In this conversation I talk with Jennifer Dennard and Dan Pupius, the co-founders of Range, software that helps teams be more connected, focused, and productive no matter where they’re working. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range.
Jen is the co-founder and COO. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband.
Dan is co-founder and CEO of Range. Prior to Range, Dan was Head of Engineering at the publishing platform Medium. And before that he was a Staff Software engineer at Google, where he worked on Gmail, Google+, and a variety of frontend infrastructure.
He has an MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives he raced snowboards, jumped out of planes, and lived in the jungle.
This is a fairly meta conversation (in the old sense of the word!) since we talked about how Dan and Jen structure their relationship and how they built their company…which is a company that builds software that structures relationships - specifically, effective teams.
As Dan outlines, “Human behavior requires structure to facilitate it…in an organization, software provides a lot of architecture, which shapes our behavior, but we're (often) not intentional about that software. The whole theory of Range was… how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams?”
My book Good Talk is built around the idea of a Conversation OS, or Operating System.
One element of the Conversation Operating System is error and repair. As Jen says in the opening quote, conflict and collisions will inevitably happen in relationships.
Dan suggests that “if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing, in how you recover.” In other words, how you repair the error or breach in the relationship is often more important than the error itself.
Many folks shy away from conflict, or hope it never happens. Planning for it and knowing it will happen is a fundamentally different stance, a more effective Error and Repair Operating System.
I also love the “reasonable person principle” that Jen and Dan use in their relationship, as long as it never slides into gaslighting.
We unpack a lot more great stuff, from uninstalling Holacracy at Medium to the importance of being journey-focused in entrepreneurship relationships, and the power of crafting explicit processes ahead of needing to use them.
Dan and Jen are also big believers, like me, in the power of the “check-in''. For example, in my men’s group we share in 30 seconds how we're doing emotionally and physically at the start of every group. At Range, it can be as simple as a “green, yellow, red” check-in or as deep as going straight to the question “how are you…really?”
They suggest that baking human connection into each and every meeting is much much more effective than trying to isolate connection into one “vibes” meeting.
As with many of my co-founder conversations, there is a common thread of clear roles along with an awareness of and respect for the Venn diagram of skills between the co-founders.
Another common thread, as Dan says at the end of our conversation: looking after yourself and attending to yourself is key, because “if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader.”
Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist.
You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship. Paired creativity is a thing!
And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.
Links, Quotes, Notes, and Resources
Lawrence Lessig’s Pathetic Dot theory
Daniel Coyle’s Belonging Cues: Belonging cues are non-verbal signals that humans use to create safe connections in groups. The three basic qualities of belonging cues are 1) the energy invested in the exchange, 2) valuing individuals, and 3) signaling that the relationship will sustain in the future.
Kegan’s Levels, specifically, Stage 4 — Self-Authoring mind
Minute 8
Jennifer Dennard:
Part of why we chose to do a company was thinking about the journey and not the outcome, so startups are very unlikely to succeed, statistically. And so I think it can be similar when thinking about a conversation. Instead of going into it saying like, "This is what I want this person to say or do at the end of it," it's more like, "How do I want to feel during it?" And like, "How do I want the experience to be for both people?" And I think that's kind of how we think about conversations, but also more broadly, as a company, like, "What's the experience? Cool. Are we still having fun? Are we enjoying the adventure?" Certainly there are downs amongst that, but I think part of what has made us successful as a founding duo is that we are in it for the journey versus any specific moment or specific outcome, which I think can be really hard to then deal with the journey, which is quite long.
Minute 9
Daniel Stillman:
Well, so now we get into the point of the story where the beginning can seem organic and emergent, and then at some point, you do start to have that question of, as you said, Jen, values versus tactics alignment, right? And how are we going to do things around here, right? Building the culture and the process of how we're going to do things. How do you feel like you have managed that conversation of aligning on how to align?
Dan Pupius:
Yeah, to some extent, this aligns with the whole purpose of Range in the first place, which is that I think human behavior requires structure to facilitate it. Part of the inspiration for Range is from Lawrence Lessig's pathetic dot theory, that human behavior is manipulated by the forces of laws, markets, norms, and architecture. And in an organization, software provides a lot of architecture, which shapes our behavior, but we're not intentional about that software. So the whole theory of Range was about, how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams? So we kind of like thought about the processes ahead of the problems, so what's our cadence of work? How do we communicate? How do we run meetings? How do we talk about things? And just really thinking about the architecture of which we set things up.
And I think we're not super dogmatic and we're flexible, but I think it's something to fall back on.
Minute 17
Daniel Stillman:
I've heard this before, that some clarity around roles and division of labor is really helpful. Otherwise, there can be unclarity, for lack of a better word, but it seems like the other side to the coin is also true, which is flexibility to pass things back and forth and to shift and alter who's doing what is also really powerful. I'm curious how you navigate that conversation.
