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A
One of the things that we're really interested in in Virtual first is productivity. Our original hypothesis was we're in too many meetings. But when we go through this HR as a product framework, when we actually look at is that the right problem to solve? What we discovered was it's not because actually the number of meetings that we have across Dropbox is below the industry average. So it's not the number of meetings that is the problem, but things that are the problem are constant distraction, continuous context switching. It's where meetings are actually staged on your calendar. So you'll have an hour 15 minute break, another 2 hours 30 minute break. You can't do anything meaningful in those breaks, right? And so there's not enough time to do this deep work that is so critical for productivity.
B
Welcome to the Work for Humans podcast. This is Dart Lindsley. When most companies talk about HR as a product, they mean applying product practices to HR services. But at Dropbox, it means something different. As Chief People Officer Melanie Rosenwasser describes, their focus goes beyond HR services to include how work itself gets done. After the pandemic, Dropbox HR joined forces with the Dropbox employee design team to conduct user research and qualitative studies to understand employees deeper feelings about transforming the way they work, including being remote first and without traditional offices. They set up trials, tests and experiments and then, backed by data, made the leap to their virtual first operating model in which the huge majority of the workforce is remote and physical spaces are used primarily for planned team events. They redesign collaboration techniques and meeting norms, including distinguishing set times for collaborative work and deep focus and establishing meeting free focus days. In our conversation, Melanie and I talk about how Dropbox leadership supported the move to work as a product, how design thinking has fundamentally changed the the people function and what it takes to build human centered systems at scale. We explore the mindset that drives their approach. Be human centered, simple is sophisticated, stay curious, outcomes over outputs, and iterate to innovate and how these principles can reshape how every organization designs work. All right, enjoy the show, follow or subscribe. Wherever you listen to podcasts, it helps us to win our dream guests. All right, now here's my conversation with Melanie Rosenwasser. Melanie Rosenwasser, welcome to Work for Humans.
A
Thanks. Thanks for having me.
B
Dart Dropbox did something really interesting during COVID when it came to moving to remote work and you used self consciously and explicitly a design approach, actually bringing together the product, design team and human resources to decide what remote work was going to be. It's a very unusual Best practice. And the reason is that most HR departments, when they are taking a product approach, focus exclusively on HR services. But this is something broader than that. This is something that's the experience of work itself and how work is delivered and the route to market for work. So you've gone on to continue to use design practices for a lot of what you do. And that's what I want to talk about today. Before we actually get into the part about how you do hr, I want to set the context, the business context that you are in at Dropbox. So recently we had Susana Kubrick on and she's at Nubank, and Nubank has this crazy growth path and all these different things that actually govern a lot of the ways that they think about delivering human resources or people operations. And so what is the context of Dropbox and how it relates to how you think about work?
A
That's a great question. So for those that don't know about Dropbox, it's a content collaboration platform. We have over 2,000 employees, we have over 700 million customers. We offer a suite of products that's basically designed to simplify workflows, so finding, organizing and sharing information. We just launched a new product called Dash, which is effectively an AI teammate that offers context aware intelligence. So intelligence, search answers and summarization. But Dropbox connects distributed teams at the end of the day. And so our operating model, which you touched on, we call virtual first. This operating model enables basically a distributed team, Dropbox, to build for distributed teams. So the way in which we work also goes hand in hand with the customers that we serve and the ethos of our product.
B
That makes a ton of sense. And one of the things I noticed when I was researching this show is how much of the content on Dropbox's site, it's not even necessarily specific to working virtually. It's just how to do great work, how to be on a team whether it's virtual or not, or how to communicate whether it's virtual or not. And so there's a way in which your product line is at the center of how we work and you've taken as a concern how we work in general.
A
That's right.
B
When did Dropbox first start using Design for People practices? Did it emerge during COVID and the pandemic, or was it something that was already kind of going on?
A
There were pieces of it that were going on before the pandemic. So things like the evaluation and iteration of an HR product. So are we meeting the success metrics? How are we learning and how are we making improvements too? Basically, employee experiences. But I would say that the pandemic was a catalyst to reimagine just work in general. So not just where we work. Do you work in an office, do you work at home? But to fundamentally reimagine what work is all about, what is the purpose, which is very different than just porting an in office experience to an online context, we really wanted to dig deeper. So I would say that we really started to flesh this out fully in the pandemic with our Virtual first product, if you will.
B
And I remember that right then you had a new VP of design.
A
Yes, Alistair Simpson.
B
Yeah, Alistair Simpson. And so first of all, there's lots of companies that don't have a VP of design. Most tech companies do, but lots of companies don't. So you had a VP of Design, you had a design practice going on in house already because of the design of your product. I actually find that a lot of times this is the way transformation happens, which is, this is called my law of just lying around, which is if you assemble something completely innovative, because the parts of it were just lying around and you didn't have to invent them to actually assemble them. And so it's one of the reasons why I think a lot of the design of people practices is coming out of organizations like Dropbox, where there is already a design practice in house. So since the Virtual first, have you explicitly become increasingly a design house in terms of how you create your people practices?
A
Yeah. So Virtual first really was like our tent pole product. And we learned so much of how to apply product management and design thinking principles to employee experience. But now we actually have a more formal framework that we follow on the HR team for everything that we do. It's not very catchy, but it's called HR as a product, or HRAP is what we call it. So we think about this as a set of products across our people team endeavors. So Virtual first is an example, but performance learning those types of things where effectively employees and candidates are our customers. And if you look at the product funnel, there are inherent similarities between that and the people funnel. So for example, on the product side you have marketing campaigns to drive awareness, and on the people side, we run talent brand campaigns to drive awareness. And further down the funnel, conversion on the product side equals gaining a paid user, whereas conversion on the people side is an offer accepted and so on. Right. So with this in mind, we looked at a number of product management and design best practices and frameworks. So design thinking and lean startup A double diamond, jobs to be done. And we created this sort of tailored approach that aligns to our needs as a people team. That became hrap. And it's a four step model and it's Discover, Build, evaluate and Iterate. Where discover is truly understanding the customer problem. Build is around creating prototypes or MVPs. Evaluate, analyzing outcomes against certain success metrics, so things like adoption and engagement and retention. And finally iterate, which is taking the feedback from that evaluation process and essentially debugging your product. Right. Fixing the things that weren't working and then scaling and that evaluation iteration cycle is continuous.
