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Show Notes

There’s no secret knowledge: This week on Track Changes, Paul and Rich are joined by Postlight managing partner Gina Trapani to do a follow up on our previous episode about intranets. Gina explains why she was annoyed that we didn’t know we had an intranet. From there we discuss why management and employees often need different tools and talk about what makes a good leader. Protip: a good leader is someone who knows how to limit stress, not spread it.

Transcript

Paul Ford Gina turned to us the other day and she’s like, “Oh yeah, it’s great!” And she looked at you and she was like, “You’re the one who creates anxiety,” and then she looked at me and she was like, “And you’re just incomprehensible.” [Music plays alone for 17 seconds, ramps down.] Rich!

Rich Ziade What’s up, Paul?!

PF You and I are pretty good at taking critical feedback from the team. 

RZ Long pause. 

PF Well there’s been a lot of critical feedback from the team over our time here, at Postlight. 

RZ Yeah. And we build on that, and we learn. We’re in a state of learning [music fades out]. 

PF So you and I said something [Rich chuckles]. We said something we shouldn’t have said on a podcast a couple podcasts ago. 

RZ What did we say? 

PF We said that Postlight didn’t really have an intranet and we needed one and we were gonna have an intranet within six months, dammit, and we said, “Let’s commit to this. Are we gonna commit?” And you said, “Yes, let’s commit.” And I was like, “Yeah!” 

RZ I don’t remember any of this but it’s in the transcript. 

PF So it went out and Gina Trapani—Hi Gina. 

Gina Trapani Hey Paul. 

PF Who is a listener of the podcast as well as a managing partner here at Postlight [all laugh]. 

GT “A listener to the podcast.” 

PF Well that’s part of your job! 

GT It’s well—yeah. 

PF Now that there’s more people working in marketing are you gonna stop listening? Be honest. Be [sing songy] honest!! 

RZ Do you ever think maybe she enjoys it, Paul? 

GT No comment. 

PF No! [Laughs] No, she spends so much time with us. Do you imagine what it’s like to have to be like, “I have to give up a bus ride.” 

[1:29]

RZ Well let’s start this podcast that way: why do you listen to Track Changes?

GT Because it’s important to know what y’all are putting out in the world in the name of Postlight [Paul chuckling]. 

RZ Fair. 

GT Also, I just like to bust your chops. So, listen, it was a couple of weeks ago, I’m walkin’ down, like, Caton Avenue, I’m walking to my bus—catch my express bus. 

PF For people who aren’t from New York City, that’s a very legitimate place to be walking. 

RZ Yeah [chuckles], she’s not playing games. 

GT And I got my headphones on and Siri gives me the little prompt, “There’s a new episode of Track Changes.” I’m like, “Oh, let’s see what Rich and Paul are up to today.” Next thing you know I’m doing the thing where I’m talking back at you, in the podcast [Paul and Rich laughing], on the street. Like it looks like, you know, normally you’d be in your car yelling at the podcast but I’m walking down Caton Avenue. 

PF [Angrily] “Are you—”

GT I was like, “Are you serious?!? What are you talking about you don’t know where to go to get policies?! Of course everybody knows that you got to Basecamp! That’s what we use here at Postlight, except for Rich and Paul.” 

PF I’d like to use Basecamp—

GT It’s so funny. We—

PF Except it is a giant jumbled pile of stuff. 

GT You know, it was, I dunno, it was about a year ago and we were like, “Ok, stuff in Slack all gets lost. Everything in Google Drive is sort of hidden. We need a place to organize our stuff. To have our schedule and our tasks and our documents.” And so this sort of committee—

PF What some might call an intranet. 

[2:37]

GT Some might call it intranet. And this kind of committee formed inside the company that was like, “You know, we need an easy way to track these things. We need a little bit more accountability, we need a way to create a task, and assign it to a person on a date.” And so we did a bunch of research, this committee, led by one of our managing partners, Jeremy Mack. And we were like, “Alright, look, it’s not the best tool in the world but it’ll fulfill a lot of our needs. Let’s use Basecamp.” And so got managers on board; got people on board; we spent all this time moving over our policies and documentation, and the company calendar, and all the all-hands notes. And we roll out Basecamp. And Rich and Paul hate it. 

PF I wouldn’t say ‘hate’. 

RZ [Under breath] I hate Basecamp. 

PF No [Paul and Gina laugh]. Here’s—I mean—

GT See. 

