The Culture Code

With their deep involvement “on-the-floor” frontline managers are a lot like player-coaches.

That’s how the CPO of Box Jess Swank likes to think of them. And I think it makes a lot of sense!

Jess shared five critical ways she develops her frontline leaders
  1. Monthly manager power hours on timely skills
  2. A bi-weekly manager newsletter
  3. A Slack channel for Q&A
  4. Focused development programs and coaching
  5. New manager training
She also shared that moving in 2024, she’s focusing on locally tailored training: “We're working on understanding the commonalities across locations and how we can support local managers with local issues in a customized way.”

In addition to the above, she dived into what culture looks like at Box, how they scale and sustain their culture, and her number one book recommendation.

Hope you enjoy this one
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What is The Culture Code?

Welcome to The Culture Code podcast. On this podcast, you’ll learn how to grow, shape, and sustain a high-performance culture with the CEO of LEADx, Kevin Kruse. From designing and delivering highly effective leadership development programs, to measuring and improving the employee experience, you will understand what it takes to cultivate a thriving company culture. Through interviews with Chief People Officers, deep dives into key topics, and recordings of our invite-only community sessions, we bring you cutting-edge, data-backed insights from the most desirable companies to work for in the world.

Kevin Kruse - LEADx: Hello, everyone. I'm Kevin Kruse. Welcome back to another episode of The Culture Code. Super excited for our guest today, the Chief People Officer at Box, Jessica Swank. Jess, welcome. And where are you joining from today?

Jess Swank: Well, hello, Kevin! Hello from around the world. So excited to be here today. So I'm joining from Redwood City, California.

Kevin Kruse - LEADx: Love it, Redwood City. And we're here to talk about culture. And I just want to put it in context first. Can you share with us, you're in Redwood City, and a big question among Chief People Officers is the whole like, do we call people back to the office, remote-first, hybrid, etc. Where has Box landed on that? So as we think about culture, we know the context of that conversation.

Jess Swank: Yeah, no, it is definitely a really important question. And I think we're all in kind of this grand experiment. So we have taken the approach of being hybrid, which means we have, you know, a couple of times a week, we have what we call IRL days, and real-life days, Tuesdays and Thursdays, where we try and come together, create that community and connection in real life. But we also have about 30% of our Boxers around the world who are remote. So we want to make sure that no matter where you're working, no matter what you're doing, that you can be successful. But yes, we are really committed to this hybrid with a lot of flexibility.

Kevin Kruse - LEADx: Jess, anyone in the tech space knows your company Box, a super successful company. For those who might not be familiar with Box, how big is your organization and in plain language, what do you do?

Jess Swank: Yeah. So Box, we are the leader in the content cloud space. And what that means is, you know, we all have a lot of data these days. And so we provide a way for customers, for employees, to, in a highly secure way, capitalize on that content, share, collaborate internally, externally, and then we have a lot of integrations with other software tools. So, you know, Microsoft, Google, Slack, Zoom, you name it. So, again, it is really this way to take your data and provide it in a very highly structured way.

Kevin Kruse - LEADx: About how many Boxers are there?

Jess Swank: Yeah, we have just shy of 2,600 Boxers around the world, and we have a number of customers. So we have almost three-fourths of Fortune 500 customers and over 120,000 customers. So we are definitely global, and we're growing, which is also the exciting part.

Kevin Kruse - LEADx: Do I get a gold star for using the phrase "Boxers"? Because I did hear you reveal that internal word in your very first answer, which is a sign of a strong culture.

Jess Swank: Yes, I say that without even realizing it. Sorry, I didn't even realize I said that. But yes, Kevin.

Kevin Kruse - LEADx: How would you describe your company culture in just a few words?

Jess Swank: Like you said, it's, I think, often hard to really describe. However, I think a couple of key tenets through our culture is one, we are a founder-led organization. So our CEO, Aaron Levie, is one of the co-founders, and he's still CEO, as well as our CFO, Dylan Smith. And so I think that has a lot to do with the sense of, you know, kind of a startup mentality, scale, and growth. And so we deliver, you know, kind of high drive. You know that. Dst, which is one of our values, but also an incredible focus on culture, on people, on communities. And I think that, to me, is part of our secret sauce as well as, I'm saying, we have a lot of fun. We laugh. It's a very open, transparent culture, which I think makes a lot of the hard work a lot more enjoyable.

Kevin Kruse - LEADx: Yeah, and just, you know, shout out, like I said, to your founder, CEO. What are some of the ways you foster or sustain this culture? Any unique rituals or traditions related to your culture?

