Doing Difficult Work

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Episode Transcript

CHRIS MARTIN: To kick off this episode, let’s start with introductions and the hardest project you’ve ever worked on.

JAMON HOLMGREN: Hi, my name is Jamon Holmgren and I’m one of the co-founders of Infinite Red, Chief Operating Officer.

Chris asked what’s a difficult project that I’ve worked on in the past and I think early on when I was first sort of getting outside of just building marketing websites, I took on a project for a social media platform. Of course, this was probably 2009, Facebook was sort of coming into its own and they wanted to build a social media. It was a guy that really didn’t understand what social media was. He was on no social media platforms himself. He was an older dude who was annoyed that his daughter-in-law kept inviting him to the Facebook and he did not want to deal with that. So he decided instead that he was going to build his own, so he wouldn’t have to join Facebook. It was … it sounds kind of ridiculous and made up, but I swear this was an actual project that we did.

KEN MILLER: Well, that is my kind of lazy. (laughter) Really, I mean I’m serious. Where you will recreate the site, from scratch, in order to not have one annoying experience.

Ken Miller, CTO/CFO, founder of Infinite Red. I’m trying to think about a hard project. For me, the hardest projects are the ones where you have to keep at for years. A massive, blast through it, kind of hard project is much easier. I’ve always been a little ADD and I think that some people thrive on that emergency situation, but a long haul where you have to keep at something for a long time is harder. In terms of work technical things, a couple companies ago, we had a very email dependent company and so we had to get a huge number of emails sent in a very narrow window every day. That was a very long back and forth process because you have to keep up with the amount that you are sending out physically, you have to manage the deliverability, you have to monitor your changes and make sure a small change in your rendering doesn’t completely blow up your delivery window. And so the process of managing that over time definitely taught me a lot about how you set something up so you can do it over time.

TODD WERTH: How many emails did you send out Ken, just curious.

KEN: I think we were at 3 million. This was pre-Mailgun, pre-AWS. This was, we had to actually size the hardware-

TODD: Is that per week?

KEN: Appropriately. Every night. And it had to be finished in about a two hour window.

TODD: So you’re responsible for most of the spam in the early 2000s.

KEN: Yeah, that was me. I’m sorry. (laughter) My bad.

Delivering legitimate email is actually pretty tricky because of all the anti-spam measures that are a necessity of modern communications. So that was probably, in terms of the technical project, that has been the most challenging. That, organizationally, was the most for me.

TODD: Hi, I am Todd Werth. I’m the CEO and the founder of Infinite Red; long time listener, first time caller.

So Chris asked us to talk about a hard problem we’ve had in the past. So I think most hard problems I’ve dealt with in the past haven’t necessarily been technical, because even though they’re difficult, they’re fairly straight forward to go through. Some just take a little longer.

KEN: That’s true.

TODD: Most of the problems have been human related. One that comes to mind, and I’m sure there are better examples but, circa 1998, 1999 or something, I did a project for the San Francisco 49ers. The scouts would go out preseason and they would scout out new people and they would go all over the country and they would take notes. Traditionally this was done on paper and then when they finally made it back to the home office they would go over their notes with whomever and what not. So we were developing a system where we gave these peoples laptops for them to take out and then when they got back to their hotel room they would hook up to the phone line and use a modem and upload the data to the database; which was hugely advantageous to the San Francisco 49er corporate office.

The problem is, none of these gentlemen have every used a computer before. Didn’t know how to use a mouse, didn’t know how to use a laptop, so the challenging part there …actually, a colleague of mine, his name was Milton Hare, he did the training and taught them the very basics of using a computer. That was actually quite challenging. The user interface that we designed had to be geared towards that. It had to be, not just simple, but absurdly simple. It was very fascinating. The bad part of that project was that I got to see a lot of data on professional football players, including things like their criminal records and I will not go into it, but it’s not a pretty picture.

CHRIS: What we’re going to do in this episode is we’re gonna look at the art of doing difficult work in three main areas: extreme personal support, collaboration, and transparency. But before we get there, what is difficult work? We’ve had a couple of different responses. We’ve had technical, we’ve had human, but what is difficult work?

TODD: I would say…that’s a hard question.

KEN: Difficult work is work that is not easy. (laughter)

TODD: Yes, Ken. That’s why we have you here. It’s tough to say. As far as from our culture and our perspective, difficult work is what’s difficult for individual people. So for example, I’m an engineer and designer, not a sales person. Jamon is also an engineer, not a sales person, but Jamon and I for a long time did sales together. That is difficult work for us, we didn’t come natural to it, we didn’t have any experience with it. So one of the things we decided early on is, we have a couple of rules.

