Employee Productivity & Wellness In Remote Work With Dan Pupius

Chris Ronzio (02:00):

Hey everyone and welcome back to Organize Chaos. I'm your host, Chris Ronzio, and today our guest is Dan Pupius. Hey Dan.

Dan Pupius (02:08):

Hey, thanks for having me.

Chris Ronzio (02:10):

Thanks for coming on. I appreciate it. You've got a really cool software product called Range, and I want just dig right into it. Can you just tell everyone if they haven't heard of it, what is Range all about?

Dan Pupius (02:21):

Cool, yes. I'm an engineer by background. I worked at Google for a long time, then ran engineering at Medium, which is a publishing platform. Really, the idea for Range came about because I felt like I lacked the tools to help me run the team the way I wanted, so I was building scripts, building spreadsheets, I even had two engineers doing some internal tooling. Then, as I look closer, it really just felt like there was a big hole in the market and I wanted to solve that.

Chris Ronzio (02:46):

You just didn't have the tools you needed at those companies and you started building one yourself. I feel like that's the common, the ideal case. Were you a solo, just a one person team at the beginning, or did you start with a founding team?

Dan Pupius (02:59):

Yes, we had three people at the beginning and one of my co-founders is still with me. She was the people partner at Medium, so we worked really closely there. I had a bit more color about the whole, instead of just being scratching our own itch, we looked at product management tools and they were really task and project focused, but they kind of ignored the human side of collaboration. Then, you have communication software, which is really noisy and distracting, and also it's decoupled from the actual structure of the organization. If you think about people's usage of Slack, so much of it is based on norms and etiquette that it takes a ton of work to actually manage Slack. Then, the third piece is engagement software, it measures how teams are doing, but it really doesn't guide action. It requires a lot of work to process the information that comes out of the surveys and then come up with next steps. We imagined this new type of software that actually helped teams work better together, which is built around the needs of modern teams and kind of blurs the line between some of those traditional categories.

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Where Does Range Fit Into Other Remote Tools?

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Chris Ronzio (03:55):

If the average person listening has some of the big name tools, the names like a Slack and a Zoom and Asana or something like that, where would Range fit in or what does it replace, just to get everyone to wrap their heads around it?

Dan Pupius (04:13):

It's true there's some overlap with several different types of tools, but typically we replace bad processes, a lack of process or things that are just done informally in say Slack or a Google Doc. We integrate with Slack and Microsoft Teams, we see those products as the engagement layer. Then, we also integrate with all the systems of record, so Asana, GitHub, Calendar, Google Docs, eventually CRM systems, pretty much anywhere you're working. The typical employee might be working in their own [inaudible 00:04:40] systems of record today. Range slides in-between these two and becomes the sensing layer, the intelligence layer, that helps you get a more complete picture of what's going on your team.

Chris Ronzio (04:50):

Got it. Okay, that's helpful. You mentioned starting with a team of three. How big is the team today, or what's been the growth story over the last few years?

Dan Pupius (05:01):

I mean, this is wild time to start a company with COVID and economic crises and whatever, but we're 18 people today. It really feels like that we started the company when we saw these trends in the workplace, and over the last few years that's really come to reality and come to fruition, pretty much everyone has experienced remote work now and pretty much every company will have some element of remote work going forward, whether it be hybrid or fully remote.

Chris Ronzio (05:29):

I think it's an incredible time to start a company. Over the last few years, we saw so many big macro shifts and trends and a lot of the existing software players had to pivot or had to figure out how they're going to exist in this world. Starting from scratch is almost easier, building with a fresh code base rather than a refactor. Am I saying that right to an engineer?

Dan Pupius (05:52):

Yes, that's right. Yes, maybe. I think that the world is definitely changing, and it's kind of a cliche to say it's changing faster than ever, but I think it's true. Norms and expectations around work are so different today, and the implications of even the 2008 crisis affected how people worked, how people show up, how people... What they expect from their career and we should expect COVID and the current financial situation to continue that trend.

Chris Ronzio (06:19):

As I was looking at the videos on the website, it seemed to be that one of the main focuses was people-to-people meetings and group meetings. Is meetings really central to the application?

