The Culture Code

Culture isn't magic. It's the product of thoughtful effort.

As Josh Bersin puts it, “To change the culture, don’t start with the culture. Start with the problem that you are trying to solve, what success looks like, and why it matters to your company.”

Nowhere is this mentality more present than at Headspace, where Chief Operating Officer (COO) and Chief People Officer (CPO) Karan Singh fittingly operates under the mantra “less but better.”

Here are a few highlights from our interview:
  1. how he creates a culture that reflects the company mission
“Culture certainly doesn't happen magically,” Singh pointed out. “You need to create it.”

Here are three ways (of many) that he does so:
- Beginning every all-hands meeting with a guided meditation
- Flexible time off for employees to catch up on life, recharge, and get away from laptops
- peer-to-peer recognition where employees express gratitude for each other’s contributions and adherence to company values

2. how a team’s engagement and workload capacity go hand-in-hand

As a dual COO and CPO, Singh shared the following unique perspective:

“Wearing my operational hat, I think a lot about capacity planning and how much a team can take on. I think those areas are directly related to employee engagement scores. As engagement decreases, so will the load that your team can handle. If you wait every six or 12 months to measure team engagement, you clearly can't plan effectively.”

3. how he develops “superhuman” leaders

A recent example of “less but better” in action:

The “Superhuman” Program—In collaboration with a team of neuroscientists and faculty members from UC Berkeley, Headspace created a program centered around this question: “How do you create a workplace that is remote-first and creates space for people to work smarter, not harder?”
Singh and his team strove to make these concepts explicit and operationalize them. Every employee at Headspace completed the program.

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This one is a must-listen! Enjoy! 


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 Kruze. Welcome back to another issue and episode of the Culture Code. Our guest today, I'm very excited because I'm actually a customer of his company. He doesn't even know that until right now. The COO and Chief People Officer at Headspace, Karan Singh. Karan, welcome! Where are you coming from today?

Karan Singh: Kevin? Thanks so much for having me. I am dialed in from the Bay Area.

Kevin Kruse - LEADx: I'm all the way out in Philadelphia but have been spending more and more time in the Bay Area and really had fun in San Jose the last trip out. So you're a lucky man to be living where you're living.

Karan Singh: Certainly feel that way.

Kevin Kruse - LEADx: So let's start at the beginning. For those who might not be familiar with Headspace, how big is your organization and in plain language, what do you do?

Karan Singh: Certainly, what we are is a comprehensive mental health care platform. Everything from mindfulness and meditation resources that many of you would love to hear that you're a member here. You know the Orange dot on your phone for access to support. But all the way now to clinical support, coaching, therapy, psychiatry, even serving as your company's employee assistance program, your EAP.

Kevin Kruse - LEADx: It's great, how many employees worldwide?

Karan Singh: We have about a thousand people across the country, everything from licensed coaches and clinicians to award-winning producers and data scientists. So quite a collection.

Kevin Kruse - LEADx: I love it. Kuran, before we talk about the culture, point of the interview, I think it's important also to clarify, like people are so curious in this moment of time, like Headspace. Where have you guys landed on the whole work remote work, hybrid, you know, that issue? Where are you guys at with that right now?

Karan Singh: The strategy has been evolving as we continue to learn. Let's say the headline is still remote first, but recognizing the importance of what I like to call in-person booster shots, the opportunity to get together on some sort of regular cadence to really build psychological safety and trust, which, you know, can get degraded if you're fully virtual at all times. So I think the virtual first has been incredibly valuable, just as a recruiting strategy, and to find the best talent. I think it's both. And you also need some opportunities to be together.

Kevin Kruse - LEADx: Yeah, I appreciate you sharing that. It's certainly not an easy issue. How would you describe your company culture in just a few words?

Karan Singh: Well, we define our culture as really who we aspire to be as an organization. I think our culture is, give me a couple of keywords. One is inclusive; we want to be representative of who we serve. Two is impact-driven; we ultimately want to be delivering real member value. And the third is curious - we start with a beginner's mind, a fundamental practice, part of mindfulness practice.

Kevin Kruse - LEADx: That's great. What are some of the ways you foster or sustain this culture? Any unique rituals or traditions related to your culture?