One, you don’t have to do something the way other people in the world do it. We’re engineers, we’re doing sales, we approached it from an engineering standpoint and we engineer our sales process. Later we can talk about that.

Two, is anything that is difficult for individuals, they shouldn’t be doing alone. They should never be alone on an island. If someone, whatever it is, talking to a tough client, dealing with a tough technical problem, doing something that’s outside of your comfort zone such as sales or maybe giving a presentation or whatever it is, we do at least in pairs or more. It’s one of the things I really, I beat the drum beat with our team is, if there is something you’re dreading, use the buddy system and get people to be there with you because that helps a lot. For example, in our sales calls, Jamon and I would do this thing where if I’m talking and I’m starting to fumble, he would interrupt me and take over, or if I felt like I had nothing to say and I was having a particularly anxious moment or something, Jamon would take over and we would support each other that way. Eventually we became pretty decent sales people.

KEN: If I were to take a crack at defining difficult, I would say, something like work where you don’t already know how you’re supposed to do it. As distinct from hard work, for the purposes of discussion, I would define as more you know how to do it there’s just a lot of it and you need to do it quickly or intensively for some reason.

One of things that we actually like to do around here is turn hard work into difficult work. Find a way to automate in terms of process or literally automate in terms of code, things that would otherwise be hard work. It’s not always possible, but we try to when we can.

JAMON: I have a personal example of this, wasn’t done within Infinite Red per se, but on Christmas Eve I suffered a house fire and it obviously was quite traumatic but one of the things we have to deal with as sort of a fall out of this house fire is submitting personal items to insurance for reimbursement, to kind of restore what we had. It’s a very labor intensive process, to go to the insurance company’s website and individually type in items because most people with a normal sized home would have thousands of items. The restoration company had done a spreadsheet for us and they had done a lot of the work, where they had gone through, and I would characterize that as very hard work, where they had to go through a bunch of soot-stained things and inventory them, take pictures of them, describe them in a spreadsheet. They did a really good job with that and they put it into a spreadsheet, but to put those items in was still a manual process of transferring from a spreadsheet over to the State Farm website.

I decided that, maybe what I’ll do is I’ll figure out some way to automate that and that took me like an hour. I could’ve gotten a lot of things done during that time, I could’ve entered quite a few items in that amount of time. It took a lot of frustration, of like going down the wrong road, and kind of reverse engineering the web app. But once I had it done, I got it to work and I ran this cURL script for like 45 minutes and at the end of 45 minutes we had 3,000 items entered into the website. So this was a situation where we could’ve just buckled down and done the hard work, but instead of doing that I did more difficult work of thinking of a way to automate it and that was a net positive.

KEN: And if the FBI or State Farm are listening, we had no knowledge of this. (laughter)

TODD: State Farm is definitely not listening.

KEN: For the record.

TODD: Jamon, two questions. One, do you think State Farm intentionally makes it super hard to enter items that they’re going to reimburse you for? Two, how long do you think that would take you if you hadn’t automated that?

JAMON: You know, we’ve been asked that before. I don’t actually think that’s the case necessarily, because I’ve been involved in enough software projects where you’re not intentionally making something difficult for users, but when you don’t use it, when you are not the end user, when you are not the person sitting there whose been through a fire who has to go through it and do it. It’s not as easy as it seems when you’re testing it with 14 items, 14 test items. I think actually this speaks more to a lot of what we do where yes, entering 8 dummy items in the course of testing it on localhost, it’s actually a pretty good experience. They’ve actually done a pretty good job of making that pretty decent, but the overall user experience of a real person in a real position of needing to do this-

KEN: For a large loss, not just like hey someone stole my bike, but yeah …

JAMON: Exactly, it falls on it’s face. So I actually don’t think at all that this was intentional. I think that it’s entirely within the realm of possibility that this is simply they haven’t user tested. It’s a fairly new system, hopefully they’ll add bulk import at some point.

As far as the second question which is how long do you think it would’ve taken to enter those items. I think I’d gotten through maybe a couple hundred in the previous hour. It was taking me probably between 15 seconds to 30 seconds to enter each item. It would’ve taken a long time and been very tiring.

TODD: We’ll give State Farm the benefit of the doubt.