B
You mentioned briefly your talent brand or your employment brand. And there's the part of marketing that is essentially communications and public relations. And then there's the part of marketing. The quote that I like a lot is, I think it was Theodore Levitt at Harvard who said that the job of sales, which in this case would be recruitment, is to get rid of stuff you have. And the job of marketing is to make sure you have stuff that sales can get rid of. And so the question of how far back do you go from how you communicate brand to actually how you create a work product, a work experience that can be sold? And so I think in Virtual first you really dove into do we have a product that people want to buy that's actually going to satisfy their needs? Do you get involved in other parts of the experience of work that have to do with that? With are we creating the kind of work experience that people want to buy?
A
It is a great question. So because Virtual first is effectively an operating model, it's not about just performance management and compensation planning, learning and development. Right. It's about how we actually work as an organization, how we work as a culture. So I'll give you an example. One of the things that we're really interested in in Virtual first is productivity. Everything from the AI tools that we are using to how we're measuring productivity within our respective teams, to something that we're exploring recently, which is this notion of time and energy spent at work. So our original hypothesis was we're in too many meetings, so let's have a goal to reduce the number of meetings. But when we go through this HR as a product framework, when we actually look at, is that the right problem to solve? What we discovered was it's not. Because actually the number of meetings that we have across Dropbox is below the industry average. So it's not the number of meetings that is the problem, but things that are the problem are constant distraction which take away from productivity, it's continuous context switching. So you'll have a one on one with somebody, a strategy meeting, a leadership meeting. Right. All in a row. It's where meetings are actually staged on your calendar. So you'll have an hour 15 minute break, another 2 hours 30 minute break. You can't do anything meaningful in those breaks. Right. And so there's not enough time to do this deep work that is so critical for productivity. And so when we actually look at what is the real problem now we're working with our product team. We acquired a company called Reclaim, which is a calendar management company a while back. So now HR is partnering with the Reclaim team on how do we actually think about not just how many meetings are we having, but how do we increase the quality of our meetings, the cadence and how we think about the importance of deep work. So that's an example that goes beyond a typical HR use case.
B
It absolutely does. And so let's take that as an example and let's talk about discover, build, evaluate and iterate. So how did you discover that in the first place?
A
So, so the way that we discovered it was we have a number of work streams around productivity, our own internal productivity, but also our visions for could we build a company operating system where this can be tracked and then like productized later for other companies? So we're starting with ourselves, right? And we know from employee engagement surveys that this notion of barriers to getting work done is a huge problem for our employees. We also know that in a remote context, we have lots and lots and lots of meetings. Frankly, even before a remote context, you know, we had eight straight hours of meetings. We were just sitting in an office together. Now we're having eight straight hours of meetings and we're just doing it on zoom. We haven't really solved that problem. And so this is kind of where the Discover piece came in. We know we have an issue around this. Employee engagement sentiment surveys are emphasizing this. And so part of also the Discover is doing a lot of internal research. So we did some surveys on our highest performers in less meetings than everyone else. How do our highest performers manage their time and why is that helpful? So things like that. And that's where we started to find actually our highest performers are in more meetings than everybody else. So being in more meetings is not prohibiting them from performing. But what we did find is that they're very diligent about chunking their meetings. So four hours of one on ones that I have every Monday, Tuesdays is where I do strategic meetings every day. I will have a two hour block for deep focus time. And I'm laser focused on protecting my time outside of work. So I don't really allow for a ton of distraction in my off hours. These are all things that our highest performing employees exhibit, despite what we initially thought.
B
Do you remember what the survey question was? That was a part of this discovery that's really detailed and there's no reason you should remember it. But if you do remember, it's about.
A
Barriers to getting work done. But it's the way that we posed it.
B
It's not exactly how you posed it, although I think that's interesting. It's that you asked it at all.
A
Yes.
B
So you took as being within scope whether or not people feel that they're being effective at getting work done regardless of where it sat in the company.
A
That's right.
B
So it wasn't just, are our HR services easy to use? It was, is there something blocking your work? And so just the fact that you asked it is already an unusual scope.
A
Yeah, I would agree. And I will say our CEO is deeply passionate about the future of work, about unleashing potential, on minimizing distraction. And so there's a really important partnership there where his expectation is that the HR team is leaning in and redesigning work, not just redesigning HR policies.
B
Yes. Many organizations that I talk to who do not have all of work in scope say I'm not granted that scope. In other words, they haven't been granted that scope by leadership and so they focus on what is within scope. Tell me about the Reclaim team and what that name means.
A
Yes. So Reclaim is about reclaiming your time and energy. We acquired this company called Reclaim and again, they're a calendar management company.
B
Oh, I see, I see. The name of the company is Reclaim, but also the name of the team is Reclaim, which is about reclaiming time.
A
That's right.
B
It's come up a lot recently in interviews the degree to which experience design is the design of time and also transformation design is the design of time. And we recently had Ashley Willins on the show who talked about time poverty and how so many of us who are doing the best financially and are the farthest from financial poverty, are the deepest into time poverty. And so this idea of having a team, even if you didn't have a product called Reclaim, having a team that is called Reclaim is really an interesting concept. So let's do talk about the build phase in the Virtual first project.