Karan Singh: It certainly doesn't happen magically. You need to create it. And it's really special when it does happen organically. I think we're really proud of the culture we've built at Headspace. And I think a large part of it is because we know that mental health and culture are just intricately linked to our mission. Our vision is, in fact, supporting the mental health and well-being of employees. We take a lot of those lessons and apply them to create our own healthy and happy workforce.

There are a few traditions or rituals that we use to reinforce this. Everything is as simple as daily company-wide meditations. Every all-hands meeting starts with a guided meditation by one of our teachers, which is a great opportunity to pause, center, and set an intention going into a meeting. We have twice-a-month mental health days, what we call Mind Days, to create boundaries and ensure there's space to recharge. One of my favorites is our peer-to-peer recognition program, which effectively allows employees to give points to recognize colleagues when they really live our values. It's part of our gratitude practice, which we think is so important in mindfulness and meditation, allowing people to share what they're grateful for in small and big ways.

Kevin Kruse - LEADx: You packed a lot into that short answer, and I just want to make sure everyone got it, and I'll start at the end. It's a gift to me because I'm a big believer in having an attitude of gratitude. One of the only expensive pieces of art I own has the word "gratitude" right in the middle of it. I have a morning gratitude practice, but I never really thought about the recognition practice at work as a sort of a deeper, spiritual, almost gratitude practice, which it definitely is. I know from the cold-hearted LEADx research that recognition is a top-10 driver of employee engagement, but I never really linked that to my own personal gratitude. So you just enlightened me there. Thank you for that one.

Karan Singh: And, Kevin, if I could add, I think it's such a critical part that we learned over the years. We didn't have that right out of the gate. Gratitude in recognizing when we live our values is part of the conversation. When you're recognizing someone else, it's actually an opportunity to say, "Hey, I saw the specific behavior or action or decision," and tying it then to an explicit value. So it becomes ingrained into our operating system, and people start to really unpack what these values mean. So it's been really valuable in a way to put some life into otherwise words on a sheet.

Kevin Kruse - LEADx: Okay, and I'm going to put an even finer point on it. This is great. So, Grant, over the last 20 years, I don't know, I've done 100 keynotes on the topic of employee engagement, and one of the top three practices is recognition. The one slide in the hour, the one slide where everyone pulls out their phone and snaps it, it's a slide that says "3 Steps to Strategic Recognition," you know. So step one is say thank you, make sure they know they're being thanked. Step two is to mention the behavior, so there's no misunderstanding about what the behavior is. Step three is to link it back to a corporate value, something that you care about. So it's that reinforcement of what good looks like and how you did it. So brilliant, love that. Love that. Hey, tell me more about these twice-a-month mind days! What should I do? Do I just take a long nap all day? Do I meditate for eight hours on the cushion, or is it a little less intensive than that?

Karan Singh: It's flexible. I think what we've realized is that every individual is really different. Teams have different ways of recharging. So there's no replacement for creating space and making sure that's also consistent across the organization, so that everyone might be off at the same time, if you will. So different people use it in different ways. Everything from catching up on life or personal chores to spending time with family or friends or spending time out in nature. Largely, it means being off the laptop and outside in the real world in some way. But we found that it's just really important both as a boundary that then work gets done in the four days prior, a space to then have an extended weekend in many ways when we have those nine days, and then it just becomes part of reinforcing that we live what we practice, what we believe in, and that taking care of your mind will ultimately create a better output and a happier workforce.

Kevin Kruse - LEADx: And I haven't forgotten the first ritual you mentioned is talking about meditation, starting the all-hands with a mindfulness experience. I just came back from a conference in Nashville last week where the keynote opened it up with one minute of box breathing. You know, 5 or 10 years ago, you would never see these public meditation and mindfulness experiences, right? And now they're pretty common. It's like, if you want, join us at 6:00 AM for sunrise yoga, and we're going to kick off with some mindfulness. I think it's great. I'm into that stuff, and I notice that maybe some others thought it was a little unusual, or maybe they just wanted to get to it right away, kind of a traditional mindset. But I think even how we start our meetings, certainly our all-hands, but this is a stealable idea. I'm always listening, and you're the first I've admitted it to in all these interviews I'm doing. I'm just trying to mine ideas that your peers can steal. So this doesn't cost any money to start a meeting, and if your corporate culture isn't ready for actual meditation or mindfulness, pause and say, "Hey, everyone, can we just take a minute to think about what do we need to let go for the next 30 minutes to have an incredible meeting together?" It doesn't always have to be meditation. Getting people in that right state can just lead to so many better results. Agree?