KEN: I think this impulse, this is exactly the kind of impulse that leads some people to computers, to programming. This allergic reaction to tedium and repetition and when you find computer programming for the first time, if you’re that kind of person who hates that sort of tedium, you’re like ‘this is the best thing that I’ve ever seen in my life,’ right? I only have to think in enough clarity about what’s happening to describe it to the computer, and then it’ll do it for me. That’s a really powerful feeling and as you get into it of course you discover that you’ve just traded one problem for another problem, but we’re the kind of people who find that to be a higher class, more interesting, better, more rewarding problem.

CHRIS: There was an intriguing phrase used the other day: We make difficult things doable through extreme personal support of each other. So can you paint a picture of what extreme personal support means to you at maybe the founders level and then maybe at the Infinite Red team level?

TODD: Who said that Chris?

CHRIS: That was the brilliance of a guy named Todd Werth.

TODD: I do not recall saying that. I wouldn’t phrase it that way, even though I literally phrased it that way. (laughter) I don’t remember saying that, but it makes sense. It’s not only do we give people support when they’re doing work that’s difficult for them including all of us, and including the three people here as well. Let me tell you a little story.

When I was a young man I worked in a warehouse, I drove a forklift around at a job. One thing I noticed in that job, it didn’t suit me very well because I like to talk and I like to think about stuff and it was just very tedious. What I noticed a lot of the people in the warehouse, all different ages, young person like myself all the way up to older people, is a lot of people in the warehouse were not in the right job. This one gentleman would constantly get in trouble and the bosses did not like him because he loved to chat and he was really good at it and he was really personable and I have no idea why he was in the warehouse, it made no sense at all. Later on he went to become a successful real estate agent, which is completely appropriate. Now this company I worked for, it was a big company, it was one of the largest companies in the state, so it’s not like they didn’t have a place for this gentleman to work well, so he ended up leaving.

The reason I tell that story is because you have to know everyone individually and what’s hard work for one person is not hard work for another. If it’s not hard work for another person, one way they can support people rather than just direct interaction is for them taking on jobs that other people find hard. So that’s kind of support and of course there’s just day to day, I will show up with you on the battlefield, type of support and that kind of stuff.

JAMON: I think one of the ways that this manifests itself is how we deal with failure and the inability to get something done here. We’re not quick to reach for blame the individual who’s there. Sometimes that’s the case where someone just falls down and they kind of do their own thing and that needs to be corrected and move forward.

TODD: We so don’t look to blame.

JAMON: We don’t look to blame. No it’s really, let’s look at this from a collaborative approach. How can we, as a group, do this better in the future? How can we adjust our systems? One of the things I don’t like is to identify a gap in our system, for example, and then say that the answer is that the people involved need to just try harder. I really don’t like that answer. Unfortunately that’s something that a lot of lazy leadership will do. They’ll just be like, ‘you need to get your act together,’ and that’s the answer. The reality is that’s often not the answer. The answer is usually to work with the system until it’s at a point where doing the right thing is the easy path, where doing the right thing is the natural and intuitive path. That takes thinking, that takes understanding the problem, it’s harder for leadership to accomplish that.

KEN: It is occasionally the right answer though.

TODD: It sometimes, sure.

KEN: But not very often. It’s rarely that simple, but I think one of the hard things that I’ve found in leadership was actually saying to somebody, ‘Look, you need to step up. You have what you need right in front of you, the next part is up to you.’ Actually saying that is part of it. I think what Jamon is referring to is that if the support is not there, then saying that is meaningless.

JAMON: Yes.

TODD: Well, I mean, it’s like someone is pushing a rock up a hill and you’re just saying you need to push harder, push harder. When the person’s telling you and you’re not listening, why don’t I just walk over the hill and get the rock that’s already over there? You know what I mean? So-

KEN: Yeah, I completely agree with that.

TODD: I do agree that asking somebody to step up in a real way, not just a nose against the grindstone type of way.

KEN: When you get to the point where you’ve got all of the easy rocks on one side and what we actually need to do as a team is get this one huge freaking rock on the other side of the hill, and some people are not pushing with you, that has to be addressed.

JAMON: Right

KEN: But it’s much smaller part of the pie than I think some management philosophies would tell you.

TODD: I personally convince everyone that pushing rocks is one of the neatest things in the world, it’s a rarity, and for a low price they can push my rocks for me. (laughter)

JAMON: I think one of the things Ken has said in the past is what we want to be is a high support, high expectations company. Low support, high expectations is just toxic.

KEN: That’s a sweat shop.

JAMON: Yeah, it’s a sweat shop. High support, low expectations is a nursery and low expectations, low support that’s-

KEN: I don’t even know what that is.

CHRIS: How does this picture of extreme personal support enter your relationship as the three founders?