Jess Swank: Yeah, I think a couple of ways. One is we have really strong values. We have seven values that are absolutely embedded into everything that we do. So, you know, everything from, as we hire, we look for culture adds. So, you know, again, we want diversity. We want the sense of, you know, one of our values is "bring your whole self to work." So we want that sense of diversity, equity, inclusion, top of mind. But also, we want people and potential Boxers who actually really align to our values, those seven. So everything from hiring to development, to promotion, to compensation, right? We even, in our performance management, look at the "what" and the "how" with the underpinning of those values. So, again, like you said, Kevin, it's not just, you know, kind of the platitudes. They actually are embedded into how we talk, but also the actions that we take. So I would say that's one, two, three, I would say the second part of our culture, and I mentioned this, is a real commitment to creating a sense of belonging. And with that, it's yes, it's creating, you know, diverse voices and welcoming those and creating that sense of inclusion. But it is that real warm sense of, "Hey, we want, no matter where you are, no matter what you're doing, to be able to feel like you have a place, and you're seen and heard here at Box." And I would say the third one, that for me is incredibly important, is we're a very transparent, open, collaborative organization. And so I think that sense of culture where, "Hey, we, you know, kind of be an owner" as one of our values, and that sense of like, "Hey, we are all part of this, and it is up to every single one of us to make sure we're exemplifying, adding to, building that culture, not only looking back at what it's been, but really thinking about the future and where we want to go."

Kevin Kruse - LEADx: Jess, you packed so much gold in that answer.70% of engagement is correlated to the manager, and front-line managers touch more employees than any other leadership group. What are some of the ways you develop your front-line managers?

Jess Swank: Yeah, and I, as you believe, Kevin, it's one of the most challenging roles in organizations, right? Because even now we have managers who are not just managers, you know, that's not just all that they do. They are player coaches, they're managers, and yet they have their own deliverables. And they, as you said, are at the front line of so much in incredibly challenging times. And they're, you know, what they're having to filter and communicate and be aware of and deliver on. And, you know, personal, professional. It's immense. I have a lot of just compassion and gratitude for all the managers around the world. And a couple of things that we do. So. One is, we have a monthly Manager Power Hour, and this is an hour-long, you know. I lead it. Our team leads it. It's full of, you know, kind of strategy, what is going on. But then, enablement. So you know, what are programs? What do they need to know? We do some training. So that's one. We also have a bi-weekly manager newsletter that we send out. We have a Slack channel for questions. We also do a lot of focused development. So we have some development and coaching programs available for our managers. And then we also look at if you're a new manager, whether you're a new manager to Box where you might have external expertise and experience, or you're an internal, you know, promoted manager. We have what we call Manager Accelerate program, which is a 6-month program, where we put people through, again. A very robust training. But also it's not only training, it's coaching, it's sharing. It's about enablement, making sure that the managers are best set up for success. So we're working on that, you know. One of the challenges. And again, observations, as you mentioned, you also know what that looks like around the world differs. So what that looks like in the US is different than what it looks like in our full inside, versus what it looks like in, you know, kind of Japan. So we're also trying to think about what are some of those commonalities. But then, where and how do we also need to support local managers with local issues.

Kevin Kruse - LEADx: Yeah, and and again, just to build a little bit. I just did some LinkedIn rants on this topic about how we love to see developmental nuggets sent through their Slack, or the Teams, channels, etc. Because you want to deliver things in the flow of work where people are hanging out, right? Bite-sized. Yeah, everybody's too busy for work, but they're great. And at LEADx, we're seeing a huge drop-off in people doing pre-work in a flipped classroom model. But people do what's on their calendar, right? So they always say it's old-time management, you know, if you really want to do something, put it on your calendar, not your to-do list. So those monthly, and this is stealable for all the listeners. Listen to the Leadership Power Hour, right? So once a month have a Power Hour where you get people together, and then it's on the calendar. There's that cadence, and perhaps I, we won't have to go into the details. But maybe there's some breakouts. Maybe there's some cohorts. Maybe there's some peer buddy study, study buddy conversations, lots of things you can do. It's not one or the other. The big thing I love, Jess, is, unfortunately, what I hear too often in these conversations is people say, "Oh, we do great leadership development. We cover these 18 competencies in a two-hour webinar period." Well, how many of those things are gonna be remembered and applied in the weeks ahead? Right? So it's not a program. It's a system. It's an ongoing thing. And it sounds like you've got a robust system in place.

