3 Rules for Building a More Caring Culture — This Chief People Officer Shares Lessons from Lambda School & InVision
People & Culture

3 Rules for Building a More Caring Culture — This Chief People Officer Shares Lessons from Lambda School & InVision

Mark Frein has served as Chief People Officer at Return Path, InVision, and now Lambda School. Here, he shares his approach to spinning up the people function, as well as tactical tips for creating a great employee experience, enabling a workforce that feels seen and heard, and making an environment

Over the course of his career, Mark Frein has tackled everything from running a leadership development consultancy, to earning a Ph.D. in Education and teaching organizational theory as an adjunct professor. But for the last decade, he’s carved out a signature focus: serving as the Chief People Officer charged with building up the HR function at venture-backed startups.

After a three-year stretch at Return Path, Frein joined InVision in 2017, when the design platform was around 250 people. He spent the next few years setting up the HR departments that under his tenure grew the company to almost 900 employees and rolled out programs around performance management, development, total rewards, onboarding, and people analytics. In early 2020, Frein signed on for his latest adventure when he joined Lambda School as the Chief People Officer & Head of Alumni Programs.

Few have been able to spin up several startup people orgs across so many different spaces. Eager to tap into the collection of top-notch people practices he’s accumulated over the years, we sat down with Frein for a conversation about the lessons he’s learned as a repeat Chief People Officer — and some patterns quickly surfaced.

“Every single company that I walk into, if I'm in charge of the people function, there are a few fundamentals that are really important to me: creating a great employee experience, enabling a workforce that feels seen and heard, and making an environment where people feel developed,” says Frein.

In this exclusive interview, he walks us through each of these elements in turn, opening up his playbooks for building the people function from the ground up. Frein sketches out what a great employee experience looks like and offers tested practices for training managers and developing talent.

He shares plenty of more philosophical musings — such as why leadership is an exercise in caring and why supervision is fundamentally about development. But there are tons of tactical nuggets as well, from how to custom-tailor employee onboarding to his unique approach to skip-levels. We think it makes for a particularly helpful read for both founders and early-stage people leaders trying to set a thoughtful foundation for this function, but managers of all stripes will walk away with practical pointers and thoughtful perspectives to pocket for later. Let’s dive in.


When it comes to figuring out what a great employee experience looks like, it’s natural to seek out inspiration. But Frein suggests taking a different tack. “Everybody's going to point to companies that they feel have been great examples of doing this. For example, Netflix’s famous culture deck about how they foster talent,” he says. “But the problem is that you can't copy-and-paste what they do to make their situation work. At Lambda, our situation is completely different — different company, different culture, different values, different talent base. There isn't a playbook of cookie cutter recipes from other companies. It's really about figuring out what drives the values and the culture of your company,” he says.

That’s why my people philosophy is almost always going to start with the strategy of the company. One of the things that I always think about is how can the people team or HR function create an employee experience that matches what that company exists to do in the world,” says Frein.

In many ways, building a great culture is about matching the employee experience to the competitive positioning of that company.

This can take several different forms, and should be infused into every aspect of the people team’s work. “It’s about finding all the ways in which we can help someone feel connected to the mission and the values very early on and ways in which they can feel connected to each other,” says Frein. “We've tried to really hit very early and very deeply how people can identify with how the company is different. Because ultimately company culture and company values — no matter what words you use — are about the experience of those that's unique to a company in question.”

Here, he shares several examples of how he’s operationalized this philosophy in his own roles:

People team’s approach:

“At InVision, one of the things that defined a lot of the cultural work that we did was design and user empathy. Because InVision is a leading design platform, we took user research and design thinking concepts and we applied that to the ways in which we built the architecture of the people function, and even in the creation of the services that we launched internally for the employees,” says Frein. (As he shared in this Medium post, this extended to hiring UX designers by trade onto the people team, building visual prototypes of employee handbooks and learning portals, hiring an agile program manager, and embracing the language of design thinking by speaking of “launches,” “iterations,” and “use-cases.”)

At Lambda School, there’s a different flavor, of course. “One of the reasons why I was so excited to come to Lambda is that we're in the world to educate. We exist in the world to help people be their best selves and to help people get a career in technology. Our founder and CEO Austen Allred once said at an All Hands that this should apply equally to ourselves as employees here at Lambda,” says Frein. “So as we’ve started to get the people function off the ground, we’ve leveraged a focus on learning — both being learners ourselves in the company, and then also fulfilling our mandate to teach. As we build the architecture of the people function, we’re thinking about how it can support continuous development of a group of people who in turn are trying to help the development of thousands of future data scientists and engineers.”