JAMON: I can kind of personally attest to this. There are certain tasks that I’m well suited to, my personality, that I enjoy doing. There are other ones that it’s like pulling teeth to get me to do and that’s just been exacerbated since I had the house fire and am kind of displaced from my normal routine and I really just want to focus on the things that I really enjoy doing. What we did, actually earlier this year, up until this point we’ve made a lot of decisions together, we’ve done a lot of things together and that’s was appropriate for the first couple years of Infinite Red. But we’ve gotten to a point where we kind of understand each other, we kind of have a lot of aligned shared goals and we’ve actually started to specialize.

This was a way for Todd and Ken to support me, in that Todd could focus on a lot of team-oriented things and Ken’s been doing a lot of things with the financial and bookkeeping side of the business, which I am not good at. I can focus more on business development and that’s actually the part of the business that I find really interesting, so rather than just telling me, ‘work harder at managing your projects, work harder at being an account manager, work harder at doing these other things,’ which yeah, I could work harder and do a better job. Instead of doing that we’ve found a solution that wasn’t centered around just working harder it was centered around doing things that we felt effective at.

TODD: As we are three founders and we govern as a quorum of elders as it were, as opposed to a hierarchical company, supporting ourselves, each other, the three founders, is just as important as supporting the team in my opinion.

When there is a financial problem, thankfully we haven’t had too many of those, we all have to step up and so we tend to understand each other’s personal finances, each other’s personal stuff. It’s almost like a pseudo-marriage in a way, although there are three of us so it’d be a polyamorous marriage in this case. It’s a requirement to be more, I don’t want to use to word intimate, but intimate in each other’s lives and I think we’re really good… What’s cool about three as opposed to two or one, for example, because Jamon’s done one and I’ve done one, I’ve been in another company …but what’s cool about three is, typically it’s one person having a communications problem or arguing or having difficulties with another person and the third person mediates. It’s either Jamon and I are having an argument and Ken mediates or Ken and I are having an argument and Jamon mediates. Hey wait-

KEN: Wait, when do you mediate, Todd? (laughter)

TODD: I don’t think I’ve ever mediated, that’s funny.

KEN: I don’t think you have actually. I’m noticing a pattern here, yeah.

JAMON: That’s not true.

TODD: But it is totally true. But it’s okay. I tend to draw lightning as well away from people and because I deserve it. I don’t know if that answered your question, but I think it’s uber important, sorry, it’s Lyft important that we do that. (laughter) You know, it starts and then we can all support the team if we are supported ourselves.

JAMON: It sets the tone, all the way down and we have to. We have no other way of working. We have to support each other and it’s not just when we’re having interpersonal problems with each other, but also when someone’s just literally having a tough time. What I think we’ve done really well as a founder team is go into our shared channel and post, ‘I’m having a tough time.’ It can be for any reason, it can literally be like, I didn’t sleep very well last night; I just am so bored with this task, I cannot get started with it. All those things are valid and the answer is never just suck it up, or if it is, it’s one of those things where it’s an empathetic suck it up. If that makes sense. It’s like, I totally get it, I understand where you’re at, we really just need to get this done. And sometimes that’s what you need, you need a little boot in the rear and that’s something that you can take from the other side too. It’s been great, really, the last two and a half years having that.

TODD: Obviously we’re talking about supporting each other as founders, but it’s the same with the team. One key thing is if someone is vulnerable, they say they’ve made a mistake, they say they’re having a problem, even if you personally think ‘is that really a problem?’ Or whatever, it doesn’t matter. Whatever your personal feelings are is irrelevant. If you stomp on that person, if you make fun of that person, if you tell them to suck it up buttercup, everyone, not just them, the entire team will contract. They will put up a little more walling around them and they won’t do that in the future. They’ll do it, they just won’t do it around you. It is hard because we’re all emotional beings and sometimes you have an emotional reaction to something. But you have to be super careful to not …when that flame is just starting you need to be very gentle with it and not blow it out.

KEN: It’s more than just avoiding stomping on people, not that Todd was saying that’s all it was, but you have to go out of your way to solicit, to get people to talk about what’s going on with them, to check in with them, to reiterate that you’re available for that. You can’t say it once and assume that everyone will remember that, they won’t. Right? People’s own internal dialogue about how worthy they are, all that stuff will keep coming back if you don’t actively do it. Also, we will make mistakes sometimes, right? So you have to keep doing the active things as well to keep the ship steered in the right direction.