Karan Singh: I love that. And I think that the adoption curve is such a critical part of this equation. There are certain companies and teams where that might be easier to implement, and there are others where they're not yet there. But just creating space and setting an intention, this is such a powerful practice. And then the other thing I would say is, it's also modeling that behavior from the top, you know. That's both myself and other leaders of the team being really explicit about preserving that time, but also being explicit about reducing the stigma. And that might mean talking about when I'm working with a coach or when I might be seeking a therapist, and things that clearly might be more challenging in certain environments, but start to open the door to that conversation, that dialogue, because we know everybody's going through something. But most people aren't talking about it.

Kevin Kruse - LEADx: Let me shift over a little bit. 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?

Karan Singh: We focus on less but better for sure. And I think that's both in how we think about where we make investments, but also how we encourage our managers to operate in a sustainable way because we know that the stress and burnout amongst that manager layer is rampant across the economy and certainly can be in a high-growth organization. So we spend a lot of time thinking about how we make sure that they're supported and giving them the right resources. So, you know, monthly leadership development training around creating accountable spaces. There's actually a program that I think may be one of the most important things we've rolled out over the last year, which is becoming superhuman. This collaboration we did with a team of neuroscientists and faculty members from UC Berkeley where we really talked about how do you create a workplace that is both remote-first but creates space for people to work smarter, not harder. And I think we all jumped in, you know, post or in COVID, and just worked as hard as we could and realized we didn't have the dial at the right level. And so this is things like focusing on MITs (most important tasks), doing calendar cleanses, scheduling blocks of time for deep work, you know, things we know that are on the periphery but haven't actually operationalized. So we made it very explicit. We had everybody across the company run through this program. We've done subsequent training to ensure that we're actually following some of those best practices. And we tweaked it based on, you know, what was specific and explicit about our own culture to make it work most effectively.

Kevin Kruse - LEADx: Becoming superhuman, not worried about setting the bar a little high there, huh?

Karan Singh: Yeah, you know, the only task worth doing is the impossible.

Kevin Kruse - LEADx: I love that. Yeah, no, I mean, make a big, bold promise. How do you solicit feedback from employees about the culture and their engagement (e.g., engagement or other surveys, town halls, ?)

Karan Singh: It's something I'm so fascinated about, and I've actually really enjoyed the questions you've asked a few of your other interviewees before. I think it's a combination. There's both qualitative listening, better in multiple forums from all hands to AMAs (Ask Me Anything), to more quantitative surveys, pulse surveys. We typically do a quarterly survey to gather that feedback. Change up some of the questions, although there's always a base set of questions we ask to drive some level of consistency. And then create forums for both, direct as well as anonymous feedback, should you need it, to make sure that we both hear what's working or what's not, prioritize that list, and then roll out strategies to address that list. And then rinse, wash, repeat. So a big part, I'd say, the last part of this is being able to share what we heard and making sure that that's giving people a chance to confirm or edit that list. So we got it right. I think that's where I've seen this fall down before is maybe the feedback loop tends to be broken.

Kevin Kruse - LEADx: Yeah, for everyone who's listening to a lot of episodes, I'm a broken record on this. I won't go deep, but what I most want people to take away is that you're actually doing quarterly surveys. You're doing surveys quarterly. Many people feel, "Oh, everyone's over-surveyed," and things like that when it comes to manager effectiveness, engagement, etc. Quarterly is usually the right pace. If you have to report your finances quarterly, why aren't you measuring your culture, your people's stuff quarterly? If someone gets disengaged, you might have, depending on how hot the economy is, you might have 6 weeks to 12 weeks before they've found another job somewhere else. So you can't wait until 12 months go by to address an issue. So that's the big takeaway to me.

Karan Singh: I'm just working hypotheses. I'd love to get your thoughts on it because wearing my operational hat, I think a lot about capacity planning and about how much a team can take on. And I think that's directly related to your employee engagement scores. And so as the load that your team can work on will dip as engagement decreases, they have the ability to potentially do more. And so I think if you wait every 6 or 12 months, you clearly can't plan effectively.