Dan Pupius (06:33):

Essentially, we envisioned the platform for teamwork going forward and we needed a wedge. One of the big pain points we heard was around meetings, so the first product was actually around in sync check-ins, which kind of replaced a daily standup where you share what you're working on, what you've done, and then there's a few team building components built into that. The goal of that was to reduce the number of meetings you have, and we hear people actually cut their meeting time drastically through those in sync check-ins. Then, the second pillar of our product is around the meetings that you do have. When you do have a meeting, we have an agenda management tool which makes it super efficient to run the meeting. It helps you keep track of topics, manage pre-reading, take action items and notes, and then it creates accountability loops for those.

Chris Ronzio (07:21):

I think the meeting thing is... It creates chaos, so many people have chaos, and this podcast is all about organizing chaos. Meetings to me are about staying productive, keeping your people accountable, and then helping deal with the person on the other side of the meeting and make sure that they're in a good place, that they're happy, healthy, and staying sane. Let's kind of talk about those two things one at a time. We'll start with just the general productivity of a business. First, is Range remote? Is your business remote too?

Dan Pupius (07:58):

Yes, we're completely remote today.

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Is Range For Remote Teams Only?

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Chris Ronzio (08:00):

Do you think the product is built for remote teams or any business?

Dan Pupius (08:07):

When we started, remote was considered fringy, so we didn't build it specifically for remote teams. We looked at what teams needed in order to be productive. What we found over the first couple of years was that really remote amplifies the problems that exist in existing workplaces. There's some new problems, but a lot of the problems existed already and they're just amplified and there's fewer get-out-of-jail-free cards. That meant our early market was... We had a lot of remote teams in that early market, so we have focused on their needs specifically. But, what's interesting is that say you're in an office building in downtown San Francisco and your team is split over two floors, you have a lot of the same symptoms that a remote team will face, a lack of belonging cues, a lack of context, a lack of informal ad hoc communication. Remote is a spectrum, it's not binary, and it's just how remote you are. Do you see your team once a year or never? Or, do you see your team maybe once or twice a week? I think you make remote work, and then you make work, work for everyone.

Chris Ronzio (09:13):

That's a good point. I mean if you're split between a couple different floors, it's like you're remote, you don't see those people hardly ever. We're moving into a new office and we are predominantly remote, but we do have an office for anyone that wants to come to it, and we'll have a few different floors and I wonder how that'll go. It's going to require us to have really strong communication.

Dan Pupius (09:34):

I have a funny anecdote.

Chris Ronzio (09:36):

Yes, go for it.

Dan Pupius (09:37):

Sorry. I was just going to say, it will fundamentally change the culture. When I was at Medium, we were on the same floor, but there were two sides, there was the referral side and the market street side, because we were in this weird flatiron building, it was a triangle. Literally people would say, "Oh, those people on the referral side or those people in the market street side," that became an identity and it caused some tension, for real. The structure and the architecture of how we shape our offices and our buildings affects the communication, and then that affects how we behave to each other.

Chris Ronzio (10:06):

Well, I hope we don't start talking about the upstairs people and the downstairs people. We may need a camera and a huge monitor to see what's going on each floor.

Dan Pupius (10:18):

Yes, I mean I think you will. I think that's what's funny. I think it's like how do you intentionally cultivate the connections between floors and diffuse some of those tensions?

Chris Ronzio (10:25):

Well, do you have any tips while we're on the topic?

Dan Pupius (10:29):

Yes, I mean think you have to think about... If you are going to be co-located instead of fully remote, one of the pieces of research is around belonging cues. If you and I get in the elevator together or go to say the cafe together, even if we don't talk, there'll be an informal belonging queue, we'll make eye contact, we'll smile, maybe nod, and that kind of reminds each other that you're on the same team. Now, if you don't have these belonging cues, they kind of degrade and decay over time and then you end off with less trust, and that trust actually erodes psychological safety and the connection on the team, and that's what gets underneath the effective teamwork.

Chris Ronzio (11:09):

How do you simulate those belonging cues through an application like yours with a remote team?

Dan Pupius (11:18):

In our product when you do check-in, you check-in with your mood. I check-in with a I'm green today and I'm feeling nerdy, so I put on the nerd glasses or feeling a bit like a cowboy, put on a cowboy hat, and it kind of just humanizes you a little. Then, we also have team building questions every day. It might be a question about what do you do this weekend or what type of books do you like to read? Again, it's just humanizing each other. Then, you also see teams using Slack for this so they might have... I think Zapier does a GIF party where they all just start throwing silly GIFs in the channel. It's just anything that humanizes your colleagues can function as a belonging cue.

