery?
Greg Kunkel: One expression I use is big M versus little M. Big M is your bigger mission — start there. Little M might be your current projects or where you're at personally.
It's very normal to show up and think, "My job this week, I have this project due, I have this going on." It's easy to start with the little M. I try to train our team to start with the big M — early in the week, take a step back and zoom out. What's the big M? If I'm working on the client side, where does that fit in the bigger picture?
In the mornings, I have a ritual I call visceral drafting. Instead of starting with emails or reactive work, I start with a blank piece of paper — just like a writer would. I don't look at notes or anything else. It may be the bigger mission, or a bigger project within that, or how things fit together. Even just 10 or 15 minutes of getting my thinking out on the table helps me sharpen my thinking and make it a little less fuzzy.
Those kinds of rituals, especially with AI and more technology now available, help us tap into what we authentically think, how things make sense to us, what our questions are, and what we want to do with all the capabilities we now have. Those are going to be increasingly important human skills.
Anita Grantham: Does everybody at Next Jump do that — the blank paper in the morning?
Greg Kunkel: I would like more people to do it than probably do. But it's a good example of something people really struggle with when they're busy, have clients calling, deadlines due, emails piling up, and life stuff happening. It's very easy to stay within routines.
One of the things we've learned on the culture piece is that rituals, behavior, and habits are such a lion's share of what enables adjustments to be made. My closest team — I basically ask them to do the visceral drafts, to think about it, to expose it, share it, and sharpen their thinking. But it's a current challenge of mine right now.
We're in a transition where people could do their jobs before, but now there are tools that can make their jobs so much easier — and that begs a scary question: what would you then do with that time? What would you do with your energy? What would you be able to build? If you're in a role that had a very specific function, that is changing. So the rituals need to change with it.
Anita Grantham: For people who are scared about it — we talked about this a little bit at dinner last night — what advice would you give to people who are automating so much and don't know how to redirect their minds?
Greg Kunkel: First, I think recognize the truth of the situation. Has the situation changed? What am I doing that's ineffective or that could be improved? Be able to talk about that, recognize it, own it. That's a hard journey for all of us.
It helps to have colleagues who may be going through difficult things too and to be able to have that conversation and train together. We try to do a lot of that kind of training in small teams so you don't feel alone in it.
Anita Grantham: What kind of training do you do together?
Greg Kunkel: It could be in teams of three, sharing your visceral drafts. We also have small coaching training groups once a week where people come together, more on the development side. One of the things we've found is to normalize it. Coaching can sometimes feel finger-wagging at its worst, as opposed to normalizing those emotions and acknowledging that change is hard and increasing your resilience through it, not despite it.
I think there's also an element of vulnerability — not my favorite word, but what I mean is being able to put out what you really think, what you want to do. It's a scary feeling because you can get criticized, and people may predict it won't work.
To be able to try it, iterate on it, and stick with it is scary. Having practice ground where you can go try things — those are skills that I think are going to be more crucially important. We built a mobile app with three people, for example, and for me that was just eye-opening in terms of what's possible. That would have been a 30-to-50-person effort in our Perks at Work business before. The tools are changing so quickly. It really begs the question: how do we service our customers better? How do we run our operations better? How can we dream of things that before felt impossible? Those are hard questions.
Anita Grantham: In thinking about AI and how much more can be developed so quickly, people can view it as hard, but part of what I'm learning from you is it's the lens you put over the top of it. It can be viewed as hard, or it can be viewed as really invigorating and exciting. At Next Jump, how do you think about gauging that so the fear doesn't become too big and you can innovate to create better solutions for your customers?
Greg Kunkel: The way I think about it is that as a leader in the organization, you have to go first. You have to experiment, and when you do, you also have to share the challenges and struggles — something I've had to learn and still struggle with. I'm more of an optimist, so I grew up not necessarily talking about the challenges. But I think that does a disservice to others, because those struggles are real and part of what actually happens.
With that said, I've been as invigorated over the past year as at any time I've been at Next Jump, and a big part of it is that things that felt impossible to me now feel amazingly possible. It's an exciting time, and I think people feed off that energy — and off the belief in people's endless ability to upgrade if they want to and are willing to work at it.