Dan Pupius:
Well, I think, we have a Venn diagram, so there's the stuff that's clearly mine and clearly Jen's, and then the middle bit is the messy bit. And luckily, there's not too much there, though that's probably the most critical part of the business for the last 18 months or so, so lots of back and forth on marketing and sales, for example, but it means that we still have these areas, where's it's just very clearly our areas of expertise, where we get to have mastery and complete autonomy. And then it's really the messy middle where we go back and forth. I think if it was all messy, that would be really difficult, or if only one of us had areas of specialization, that would be really difficult as well and probably really disempowering.
Jennifer Dennard:
Yeah. A lot of the decision of who takes something usually relates to bandwidth, and that's both time available but also energy. Sometimes Dan or I will take something just because other person's like, "Oh, I cannot keep doing that," or I don't quite have capacity. And I think that's maybe another thing that we haven't talked about yet in this conversation, is we have invested in through process and tried to cultivate a sense of, I think, safety and belonging on our calls, on how we work together. And that allows me, for instance, to say something like, "I just had hip surgery two weeks ago," and to be like, "Hey, my pain level before or after that is really high. I'm just not able to be what you might consider a normal capacity for me." And Dan [inaudible 00:19:21] hear that and, at least my experience of it, to not feel blamed at all, just to be like, "This is a fact about the bandwidth that we have as a collective system." And I think that allows that kind of handing off of responsibilities in a way that doesn't feel contentious.
Minute 27
Dan Pupius:
But, yeah, if I'm sleep deprived, I will be a bit sharp and I will step over the boundary of what is safe conflict, right? And that could be a catastrophic event if we didn't have that foundation. So I think that's kind of what's interesting, is that if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing in how you recover.
Daniel Stillman:
Jen, what do you do when Dan gets a little sharp?
Jennifer Dennard:
Usually, I pause. Like Dan kind of knows as well, I'll be like... I look away and I'll be like, "Okay, let me..." And then I usually try to pull out what it is underneath, like what is he trying to say or what's the best interpretation? I think something Dan maybe came up with at Medium or we started using there was the reasonable person principle and the idea that whatever the person's sharing, there's a reasonable explanation. And so I think I probably... Took me some time, probably... So Dan at Medium was more my mentor, I would say, and so to come into a co-founding, peer relationship, as a woman who's also younger, I think it took me probably the first few years to really step more into like, "We are peers." And I distinctly remember Dan going out on a very abbreviated paternity leave, unfortunately, at the start of the pandemic. And I was like, "Oh, Dan doesn't know what he is doing either. He just comes up with an answer when I ask, and I can do that."
And I think feeling like a peer in those conversations, to the point we were talking about earlier with power dynamics and stuff, really changes how sharpness lands. It doesn't feel personal. It feels like Dan didn't get enough sleep last night. I think, if it ever starts to feel personal, I also feel comfortable being like, "I'm going to step away from this call. I don't think we're being productive." And we've done that here and there and instead come back together. And I think knowing that, just like any relationship that when you have conflict, even if it does go into a space you're not comfortable, that you have the ability to repair, in my mind, matters because you're never... Whether it's your founding partner or a friend or a spouse, you're never going to not have conflict, unfortunately. And so [inaudible 00:29:24] that you can, typically make it productive, and then when it's not, that you can repair and talk through whatever underlying issue, that feels important to me. And I think we have that really shared understanding
More about Jennifer and Dan
About Jennifer
Jennifer Dennard is the Founder and COO of workplace collaboration software company, Range. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband.
About Dan
I'm Dan, an English software engineer and entrepreneur who lives and works in San Francisco.
I am co-founder and CEO of Range, where we believe that healthy companies aren’t simply better places to work, but do better work. We build software that helps teams be more connected, focused, and productive no matter where they’re working.
Prior to Range, I was Head of Engineering at the publishing platform Medium. And before that a Staff Software engineer at Google, where I worked on Gmail, Google+, and a variety of frontend infrastructure.
I have MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives I raced snowboards, jumped out of planes, and lived in the jungle.
Full Transcript
Daniel Stillman:
Jennifer, Dan, I'm so excited you're here to join me on The Conversation Factory. Thanks for making the time in your day.
Dan Pupius:
Yeah, thanks for having us. Excited to be here.
Jennifer Dennard:
Yeah, thank you.
Daniel Stillman:
So, all right, Jennifer, you made a very, very reasonable request. When I think about conversations, turn taking is one of the most fundamental and easily identifiable ways to manipulate a conversation for good. And it actually turns out that if women speak first, it's actually best for groups in general, according to my experience, for whatever reason. I'm not sure why that is, but it is, in fact, the case. So-
Jennifer Dennard:
We've heard-
Daniel Stillman:
What's that? I'm sorry.
Jennifer Dennard:
We've heard similar things, that encouraging certain people to speak first helps create a more equal and inclusive conversation.
Daniel Stillman:
Yeah. So Jennifer, I'm wondering if you can kick us off with the question of how you and Dan met and decided to start working together on this company. I'm curious what your version of the story is.
Jennifer Dennard:
And do they match?
Daniel Stillman:
And do they match, right? We should have had this as a double blind interview, really. That would be...