A
With Virtual first, remote work is our primary way of working, but we also prioritize Intentional in person connection, at least quarterly, as we know that coming together is critical for things like relationships and teaming and even, even strategic planning. So we don't fit into the neat boxes of work, right? We're not remote only. We're not fully in person. We are not hybrid. So it's a little bit of a, a new category. And it's really based on the premise that first, modern knowledge work is flawed. But by shifting our focus to managing outcomes instead of micromanaging your presence, we believe we can increase employee happiness and performance and retention, which I know that we'll get to. But the underlying thesis is that intentional flexibility and agency are basically these new currencies of modern work. So with Virtual first and in applying the HR as a product framework and the Discover phase, our core hypothesis was that flexibility and autonomy were these two really important tenants of the employee value proposition. But we did a lot of research, right? We conducted focus groups and surveys. We stood up this future of work squad with almost 100 employees across every team and function, so we could better understand how various work models might impact certain Personas based on roles and teams. We spoke with dozens of companies, hybrid, remote first, et cetera, to really understand the pros and cons of these models. And then we moved on to building this sort of minimum viable product, which is the build phase. So we knew that it's more than just logistical changes. This is really a profound shift in the company's basically collective mindset and psychology around work itself, right? And so there's a few things that we did in this phase. So the first is we built from first principles. So we designed Virtual first to create a level playing field. That's why we are really steadfast in the notion that individual work is done remotely. So we don't allow for desk hoteling. And we intentionally avoid hybrid models because we believe it can create inequity with performance and promotion outcomes. If some people are choosing to be in the office, maybe with their manager, and another person is remote, you can see how that increased facetime might actually end up with uneven outcomes. Another thing that we did is we adopted some new practices. So we try to operate async by default, empowering employees to work on schedules, on their own schedules, while maintaining collaboration. So here's an example. We've adopted something called core collaboration hours. So this would be 9am to 1pm Pacific Time, which overlaps with 12 to 4 Eastern Time. And this provides space for real time connection, effectively meetings. We've invested in infrastructure, so we transformed our existing real estate or offices into what we call studios. So they're more designed for creativity and teamwork work that you do together versus individually. So we actually took out a lot of the individual desks. We have floor to ceiling dry erase boards and other things. Right. And we introduced these on demand meeting spaces worldwide so that you can gather when you need to from virtually any city in the world. We reimagined our perks, so we replaced traditional in office perks, of which we had many previously, with stipends. Right. And this allows employees to invest in what actually matters most to them. So it could be anything from child care to wellness to home office setups. So they can really thrive in a remote first environment. We are really focused on fostering local connections. So we launched something called Dropbox Neighborhoods. So this gives employees in the same region opportunities to gather for things like all hands and product launches, etc. We've elevated this notion of the art of gathering. So again, teams meeting at least quarterly. They're supported by self service tools like offsite in a box. We also have a dedicated offsite planning team. In addition, we actually share our playbooks that you mentioned looking at some of these resources. But we have sort of an open sourced virtual first toolkit which talks about best practices for effective meetings and collaboration and teamwork. And so that's a little bit of what we initially built. Right. And I'm sure you're thinking that seems like really comprehensive and thoughtful. I'm sure everything went well. Absolutely not true. Which brings us to the evaluate piece. Right.
B
I was going to ask what went wrong because I didn't think it would go right perfectly the first time at all.
A
So our early metrics were not good. Attrition increased. And keep in mind this is also during the pandemic. So there was a lot of fatigue from being quarantined, the great resignation, et cetera. We had really low employee engagement scores. Confidence and leadership decreased. This is all understandable. Nobody signed up to work for a remote company when they came to Dropbox and now they're being told we are remote now. Right. Which is a bit of a one way door, especially when you're doing things like selling real estate or offloading real estate investments that used to be offices. Right. Revisiting your perks program, doing all of these things that are like we are really moving in this direction. It's jarring. However, over time, those who wanted to be in office left. Those who saw the value proposition we were offering as being really important came or stayed because of it. And now we have actually seen the highest employee satisfaction scores on record. We've seen the lowest attrition rates we've ever had as a company. During Virtual first, we have record high offer acceptance rates, record low time to hire. Now that we're hiring from everywhere. Over 70% of our candidates actually say Virtual first is the reason for their interest. And over 90% of our employees say Virtual first is the reason they keep subscribing. Right. That they stay at the company. And so of course, there's also other broader industry research around this stuff. Right. That show that flexible companies actually grow at faster rates. And that even though people are mandating return to office, not as many employees are actually doing it. But this gives you a sense of some of how the metrics have moved over time.
B
What I really admire about that is there's a lot of things in our research where we've been collecting information on what people hire their job to do for them. And there are many things that are very individual, which is I like to solve puzzles, or I like to be given a stage, or I like to build things that don't exactly depend on what other people like. But one of the things people say is I hire my job to work with others. They want to be in person. And then there are other people who really don't care to be in person. And the problem is that the people who want to be in person, if nobody else comes to work, they don't get what they want. And then if you force those other people to come to work, then they don't get what they want. And so this is like one of the places where a company really has to make a decision about not trying to create a product that meets everybody's needs and by doing, that meets nobody's needs.
A
Correct? Yes.
B
And so that's a very hard decision to make. How hard was that decision. On work for humans? We've been exploring the principles of multi sided management, which is the belief that work is a product that every company designs, builds, and delivers to employees. Along the way, people started asking how they could put these ideas into practice. So I founded the work design firm Elevenfold to help your company create the kind of work that makes teams feel alive and engaged instead of dead and dull. So you can reduce turnover and build commitment. We're doing something revolutionary here. Learn more@elevenfold.com that's 11 f o l d.com.
A
Incredibly, and it's so funny because what you're touching on, and I completely agree, intentionality in the design process is so critically important. So when you're designing with intention, you actually are understanding the fact that you can't possibly solve for everybody's personal. Like this is the job to be done for me. Right. And so the other thing we learned in this process and why it was hard is that human beings are also really bad at predicting what they might want in the future. So we actually at the beginning ask people, what do you want? You want to come into the office? Do you want to be remote? Do you want to have a choice? Do you want to whatever? And people said, I want the freedom to decide if I want to go in or not and where to work from. And I also want to just go into the office whenever I want to just do work. And I think I'm going to do that about three days a week. That was the original. When we actually were able to open our studios, what we discovered was 92% of our office spaces were empty every week. So what that means is you may have thought, I'm really interested in going into the office. It's so that's what I believe I'm going to want. But in practice, people did not want that.