Jess Swank: Yeah, and exactly. And I think it's that system. It's building those habits on a day-to-day level and then helping to reinforce along the way. And again, we have a coaching mentality. Where, hey? We? We call them nudges, right? We might nudge you and say, "Hey, you know this might be, you know. Have you thought about it, you know? Let's make sure that we talk about why to reinforce. We also have a bi-annual what we call learn fest so twice a year, where we also have manager-specific content. So everything from, you know, how to be a better manager or leader to, you know. Make Mom proud, one of our values. We have a whole session around it. So we have full, you know, kind of Boxer editions, but then also managers to say, "Hey, what? This look like? Situational leadership? One of my personal favorites is that we roll out across all of our managers as well."

Kevin Kruse - LEADx: One of your values is actually "Make Mom proud."

Jess Swank: Yes, "Make Mom proud." It's my favorite.

Kevin Kruse - LEADx: See how sticky is that right? Instead of, you know, just integrity, "Make Mom proud." We all know what that means. We know, right? I love it, absolutely.

Jess Swank: And we've tried, and we've tried to also have an aspect of, you know, or whoever you admire most, right, because we want to also be inclusive. But again, that sense of we want to act with integrity, no matter what we do, no matter where we are.

Kevin Kruse - LEADx: Yeah, I absolutely love that. As you know, this is a short format podcast. What book would you recommend that your colleagues read? (or podcast, video, etc.)

Jess Swank: I am a big fan of Adam Grant, "Think Again," both the book and the podcast. And to me, yes, it's the book and the podcast, but it's the way of thinking. It's to be able to say, "Hey, you know, we question our assumptions. Do we have biases there? Is there a different way that we could think about and do that?" So again, just, I think it's great framing. And I use just that thought experiment often in my day.

Kevin Kruse - LEADx: Great! Related to culture, are there any special initiatives or results you’re most proud of?

Jess Swank: I think probably the only other one that I would note is we are just constantly trying to pilot and learn new things. And so one that we are actually piloting is integrating DEI into our leadership and development. Because, again, going back to managers, I think that right now, this sense of how do you train? What do you think about this across your organization? It's incredibly important. So that is one that we are piloting, and we're getting a lot of positive feedback on. We're looking to roll out next year globally.

Kevin Kruse - LEADx: Now, I'm gonna ask you to go back in time to the first day you became a chief people officer. You probably know some things now that you didn't know on that day. So, write a Slack message back in time to a younger version of Jessica Swank. Like, what advice would you give her?

Jess Swank: I would say, make sure you understand compensation and executive compensation, because a lot of work that you do is with the Compensation Committee. And I think for many of us who grew up, like I grew up through recruiting and people partners, I didn't have that expertise. So, day one, I remember my first Compensation Committee. You need to be that expert. So, either formal training or informal training. Make sure you understand at least the fundamentals of compensation, especially.

Kevin Kruse - LEADx: We're talking now, this interview's late October of 2023. I assume you have your 2024 plans in place. So like, what's a priority that you and your team are gonna lean into or focus on for next year?

Jess Swank: Yeah, as I mentioned, we just passed the 1 billion mark last year. And so we have our sights set on 2 billion. But beyond that, we have what we call our "People Path to 2 Billion" that is really driving the focus areas for not only Box and how we scale, but also for our People and Communities organization. And so we've broken that down into a couple of different areas, including how do we scale talent and culture, and how are our processes fit for scale? They might be great for 2,000 people, but will they be great when we're, you know, 4,000, 6,000, for example. So that's the work that we're going to be doing over the next couple of years, which is super exciting. And then, I think, too, we are big believers in utilizing our own product. So that "Box on Box" mentality. We're also super excited as a team and a company about Box AI, which is a product that we're launching, as well as Hub, which is kind of a central way, and Compository, which is gonna be a game-changer, that links with the Box AI, not just for our own People and Community team but for a lot of functions and organizations in this coming year. So super excited about both of those.

Kevin Kruse - LEADx: I love that. In the last employee engagement survey LeadX did, a future vision was at the top of the list for the most motivating factor. We all want a strong, compelling future, and yet too often, company strategies and things are too complicated for us to really remember and get motivated by. But I love what you just said: "People Path to 2 Billion." Like, inside that is a whole bunch of drivers, and inside each driver are a bunch of actions. I know you've got those details, and yet everybody can remember and get excited by the "People Path to 2 Billion." So I applaud you on that. The AI part is probably the most exciting thing going on in Box over the next year. I assume?

Jess Swank: Absolutely. It is our... you know, we've developed it internally, taken the best of external. So we're building on that. But again, using that on the Box platform, it's secure, it's collaborative. I think it's really going to be a game-changer. I'm super excited.

Kevin Kruse - LEADx: Chief People Officer at Box, Jessica Swank. Jessica, thanks for all the work that you do and for giving me some precious time on a Friday afternoon.

Jess Swank: Oh, thank you so much, Kevin. Thank you for all you do. Appreciate it.