Jennifer Dennard:
So Dan and I met when we were both working at Medium, the blogging company. Dan was leading engineering and his team had actually set up a regular set of meetups or talks, a way of engaging with the community, and I ended up being a guest speaker at one of the events. And so a bit later, I actually ended up joining Medium full-time on the people operations team. And Dan and I ended up partnering a lot on organizational design. So Medium had been using something called Holacracy, which is a specific way of operating that I'd say Dan and I are pretty values aligned with, maybe less tactically aligned with the implementation of. And so Dan and I were partnered with designing a new system as it had been... Medium was moving off of Holacracy. And so we worked a lot together on a tool, internally, to really help the company operate, to showcase what people were working on, and it's, in many ways, a precursor to what we do today, but like company, Medium had ups and downs. And Dan and I were often supporting one another during those ups and downs.
Jennifer Dennard:
And so during one of those downs, I would say we were talking and Dan came in and he was excited. And I was like, "It's a hard week. It's not really an exciting time." And he was like, "Okay, but do you think, generally, we could build better tools to support companies beyond just Medium," and taking what we were learning with the tool that we were building there, and the things we were seeing about how companies operate, and where things broke down to really help other companies? And from there, we just went back to work, but a little bit after that, Dan and I had both left Medium at that point. And Dan was starting to think about starting a company and ended up chatting with me about whether there'd be interest in starting something, like Range, around building tools to support teams and companies and being more effective in their operations. And yeah, it really stemmed from our experience working together at Medium and seeing some of the problems that different companies faced.
Daniel Stillman:
Dan, what would you add to that story? What's missing, from your perspective?
Dan Pupius:
Yeah, I think that's accurate. Yeah, I think, basically, as I was looking around things to do next, leading other teams, bigger challenges, I just couldn't imagine working in a traditional company again and using the traditional tool sets, so I was like, "Well, if I'm going to staff a team to build tools to help us actually work better together, maybe I should actually evaluate whether that's a real opportunity." So I met with investors and then met with Jen and it kind of just... I don't know. It wasn't a decision point. It almost felt like it just gradually happened, and before we knew it, we had a company we'd incorporated and then raised some money and built a team, and it just kind of... I don't know. It felt natural and there wasn't a discreet moment where we were like, "Okay, let's do it." Maybe Jen remembers differently, but I don't really remember the specific decision point.
Jennifer Dennard:
Well, I remember you were actually very specific and intentional on like, "This doesn't have to be a specific decision moment. You can take time and think about whether you'd be interested in starting a company. It's a big decision," which I think was a precursor to some of the ways that we work together now, but it felt very egoless and felt very, like, "I'm not going to be offended if you don't want to do this crazy thing called a startup." I think that level made the conversation much easier and much more of a natural progression, where we got to keep talking more deeply, and then eventually do the official parts around it.
Daniel Stillman:
What was that word that you said, equalist? I couldn't-
Jennifer Dennard:
I don't know if it's an actual word, egoless, like [inaudible 00:05:09].
Daniel Stillman:
Oh, egoless. Yeah.
Jennifer Dennard:
I haven't been subject to too many of these conversations, but I think sometimes when people pitch you their company idea and wanting to work together, if you say no, it can feel very like an attack on them personally, which I get it. It's their company. And Dan approached that very differently of like, "Say yes. Say no. Do what you think is right. Here's some fun stuff to think about." I think he either knows me well or approached it kindly, but the giving me an [inaudible 00:05:37] to think about is certainly a way to get me intrigued about a space.
Daniel Stillman:
It's so interesting because, Dan, I saw you nodding your head. Is there anything else that what Jen said evokes for you?
Dan Pupius:
Yeah. It wasn't intentional. I wasn't scheming of, like, "Okay, how do I get Jen to sign onto this?"
Daniel Stillman:
Well, if you were, you wouldn't admit to it at this point, but fair enough.
Dan Pupius:
Yeah. Yeah, I do have Machiavellian tendencies sometimes, but, no, I think it was just that it is a big decision and I didn't know if there was a there there. And I figured that I needed a team to help me explore that, so started putting the team together. It's like getting the band back together almost because we'd been doing a bunch of this exploration work at Medium. And then we started doing customer conversations, product development, and exploration, and talking to investors and, yeah, it just kind of snowballed.
Daniel Stillman:
It's very interesting because the idea of an invitation begins a new conversation, and there was this in invitational... There was conversations that sort of emerged while you were at Medium, but then there was this moment where you reached out and said, "I'm thinking about this. What do you think?" And it incited another arc of conversations for you all. And it sounds like... It's really funny to think about. This is stuff when I first started thinking about, "What does it mean to design a conversation?" This idea of it can feel like manipulation if you're doing things too intentionally, but you did bring a certain essence, a certain approach to the invitation, which said, "I'd like you to be involved and let's think about it." So I think that's a very interesting moment to look at in the story arc of, "This is a liminal space and it's a generous question." And it sounds like it created a very spacious opportunity for you, Jen, to really step into it intentionally.