TODD: When we make mistakes it’s important that we apologize to the team. Not fakely like ‘oh, I’m so sorry.’ Everyone can smell fake, but if you’re genuinely made a mistake because you had an emotional moment and you didn’t act appropriately, you have to apologize to them as well.

CHRIS: So the interesting thing as you’re talking, I get a sense that this isn’t something that you just read in a book and you’re like, ‘I’m an expert at this.’ I sense that there are some really real stories behind learning what it means to be not only supporting others but to feel supported.

TODD: Yes, for sure. Ken actually is super good at advice in this kind of thing, having been a leader in the past. Typically, leader of only senior people in the last two jobs. Actually, the last one I had some more junior. Infinite Red, when we first started, we had quite a few junior people, so that was a little new to me.

One of the things you have to learn …leadership is hard by the way, I just want to interject that. Leadership is very difficult, it’s hard work and that’s why we get the support of each other. We not only get the support of the three founders, but the entire leadership team here at Infinite Red and there’s a variety of people: Gant Laborde, Shawni Danner, Jed Bartausky, Justin Huskey. It’s difficult and not only are we supporting each other, we’re coaching them, especially the more junior leaders on how to do it and one of the things Ken said and it’s just one of the great gems of wisdom that he gives, is he goes “you have to remember you have very wide arms, when you swing them you hurt people.” So you don’t have the luxury to be how you were when you were as an employee. I could say things as an employee, I enjoy making people laugh, it’s one of my things. I can do a lot of things as an employee that I simply can’t do as a leader because when I say something it’s taken much more seriously, whether I meant it or not. When I hear other managers, let’s call them, say something like employees suck, it’s like, ‘no they don’t, you suck.’ Employees don’t suck. That’s crazy, that’s like the coach of the San Francisco 49ers saying my players suck. Well, you chose the players, you’re coaching the players, so they don’t suck.

KEN: One of the things that we do when we’re working on a difficult project as a team is make sure there’s an owner. One of the things that will kill any difficult project is diffuse responsibility. Partly what we’re striving for is that everyone can take responsibility for something. Everyone can be like, ‘I’m going to execute my part of this as skillfully as I can,’ but if there’s not one person who owns the whole vision, it’s going to fail. Almost guaranteed.

Creating an environment where it’s okay for that owner to say, ‘hey I need your help to get this done.’ Where the culture is like, somebody needs something from you and they specifically ask you, that you try to do it. And that makes ownership less scary. One of the things that I’ve seen go wrong, if someone is given responsibility but no power, no ability to actually follow through on that responsibility-

TODD: That happens all the time.

KEN: That is the most demoralizing position, possible.

TODD: That’s toxic.

KEN: Yeah, so that’s how you kill your budding leaders by saying ‘hey get this done and by the way, all these people over here have their own priorities and they’re not going to help you.’ That is the worst. So, assign ownership and then back them up. That’s been one of the keys to getting certain things done. Chain React is a good example of that.

Chain React is our conference for React Native in Portland this July 11-13. So we did it first last year and now we’re doing it again this year. Shawni, who basically runs it, had ever run a conference before, had never been to a conference before, but is good at just marshaling resources and taking charge and that’s a great example where she could pull on whoever she needed for help. When it came to actually knowing specifically what to do for other peoples’ expertise, like we flew somebody up who was a serious foodie, to go and test the caterers, for example.

JAMON: That was our team member Derek Greenberg and Derek is such a foodie and it was just a joy to watch him work on that.

KEN: He had the most comprehensive report for that kind of selection process that I have ever heard. It was amazing, anyway.

None of these things that we’re saying are we perfect at. We’re not, we don’t hit this every single time and I hope that we’re not saying that’s the standard. What we’re saying is here’s our guiding star, here’s what we try to do, here’s how we evaluate whether we’re doing the right thing or not. So this is how we nurture leadership within the team, is to say ‘here’s what we need you to do, and by the way, the team is your oyster.’ You can go and pull in what you need in order to make this happen.

**CHRIS: This is really bringing up a really interesting point now, we’ve got this extreme personal support but then when you add the component of leadership and helping each other out, it introduces the layer of collaboration. So how is collaboration different from extreme personal support?

TODD: You can have a group of people who hate each other and they can collaborate if they’re given the proper motivations. This happens all the time in corporations every day. Sadly, many people work at those corporations. So I don’t think those are necessarily required for each other. I do want to digress just for one second. So Ken was saying how we try to give people in leadership positions or in a leadership role in a particular project, whatever it is. We try to do empowering stuff, but we’re not perfect at all.