Frein adds on another example from his career. “Years ago, when I was running my own consulting company, we had a client that was one of the biggest mining companies in the world. And safety was something that was extremely important to them, for obvious reasons,” he says. “So when we were doing programs with them, even if it was learning about finance or manager training on how to give and receive feedback, we interwove aspects of safety and safety culture, just to hammer home the values that that company had.”

It's not that the programming of building a people function in a startup is radically different company to company, but that the emphasis and the things you hook the programs off of can be really distinctive.

Who you hire:

“At InVision, we had a very strong design bent. Now at Lambda, we have a very strong student bent. So while you could say both things are just a common value around being customer centric, there are different kinds of people you might hire as a result,” says Frein. “So at InVision, we had a lot of people who had a design background of some kind, even if they weren't properly a designer. At Lambda, we have a bunch of people who have an education background of some kind, even if they aren't the people teaching the students,” he says.

The impact of these differences? “Because a high number of people are from educator backgrounds, some of the things that we're doing here that are different than what I've done in the past,” says Frein. “We're rolling out programs with a focus on using people in the company. For example, in maybe my first month at Lambda, I asked on Slack what we were doing in terms of supervisor development on things like feedback. And I had at least half a dozen managers contact me and say, ‘I'd love to be involved in how we think about and roll that out.’ So we have people who are already employees who have experience and an interest in facilitation helping roll those things out to the rest of their peers. And that’s something that wouldn't happen at every single company.”

You want to leverage the way you think about your company as a way to think about talent.


A startup’s competitive edge can also be woven into the new employee experience. “At Lambda, we've designed our first version of new employee onboarding, and especially with some of our key senior hires, we ask them to be a student for a week. So you get through employee onboarding, and then we ask you to go and sit in the seat of one of our students to really get a sense of it,” Frein says.

“At InVision, we actually had folks who were onboarding use the InVision product suite to design their own mockup of a web app. Even if they were coming into the finance department or the HR team, and even if they would never touch the platform again, we wanted them to walk in the shoes of a customer,” he says.

Mark Frein, Lambda School's Chief People Officer

The common thread? “Can we get them to really deeply empathize with those who the company impacts? If we can get them to feel what the experience is like on the other end of the company, that's going to translate very powerfully back into understanding what the company is all about,” says Frein.

If you’re thinking about making the values live in a company, add them to every touchpoint of how you both develop and evaluate people. If you weave them into all of those touchpoints, the values will really have strength. If they're just up on the wall, they won’t do a lot of work for your company culture.


“It’s really important to me to make sure that people understand that one of their most important roles as a manager is ensuring their people feel heard and empathized with. And it's harder over the screen. It takes a little bit more effort to punch through and connect with people on the other end,” says Frein.

“But we want to be our whole selves at work. We want to be treated like a person — our name first, our role second. And that just requires cultural and leadership reinforcement. So one of the things that I probably preach and talk about at every single company I go into is how can leaders model empathy? How can leaders create places where their teams can feel like they're truly themselves?”

These are thorny challenges for any leader to tackle, but Frein brings his decades of experiences as a people leader to share some of the behind-the-scenes mechanics for engineering this empathetic ethos.

How to hire for empathy:

“There are leaders who are very talented at creating a safe environment naturally. There are leaders who aren't. And then there are leaders who don't care about it,” says Frein. “I can help a leader who cares about this but maybe isn't naturally gifted get better at it.” (More on that later.) “But I haven't yet figured out a way to get someone who doesn't care about this to care.”

For that reason, Frein places a premium on empathy during the hiring process. Since it’s tough to suss out in an interview, he offers up his best tips:

  • Create a conversation, not a hot seat. “I try to get into a natural conversation very quickly, trying to get to a point where rather than feeling like you were onstage to do an interview, instead, we're just having a really good back and forth. And some of the elements of that conversation would include questions that ask you to self-assess yourself — your performance, your career history, things you learned by succeeding, some things that you learned by failing or failing and trying again.”
  • Surface humility. “I remember when I had a hand in designing a sales recruiting process, we baked in a set of questions that were specific to failure. Good SaaS salespeople have a lot of confidence, but I wanted to see evidence that they were capable of self-assessing with humility,” says Frein. “You will see if they are able to pick a story that allows them to be authentic on what they learned in their struggles and if they’re at least capable of being humble. If they're humble, they're almost certainly going to be empathetic or capable of empathy. If they’re effectively incapable of talking about things that they might've done wrong, it's a warning sign for me.”
  • Push past practiced stories. As part of the prep process for tough interview questions, every candidate has a rehearsed story about a time they failed ready in the back of their head. How can interviewers push past that practiced veneer? “You can start with the ‘Tell me a story when something didn't go your way’ behavioral question, but some follow-ups that can really help you get a little bit deeper are: ‘Talk to me about how that impacted you. How did you feel?’ You can really catch someone when you ask them how they felt about something that was a struggle. Sometimes they blank and don't even remember how they felt. Or they’re surprised that you care about how they feel, or they don't even know how to answer that,” says Frein. “I find it relatively easy to see someone who has a pat story about a failure, but they don't really think it was a failure — watch out for when you ask them about their emotional journey and they can't talk about it with feeling.”
If a candidate isn’t capable of being in touch with their own emotions and self-reflective about a time they failed, it's highly unlikely — especially as a leader — that they will create environments where their people can be in touch with their emotions either.

How to train on empathy:

Back to the part about training leaders who have their heart in the right place, but don’t yet have the empathetic leadership instinct. Frein opens up about what’s worked for him over the years.

“The most important thing is practice. That’s why almost always within the first six to 12 months of joining a company, I've already launched a management development series. I often start by leading it myself, and then when I get up to scale, I pass it on to somebody if I'm able to hire a manager of L&D,” he says. “But what’s fundamental to me in getting that first round of management training going is that most of what we focus on is empathy. How can we listen deeply to both each other and to our people? And how can you practice it?”

He walks us through how he recently applied this approach at Lambda School. “Within the first six months of joining, I had booted up my first management session with a number of managers here at Lambda. And out of my old chest of goodies, I dug out these videos that I recorded when I had my own consulting company,” Frein says. “And in these videos, I took some people that were working with me and asked them to tell a story of when they were really blank — with blank being a strong emotion. So tell us a story of when you felt really angry, sad or happy.”

This approach comes out of research on emotionality. “When people recount a strong emotion, they usually begin to feel it again, or at least they have to handle it again. You could see in the videos one of them in particular got angry and worked up again. Another was much more in tune with her emotions. She didn't get angry, but you could see her processing,” he continues.

“So I showed these videos to my management class and I asked them to get curious about what they're seeing. And what I really do is focus on stopping them as soon as they want to judge. Because there were great managers in the class who still could not quite resist the urge to start diagnosing and fixing, a ‘Oh, I know exactly how to deal with this person, he needs to do XYZ,’ kind of response. But that’s trying to solve his problem before we even understand what the problem might be. So let's back up a second and just talk about what we're seeing and hearing.”

This is where Frein pulls out a trusty metaphor. “A manager's ability to read emotions is a little bit like training yourself to be a sommelier. You pick up a whole new language about it. Is that anger? Is that just frustration? Is that person in touch with their emotion right now? Through training, you're developing a little bit of a vocabulary and that vocabulary helps you step back, not judge.”

If I can start to get people to really work that muscle — the curiosity before judgment, the listening before developing an action plan — I know I can get them down a road where they become empathetic leaders and amazing listeners who will create very safe, transparent environments for people to feel seen and heard.

Quick tip: Outside of attending or developing your own training, Frein recommends Brené Brown’s work as a starting point. “It's very accessible. Her TED talks on empathy and listening are the resources I probably fire around quickest — they’re both famous and very good. Also, Goleman’s work on EQ is one that's standard and a very strong piece of work,” he says.

How to fire with empathy:

Frein notes that this empathetic approach extends beyond hiring and development practices — it applies just as forcefully to the end of an employee’s experience with your company. “It's really important to me that I exercise my direction of people in the workplace through caring. When I have to discipline someone, when I have to fire someone, I'm going to do it from a place of caring,” he says.

Organizations that I want to work for care for people from the point of entry to the point of departure.

“It's really easy to dehumanize. It's easy to just shrug and say, ‘It's a talent market and they’ll find another job right away.’ As soon as you go down that slippery slope, it's easy to do that over and over again, and think that people are replaceable,” Frein says.

Here, he gives us a window into what firing someone from a place of empathy might look like. “When someone has reached the end of their line with a role or with a company, you want to be clear. Good, basic firing technique is getting to that quickly — not beating around the bush, not apologizing about having to do it,” he says. “But what you can do is feel for them.”