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Why Are Businesses Afraid Of Remote Work?

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Chris Ronzio (11:54):

That's fun. We'll try out a GIF party ourselves. Do you think a lot of companies are still afraid of remote work, and why do you think that is?

Dan Pupius (12:04):

There's kind of two theories of motivation, theory X and theory Y. Theory X is that you're inherently lazy and will do the minimum amount of work necessary. Theory Y is you inherently want to be good and want to cultivate craft and want to grow. People who come from this theory X school of... They worry that if people are at home, then they're just going to be slacking off and playing on their computer instead of doing work. If people are sitting in the cube, then they can at least see people are kind of working, but we all know that's a fallacy because people could just be checking TikTok or whatever all day in the cube, let alone they don't need to be at home to do that. I think it predominantly comes out of fear. Then, the second element is not knowing how to manage teams remotely. There's all these practices that people use to run teams that kind of break down when you go remote, you have to evolve them and learn new ways of doing it, and that I think is always scary for new people.

(12:55):

Scary for people, yes.

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Managing Employee Productivity In Remote Teams

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Chris Ronzio (12:56):

No, I agree. I think it is fear. I think it's fear that if you can't see what people are working on, you don't know if they're getting anything done. How do you recommend that managers, leaders can keep tabs on what their people are doing without feeling so micromanage-y? I think I made that word up.

Dan Pupius (13:19):

No, I think it's a legit word. I mean, I think for managers, you can't expect to not see anything that's going on. Part of your job is to understand how work is progressing and what's going on. The expectation that managers can't get visibility into the progress of work is kind of ridiculous, but at the same time, we don't want it to feel micromanage-y. I think there needs to be a culture of transparency and the transparency is about sharing context with your team, and one of those teammates is your manager who has a certain role to play. Then, how do we create transparency? We can work in the open, we can use tools like Slack, we can use tools like Range to create more visibility, we can also set up a cadence of communication where information gets shared and transmitted.

(14:02):

Meetings are much aligned, but I actually think meetings are really important and you need to think about this cadence of meetings that actually allows you to check in on what is the plan, how are things progressing, who is blocked, what decisions need to get made? All those things need to happen, and if you can do that, you can kind of calm some of those anxieties and fears that then lead to the micromanaging behavior, because I do think micromanagement comes from... For most people, it stems from fear and a lack of trust that things are going in the right direction. I don't think most micromanagers are honestly Machiavellian, tyrannical, authoritarian control freaks. They worry that the project isn't going to ship on time and they're going to get blamed for it.

Chris Ronzio (14:45):

Yes, like you said, there's a lack of trust, they're kind of leaning in, and they're over your shoulder. What have you seen as the best cadence of check-ins to make sure that work is progressing?

Dan Pupius (14:57):

Yes, I mean, I'm biased of course, but I quite like the way that we work, and it's been tuned over a couple of decades of working elsewhere. We work on two week cycles, and we think about a cycle as having bookends. At the start of the cycle, we have a full team meeting where it's an all-hands, and at the end of the cycle we do a recap. It kind of creates this sense of closure and pace to the work that doesn't feel like it's a constant grind. Then, each team will have a planning meeting at the start and then a couple of in person check-ins along the way. Then, we of course use in sync check-ins every day as kind of a background drum beat where you can share what you're working on that particular day, any updates, ask for feedback, things like that.

Chris Ronzio (15:43):

Well, we did not talk before this podcast, and we do the same thing with two weeks sprints or two week sessions, so that must be correct. Two for two.

Dan Pupius (15:52):

Yes, I mean I think it depends on the nature of the work. It's possibly that our work is in a pretty similar stage, but I think work has... If you're working on an infrastructure project or a two year build, that's going to be very different than if you're in a growth mode or R&D mode, and then faster than two weeks, I think it's just the pace is too high for... It's too much overhead for a team of a reasonable size, it might work for a small team.

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Goal Setting & OKRs For Remote Teams

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Chris Ronzio (16:19):

Where do you think goal setting, goal tracking, goal reporting fits into this whole check-in thing?