It also goes back to investing in people who are showing progress and changing. People aren't linear — some grow in bursts and then stagnate, and for others it takes a while. To be able to be flexible in how you view a traditional org chart — one that looks more like a sports team than a traditional, linear promotion track — I suspect that's more where work is going.
Anita Grantham: I love that you're bringing up the sports team analogy and that it could be the future of the org chart. When you say that, I think more of a spider web — is that the way you're thinking about it, where we're passing back and forth?
Greg Kunkel: My prediction — and it could be completely off — is that it will be a collection of small teams. Teams that are nimbler and can work with each other. Yeah, the spiderweb is a pretty good analogy. We use the idea of a community — and that community may be tightly within your team, with collaborators, or with partners. I think the definition of what it looks like for your organization to achieve its mission is just going to look different.
Just like in any sport, you go through slumps, and there are times when you need to reset, and other times when you're on fire. In a traditional organization, if you're at a certain job level, you either get promoted, stay, or get fired. To be able to shift — to take on a bigger mission, pause on some mission work, or step back to something a little less central because you need time to recover — those aren't principles that typically align with corporate America.
Anita Grantham: I think we're going to get pushed into this conversation because already founders are saying, "What's happening between product and engineering? How are we working together? What's happening between customer service and sales?" I think our org charts are going to be pushed more than ever in this next phase.
Greg Kunkel: I do think there's a real need and opportunity for individuals, teams, and organizations to blend that. It's never been easier to talk to customers. It's never been easier for someone like me, who isn't on the tech side, to build product that can get released with a code review in a matter of hours.
Anita Grantham: You're doing that now, though.
Greg Kunkel: Yeah, I'm doing it now. To be able to be a product person who builds, who sells, who talks to customers, and who understands problems — the tools are there for almost anybody to do it. But historically, you had an engineer, a product person, and a salesperson, and those lines were very clear and siloed. "It's not my job." Yet the tools are now there. So how do you train individuals to embrace that, accept it, and want that? That's the challenge in front of us.
Anita Grantham: For sure. So if we go back to the audience — we're having CEOs watch this, we're having heads of people watch this — if they say, "How do we decide if we want to be more developmental?" What would be the advice you would give to go in the direction that Next Jump has gone?
Greg Kunkel: I think it's incredibly empowering to think of two levers versus one. It's not to say you can't hire someone who has experience, is a good cultural fit, and can plug in and be immediately productive. But having the confidence that you can also grow individuals — maybe younger ones, or others — into positions they didn't dream they were capable of, gives you a lot of confidence that you're not stuck with just one lever. I would advocate for building programs on both sides of the organization, because it's empowering and gives you more leverage.
Anita Grantham: Are there examples where there's still a chief people officer but they're building this way? Is it possible for the role to still exist, or is it just additive and not as useful?
Greg Kunkel: My observation is that where I think senior leaders — CEOs and others — get into trouble is when they're delegating the people side entirely to HR. I think we have the biggest impact on the people side. HR can absolutely surface data points, flag feedback about things going wrong, and drive innovation.
On the HR side, I think understanding the mission is critical. In our Perks at Work business, we sit within benefits, and I work with thousands of HR leaders. I've seen a correlation — more qualitatively — where those who come from a business background, whether sales, product, or marketing, are often more effective at communicating and bringing in elements from the people side. Our enterprise exists because we have a mission and are driving and innovating on it, which enables us to take care of our customers and our people. Where it can go wrong is when it becomes an either/or.
Anita Grantham: It has to be both.
Greg Kunkel: It is both.
Anita Grantham: And so how would you advise CEOs who are delegating the function to take it on?
Greg Kunkel: Recognize that the people side is a lever, and that people are watching you. It can depend on where you are situationally — if you're trying to maximize things to go sell, that may be the right call. But if you're going to build something and want a high-performing organization, it starts with yourself and your impact. As a senior leader, certainly at the head of the group, you are being watched more than anybody.
Anita Grantham: Every day. You've talked a lot about predictability. I read that you built a kind of Moneyball predictor. Is that something you still use? How would you look to measurement for people to assess topics like this across their organization?