Frein unpacks the first step: “Be there for that act with the gravitas it deserves. If you walk into a dismissal conversation and have psyched yourself up by saying, ‘This person is no good, I'm here to make sure that the only thing that matters in this organization is top talent,’ then the likelihood that you're going to be dehumanizing in that firing conversation is very high,” he says.

As for how to handle the conversation itself, Frein offers up these thoughts: “I would look them in the eye. I would wait to let them breathe. I would, in my own mind and my own heart, be letting them sit with that news and reminding myself that it's important that I care about their reaction to that — meaning they might get angry, they might get very sad,” he says.

Frein shares a method that seemed helpful in a real-life conversation he had: “The manager came in and said this is your last day. And then I was with the person, as often is the case with HR, telling them what was going to happen next. And the person was very emotional. And I remember telling myself, ‘I am going to give this person back all the power. I’m going to let them decide when this conversation is done.’ I looked at my calendar and made sure I had a lot of time. And of course, this is up to a reasonable point. But I thought to myself, ‘I'm not going to try to get off this call. I'm going to walk this person through the basics of the HR transactions around being let go. But then I'm going to basically be here for them,’” Frein recounts.

“So I was answering all of their questions, and at one point the person said, ‘Don't you have anything you need to go to or anything better that you need to do?’ I said, ‘No, I'm here, as long as you need me.’ And that completely changed their demeanor. I mean think about it — you just got fired, you’re probably feeling about the most powerless you felt in a long time. Even something as simple as, ‘Oh, he's going to be here on this call with me until I also feel done,’ that changes things a little bit. Did it make the person feel great about being fired? No. Did it make the person feel differently about that situation? Absolutely.”


Another key indicator of employee engagement? When people feel like they can grow and they have grown. “There's very good reason to believe that one of the things that people value the most when they're in a company is if they're growing —  when people feel like they're learning, it provides some of the highest spikes in engagement,” says Frein.

Here, he takes us through the tools available to managers and people leaders for reinforcing this at every touchpoint.

Handling interpersonal tension surfaced in skip-levels:

“People likely don't do anywhere near enough skip-levels, and probably don't do them in a way that really helps. I typically hold on to my skip-levels as long as I possibly can for a couple of different reasons,” he says. (As a result, Frein estimates he’s done perhaps thousands of skip-levels over the past couple of decades of his career.) “First, it just keeps me connected to everybody in my downline. Second, it also helps make sure that my direct reports know I'm keeping them honest, in a friendly, open way.”

Standard fare so far, but we found that much of Frein’s approach to skip-levels was unexpected. “I don't go in and hammer these oftentimes much more junior employees with a whole bunch of questions. Instead, I say, ‘This time is 100% yours. If you have absolutely nothing to talk about, I have some questions I will ask you, but I’m giving you this time with me as entirely your time. That means you can ask me questions about how we're doing as a business, my vision for the team, struggles you're having at work, or your career. You own this time — including if you want to cancel it,” he says.

“It usually takes a few times for folks who are new to working in my organization to get used to this. And the first or second time we meet, I know I might not get much. But then eventually, things start to come out.”

Skip-levels aren’t about dropping in as their executive officer and peppering them with probing questions. It’s about the reverse — giving them a chance to have complete control of the mic.

When it comes to handling the problems that inevitably tend to bubble up in these conversations, Frein shares his take: “If someone in a skip-level says, ‘I’m struggling working with your direct report,’ then I ask them about what they've tried out so far and what they intend to do next. I may gradually go into coaching mode, but what I don't do is say, ‘Let me take this and go do something about it.’ Even if I feel that way — and honestly, sometimes I do feel that way,” he admits.

“But I don’t because I want to teach everybody in my organization that the first step when something isn't quite the way they want is to begin to problem solve as best they can for themselves. I don't want them to get addicted to this idea of ‘I'm going to complain about my manager, and I know Mark’s going to go and yell at that person.’ That creates a lack of trust, and it also can create a situation where people don't take it upon themselves to do the work of communicating with their own managers.”

When asked to spot patterns in the issues he often sees here, Frein makes this observation: “80% of the time, the issue is problems in relational communication. It's people not being able to talk about what matters to them as a person. It’s a feeling of not being listened to because someone shut me down, or a feeling of not being respected because a manager is not showing interest in one's opinion or one's life circumstances. It's about a failure in human-to-human communication, as opposed to say a failure in process or a failure in transactional communication,” he says. “The remedies — when they work — are almost always about sitting down and having a more direct and caring conversation.”