Dan Pupius (16:27):

I mean, I think this is really interesting because there's a whole host of OKR tools and OKR practices, and the way I think about OKRs and goal setting are they're tools and they serve a purpose, and what is that purpose? Too often, they're essentially used for executive oversight, so it's essentially an abstraction that allows an executive to understand status for a project. I think that misses out on some of the value of OKRs. If OKRs are around... If you think about it from a team perspective, the goal in the OKR or the objective, whatever model you want, the V2MOM, whatever it is, it can help the team understand what to prioritize, what is important, and how to make decisions better. I think about it through that lens.

(17:12):

The irony of working at Google, which is the poster child for OKRs, is as an engineer I often didn't know where my OKRs were, team OKRs. I was completely disconnected, so I was just working on projects, and then some middle manager knew how to connect those projects to the OKR, and that's a huge failing. If I knew the material impact of my day-to-day project on a KPI or a business metric, I would be able to make much better decisions and probably feel more motivated as a result.

Chris Ronzio (17:37):

I think it's important to keep tabs on those metrics and feel attached to the bigger goals. I think that they get missed a lot of times because check-ins can feel just very operational of the project that you're working on. Should it always be an element of the agenda to talk about those bigger picture OKRs or whatever they're called?

Dan Pupius (17:57):

We do it at the start of a cycle. At the start of the cycle, we check-in on our objectives. I think this is where having rituals is really helpful. If the ritual is at the start of the cycle, you check-in the goals and everyone shares plans, progress, problems, whatever it is, and there's a bunch of these formulas, but it kind of just standardizes it and makes it habitual. If every single week someone has to think through, "Okay, what information do I need to find out? How do I phrase it? How do I share it?" That's a lot of overhead. Coming up with these simple formulas that allow you to quickly gather and express the information that's helpful to the team is really valuable. When I was at Medium, I had a script that would send out an email every Friday asking four questions to each of my team leads. Then, I would use those four questions to roll up a report for the executive team. That made it a very quick habit for my leads and also for me in writing that executive team report.

Chris Ronzio (18:54):

You said yours was plan, progress, problems, is that what it was?

Dan Pupius (19:00):

I actually used what's the goal, what's the reality, what are obstacles, and what are some opportunities?

Chris Ronzio (19:10):

Oh, that's cool. I like that.

Dan Pupius (19:12):

Goals, reality, obstacles, opportunities, and then you can add wins [inaudible 00:19:16] for growth.

Chris Ronzio (19:16):

Yes, just having the ritual, I mean it makes it so you don't have to think about each week, "What am I reporting? What am I presenting?" I think that's a great suggestion.

Dan Pupius (19:22):

Exactly. Humans are... We're super ritualistic beings. Every morning, we make coffee, we make the kids breakfast. Every weekend, you go for a run, you go see the football game, watch your movie. We like this rhythm and this ritual. When there's chaos, to the point of the podcast, that increases the anxiety and it actually increases uncertainty and it then gets you out of your groove.

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Monitoring Employee Wellness In Remote Work

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Chris Ronzio (19:47):

Yes, exactly. All right, so shifting into wellness, the other side is checking on the person, not checking on the progress or the work, but on the person. How do you actually keep a pulse on your employee's wellness, on how they're feeling as part of these check-ins or part of this remote work?

Dan Pupius (20:06):

In Range, the check-in has a mood, it's self-reported of course, and there's a lot of caveats into the effectiveness of that, but that is kind of the backbone pulse. That's kind of a quick checker. Am I green? Am I tired? How am I showing up today? Am I really sick? Am I red? It's kind of this ambient information, but that on it own is not going to be enough because you have to have that level of psychological safety in order to share that. Then, also, you need to get more color. We try and sense in a bunch of ways, we have a lot of openness around how we're doing. Every meeting starts with a check-in round where you say how you're showing up, if there's anything on your mind. As leaders, we try and role model that very openly. I've had a lot of sleep problems with my children, and I will often say, "Oh man, I've been up all night with my kids, so I'm pretty tired," and the other leaders model it, and then that helps surface information.