One of the coolest things about having Ken and Jamon around is when I do something boneheaded, typically Monday-Friday, they let me know and they help me get through it and they identify it and on the flip side for whatever reason the team is pretty comfortable talking to me. It’s just my personality, I talk to people a lot. And so if they have a problem with say Ken or Jamon, they’ll let me know, and then I go talk to that person or we talk and try to do it in the most supportive way possible with the goal of improving that person’s, how they’re performing as a leader and that’s awesome because we’re all human so having the support.

For the team it’s the same way. A lot of programming, I wouldn’t say design because design’s a little different, we do design and development. A lot of development shops are kind of little dog eat dog, kind of situation. People can be arrogant, they can make fun of other people’s work, and that kind of stuff. We really hire and try to promote a, you can be critical and explain problems, but do it in a supportive way and that can’t be in a mission statement, it can’t be something you announce in a meeting. They have to live it every day and especially new people, it takes them awhile to get deinstitutionalized and understand that you can make mistakes, you can put your head above the fray and it will not get chopped off. Every once in a while someone does and I have a private conversation with them and let them know how they were really not being supportive and our team’s awesome, they all want to be. It’s almost never malice, it’s always just they miscommunicated and they didn’t understand what they were doing.

KEN: Well people are messy, right? That’s just the nature of the beast.

JAMON: This highlights one of the aspects of almost everything within Infinite Red and that’s where we try to design things for iteration over perfection. So even things like support, supporting our people we are iterating on how to do that. We’re trying to have a feedback loop, there has to be some level of learning from our mistakes and then continually getting better.

There are some things where someone will take on a task as a group that we decide, were going to do this thing and it’s actually a very difficult technical thing or it’s a very difficult societal thing, where we’re going to build a new AR system or something and the tools are not there and we have to build all that. So there are hard technical things that are…

KEN: There are, but-

JAMON: But I think you’re right Ken, in the interpersonal stuff kind of always comes back to that, as far as the things that end up feeling very difficult and very hard.

KEN: So just to take that, so let’s take like, the Manhattan project.

TODD: Why not, take it…

JAMON: And of course that was the project in World War 2 where they were developing the nuclear bomb.

KEN: Right, so definitely some complicated ethical angles on that one, but how do you do that? Well, you attract the world’s greatest scientists and put them in one place in New Mexico, and then you give them the tools that they need to work with and you give them a goal that you can align on. In this case, win the war.

TODD: Kind of like Breaking Bad.

KEN: Boy, our examples ar going really dark here. (laughter)

TODD: Well they brought world class scientists to New Mexico-

KEN: Let’s pick a better one because it still works, right? If you’re not just one person sitting in a room, working on something hard. Not to take anything away from that because a lot of amazing things have come out of one person sitting down with a problem. I think that’s a different question than what we work with ever, right? I think we could probably have a whole podcast on how do you recognize a good engineer for example and I think that’s an interesting question but it’s a little different from the question of how do we as a company work on that. Because that really is about: how do you set up an environment where people can do their best work? And how do you hold people accountable? But also make sure that they are not held back by lack of resources. And those resources can be physical, tangible but in many cases they are emotional resources or organizational resources.

Especially in a software business, I think that it’s exaggerated in a software business and that dynamic also is worth a whole podcast because of the dynamics of software and how they’re different. Because there’s nothing to buy, right? Once you have the computer, you’re done. What that leaves is all these other kind of softer, squishier resources that people need to do their best work.

JAMON: One example of this is an internal tool that we’ve been working on that is intended to increase the efficiency of certain types of tasks. It’s not something that’s open source at this time, so I’m not going to go into a lot of detail, but I asked the team that was behind it why we weren’t necessarily realizing some of the gains that we had anticipated to start with and interestingly, a lot of the responses were, really had nothing to do with technical issues or anything like that. It was policy related things. Some things that we were doing that were sort of handcuffing them in some ways and there were reasons behind those, there were sort of organizations reasons, strategic reasons behind some of those policies, but it allowed us to look at the end result of this difficult problem that we were trying to solve, and make some decisions based on values and trade offs that were more strategic in nature that we didn’t realize were holding them back as much as they were. So that’s an example where we had a hard problem and, unbeknownst to us, we were making some decisions that were making it more difficult for them.

CHRIS: When does extreme personal support diverge into collaboration? Todd mentioned that you can hate the people that you’re with and still collaborate, but what does successful collaboration look like?

TODD: I would say successful collaboration is a multi-faceted thing. One, is the stress level of the people doing the collaborating. Two, the most obvious, is a successful work output of that collaboration. Meaning you accomplish your goals, hopefully in a creative, high quality way. And then three, from a business standpoint, that it was the return on an investment of that collaboration was good.