Giving advice in career conversations and teaching — not assigning — in 1:1s

“One aspect that's important about environments where people feel very strongly that they’re developing is that they're also safe. The best thing you can do to help people feel like they're on a great career trajectory is to make it okay to talk about careers openly and really ask questions about what's next,” says Frein.

“If you've made it so that they feel, ‘Oh, I better not really tell anybody when I'm thinking about my role or my career because somehow it's going to get used against me,' you're often going to get the most political people advancing in the organization — because they recognize that what they say about what they want is more important than what they actually feel,” he says.

“Instead, you have to create a context where it's okay for someone to say to you as a manager, ‘I'm struggling because right now I'm increasingly bored with my role, but is there anything else I could do?’ If you've created an environment where that's true, your best people are going to want to stay there and do their best.”

Here’s how Frein tries to cultivate this open culture on his team. “For my directs but also my skip-levels, I try to get a sense as early as I possibly can of where they are in their own journey of thinking about their career,” he says. “Maybe one of my directs is one step away from being a Chief People Officer. Maybe it’s a situation where it's not 100% clear exactly where they want to go, but I want them to be okay articulating that. Then I ask a series of questions, gradually helping that person see for themselves. Where do you find your most joy? Where do you find your biggest contributions? Where do you just get absolutely jazzed during your day?”

The art of career conversations is helping a person discover their own answers.

“And as they see that for themselves, then it's getting them involved in some work if possible, getting up their taste for that,” says Frein. In his view, it’s all about the follow-up. “When I begin to understand how concrete they are about what they want as their next rung on the ladder — even if it's crosswise — then I try to build it into almost every conversation I have. How are you thinking about what we talked about last time? Did you go and try that piece? How did that go?”

Here’s why: “I think supervision fundamentally is development. A lot of people might think, ‘Well, as a supervisor, aren't you trying to make sure they get the work done’. It's like, well, yeah, of course. But that's the easy part of supervision. Quite frankly, the hard part of supervision is to develop your people,” says Frein.

“So most of the conversations I have, or at least try to have, have some aspect of, ‘I know that this person is close to being a Head of People, how can we talk about things in a way that gets them to see the way the world looks from my point of view in almost every chat we have? Gradually introducing them to the world that I'm living in, even if they're not quite there yet.”

This trickles down into how Frein approaches his weekly 1:1s as a manager. “How can I use 1:1s as opportunities to teach? I can give them work in a Slack message. During that time, I want to talk about what they're thinking about, and I want to have them put things on the table for me. If I'm going to a 1:1 with my manager every week waiting to get a list of things I'm supposed to do, it just fills me with dread and depletes my energy,” he says.

I tend to think one of the worst ways a manager can spend a weekly 1:1 with an employee is to give them work. I want to find out how my direct reports are doing and what I can do to help them.

Making decency the centerpiece of development programs

“When I think about when something really magical happened in terms of helping people feel like they really grew, in some cases it wasn't even so much about the design of a program, as much as the context,” says Frein. “The common theme was the links between where a person is at in their personal journey and where a person is at in their career journey.”

Take this real-life example. “Back when I was running my own consulting company, I was working with a general manager who was known to be very tough with his employees and was almost proud of that. He was in a managerial development program and I was his coach. And he said to me at one point that it's really important to not show weakness when it comes to my people. So I asked him some questions and I sent him home with some assignments, one of which was for him to go home and just get some feedback from your family around the dinner table. Just ask some simple questions like, ‘When am I at my best? And when am I not at my best?’ And he came back to me and he was really struck. Without going into detail, he basically said, ‘You know, I need to make a change. I realized that the way in which I've built myself up at work is also what I take home. I've taught myself that the way to manage my people is to have them be afraid of me. I don't want that to be true of my home.’ And he did a 180-turn on his management style.”

The lesson Frein took away? “Over the years, when I've done the most successful deep development of people, it's almost always about catching them at a time when the work that we do in the workplace is about being a good manager or a good teammate is just about being a better human being,” he says.

We're all in this journey in our lives of trying to be decent people and the best development in the workplace is often just about exploring what it means to be decent with each other.

“I know it sounds kind of silly, but it's about how do we just be good to each other? Work is very stressful. It puts us into weird situations where we feel competitive, where we might have politics creep in. If we're going to develop each other, let's do development in a way that injects decency, caring and generosity back into teammates and workplaces. And on that basis, you can make magic happen.”

This article is a lightly-edited summary of Mark Frein's appearance on our new podcast, "In Depth." If you haven't listened to our show yet, be sure to check it out here.