Jennifer Dennard:
Yeah, and I think like when Dan says he didn't know if there was a there there... I at least speak for myself and I think this is probably true for Dan as well. Part of why we chose to do a company was thinking about the journey and not the outcome, so startups are very unlikely to succeed, statistically. And so I think it can be similar when thinking about a conversation. Instead of going into it saying like, "This is what I want this person to say or do at the end of it," it's more like, "How do I want to feel during it?" And like, "How do I want the experience to be for both people?" And I think that's kind of how we think about conversations, but also more broadly, as a company, like, "What's the experience? Cool. Are we still having fun? Are we enjoying the adventure?" Certainly there are downs amongst that, but I think part of what has made us successful as a founding duo is that we are in it for the journey versus any specific moment or specific outcome, which I think can be really hard to then deal with the journey, which is quite long.
Dan Pupius:
Yeah, I think we've seen a lot of the power of intention at Medium. So when things worked well and how we laid intentional, explicit processes down ahead of needing to use them, we saw the value in that, and then also we saw when it broke down. So from very early on there, we talked about, how do we prioritize decision making, prioritize ourselves, our families, the founders, et cetera? And then we were very clear about how we want to communicate, our values. And I think some people would probably say that's a waste of time, but I think that sets the foundation and just makes everything easy down the line.
Daniel Stillman:
Well, so now we get into the point of the story where the beginning can seem organic and emergent, and then at some point, you do start to have that question of, as you said, Jen, values versus tactics alignment, right? And how are we going to do things around here, right? Building the culture and the process of how we're going to do things. How do you feel like you have managed that conversation of aligning on how to align?
Dan Pupius:
Yeah, to some extent, this aligns with the whole purpose of Range in the first place, which is that I think human behavior requires structure to facilitate it. Part of the inspiration for Range is from Lawrence Lessig's pathetic dot theory, that human behavior is manipulated by the forces of laws, markets, norms, and architecture. And in an organization, software provides a lot of architecture, which shapes our behavior, but we're not intentional about that software. So the whole theory of Range was about, how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams? So we kind of like thought about the processes ahead of the problems, so what's our cadence of work? How do we communicate? How do we run meetings? How do we talk about things? And just really thinking about the architecture of which we set things up.
Dan Pupius:
And I think we're not super dogmatic and we're flexible, but I think it's something to fall back on. In [inaudible 00:11:09] and everyone culture, they talk about it being the groove. So high performing teams need a home where you feel supported and safe, a groove where these processes you fall back on, and then if you have those two, then you can push people to the edge of their ability. And having a startup and trying all these new... We're doing things we've never done before. We need that to fall back on so we can be at our edge without getting burnt out, and touching against burnout, I guess, instead of going over the edge.
Daniel Stillman:
So Jen, is there more you wanted to "yes, and" on that?
Jennifer Dennard:
Oh, I was just going to say a very simple example of that is, very early on, we set a cadence of meetings of a time for us to kind of connect, a time for the whole team to connect, which at that point was two or three more people, not a huge group, but even just having that simple amount of process or structure of like, "This is when we are going to talk," is really helpful, because then it didn't feel like... It wasn't as hard to raise a conversation or to figure out when we were going to speak about something that we were disagreeing on and you get to resolve. I think those two... "Process" can sound really heavyweight, but for us it started as just like, "When are we going to meet?"
Daniel Stillman:
Yeah, just [inaudible 00:12:26].
Dan Pupius:
[inaudible 00:12:26]. And then names are important as well, so what we're going to meet about. So when Jen and I have our one-on-one, we have a tactical one on one, and then we have a strategic one-on-one and many times we'll talk about tactical things at the so-called strategy meeting, but it keeps us on track, more often than not, to just like, "What are we talking about here?" And then our team meetings, we have an operations meeting with our VP [inaudible 00:12:51], so we're only talking about operations. We're not talking about product strategy or things like that. And then we have an alignment meeting with the leads of all the teams. So the names of these meetings actually set the context and help us keep it on topic and it does deviate, but it is easier to bring back to the core topic.
Daniel Stillman:
Yeah, those names are invitations, right? They set the tone for the-
Dan Pupius:
And the purpose.
Daniel Stillman:
Yeah, the tone and the purpose for those conversations. So you're meeting, the two of you, twice a week?
Jennifer Dennard:
Mm-hmm.
Dan Pupius:
Most times, yeah. We sometimes take a [inaudible 00:13:27], like we'll... If we're exhausted on Friday or one of us is out, we'll, of course, skip, but I think we have, yeah, these two one-on-one touch points.
Daniel Stillman:
Yeah. One thing I'm kind of curious about is I was looking over your website before I came on the call with you all and one-on-ones are one of these things that people sometimes step into these conversations with no plan or with the inkling of a plan, but I think a lot of one-on-ones, there's a clear power differential, right? It's a manager having a one-on-one with somebody who they manage, and you two are co-founders. So I'm curious, in your one-on-ones, how do you... What's that like, right? It's a one-on-one of equals,
Dan Pupius:
I think, before I even talk about our one-on-ones, I think, in general, it's the person with the implicit authority or explicit authority, in some cases... It's incumbent on them to make the space safe, and I will always start the... When I have one-on-ones with people who report to me, it's like, "This is your time. This is where I support you. I am here in service of you, so this is your meeting. It's not my meeting. I get my needs satisfied elsewhere, ideally in a team environment." So that's never going to negate all of the power dynamic, but it does help set the context for that conversation. And I think that's pretty important because if managers use those one-on-ones in a way to have the person report to them, like, "I report to this person," that sets up the tone of the conversation and the purpose of the meeting, whereas if it's actually oriented much more, "This is where I support you," that's how you help people achieve... That's where they're honest with you and when they're open and vulnerable and where you're most likely to learn more things, so I think that's some framing, but I don't know about our one-on-one, Jen, how you feel about that.