Greg Kunkel: One of the dangers of the data analysis piece is that people can get so into data-driven decisions. Most data is captured from the past, so you're looking at past data exhaust to predict the future — and there can be giant lessons in that. But it also makes the assumption that the future will be the same as the past, and I would argue that's increasingly less true.
Intuition and judgment matter. Being able to take past data as valid data points and think, talk, and debate what those indications might mean — while also asking how the situation may have changed and how to put those pieces together — is what can sometimes get missed in purely data-driven decision discussions.
Anita Grantham: And full circle, back to the AI conversation — if we're just relying on AI to tell us what's happening, we have to be able to apply our intuition over the top of those situations.
Greg Kunkel: I think it gets to what you want to build and what would resonate. AI is just the tool — the tools to effectively build that are amazing.
The amount of limits we put on ourselves and what we think we can do is often unchecked: "My boss wouldn't let me do that," or "I can't do this because of X." There's a part of being able to be more truthful with ourselves about what those narratives are, exposing them, and trying to get them challenged — which is where a coach can really help. Actually challenging you and helping you think, "That may not be true."
I see that a lot in HR — people waiting to be told what decision is coming down, what AI tools they can or can't use. Sometimes those limits are real, but in many cases I can see how they're self-imposed. I see others who are innovating, trying things, experimenting — and they're also getting promoted and making progress. I think we badly need leaders who are willing to take those risks and try things. I would hope for each of us to recognize some of those limits.
Anita Grantham: What I hear you saying — which is so incredible, and I think it's always been true but is now spotlighted around AI — is that no longer do we have the luxury for somebody to come to us and say, "Go do this." The value creation now is saying, "I see a problem. I'm going to iterate on the possibilities for how that can be solved or delivered, and I'm going to take a chance and deliver it even if it might be outside of my scope." And continuously deliver value even if somebody says, "Hey, I don't want that right now." Especially in HR — not sitting back waiting, but jumping ahead and saying, "I think I can be better here for the organization."
Greg Kunkel: I think that's right. There's a part of tapping into what would I want to do, what problem could I solve — and being open to the idea that ideally you want to build something you're proud of.
I do think it starts with yourself. If you build something and other people think it's amazing, but you know you cut corners and it wasn't something you truly gave your best to, that's not a good feeling. On the flip side, when you build something you're proud of but it doesn't resonate with others, that's missing half the equation too. Ultimately, I think you want to strive for building something that does both. That's not easy, but it's something worthwhile to strive for.
Anita Grantham: It's very difficult. Kind of a corollary — you've talked about making sure you know where the business is going and building a culture to support that. Where am I going on my career path, and making sure I'm doing things that are additive to that vision?
Greg Kunkel: The only thing I'd add, even to the career path piece, is that if individuals can start with the bigger mission — whatever that mission might be within their organization — and live in that space for a moment, even with some discomfort, it will bring up more questions and thinking. Then coming back to, "How can I impact that?" — if done in that sequence, and done more often, it will be beneficial to both the organization and to the individual's ability to create impact. And if you bring impact to an organization or team, you're going to have more opportunities in your career.
Anita Grantham: And so inside the Next Jump culture, I can continuously deliver to you. Sometimes it will land, and sometimes it won't, but both will be learning opportunities.
Greg Kunkel: Exactly. And if I had two choices of where to invest, I would put more weight on someone who is trying new things, developing, and staying open-minded — even if the outcome isn't there yet — than someone whose outcomes are there but who is largely living on what someone else has already done. My prediction would be that the first individual will grow further and have a bigger impact in the future.
Anita Grantham: Definitely. You love using the word "prediction." Am I missing anything inside of that?
Greg Kunkel: When we make decisions, we're all factoring in predictions. If you don't think it's going to be a good outcome, you likely won't take action. I use the word "prediction" a lot because we are prediction machines as humans, whether we talk about it or not. Being able to put those predictions on the table and state them more openly and transparently enables much more real conversations.
Often our prediction will be negative, but we don't really want to say that, so we'll couch it or be more passive-aggressive. Being more honest with ourselves — good thing, bad thing, why am I making that prediction? Is it a fear? Is it an emotion? Is it because of a past experience? Is that experience the same as what might apply here? — is a very important part of our decision-making framework that we're making unintentionally. If we can be more intentional with it, we'll ultimately make better decisions.