B
The say do gap there, I get that. Which is, am I going to go into work today? Well, you know, it's going to take me an hour. And so in theory it makes sense that you're going to go in three days a week. But when the morning actually rolls around and you're deciding whether or not to go in, you're like, maybe tomorrow.
A
That's right. And also so much of this hybrid work experience now is. And if you go into the office, if your colleagues choose not to, you're on zoom anyway. You're just on zoom in a conference room versus in your home office or at home, your apartment, wherever.
B
But what you had to do in that moment is you had to say, we are going to have a differentiated product, our product. We're going to specialize in something and we're going to be decisive and clear headed about. We're making a big decision here about what kind of a company we're going to be. How long did that take? How long did it take from we're going to have to make this decision to making the decision I would say.
A
It probably took nine months from, oh, this is interesting, this is happening. But wait, we're still performing. We're meeting all of our product launch dates, we're meeting all of our financial objectives. Should we explore this further to we announced it to our employees is probably about Nine months. And during that time, we did lots and lots of research. We needed to get our executive team aligned, we needed to get our board aligned. There were a lot of downstream impacts to making the decision, but the alignment on the first principles was probably the most important piece because one of them was a level playing field. And therefore we knew that we couldn't just allow for this hybrid work environment because we truly believed that that would do the opposite. Right. That one was really hard because what we are saying is all of your individual work is done at home and you will come together in person, but for very intentional reasons. Right. The other thing that we wanted to do, though, was when people are coming together in person, our mantra is effectively make it special if you're going to bring people together. Incredibly thoughtful agenda. A mix of team building and strategy setting, maybe something to do with the community or social impact. And what ended up happening was that's where our offsite planning team came into reality, because we knew if we wanted to make it special. If you're an accounting manager, you're probably not also an event planner, so you need help. Right. And so we created these three books that made this process much easier. The results from our gathering have been absolutely incredible, especially since we launched our offsite planning team. And so you may have a preference to I want to be in person or I want to be at home, but this kind of allows for the best of all worlds.
B
Right.
A
Because you are working, you have flexibility and autonomy, but when you come together, the experience is worth it and it's memorable.
B
Does your offsite planning team also provide facilitation services?
A
They'll make recommendations on facilitators. We do have some internal facilitators and there's a number of external facilitators that we use for these. Right. That they can match us with.
B
I think that's a really underestimated service. I say as a professional facilitator for.
A
Many years, well, I'd love to have you.
B
No, it's just one of those things where people think it doesn't take a lot of practice to be good at it. That's all. And by the way, one last thing on that part where you're making the decision about which way to go. This was a time when lots of people were saying, we're going to split the difference. We're going to go to hybrid. So all around you in industry, you were hearing people say, oh, no, we're going to hybrid. And you said, that's not what we're going to do. One of the things we've talked about on the show is that virtual work can be very tough on the experience of leaders. So if you're doing experience design of leaders and thinking about that, it can feel like your company just died. We went virtual at Cisco decades ago, at least 15 years ago, and man, those buildings became tombs. People were working their ass off. You just couldn't tell. And so anyway, I think you did a really big thing and that was really hard. So let's talk about the iterate phase. Debugging.
A
Yes, the debugging. So first, this phase continues. There's likely not going to be a time anytime soon where we say we're done, right? It's a constant iteration. And so we are continuously tweaking our virtual first model based on feedback, whether it's from large scale employee surveys or narrower focus groups that we do throughout the year. But we've had some pretty important lessons learned, or missteps, if you will. Right. So I'll give you a few examples. So with virtual first with gathering, what ended up happening was you would be gathering a lot with your immediate team or your leadership team. You would not be gathering with your cross functional teammates. Right. But that is so important. So much of our work is cross functional. And so to that end, we created this company wide off site calendar so that you could actually pair your gathering with another cross functional team or several cross functional teams so you could do your own thing, but then also come together because you're all in the same place. The other thing that we noticed with remote work, it increases sedentary work. You're sitting for a long time, you're not getting up between meetings like you would in an office. You're not getting that physical break which is so important. So we've been doing these meet and move pilots where basically participants took walking phone calls versus sitting in a Zoom. And it's interesting because over 90% of our participants actually reported feeling more energized, which is like a 30% live from where we originally surveyed. And there's more to do here. Of course, the other thing on gathering, we learned that different teams actually require different gathering modalities based on the goal of their gathering. Right? So for example, in our new product team, so teams working on kind of like zero to one products, they actually require more coworking for things like bug bashes ahead of a specific release. Right. So we added this new modality that we call anchor weeks, which allows working groups to focus on very specific execution goals that they set before they come to the gathering. Right. And so they're collaborating on these really urgent deliverables and overlapping projects and they're able to streamline decision making. And so those are just a couple of the lessons that we learned. And we continue to. And not only do we constantly do this, we also publish our results with the world. So we do like a virtual first year interview where we talk about the things that worked well, but all the things that didn't and what we learned and the new pilots that are coming up because of that. And then again, we've open sourced our virtual first toolkit in the spirit of sort of optimizing this, you know, how do we work better together? But again, that iteration work is never done. Right.
B
So you have these physical gathering spaces. Are those geographically distributed?
A
We don't own them. We rent them.
B
Got it. On demand. You rent them on demand when it's needed. And people get to choose where they're going to gather.
A
That's right. And we have these playbooks that will say, oh, you're interested in gathering in Nashville? Here are four different hotels that can accommodate the number of people you have. Here are some local restaurants you might want to look into. Here are some community service events that you may want to look into. So we're trying to help folks, again with the playbooks, get to the planning. And it's based on the experiences that other people have had going to those cities.