(21:04):

Really the goal of that is not about... It's not about tallying who's feeling good and who's feeling bad, it's about sharing context because that's how you show up to the meeting, and then it diffuses some of those tensions. If you are tired or stressed, you'll react to me differently than if you are super happy. If I don't know what's causing that stress and anxiety or I don't know that you are stressed and anxiety, I will write a story and I might think, "Oh, Chris is just... He's pissed off with me or he's upset with me," and the reality is you're just tired. So much team and organizational tension arises from these subtle interactions that were relatively mundane or honest.

Chris Ronzio (21:45):

Yes, it's true. If you think that someone's upset or disengaged and you have to fill in the gaps yourself, you might make up a story that's way worse than the fact that their kid's sick or something like that. How do you take all these individually reported moods and see some kind of macro picture for the organization? I assume you have something like that.

Dan Pupius (22:10):

Well, at the moment, we only have a two week history because we don't want... I think there's a fine balance here. You don't want someone to draw the wrong conclusion or use it for... You don't want someone to come and say, "Hey Chris, you've been red three times this week. What's going on? You need to shake it up." It's kind of like the office day thing where you're not wearing enough flare. We currently only show two weeks history, and that gives you a good pulse and that helps you understand whether projects need to be reprioritized. We had a customer who said that their entire team checked in yellow one day, and as a result of it, they pushed the deadline out of that project two weeks. It was this really good sense sensing signal that the team was getting burnt out. I think in the future we will show more historical trends, but I think we need to do it very carefully and really think about how this information's going to be used and how to avoid it being used for nefarious purposes.

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Creating Psychological Safety In Company Culture

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Chris Ronzio (23:10):

Right, data mining. If a manager is listening to this and they're doing check-ins with their people, they may say that my people aren't being honest with me and they're not sharing if they're not in a bad mood. How do you create a culture that has the right psychological safety and to make people feel like they can share?

Dan Pupius (23:33):

One way to think about it is it's kind of contagious, psychological safety is contagious. Daniel Coyle talks about this in Culture Code. Really, since Google's project Aristotle, a lot of people have talked about psychological safety, but we haven't really talked about how to create that psychological safe environment. The formula that I like is actually pretty simple. It starts with vulnerability, and the vulnerability leads to trust, which is a little bit unintuitive. You think you have to trust someone in order to be vulnerable, but if I share a little bit about myself with you, you will trust me more and probably share a bit more about yourself. We start with vulnerability, that leads to trust, trust then leads to belonging. Belonging to me is much more tangible, and I can understand what sense of belonging means. Then, if you have that sense of belonging, then that leads to psychological safety.

(24:21):

As a team, how do you create a sense of belonging? It has to be about the connections between each of the teammates. There has to be opportunities to share bits about yourself or at least be vulnerable. It can be a relatively superficial level. It doesn't have to be bear your soul and talk to your team in the way that you talk to your therapist. It can just be, "I like football," or "Man, I really hate mushrooms. I can't believe you have mushrooms on pizza." These little things are... They humanize you and they express parts of your personality, and that's like what leads to the trust.

Chris Ronzio (24:52):

It's almost like the little fun icebreakers at the beginning of a meeting that just share weird facts, it sort of disarms people, right?

Dan Pupius (24:58):

Yes, exactly. Our meeting tool does have a... We have a module that allows you to run an icebreaker at the start of every meeting, and it's kind of fun. The funny thing is we have this agency we work with, we do the icebreaker at the end of the meeting, and they find things about each other. They're working together all the time, we just have one meeting a week with them, but they find things about each other through these icebreakers that they would otherwise wouldn't know. It's kind of funny.

Chris Ronzio (25:24):

That is cool. At our all-hands meetings, we do breakout rooms with the whole team and so they'll get randomly put with four or five others, and we always have these random prompts. Those are some of my most fun times. It's a 10 minute thing, but it's with people that you don't often work with and they're across departments and you learn so much about people, and then when you see them or work on a project with them, you're that much more comfortable because you remember that story they told about their Halloween costume.

Dan Pupius (25:48):

Yes, totally. It's essentially building a strong fabric of connections in the organization, and it has to be human fabric of connections.

Chris Ronzio (26:00):

From the top-down I guess, how can business owners or leaders you think be even more supportive of their employees wellbeing? Is there anything that we should be doing?