JAMON: I think those are good kind of high level metrics that you can use. Another way to do this from a more granular level is to watch how people interact. So some people, for example me, may come into a meeting and may want to kind of expose that this other person is not doing their job or something like that and that’s not a very particularly constructive way to approach this. But if you watch the successful collaborations that happen, they go into the meeting with a question and they go into the meeting, we have a challenge in front of us. How can we solve this? They get the people involved that need to be involved and don’t make the meeting too big, but they make it just big enough and that’s a characteristic of a good collaboration when everyone can go into it with an understanding of a problem, be able to provide their perspective and then the group can come to a conclusion. It’s part of this overarching concept of psychological safety that we talk about a lot at Infinite Red that leads to better and better work.

CHRIS: We’ve got extreme personal support, we’ve got collaboration, what about transparency? How critical is transparency in difficult work and in doing remote work?

JAMON: One of the things about transparency that’s important, or why transparency is important is this idea of trust. Because trust underlies a lot of dynamics within a company and if people feel like you’re being purposefully opaque, they may feel that you’re hiding something, they may feel that you don’t trust them with the information, you don’t trust their opinion, you don’t trust …and then when you don’t have a high level of trust than a lot of other things fall apart. You don’t get that collaboration, you don’t get a lot of other things that you really need. So transparency is a prerequisite to building that trust. When we’re able to be open and honest with our team about struggles or how we approach things or issues, were not necessarily saying wide open, everything is just hanging out there, but at the same time we do want to have a high level of transparency and ultimately we have to actually trust our team in order to do that. It can’t just be something artificial, it has to be something where we actually do trust our team.

Again, it’s like there’s not this formula where you just say do a whole bunch of transparency and everybody will trust you. No, what you have to do is do the hard work to build that trust. The transparency is a part of that and then that is something that you continue to do.

There was a situation where we implemented some new business policies, business way of doing work. Todd was intimately involved with that throughout and all of us were really and some feedback we got afterward was that they didn’t feel that there was quite the transparency that they had expected. Felt like a bit of betrayal of trust, and we heard that, we heard that loud and clear. We told people we heard that loud and clear and we changed the way that we implemented larger company-wide changes in that way. It can be a little difficult, just being wide open sometimes will expose you to knee jerk reactions, or a lot of different things that can sometimes bite you, but it’s worth it in the interest of establishing that sort of trust.

TODD: In what ways are we transparent and what ways are we not transparent?

JAMON: Well one obvious way is that for most of our engineers and designers, we actually have a transparent pay scale. People actually know what other people make salary-wise. We get this feedback sometimes, someone will say, ‘I think this person is leveled too low, I think they need to level up, I think they’ve been doing good work.’ Without that level of transparency we’d never get that feedback because people wouldn’t know and you could easily have a situation where someone is underpaid and we’re not getting the feedback that that’s the case.

KEN: Chronically underpaying someone can be extremely expensive.

TODD: Ironically.

KEN: Because you can lose your best people that way. So we try to be super involved and see everything. Of course, we try, but that stops being scalable after a while so we have to have mechanisms in place that encourage the right information to come forward.

TODD: Jamon mentioned our transparent pay scales. If your company is telling you not to talk to your co-workers about how much you make; A, it’s ridiculous because you’re going to do that anyways, especially with people you’re close with and B, it’s a red flag because why? I know why they do it because it’s easier. Having a pay scale, everyone can look at a spreadsheet to see where everyone is placed and that kind of thing. It’s much more challenging from our perspective because you can’t just, such and such you know we want to give them more money for whatever reason, maybe a political reason or whatever, it doesn’t matter. You can’t just give them that because that’s not the level they’re at, so it’s very fair and the transparency is nice but, I’m not going to go into it right now but we’ve had many situations where that’s been difficult for us. Would’ve been easier just to have a normal secret pay for everyone, but not all of our team enjoys that as much as some other people. Some people really enjoy that and it also gets rid of problems like inequity between say genders, or race or anything like that because everyone knows what everyone makes.

So that kind of transparency is great. Some transparency, I don’t think we are transparent, not because we don’t want to be, we’d love to be, I personally am a very open book person. Literally if someone asks me a question I’ll answer pretty much anything. I won’t answer about someone else, like if someone’s told me something in confidence, or I won’t talk about my wife or whatever but anything about me I’m very open. But, I know not everyone is that way and there are various reasons why but as a company, we try to be as transparent unless it’s actively going to hurt people and sometimes that happens. You have to weigh hurting people against transparency sometimes.