B
Your walking meetings, are they treadmill meetings or are they walking around the neighborhood meetings?
A
Whatever people want.
B
Okay.
A
It's just not sitting at a desk on a zoom.
B
I've never known what to do about wind. I live in a windy town. I guess it's like.
A
And service can sometimes be. Yeah, frankly, sometimes I walk around my house carrying laundry, doing whatever. I feel so much more energized just having a conversation with somebody on the phone without having this sort of video interaction. It's a really nice and welcome break from the zoom fatigue.
B
You mentioned intentional flexibility and we've talked about intentional. You also mentioned agency. How does that manifest?
A
Teams will basically contract. What are the best times for us to meet as a team? What are the personal preferences and things that other people have going on? Other time commitments, other things. And how do we basically optimize such that we are able to meet the needs of everyone on the team without causing this consistent fatigue? So teams will contract and say, we are only going to have team meetings in the first half of the day, let's say, and the rest of the day is for emails, work, deep work, Whatever it is. Because our teams are highly cross functional. We also have international teams. You have to have, we call it Flex for friends. There's sort of like a directional agreement, but there's also, of course you need to be flexible. But there's a lot of agency and ownership over your time and your team has their own rituals around time. That's probably the biggest in virtual first in terms of agency, just with your time. But I will say there's also this encouragement of work life harmony. So there really aren't expectations of if I am your manager and I am working at 9pm, you must also be working at 9pm that's not a concept that we buy into. You should still have SLAs, right? With your client groups, with your internal customers. But that does not have to do with necessarily responding within five minutes of your manager or you know, at all hours and that type of thing. This notion of work life harmony is really important in virtual first and that's where the agency piece comes in. Right. So I might have some meetings in the morning, I might take a yoga class in the afternoon and I am back. Right? Or because I work on the east coast and a lot of my colleagues are on the west coast, they know that I protect my time between 5 and 8pm because I am with my children, I'm feeding them and putting them to bed, but then I get back online at 8 when I need to. So there is that understanding of life is happening. We're going to get our jobs done, but we're going to have understanding and empathy for the fact that not all of our schedules look exactly the same.
B
I noticed that so much of this depends on who you think people are. And one of the things that I think we see with a lot of return to work mandates is lack of trust. And so where do you think that comes from in your organization, the belief that people can be trusted to do this sort of stuff?
A
It is a great question. I think it starts with having the right operating model around goal setting and performance management. So if you're aligning on the right assertive goals for the year, it's up to the person to deliver on the goals however they want to do it. Again, they might do it during different hours. Some people like to work in the middle of it. Whatever it is, if you are delivering, we are aligning on what that looks like at the beginning of the year. Maybe there are some pivots, but effectively you are responsible for delivering those goals. Right. And I think having really tight performance management processes which really just includes frequent feedback loops. Right. Really strong kind of one on one hygiene between a manager and an employee. Really strong and calibrated performance management processes. So ultimately it starts with you got to have the system that enables the trust. It's easier said than done. But I will say when we were in an office, even though you could physically maybe look out onto the floor and see a bunch of people on your team, you don't actually know what they're doing and what they're working on. So it's a little bit of a misnomer to assume that just because you're in close physical proximity to someone means that they are performing better.
B
Right. Especially in knowledge work, which is. Knowledge work is invisible.
A
That's right.
B
And that's absolutely right. You mentioned that some employees, this wasn't for them. Did you face any resistance from leaders in terms of this is not how I want to lead a team or manage a team.
A
We did face some resistance for leaders, particularly around the notion of core collaboration hours, right. Where you would compress time during the day for meetings and they would say, I can't do that, I need to have meetings all day long. And so I will not abide by that. But what ends up happening is then your team can't either because you are the role model, you are setting the pace and the standard. And so now you're making a personal decision. But that's actually going to impact every single person on your team. Right. Because who's going to be in those all day meetings? It's people on your team. Right. Or your colleagues. And so it did take a little while, but I think so. We had one senior leader, vice president and she said, this is absolutely not for me. I'm gonna have meetings all day long. And that's just what it takes to do my job. And then she went out on parental leave and came back and said, I will never ever work for another company again unless they are remote. Because now the time she would've spent commuting and all of the time for unnecessary meetings that she can now cancel or she can handle in writing, asynchronously, et cetera, et cetera, this actually allows her to be like a more well balanced parent in person. And so sometimes it takes some time to experience it, but even when there was resistance, we didn't change course. And this kind of some of the same principles with products. If you launch something and it's buggy in the first X number of months and because there's friction, you're like, oh, forget it let's just abandon this project. We wouldn't have any products. Right. And so you have to have some ability to navigate some of those bumps and work through them and around them. And you will have some turnover. You might have turnover with your customers, you might have some turnover with your employees. And you need to be okay with that. Right. In a major change management transformation. But I will say with employees. So we did have employees that left. I want to work in an office. Okay. Dropbox has this program that we call Boomerang. And what it means is if you are in good standing and you leave the company, we will reinstate all of your equity so all of your stock to 100% of what it was before you left. And since we rolled out virtual first, we have had over 200 boomerangs, meaning 200 people that left experienced something different and then came back.
B
That's a great policy. I love that there's something important in what you said just now, which is that we've said the word design and we've said the word product. And when you talk about products, products, iterate, everybody knows that there's something about how the traditional model, when it sees employees as assets to be optimized, there's no product to iterate. In other words, there's no thing that you can point at that's a separate thing in the world somehow that is going to be iterated upon. And so it's interesting to hear you talk because you said, well, we would have no products. So there's already this assumption that there's this thing in the world which is a productized experience of work. I want to talk about some of the principles and I'm going to go through them and we'll pick which ones we want to talk about. Human centered, simple as sophisticated. Stay curious. Outcomes over outputs. I want to go into that. Iterate and innovate. Interesting that that's not switched around. It's not innovate and iterate. It's iterate and innovate. Discover, build, evaluate, iterate. So we've got actually iterate twice there. But let's pick simple as sophisticated.