Anita Grantham: So coach me through this one. I'm working at an organization. The pattern of my leader is that they're not connected to the mission. They're not able to articulate what the mission is for the team or what the goals are. They're changing very frequently. In this time with AI and rapid development, we're shipping product and releasing it faster, we're changing dates, and it's very chaotic. Where would I start to highlight this and create a more streamlined organization around what we're delivering?
Greg Kunkel: There's a part of being able to take a step back and, on one hand, do the visceral drafting of what would I do in that position and how does the system work. What is the mission?
That would probably give me more respect for how difficult that role is and the challenges it carries — and I think people can feel that. If you're going in with an attitude of "I'm not responsible for it, you are, and I'm just passively giving advice," people can feel it. Versus someone who has taken time to sit with that challenge, understand the complexities and nuances, and thought about what we could do in the future. People can feel someone wrestling with that challenge.
A mistake I've sometimes made — and others make — is being too certain on the action without doing the investment and thinking in terms of understanding the situation, the challenges, the nuances, and the limiting factors. If you can do that, you'll have a more authentic conversation and be able to find places where you can create some momentum. And I've very rarely met a boss who would not notice that and want more of it.
So often you can build trust and goodwill by both understanding where they're coming from and how difficult it is, and then creating momentum. Now you're in a place where they're probably coming to you for advice. Whereas the easier path — not doing anything yourself because you think they're the issue — will come through in tone, even if you don't say it explicitly. And it doesn't go so well.
Anita Grantham: It doesn't. And then what happens when I feel like I'm giving feedback to the leader and I don't feel like I'm being heard?
Greg Kunkel: I look at that in terms of what's my intention. Is my intention to fix them? Are they even asking for feedback?
There's a part where the situation differs — they may say they want feedback but not really mean it. And in some cases, maybe they're not even asking for it, and I'm trying to state my point anyway. There may be more effective ways to approach that.
I have to be honest with myself. I'll do the reverse side too — I might be giving feedback to an employee with my own agenda for what I want, rather than for what's genuinely good for that person. There's a level of self-awareness needed: giving feedback with an agenda isn't necessarily going to be the most effective way to give feedback or advance the mission.
Anita Grantham: We were chatting at dinner that there really isn't a company I can think of that is excellent — outside of Next Jump — at developing people, really intentionally developing people at scale. So we have a lot of frontline leaders with no training, and then a bunch of early career people looking up saying, "Well, my leader should tell me." It feels like there's a lot of spin — new leaders who don't know what to do, and early career people who know they need more but don't know how to get it. How do we get through this? What advice would you have? I don't think management teams often recognize that it's happening.
Greg Kunkel: It's a complicated question, and one I don't know the best way to fully answer. But one thing that comes to mind is this notion of practice ground, and what we call above the waterline versus below the waterline — like a boat. If you make a mistake above the waterline, there may be a hole in the ship, but the ship is still running. Below the waterline, a hole means the boat sinks.
There's value in giving people above-the-waterline initiatives where they have the ability to make a mistake. We often expect people to learn just by listening, rather than by actually being challenged with a project. I've had to learn the patience and deliberateness of giving people space to do a project where they're going to learn some lessons — so that by the time they show up in their below-the-waterline role, they have a better skill set, better decision-making, and more experience.
That can be a work thing or even a home thing. As individuals, we often separate those two, but you can learn from the way you interact with family, or from a project that isn't work-related at all. It could be working on a softer skill — listening, observation — and if you bring that mindset, you'll find it turns up in the mission part when you really need it.
Anita Grantham: Yeah, it's so true. Well, I have two final questions for you. Is there anything else before we go into them that you'd want to share with our listeners?
Greg Kunkel: No.
Anita Grantham: Okay. From our last founder, she has a question for you. Is there a decision or something that happened that really impacted you — that you learned a tremendous amount from — a decision that had tremendous impact?
Greg Kunkel: In a lesson-learned, maybe a regret standpoint?
Anita Grantham: Yeah.