Dan Pupius (26:11):

I think that's a really tricky question. I think my sense is that the middle managers are probably the most overworked, under-supported people, and the highest leverage in making this better, because they're connected to the team daily, they're very close to the work, but at the same time they get very little support... I mean, they get very little manager training and they get very little support on how to actually cultivate effective teams. That's where I think the biggest leverage is for executive leadership. Then, I think it's role modeling and kind of demonstrating these practices that we know lead to more healthy, more effective teams.

Chris Ronzio (26:55):

Yes, absolutely. I think if you can be a good example at the top, you can support your managers and have empathy for what they're going through, and encourage them to do these sort of check-ins, then you're at least on the right path. That's probably more than we can say for a lot of companies. What's next for Range?

Dan Pupius (27:15):

Just continue to make the product better. We have our core pillars built out, so we're continuing to add interesting things around the meeting tool. Pre-meeting workflows is kind of fun, post-meeting workflows. We're working on a new consumption experience and building out a big Microsoft integration, so Microsoft Office, Microsoft teams. That'll be a big new vertical integration that we do.

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What's Your Go-To Market 'Wedge'?

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Chris Ronzio (27:39):

That's great. I want to go back to one thing from the beginning of this podcast where you mentioned that the check-ins were a wedge. I understand what that means from a product standpoint, but I think a lot of people that are listening and building their businesses may not understand the go-to-market intention there. Can you talk through a little bit of how you thought about that and how it connects to what you might do in the future?

Dan Pupius (28:06):

Yes. It's hopefully obvious that you can't just suddenly drop a whole operating system for work on the market. One, it's not feasible to build. Two, you don't really necessarily know what you're going to build. Three, how are you going to market it and sell it? We needed something that was essentially going to be a point solution that would allow us to get into the market and learn from customers and work with people. We chose check-ins because we did a bunch of research and found that these stand-ups and check-in meetings were a big pain point. Then, also we liked it because it was at this intersection of work and humanity. It's a point where you come together as a team and connect at a personal level, but then also share about your work. That felt like a really interesting point to come in and help with both productivity and team health.

(28:55):

Then, we built out all these integrations, which then taps us into the work stream data. We have huge amounts of data about everything from documents, code changes, and that's really useful for then building up ambient information about what work is happening in the organization. That sensing layer is quite valuable.

Chris Ronzio (29:14):

Yes, so interesting. I think, again, just a point for anyone listening to this, as you're going into any new business, any new market, I think you can have a tendency to want to drop the whole business plan and say, "Let's build the whole thing, let's do everything right now." I think it's a really smart lesson that you mentioned, Dan, that just starting with something, what is the easiest first thing that we can do because we can't do everything? How do we be efficient and tackle one problem, and then move on to the next? Thank you for explaining, because I think it's a strong point.

Dan Pupius (29:45):

I think we also didn't know where would we go next, so we had to listen to customers and figure out what was the best adjacent possible, because in this space there's so much potential. That's honestly one of the challenges is what is the next thing that we integrate into this product offering without making it feel confused or crowded? We work very closely with customers and then think about what is our differentiator for building this? With meetings, our differentiators that we can connect the synchronous meeting to the asynchronous meeting. For goals, we can connect the high level objective to day-to-day work stream data. Then, we have to think about what is the differentiated factor for us adding these different modules.

Chris Ronzio (30:22):

Right. Well, what is the...? I guess if you had to summarize or leave people with one thought, one lesson, one takeaway, what would you want that to be?

Dan Pupius (30:30):

One takeaway I think is focus on the team. A lot of management is point-to-point, so manager to employee, but in the future of work, the team is going to be the most important unit of work. In remote work, that's especially the case. Thinking about team health, team productivity instead of individual productivity, team communication, teamwork, that's the key. You want your team to feel like a pro basketball team and not a golf team. You don't want people going off and just putting scores on the boards, but working independently, you want them to be really fluid, passing the ball, and working really closely together.

Chris Ronzio (31:06):

Well, you must have listened to my podcast before and know about my love for basketball, so I appreciate you summarizing with that. Dan, it's been great talking with you. Thank you so much for sharing. Can't wait to follow Range's progress.

(31:18):

Hey, thanks for listening to Organize Chaos. If you like this episode, be sure to subscribe, leave a review, or share it with anyone in your network that you think could benefit from this information. For episode show notes, podcast recaps, and tons of other small business news and inspiration, check out the manual, that's trainual.com/manual.

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