Jennifer Dennard:
I think one of the things that we do is we typically have pretty clear areas of ownership, so I don't know. Just like a, I guess, regular one-on-one, we usually have an agenda. We have the topics we want to talk through. It's usually like either of us sharing updates on whichever area we're owning for the time being, and sometimes that ownership gets passed and handed off, sometimes week by week, depending on what's happening, but that is something that I have found upon reflection but upon talking to other founders about sometimes the harder areas when they work with one another. That's been really powerful for us because it lets us have, I think, one, some mind space, because each of us aren't owning everything and, two, the autonomy to go figure things out and then come back together. So I find that often the best analogy, I would say, is someone that you've worked closely with, who you're doing a one-on-one collab with, where you're just working through a problem. I feel like that's often how our one-on-ones feel to me and we just have more problems to work through than the average one-on-one collab.
Dan Pupius:
Yeah, it sometimes feels like a relay race to me, where we're handing off the baton, and sometimes we're like... I guess the analogy doesn't fit perfectly because we have a quick discussion of whether we should hand off the baton, but we do have explicit owners and I do think one of the cool things about the way Jen and I work is we pass ownership back and forth more dynamically than I've seen other people and other people I've worked with.
Daniel Stillman:
Yeah, because that's one of the things that I was wondering, is the... I've heard this before, that some clarity around roles and division of labor is really helpful. Otherwise, there can be unclarity, for lack of a better word, but it seems like the other side to the coin is also true, which is flexibility to pass things back and forth and to shift and alter who's doing what is also really powerful. I'm curious how you navigate that conversation.
Dan Pupius:
Well, I think, we have a Venn diagram, so there's the stuff that's clearly mine and clearly Jen's, and then the middle bit is the messy bit. And luckily, there's not too much there, though that's probably the most critical part of the business for the last 18 months or so, so lots of back and forth on marketing and sales, for example, but it means that we still have these areas, where's it's just very clearly our areas of expertise, where we get to have mastery and complete autonomy. And then it's really the messy middle where we go back and forth. I think if it was all messy, that would be really difficult, or if only one of us had areas of specialization, that would be really difficult as well and probably really disempowering.
Jennifer Dennard:
Yeah. A lot of the decision of who takes something usually relates to bandwidth, and that's both time available but also energy. Sometimes Dan or I will take something just because other person's like, "Oh, I cannot keep doing that," or I don't quite have capacity. And I think that's maybe another thing that we haven't talked about yet in this conversation, is we have invested in through process and tried to cultivate a sense of, I think, safety and belonging on our calls, on how we work together. And that allows me, for instance, to say something like, "I just had hip surgery two weeks ago," and to be like, "Hey, my pain level before or after that is really high. I'm just not able to be what you might consider a normal capacity for me." And Dan [inaudible 00:19:21] hear that and, at least my experience of it, to not feel blamed at all, just to be like, "This is a fact about the bandwidth that we have as a collective system." And I think that allows that kind of handing off of responsibilities in a way that doesn't feel contentious.
Daniel Stillman:
Dan, what more would you say about that?
Dan Pupius:
Yeah, I think Jen has to have a lot of bravery to bring those things up, so I think a lot of the credit goes to her in having boundaries and sharing what she needs in this situation. I do think our history really helps and we've been working together for so long now, and then some of the structure as well, but I think it also takes bravery.
Daniel Stillman:
Yeah. What's some of the structure that you feel makes that possible? You mentioned the architecture is one of the components that guides human behavior. What kind of intentional architecture do you feel like makes that safety possible?
Dan Pupius:
Yeah, so I think one of the key things is... One of the foundational things, and again, this relates to what we're doing as a company, is visibility. Daniel Coyle talks about this in terms of belonging cues, and belonging cues being these micro-interactions that remind you that you're on the same team, but I also think that if there's a lack of visibility into what you're working on and what you're doing, trust just naturally degrades over time. So making sure that we are in sync and seeing what each other are doing and just having a general pulse is super valuable as setting the foundation. And then as a company, we've just been really careful about building these moments for connection, which might, to some people, seem like a waste of time, but I think is really valuable as a way of building that trust and vulnerability, which is the only way that you can have those conversations. So giving gratitude is hard. I find it difficult, but creating structure where people are nudged to give gratitude is really powerful or receive gratitude to reflect and celebrate all these little things of what build up and create the foundation.
Daniel Stillman:
Yeah, I noticed that you mentioned a tactical and a strategic meeting, but I didn't hear a catch up or a vibes meeting.
Dan Pupius:
A vibes meeting.
Jennifer Dennard:
That's how we start all... So all of our meetings internally start with a check-in round, which is where you kind of... How you're doing, green, yellow, red, and I feel like Dan and I... Our meetings in particular often start with, "How are you really?"