A
Yes. To zoom out just a minute. The discover, build, evaluate, iterate. That's basically like our framework, right? That's kind of our amalgamation of lean startup design thinking, et cetera, et cetera. The human centered, simple and sophisticated. Even iterate to innovate. Those are our mindset shifts. So if the model is the what, these other things that you talk through are sort of the how and the reason why we came up with those principles is because we know that this is a major change management initiative for an HR team. We're fundamentally changing the way that we think about our own work by adopting this framework. And so definitely we'll dive into these. But that was the reason why we wanted to create these shifts, because we know it's not just a simple turn it on. Everybody uses this model now and it's no problem. Right.
B
It's interesting because now, because this is part of a mindset shift, what it means is that each of these is now not just standing alone, it's in opposition to an alternative.
A
That's right.
B
And so let's start with simple and sophisticated. And what's the alternative?
A
Yeah, so we have like a little infographic or a visual that shows the from to. It's based on the philosophy that simplicity is the ultimate sophistication. Right. And so the from to is from fragmented complexity to intuitive simplicity. This is so important for a user because once something feels too clunky or difficult to do, you just completely disengage.
B
So let's take as an example, hybrid work, not simple, because there's this code switching that happens when you're in versus out and when are you going to go and all these different things you say, no, we're one thing, we're virtual first.
A
Yes.
B
I think another example is we're going to defrag everybody's time. We're going to have blocks of time. And that's simple, simpler.
A
I think it's also in framing some of these solutions as user problems that we're solving because everyone can empathize with, oh yeah, my day is totally fragmented. Please help me with that thing which.
B
Goes to human centered.
A
That's right.
B
And so I'm going to say the text that goes with that, I'm going to say what that is putting employees and candidates at the heart of every decision to create meaningful solutions that adapt as our company changes and our colleagues grow. Interesting. So colleagues grow. A part of that is we don't assume that people's needs are fixed in time, that that's an attribute of them. It's an attribute of their situation and they change. And it's from HR driven to employee driven. I really see that as a switch from I'm going to stand back from the workforce and I'm going to optimize it as a third person problem. Like I'm going to stand over here and look at it as opposed to getting into the mindset of people who are existing in that system. And Drawing insights from there.
A
That's right. I could give you an example of that. HR centered versus employee centered with performance management, for example, forever we've run these surveys on how satisfied are you with the performance management process. And as you know, most are not. But what we found was we're not actually measuring the right things because what employees actually care about is whether or not it was effective. So we're moving from measuring satisfaction to effectiveness. And effectiveness means, is it intuitive? Did you actually get the feedback that you needed? Do you understand, Right. How you're going to grow? Those are the things that is employee centered. And so that is an example of this shift of previously do what every other HR team does, which is, did we hit the performance curve and promotion budget and did we do it in X number of weeks? And are you satisfied with the process? Right. But that's not actually human centered at all.
B
Right. I totally agree. We've argued in my organization that the question should be what job do you hire conversations with your manager to do for you? And vice versa, as a manager, what job do you hire conversations with your team to do for you? Let's focus on getting those things to work as opposed to what's our adoption rate, for instance, of, you know, completion rate or something like that. But and this is a challenge, I think, for a lot of organizations is that employees don't allocate budget to you as an organization. Let's talk about that for a second. We're going to keep going with the mindsets, but I think it's an important point. It's important for many organizations to create an experience for the people allocating budget so that they will allocate budget to your organization in the future. And employees don't do that. And so underlying this is something different about maybe how your organization is measured or understood. Do you think it is different?
A
I do. I think employee experience and culture are critically important at Dropbox. And I think the reason it is is because Drew, our CEO, cares so deeply about it. And so because he has a philosophy around having a culture where everyone can thrive and having meaningful employee experiences, that expectation trickles down to the rest of us. And a lot of the torch on culture is carried by your HR teams. Right. So, for example, Dropbox won the Glassdoor Award last year for best tech company for culture and values. We did this as a completely remote company. This is during a time where many other companies are saying that culture is the reason why they're forcing people back into an office. Right. So that means that culture is Actually not determined by where you're at. Desk is. And so I think, to answer your question, I think it's different because I think it's really like a top down concept.
B
Yeah, this sounds very much to me like what I would expect. A leader who sees employees as customers and work as a product and thinks of your organization as a product function, would understand your performance as an organization. And to keep going down the list, stay curious, maintain an open mind to explore new ideas, question assumptions, including our own, and continuously seek deeper understanding. The from is from defensiveness and the to it's from defensiveness to openness.
A
I think this is the hardest one because traditionally as HR practitioners we're under the impression that something really needs to be like 99% there before you're pushing it out to people. And so this notion of pilots getting feedback, not getting offended by that feedback and then iterating is foreign. Right? Because they're used to being like, I am the subject matter expert, I know how this thing is supposed to run. I've done it for 20 years, I've done it in many other companies. I'm just going to do that here. And so it's a very different mindset. Whereas if you interact with product managers, they love the idea of feedback, whether it's good or bad. And frankly, they like it more if it's negative because they know if they fix these bugs, it's basically going to unlock so much potential for that product. There's a story where Drew and his co founder, Arash of Dropbox, they used to have an apartment in north beach in San Francisco, and there was their first Dropbox office. It was just the two of them. They would go down to the street and they would pay people like $25 to come into their office and they would have them go through the workflow, sign up for a Dropbox account and share a file with somebody. They would literally watch these people stumble through this thing that they had designed, complaining, grumbling, this doesn't work. What is this? This make any sense, I would never pay money for this, etc. Etc. But what they did is every point of friction that they observed, they then resolved and then they basically were launched into this different plane of adoption. And so it's about this notion that if your V1 isn't embarrassing, then you've launched it too late. I think it was the CEO of LinkedIn actually that said that. And so having that mindset, it's foreign for HR practitioners, but there's a reason why it's so Critically important when you're building a product.