Sometimes people really, it’s not good if they see how sausage is made, just because they may not have the full information. Let me give you an example. So let’s say, this is hypothetical, this isn’t really what’s happened, lets say we’re going over financials once a month and we understand what’s going on and we’ve had lots of conversations about financials and then one month we’re going to be drastically under and us founders are going to have to put money into the company to keep it rolling. That’s one of those things where, if you just announce that we’re doing really poorly, we’re going to put money in so we can pay payroll, it can make people very nervous. Not because they’re not smart enough to understand, they just haven’t been sitting in those meetings and they don’t understand the big picture. You can say all you want that it’s totally okay, it’s fine don’t worry about it, but when someone’s doing a bank robbery with a gun, you don’t pay attention to what their wearing, you’re looking at the barrel of the gun. It’s just situations like that where we choose specifically not to be transparent. We default to transparency, but there are time when we choose not to be.

KEN: The first time I really extensively used what I would call social media at work was at Yammer, who semi-invented that.

JAMON: Ken, what was Yammer? What was the product?

KEN: Yammer was, I think it began life as basically Twitter for companies and it kind of turned into Facebook for companies. It’s very similar to that, so it’s, you have threaded conversations and notifications and likes, but it was aimed at organizations. It’s still going. They were bought by Microsoft, it still exists. Slack pretty much came in and sucked all the air out of that market, but, nevertheless, they had some pretty good norms for how you use a tool like that in business. One of them was, they had private groups, but they would always ask the question: Why is this private? Why is this conversation happening in private chat and not in a channel? Not that you couldn’t have things private, because there are certainly cases where you’d want that, but those cases had to argue for themselves, whereas, the prevailing mindset before had been private by default unless you needed to collaborate and so our default is: default to open, default to open channels and we do that in Slack too.

The things that we keep private are: client channels are private so that they don’t have to worry that random drive-bys are coming in and looking at their stuff. Few things like HR and finance are private and anybody on the team can make as many private groups as they want for themselves. In terms of the official channels, they’re as open as we can make them and that’s been part of that ethos is that it’s not all transparent, it’s transparent by default.

JAMON: But that even extends outside the company. On my Twitter I’ll answer questions and I’m often quite transparent about some of the challenges that we face. This podcast being another outlet for it, where we talk about what we do. It’s even outside of the company itself and I think that helps, it’s a part of who we are. Todd, Ken, and I initially started on some open source software and that’s the height of transparency there.

CHRIS: So kind of bringing this episode to a close; What advice would you give to other founders who are looking to build a culture of doing difficult work together as a team?

TODD: I would say the number one tip is just try, and keep on trying. There’s no magic bullet, I don’t know of any particular books you can read, every organization’s different and different type people and different type jobs have different needs, but if you just keep on trying and keep on making an effort towards it, if you stumble and you have an emotional moment and you swing your arms too strongly, get back up, apologize, and keep on trying.

JAMON: How do you eat an elephant? One bite at a time. You start there and you start in a way that is, you don’t have this master plan where you have to follow it exactly all the way through. You design something that has a feedback loop. Feedback loops are extremely important. You’ll hear us talking about that more, very often. You start with the first thing, then you start with the next thing and you keep working at it. We’ve never done a podcast together, for example, so we start with the first episode and we iterate on it and we look at what we’ve done and we see what we like and what we don’t like. We provide feedback and we provide feedback in a way that hopefully is constructive and is something that we can learn from. Todd mentioned another time when he and I collaborated on sales and how we would engineer the process. We did it that way. We started with the first sales lead and we evaluated how we did and we continue to chip away at it.

Any company that is going to take on a hard problem like that, start with the first bite and see how you did, and have a feedback loop and have a way of iterating, getting better and by the end of that elephant, you’re going to be pretty dang good at eating elephants.

KEN: That’s terrible.

TODD: Yeah, we apologize to the elephants out there.

KEN: Can we eat Republicans? (laughter)

TODD: Can we eat people at Google?

JAMON: I get the reference: elephants and GOP.

TODD: I don’t understand…

KEN: See, this is why we had to bring Jamon on because Todd wasn’t smart enough to get my jokes. (laughter)

TODD: This is all going to be cut anyways so … I know Chris.

JAMON: I hope not. (laughter)

TODD: We eat Republicans, really?

KEN: Yeah, no you’re right. They’re probably tough. (laughter)

TODD: It’s all the wrinkles from too much makeup.