Daniel Stillman:
Yeah, just go straight to the second question. "How are you really?"
Jennifer Dennard:
Yeah. I think we try to both be vulnerable with our team to the extent that we can, but there's also a level of we are the leaders and sharing how difficult things might be at a certain time is not so good for the company. And so I think that it is helpful to be able to share authentically in those meetings, even if sometimes I feel like I have to hold some of that back for the whole company.
Dan Pupius:
Yeah. Yeah. And I think even though we have the tactical and the strategy meetings, I think sometimes we're okay putting the agenda aside and just losing the time, and then we'll just... If we need it, we'll schedule a followup, but I don't know about you, Jen, but I find that also the last two years have just been so crazy that it's sometimes just nice to escape into abstract problems relating to the business instead of having to worry about the world that's collapsing around us, so there is some escapism there.
Jennifer Dennard:
Oh, totally. I think we both have that in our personalities, which is probably why [inaudible 00:23:15] helpful.
Daniel Stillman:
I don't think you two are unique in your desire for escapism, but I'll just say, and this is a really interesting thing to highlight, is there are some people who say like, "Oh, let's have a meeting that's just about human connection." And then there's baking it into all meetings.
Jennifer Dennard:
I don't know. You could kind of put that as a motto of Range, that we think that putting human connection directly next to the work is what makes it effective. And there's research to support that related to off sites that are just about happy hours and things aren't as effective as ones that incorporate aspects of work, but we found that, certainly, culture only meetings... We have game times or [inaudible 00:24:03] audio only. We certainly incorporate that as an aspect of our work, but it really does, I think, a disservice to people to have that always be a separate thing, because it makes it... To the extent that architecture and these structures influence us as humans, it makes it feel like there's work and then there's being a human. That's just not what's true. We are all humans at work, and I think that's something that we incorporate a lot into the software of our meeting tool, of our check-ins, all the different aspects, but also into how we operate as a founding team.
Dan Pupius:
I'm sure most people can resonate with this. You have a happy hour where everyone's chummy and being really friendly with each other, and then the following day, people are being passive aggressive over work email or tickets. And it's like you segment the two personalities. There's like, "We're all a team playing ping pong, and then we're arguing with each other over the work stuff." So bringing that sense of belonging into the work stream is... It's just really valuable at actually building the team aspect.
Daniel Stillman:
Yeah, very much so. One thing I think you mentioned, Dan, was this idea that in a one-on-one where there's a management relationship, it's about inverting and saying, "This is your meeting and I'm here to serve you," and underlining it was this idea of, "I'm getting my needs met elsewhere in self care." And I'm curious, you two can't manage each other without you two learning how to manage yourselves. And I'm curious what you do, Dan, and Jen, I'll ask you next, what'd you do to take care of yourself? Before we started recording, we were talking about how we get more protein into our diets, of course, but really, I'm wondering about how you fill your own cup so that you can come to the meetings with Jen in a place that's helpful.
Dan Pupius:
Well, I think the reality is that most times I probably come to the meeting with my cup three quarters full. And if we didn't have that sense of... If we didn't have that history and the foundation, it would easily overflow, especially in today's world, but because of all the stuff we do, it doesn't overflow. And in terms of self care, I have two small kids, live in the city. I don't have that much time. I just have hot baths and go for a run as my self care. And it is minimally viable, but I do think a lot of the work we've done over the last five years and then some of the coaching we've done outside has been really valuable at helping me have more capacity and helping me rejuvenate more quickly. But, yeah, if I'm sleep deprived, I will be a bit sharp and I will step over the boundary of what is safe conflict, right? And that could be a catastrophic event if we didn't have that foundation. So I think that's kind of what's interesting, is that if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing in how you recover.
Daniel Stillman:
Jen, what do you do when Dan gets a little sharp?
Jennifer Dennard:
Usually, I pause. Like Dan kind of knows as well, I'll be like... I look away and I'll be like, "Okay, let me..." And then I usually try to pull out what it is underneath, like what is he trying to say or what's the best interpretation? I think something Dan maybe came up with at Medium or we started using there was the reasonable person principle and the idea that whatever the person's sharing, there's a reasonable explanation. And so I think I probably... Took me some time, probably... So Dan at Medium was more my mentor, I would say, and so to come into a co-founding, peer relationship, as a woman who's also younger, I think it took me probably the first few years to really step more into like, "We are peers." And I distinctly remember Dan going out on a very abbreviated paternity leave, unfortunately, at the start of the pandemic. And I was like, "Oh, Dan doesn't know what he is doing either. He just comes up with an answer when I ask, and I can do that."