B
So first of all, you just mentioned another thing about the leadership of Dropbox is that they come from a design background. Yes. So there's that. But also related to that, you have some grace to make mistakes as an organization.
A
Great point.
B
And I guess that that grace needs to also come from the employees.
A
The thing that's so interesting is I think we actually gain credibility the more we own and are transparent about our missteps. Because when you try to pretend like everything's perfect and you've got it right, employees see right through that. And then actually it erodes trust. We do these things called retrospectives at Dropbox where we had like a product launch that didn't do as well, or if we ended up cutting a feature, we'll write a retrospective on it, we'll share it with the entire company. This is what we did. This is what our hypothesis was, this is why it didn't work. This is the learning and how we're going to apply it to the next thing that we build. That level of transparency again, I think increases trust.
B
You talked about stay curious. And how some people are very attached to the way they've done something for 20 years. Well, the truth is that most HR things were not designed for employees. They may have started out to be designed for employees, but they stopped being that somewhere along the way. And if you're in a very human centered practice and you're saying, well, we want to do it the way we did it for the last 20 years, and that 20 years was not human centered, you need the openness to get out of that. So are there any traditional HR practices you just don't do?
A
Well? I think there are some practices that we've completely turned on their head. And so I think we're solving the same problem, initial problem we said we were setting out to solve, but we're doing it in a very different way. So one example would be succession planning. Succession planning traditionally is a check the box exercise of you're putting somebody's name inside of a box and you're saying whether they're going to be ready in the next six months or ready in the next year or two years. And what are you doing to make them more ready? And then wouldn't you know it?
B
And then when it comes time to do succession, you go with somebody else. That's finish the whole cycle there.
A
That's right. But then you're measured on percentage of ready now successors. Oh, good job, Melanie. Gold star. We've got 80% of successors ready to go and what you're actually doing for the organization is nothing. Right. And so what we have been thinking about now are it's really more about thoughtful and accurate organizational design. So widening the aperture of what do we even mean when we say successor, someone that is going to do that job next? Well, the requirements for that job today are likely wildly different than what they might be when that person attrits. And so we have widened the aperture to include external leaders as successors. And it's not necessarily when is the internal person going to be ready, but often it's not actually a simple one for one move. Maybe the move is I'm going to have a total new reorganization and I'm actually going to pair my learning and development team with my HR business partner team. So I'm not going to backfill the person, I'm going to increase this person's scope. So reimagining the process for what's the problem we're actually trying to solve, which is ensuring that we have thoughtful, rational organizational design. Right. And so that would be an example of something that we're just like, this isn't working.
B
And let's come to grips with reality, which is that things are much more dynamic than traditional succession planning recognizes.
A
Correct.
B
I would imagine it also leads to developing people to be better at fundamentals rather than role specific things. And one of the most the greatest fundamentals is learning. Right.
A
You are speaking my language. Especially when you think about AI and its impact on skills. There are a number of these durable skills that actually have nothing to do with technical proficiency or prompt engineering and AI, et cetera. They're things like learning agility. If you have learning agility, you can actually transcend whatever the technological advancement is of that time. But it's also things like empathy, critical thinking, right, judgment. These are all durable skills that are so critically important no matter what job you're in, no matter what tech disruption is happening. Right. So I agree with you. They are fundamental.
B
Interestingly, empathy is necessary for design, but it's not necessary for standing back third person and optimizing the throughput of a process. And so to say that empathy is necessary, it's a very designed thing, I think to say your CEO clearly thinks differently than I think a lot of leaders. Does your CFO need to think differently?
A
Yes. The way CFOs need to think differently is understanding that not all dollars are created equal. So if you are looking for efficiency or savings and you go after these really beloved employee experience programs, the cost actually exceeds. Right. The savings that you are going to get. So making sure that the CFO actually understands the value of culture and employee experience is critically important.
B
One of the things I've thought recently is that once work becomes a product in the mindset of a company, then investment in product R and D is much more accountable. And I mean in the accounting sense. It makes more sense in an accounting sense than investment in employee experience, which is quite transient. But product investment is something that lasts a long time.
A
Yes. And I think because part of this model, that sort of evaluation phase, what you mean is, are we achieving the thing? What is the ROI of this thing? And because you're almost forced to, in this model do that work, it almost takes these things that previously felt a bit more intangible and actually put real roi. And that is the language that our finance folks.
B
It's roi and it's a repeatable, ongoing thing that's going to continue to generate value long after the investment. And so it's a different mindset. At the end of my show, I always ask a couple of questions and the first one is, what job do you, Melanie, hire your job to do for you?
A
That's a great question. It enables me to basically drive a world class culture and employee experience. That's one, I think. The other is I'm very, very passionate about enabling those in my organization and those at Dropbox to truly actualize their potential. And so I think there's something really important about the employee experience is the environment that you are creating that then enables employees to do that. And I'm personally very invested in this as a leader. I think this is the thing that I'm the most passionate about. Right. For my own team, for the HR team, is how do we realize our potential and how am I creating that environment to do so.
B
There's two ways that that has shown up in our research. I think they're overlapping. One is I hire my job to see others shine. But then when you tie it to culture is I'm hiring my job to build the system that will continue to help people to shine.
A
That is so much better said than how I said it in the past.
B
Yeah, you said it great. I'm just. This is the way we've captured it in the past. And what's interesting is when was the decision made to publish so much of the best practices that you've developed?
A
I think it was 12 to 18 months into this journey because we actually had enough information where we could say these practices are going to help you.
B
Right and which scales some of those insights to the rest of the world, which is great.
A
This kind of rising tide lifts all ships. I think one of the things that happened in Covid is we all sort of forgot that we were competing against each other, and instead we all came together to say, how are you going to navigate this? How are organizations going to deal with this? And so this is a bit of like a carryover of sharing best practices instead of holding them really close to the vest.
B
What does your work or your job cost you?