Kevin Kruse - LEADx: Yeah, that's right. And I love that you, and hopefully others in the employee experience space, recognize that often people think about it as a way to, you know, focus on attrition, like, let's lower the turnover rate. Related to culture, are there any special initiatives or results you’re most proud of?

Karan Singh: Yeah, copy liberally, because that's what we certainly have done. I'd say the only piece that maybe we haven't spoken as directly about is really helping employees reconnect to their why and when they feel that why, when they're incredibly passionate about it, when they see it, when it shows up is when we share member wins or member stories in a company Slack channel and all hands where they can viscerally touch or understand how maybe all of what they're doing is laddering up to ultimately serving or improving individuals' mental health. That is so powerful. Again, another one of those booster shots that help people get through the tough times, especially when you might be making a number of changes. And so that's just one thing that is certainly a mission-driven and impact-oriented culture that we pride ourselves on. And it's been a really critical part of attracting great talent.

Kevin Kruse - LEADx: You know, as a listener, this is a pretty short format podcast. But I want to shift over to, with the minutes that we have, some faster fun questions. What book would you recommend that your colleagues read? (or podcast, video, etc.)

Karan Singh: One of my favorite books is "Essentialism: The Disciplined Pursuit of Less but Better."

Kevin Kruse - LEADx: This was where the "less but better" comment came in from earlier. So you are a minimalist at heart, and I like that. What about in your own growth journey with your Chief People Officer hat? You know, what's something that you know now that maybe you wish you knew on day one? Or if you could send a Slack message to the younger version of yourself, what would it say?

Karan Singh: It all starts with trust. And if there's one equation I was most focused on, it would be, you know, continuing to build trust, psychological safety, and clarity on our why. Because the how will flow. And I think, especially in a largely virtual environment, that can be hard. Stuff can build up, gunk can build up, and it starts to slow down the operating system. Every so often, I found that I want to be even more intentional, create more space, to continue to focus, deliver, and build trust.

Kevin Kruse - LEADx: Isn't that amazing? Like trust and safety? If you get that right, almost everything else is easy, you know. You might still have a tough conversation, but it's not a conflict. You might need to argue your side of how to solve a problem. But you don't need persuasion. If you have high trust, high psych safety, like almost everything else is easier. It's just incredible. We're talking here in this interview. It's late October, and so I'm sure you're already geared up for next year, a big 2024 again, with your CPO hat on. Like, what's your focus area? What are you going to lean into on the people's side?

Karan Singh: Number one is trust. Continue to build psychological safety and an environment of inclusion and belonging. Number 2 is reconnecting with the Y and making sure that everyone really understands just, you know, thousands and hundreds of thousands, if not millions of people who are getting better. And then the third, I'd say, is really a focus on accountability and ownership, encouraging courage in decisions and being accountable for results. I think that's a never-ending quest. And I think it's part of both head and heart about connecting with the Y and delivering on the results. And both don't have to be in conflict. So, spending a lot of time and energy, making sure that those are helping well.

Kevin Kruse - LEADx: So much wisdom. There, I keep behind me. What excites you the most about your company right now?

Karan Singh: We do have a whole lot coming. So I maybe boil it down to 2 items. I think the first is really just continuing on the momentum. I think we've been building and delivering this full-stack care model all the way from the newly launched Headspace app product that we now have for employers and health plans with content and coaching and clinical services, all part of this core experience. And then the second is really bringing the promise of our merger. We merged two companies, Ginger and Headspace, back in 2021. And we've been on a journey to merge our member and customer experiences, and we are now at a point where we have a single brand and a single member app experience. And I think that largely means removing friction, keeping it simple, allowing you as an end user now to be able to get access to covered care, and we think that that's a really big part of reducing stigma and ultimately achieving our mission.

Kevin Kruse - LEADx: We're going to end it right there. COO and Chief People Officer at Headspace, Karan Singh. Thank you for, first of all, the work your organization is doing, the impact you're having. Thanks for carving out some time to let us steal your secrets for building a great culture.

Karan Singh: Thank you so much, Kevin.