Jennifer Dennard:
And I think feeling like a peer in those conversations, to the point we were talking about earlier with power dynamics and stuff, really changes how sharpness lands. It doesn't feel personal. It feels like Dan didn't get enough sleep last night. I think, if it ever starts to feel personal, I also feel comfortable being like, "I'm going to step away from this call. I don't think we're being productive." And we've done that here and there and instead come back together. And I think knowing that, just like any relationship that when you have conflict, even if it does go into a space you're not comfortable, that you have the ability to repair, in my mind, matters because you're never... Whether it's your founding partner or a friend or a spouse, you're never going to not have conflict, unfortunately. And so [inaudible 00:29:24] that you can, typically make it productive, and then when it's not, that you can repair and talk through whatever underlying issue, that feels important to me. And I think we have that really shared understanding,
Daniel Stillman:
Jen, this is such a powerful point. And I think this is something I learned from the world of couples therapy. The ability to actually pause a difficult conversation can seem like a threat if it's not done correctly, to say, "Hey, look, I'm not comfortable with where this is right now," or, "I don't feel well resourced," or, "Maybe we should just pause this and come back to this." What verbiage do you use in those moments to slow it down, to cool down the conversation and to separate and come back? I know you said it only happens occasionally, so you may have to stretch your memory to go back.
Jennifer Dennard:
I'm trying to give a best case. If we're candid, right, sometimes I'm like, "I'm getting upset." And so I'm like, "I need to take a break." And it's not like fairly said in a nice, calm way that we want to when we're in therapy, where it's like, "Oh, say, I think I should take a moment." Probably doesn't happen exactly that way, but just usually something like, "I don't think this is constructive," like we're kind of talking back and forth or, "Let's take a break. Let's revisit this later," because if we've gotten to that point, we've probably also gone over on time, so there's a clear, like, "Hey, we're not being constructive here."
Daniel Stillman:
Yeah. I call this noticing and naming. You're like, "I am noticing my own situation, naming it, and taking it." And I'm talking over Dan, which is...
Dan Pupius:
No, that's okay. No, I think having a language for it is really important and, yeah, some of the models that we've learned about around psychology. I think it depersonalizes it a little bit. So this is from Kegan, but we might say, like, "We're not in level four anymore," or, "We've got hooked," like we've got hooked by the conversation and it kind of just pulls you out of being hooked. It's almost like if you're angry, just saying, "I feel angry," is enough to calm the amygdala. So there's these really interesting language hacks that can reset things and then stepping away. And I do think the repairing and recovering is really important. You can't just push it under the rug. And then if other people were in the meeting as well, making sure that they see the recovery, which is the same as with parents. You can't have parents argue and then make up in private. They have to make up in front of the kids. Otherwise, they don't learn about conflict resolution, so it's a similar principle.
Daniel Stillman:
You mentioned, "We're not in level four anymore." I'm not sure if I know the framework that you're referring to.
Dan Pupius:
So Robert Kegan's book, Evolving Self, provides this model for adult cognitive development and it's essentially... You have the egocentric self, you have the socialized self, the institutional self, and it's ways that your mind makes meaning given the situation. And we are constantly fluctuating between those levels as adults. And it's [inaudible 00:32:39] useful because if someone attacks you on the street, you want to drop down into a level one egocentric self to save yourself, but in the work context, it's not very... We have similar reactions and our brain drops into a different mode of operation and meaning making, and it's just not helpful because we're not being attacked or anything. It's our brain being tricked. So it just gives us some language. And the egocentric self is very black and white. It's very like, "Me, them." The socialized self is all about the relationship and the connections, and then the institutional stuff is a higher level systems thinking space. And even if the model isn't correct and potentially reductive, models might be wrong, but they're still useful.
Daniel Stillman:
Yes.
Jennifer Dennard:
And I think something we do well at this point in our co-founder relationship is identifying when the other person is dropping down. For example, I think, the counter today in maybe Dan being sharp is I will start to speak... If I'm the one who's less resourced and not doing well, I'll start to speak in shorter sentences. I will just seem more flustered. I will actually sometimes turn slightly red. And I think both of us sometimes will say to each other, like, "What are you worried about?" And/or say like, "Well, here's what this is triggering for me," or, "This is what this is making me think about," and the thread I'm pulling on. And so sometimes that really helps us get out of the conversation where we're talking about a very specific thing. And it's really like, "Oh, this other problem that's triggering for us." And less in the therapeutic sense of triggering childhood trauma and more like triggering like, "Oh, I'm actually really worried about this other thing on the sales team or the marketing team, and that's pulling on this concern, even though it seems to be a [inaudible 00:34:35] question."
Daniel Stillman:
Yeah. Although I get the sense that, just from my own experience and relationships, it's hard to say to someone, "It sounds like you're kind of in level one right now, so let's start this again when you're ready and in level four."
Dan Pupius:
It's definitely an ouch. It can be a bit of an ouch, but it can also be a bit of a shock to system because, again, the label and... I don't know. Yeah, there's definitely like, "Oh, man," like a little bit of embarrassment, but then you know that we're in a safe space. There's a lot of regard and you can come back and there's no judgment, and then we get back into the space. And I think having the ability to actually jump up and down through these mental spaces is actually really valuable, instead of getting stuck in them.
Daniel Stillman:
Yeah. Well, so shockingly, our time is running nigh. I'm wondering what I haven't asked you about managing your relationship, designing your conversation, that I ought to have asked you. And Jen, I'll start with you, to see if anything comes to mind.