A
So, especially being in the people space, it's this absorbing all of the feelings, the sentiment, the confusion, the frustration of the organization while trying to guide through some of these challenges in a thoughtful way. I think that's what it costs.
B
There's one thing in this area that we call empathy burn. So is some of it that, you know, this is one of the things about working really hard to create a great experience for people and then having some people not necessarily appreciate the great experience.
A
Yeah, right.
B
It could be either of those. Do you get a bit of both?
A
Yes. And I think you. You had somebody on your podcast that talked about this notion of hope being such a critical concept for leaders to sort of exude. And I think the cost is. I know that as a leader, the most important thing that I can do is to exude hope. I truly believe it is so on the future of our business, on employee experiences, on all of that. And I think the cost is. Sometimes that can be hard to do when you get so much of the negativity right. It just comes into this organization. And so it's hard to sometimes see past that stuff to why should we all be extremely hopeful?
B
It's very related to should we try to be great or should we try to be not bad? And one of the things we've said on the show, I've said on the show, I can't remember how recently is, that being a great chef is not the same thing as being really, really good at not giving people food poisoning. You can be really, really good at not being a bad chef and giving people food poisoning, but that will never make you a great chef. And so there's something tied to the idea of hope, which is that sometimes you get negativity, which is there are things about work that are not good and that happen that are bad. A part of hope is not just anchoring on those things, but anchoring on a better future.
A
That's right. I think the answer is great.
B
To answer your question, clearly, you're striving for great. Yeah, I agree. Where can people learn more about your work?
A
We have a hub for all things virtual first. It's called virtualfirst.Dropbox.com very easy to find. We share a lot of our findings and research on our Dropbox Work in Progress blog. And then I frequently share a lot of my own thoughts on LinkedIn, which is the main platform for sharing my personal thoughts on everything from remote work to AI and the future of work to HR as a product.
B
Well, I'll tell you, I think what you're doing is really world class and in particular I didn't know what I would discover when we started talking. I knew that Virtual first was something that was a great example of design practices as it relates to the experience of work, but I didn't know how deep it was going to go. I thought it might just be that was a project we did and that was great. But we do the rest of our businesses completely different, but instead what I heard was it's infused through everything we do. Virtual first is just an example of that, but it's a big example so it ties together a lot of our work. So really exciting to hear about and thank you very much for coming on the show.
A
Thank you so much for having me. It's an honor.
B
Thanks for joining me for another episode of Work for Humans. If you enjoyed this episode, please give us a five star rating. Wherever you listen to podcasts and share the show with one person you think would get value from it, believe it or not, this really helps us grow the show and reach more people who want to build the kind of work that people really want. As always, thank you to my producer Jason Ames at 9th Path Audio for his insights into content and his high standard for quality. Final note, the opinions shared here are my own and not the views of Google or Cisco Systems. Thanks again for listening. See you next time.
Guest: Melanie Rosenwasser, Chief People Officer at Dropbox
Release Date: November 18, 2025
This episode explores how Dropbox fundamentally redesigned the very experience of work during and after the pandemic, pioneering a "virtual first" operating model. Chief People Officer Melanie Rosenwasser discusses applying product management and design thinking to HR, shifting Dropbox from traditional in-office and hybrid models to a human-centered, outcomes-driven, distributed work environment. The conversation covers Dropbox’s HR-as-a-product approach, overcoming challenges, iterative improvement, culture, and leadership buy-in, offering lessons for organizations seeking to make work irresistible to employees.
“Our operating model, which you touched on, we call virtual first. This operating model enables basically a distributed team, Dropbox, to build for distributed teams.” – Melanie (04:24)
“It’s a four step model and it’s Discover, Build, Evaluate and Iterate… and that evaluation iteration cycle is continuous.” – Melanie (07:54)
“So it’s not the number of meetings that is the problem, but things that are the problem are constant distraction, continuous context switching… and so there’s not enough time to do this deep work that is so critical for productivity.” – Melanie (11:09)
“Actually our highest performers are in more meetings than everybody else… they’re very diligent about chunking their meetings.” – Melanie (13:33)
“…this is really a profound shift in the company’s basically collective mindset and psychology around work itself.” – Melanie (18:01)
“…now we have actually seen the highest employee satisfaction scores on record. We’ve seen the lowest attrition rates we’ve ever had…” – Melanie (22:37)
“…if your V1 isn’t embarrassing, then you’ve launched it too late.” – Melanie (51:33)
“We do these things called retrospectives… That level of transparency again, I think increases trust.” – Melanie (52:50)
“One of the things that happened in Covid is we all forgot that we were competing against each other, and instead we all came together…” – Melanie (60:56)
On the Product Mindset
“With this in mind, we looked at a number of product management and design best practices and frameworks … and we created this sort of tailored approach that aligns to our needs as a people team. That became hrap. And it’s a four step model: Discover, Build, Evaluate, and Iterate.” – Melanie (07:54)
On Early Failures & Learning
“Our early metrics were not good. Attrition increased… low employee engagement… But now we have actually seen the highest employee satisfaction scores on record.” – Melanie (22:37)
On Making Hard Choices
“You can’t possibly solve for everybody’s personal… job to be done for me. And… humans are really bad at predicting what they might want in the future.” – Melanie (26:13)
On Iteration
“There’s likely not going to be a time anytime soon where we say we're done, right? It's a constant iteration.” – Melanie (31:52)
On Trust and Culture
“It starts with having the right operating model around goal setting and performance management... if you are delivering, we are aligning on what that looks like…” – Melanie (38:35)
On Sharing & Transparency
“We do these things called retrospectives… This is what we did. This is what our hypothesis was, this is why it didn’t work… That level of transparency again, I think increases trust.” – Melanie (52:50)
Dropbox’s transformation shows that when HR adopts a design and product mindset—iterative, data-driven, employee-centered—it can move beyond “making policies” and instead design work as a product that aligns with the company’s vision and the evolving needs of its people. The result is not only a healthier culture and higher performance at Dropbox but a compelling model for the future of work.