Greg Kunkel: A little bit of my history: I came in from the client relationship side. Post-COVID, I came back to lead our core business, Perks at Work. And I would say the first year to year and a half — and it shaped some of our conversation today — if there's something I regret, a mistake I made, it was that I was feeling somewhat overwhelmed. Running the business, learning all the different parts, managing the team — you're just busy all the time.
I definitely made a mistake of not taking a step back and asking, "How do I want to make this business, this product, this service better? How do I make it uniquely mine? What do I want to bring?" That's tapping into something very personal — and in a way that would be exciting and motivating to me, and ideally to others, and that would make things better.
It took me about a year to a year and a half to realize that was a real mistake — running what I thought needed to happen operationally, following the playbook of a 20-plus-year business. It was a giant lesson for me to take a step back and ask what do I want, how is that shaped, how do I let my own authenticity — what motivates me, excites me, what I think will work — guide me. It's crucially important, perhaps now more than ever, because it's so easy to build things without asking what's actually going to motivate and excite you. I learned a giant lesson in that.
Anita Grantham: That's insightful. Thank you for sharing. It is hard to take a step back and say, "What am I doing? Why am I doing this? What do I want out of it?"
Greg Kunkel: And I think also being able to say, "I am uniquely me. I have other leaders I admire and respect in our company, but in this role, what do I bring that's uniquely mine?" Allowing yourself to be seen. It's a scary feeling at times, and it can be hard work — because we're complicated. But I think it's what we need more of.
Anita Grantham: I do, too. Is there a question you would like to ask our next guest?
Greg Kunkel: I need a second on this one. I think the question I'd want to ask is around a time horizon of three months. Where do you want to be in three months? What do you want to accomplish and innovate on in three months?
People often answer in terms of five years or one year, but things are changing so quickly. It's been really helpful for me to try to sharpen the thinking across multiple levers in a three-month window — the team, myself, the product, customer service. Three months is 13 weeks. It's long enough, but not that long, so there's an element of action that needs to be taken. I've found it really helpful to think about and sharpen.
So I'd be curious what that leader sees as the next level in three months.
Anita Grantham: I love that. It's so fascinating to think about — with how quickly things are changing — not to be so far out in our time horizons.
Greg Kunkel: There's a placeholder of what you want to build and stacking it over time, but the three-month mark — 13 weeks — has been a good iteration for me. It's not next week. It's not even a month. But having your top initiatives, being able to envision them, and seeing them in that timeframe has been helpful.
Anita Grantham: We'll ask that question. Do you have a culture crush — somebody you look up to and admire?
Greg Kunkel: So you asked about this, and I've been really lucky at Next Jump — we've met thousands of leaders from military, sports, and business. I thought about this.
There's an individual, Danielle Morse, who runs a nonprofit called Shared Living Collaborative. She works with highly autistic people and has been doing this for more than two decades. She's had amazing ups and downs and has been featured in Rolling Stone for her work in autism.
She operates largely in an environment where there's not a lot of money or resources. She has a farm, and she learned that autistic kids respond really well to horses. She's innovated in remarkable ways to take kids who are often, in some ways, overlooked, and built a high-performing community and culture — even without being able to pay a lot of money for staff. The community she's built, even within the town, is extraordinary.
We've learned a lot of lessons from watching her. I often work with organizations that feel they don't have enough resources for culture. Whenever I get asked about that, I always think of Danielle — what she's been able to build through direct feedback, community, a defined problem, patience, and experimentation. She would be my culture crush.
Anita Grantham: I love that. I have one more question based on that. What advice would you give to leaders who say, "I don't have the money to do the things"? What I love is that the investment you discuss is investment of heart and soul and time — it's not purchased.
Greg Kunkel: It goes back to that discussion on limiting factors. We all have things in our heads about what limits us — not enough resources, not enough time, not enough dollars. The military will say, "I don't get to choose who comes into my organization." Others will say the newest people coming out of college are entitled, or whatever it might be.
Money is one of those limiting factors. It can expand what you're doing, but it rarely solves the deeper problem. It may mask a problem or solve a short-term one. And I think it can also limit a lot of creativity.
Anita Grantham: Amazing. Well, Greg, thank you so much for spending the time, for teaching us, and for sharing your wisdom. We're really grateful.
Greg Kunkel: I really enjoyed this. Thank you.
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