Jennifer Dennard:
I think there's often a power dynamic in founder relationships. I think just having been a part of a number of COO and collect-all groups, there's often a power tension with the CEO. There's certainly power dynamics associated with gender and with age, particularly in the tech industry. And so I think it's something that I often encourage people to think about and focus on early on. When we first were designing Range and we started talking about equity division amongst the founders, we were pretty particular in terms of what we decided would impact equity. And I would say I got a much more equitable portion than I would with most male CCO co-founders, and I think that speaks to Dan's values but also helped really set the framework and groundwork for me to feel like a peer.
Jennifer Dennard:
And Dan has put in work for that to feel that way. And I think sometimes there's stuff early on, that the co-founder relationship gets off on the wrong foot, even if it's people who work together for a long time, because that perception and that difficult conflict early on of, "Are we equals in this? How are we approaching this?" doesn't quite happen. And then so that encouraging of conflict in that discussion, I think, is really important in thinking about the different power dynamics that can emerge, even if you consider yourself to be peers. And I'm very grateful that Dan is our CEO. He deals with stuff that I don't, and I appreciate that a lot.
Daniel Stillman:
How about you, Dan? What haven't I asked you that I should ask you?
Dan Pupius:
I don't know. I think you kind of hinted this earlier, but we went a different direction, which is that looking after yourself and attending to yourself is so key, because if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader. And I think many leaders aren't vulnerable about that and they don't focus on their strengths and weaknesses and addressing them and thinking about them, and what are their personality dynamics that may be suboptimal or rub people the wrong way? I'm very aware of how sharp I can be and how scary I can be, and I've worked for 20 years to try and correct that, so I think the personal leadership is so important as a foundation.
Jennifer Dennard:
[inaudible 00:38:20]-
Daniel Stillman:
Again, you mentioned you... Oh, sorry. Go ahead, Jen.
Jennifer Dennard:
Oh, I was going to say, and being aware of one's own mental health. Certainly, in the last five years we've had ups and downs and at a pandemic and all the things that have happened. I think being able to own that versus put it on the other person or the company is really important.
Daniel Stillman:
Yeah. Dan, you mentioned coaching has been part of that for you. Is there anything else, besides running and hot baths, that is part of you sustaining yourself and coming with your cup three quarters full?
Dan Pupius:
Yeah, me and my wife... We talk about this a lot and getting out, and especially when we had a young child, it was really hard to get out of the house, but we'd force ourselves to go out into the wilderness and go hiking, and that can be really valuable. So coaching. We do couples therapy as well, which is really, really helpful, just as a way of building our relationship, making us stronger parents and showing up better for each other. I don't know. Probably too much alcohol, not sleeping enough... All these things are problems. I'm probably not super healthy right now, to be honest, but at least we're surviving.
Daniel Stillman:
At least you're getting enough protein.
Dan Pupius:
Yeah. Well, as of last week.
Daniel Stillman:
As of last week. Well, next week's going to be better. Jen, what do you do to fill your cup?
Jennifer Dennard:
Similar tactics of coaching and therapy, I think. Normally, I run. As I mentioned, I got hip surgery, so I've been... I really like reading. It's my form of escapism, to really go deep into a moderately well written to badly written or poorly written fantasy or sci-fi novel, just to be very separate in a different world. My sister's a fantasy author, so it definitely runs in the family, but... And then, yeah, being out in nature. Right now, I can't go very far, so just sitting in our backyard. We have a garden and taking that space. I think a recent thing I've been trying more is expressive writing, where you just write for 15 minutes, and it doesn't have to be... Not really a journal, per se, of what happened, but more just like, "Here's how I'm feeling." That, I've historically found useful, particularly in moments where I'm keyed up or need to process and don't want to necessarily just ignore how I'm feeling, but want to just help the emotion kind of work through.
Daniel Stillman:
Yes. I went to a workshop years ago with Julia Cameron. It was a writing workshop. I went with my mom. It was super fun. And basically, whenever anybody stood up and said, "I'm having some trouble with this, this, and this," she would say, "Are you doing your morning pages?" That was her... Just the three pages of just long hand, first thing in the morning. And whenever I get below zero, I bring morning pages back in.
Dan Pupius:
I think maybe the lesson there is it's less about the tactics, but the important thing is the ritual, so having these rituals. So rituals for connecting with your partner, connecting with your kid, getting physical health, getting good food, whatever it is, disconnecting, escaping, making sure you have those rituals laid down so that when things get hard, you have something to fall back on.
Daniel Stillman:
Yeah. Well, this has been really lovely. I want to thank you both for your time. If people want to learn about all things Dan and Jen, are there other places they should go, besides Range.co, that you'd like them to go to?
Dan Pupius:
I don't-
Jennifer Dennard:
That's the main thing. Check out our... We have a series of podcasts and interviews with other teams and how they manage some of this, called How Teams Work or Lead Time Chats. Both of those are really great resources, I think. We care a lot about educating the community. It's not just like there's some scholarly paper that has the best practice. It's also like, how do people actually do this? So we try to share a lot of that information on our blog, which we also share out on LinkedIn and things like that. Feel free to connect directly on LinkedIn too.
Daniel Stillman:
Well, sweet. I think I'll call "scene" and just make sure that you two... Well, let's do a checkout and make sure that everything felt awesome.