PF In a real way, the way that I work with and interact with people in the organization is not captured by the tool and so it’s an intense cognitive load every time I go in because I’m not living in folders, hutches, scamper pods—

RZ Basecamps. 

PF Yeah—

GT Projects.

PF Hampidamps. 

GT Yeah—

RZ Projects, is that the noun? 

GT There’s projects and there’s teams. And here’s the thing—

PF Listen, whatever the hell it is—

GT I don’t wanna get into this. I don’t wanna be necessarily a Basecamp critic or a cheerleader. I think it has its strengths and it has its weaknesses. 

PF It has a lot of users and is successful software as a service product. 

[3:50]

GT I just—I covered productivity tools and collaboration tools for years at Lifehacker and the big takeaway for me is that like it’s only whether or not you use it. 

PF Use it. Yeah. 

GT It’s not necessarily the tool. Of course you’re gonna use a tool that you really love. So it helps if you love it and you two don’t like it. So I was yelling at you on Caton Avenue because I was like, “We basically have an intranet but Rich and Paul just don’t look at it,” because it just doesn’t jive with the way you work. 

PF I’ll tell you what: you can say, “You’re welcome cuz we just saved you six months of development time.” [All laugh.]

RZ And so here we are with the intranet! [All laugh.] But! Let me ask you this case: the announcement to the company. 

GT Yeah. So when we have our all-hands, after the all-hands, we post that to the general Postlight HQ on Basecamp. Like that’s a message that gets posted and there’s a snippet in Slack—

RZ Effectively the transcript of the all-hands—

GT The transcript; the agenda; all the things that we—yeah. 

RZ Ok, but what if we just need to announce something. 

GT Like I said: it doesn’t cover all the use cases. I mean, we’re a pretty Slack-centric culture at Postlight. 

RZ There is that. 

GT So there’s General, right? Something in General. 

RZ General channel in Slack. 

GT Yeah, we don’t do the all employees memo. 

RZ The challenge with that is that stuff gets washed away. 

GT Yeah, stuff—Slack is—

RZ In Slack. 

[4:59]

GT Yeah, it’s a river that’s constantly just sweeping away. For sure. 

RZ I’m sort of persuaded by—

PF Fine. I’m happy that we—

RZ I mean it’s weird I feel like I lost the battle. I still won’t login to Basecamp [Gina laughs] but I agree with Gina. 

PF Hmm, I just feel like the six months of development time we just got back—that’s good news. 

GT I arrived at the office and I walked up to Paul and I said, “Paul, what is wrong with you? We use Basecamp. Login to Basecamp right now.” And Paul was like, “No, no, I don’t know—I don’t—” And I said, “Do it.” And I made you login to Basecamp and then I said, “Ok, Paul, click on the ‘hey’.” You got a little red ball there. And he was like, “No, no—” I said, “Click on it. Click on it.” 

RZ I hate that thing. 

GT You did it and then it was just—

RZ Can I talk about how much I hate that ‘hey’? [Gina laughing

PF “Hey.” 

RZ “Hey. We don’t know how fonts work. Look at us.” 

PF “Hey.” 

RZ “Hey.” What’s the ‘hey’? 

GT It’s your—

PF Notifications. 

GT It’s your notifications. It’s your, “Hey, you should know about this.” 

[5:41]

RZ “Things you should pay attention to.” 

GT Yeah. 

RZ Right? I get this email every morning. It says, “Hey.” And I went in for the first few times and then after a while I said to myself, “This isn’t actually lining up with how I think about prioritizing my day,” and I never went back in.

GT I mean it’s completely fair. 

RZ You know, this is interesting, we’re glossing over it but I don’t know why that dissonance exists for me with Basecamp. It didn’t click in. Another managing partner, Jeremy, also pointed out that Paul and I are terrible because we won’t use any of the tools. And that’s been said to us explicitly. 

PF That’s not totally true. 

RZ Which is—by the way, speaks to the open communications that exist amongst partners at Postlight. 

GT Yes. 

PF Absolutely. 

RZ But also how much it hurts to hear that. . .in my heart. And I thought about it some more and I said, “Well wait a minute, am I like slowing people down? Am I unproductive? Am I hurting other peoples’ productivity?” 

GT Wow. That’s a moment of self-reflection. Ok. 

RZ It is! And I also realized another thing which is, look, I’m sitting at the top of a company, who’s gonna drag me by the ear into the room and say, “Dude, could you just open up Basecamp for a minute and just do some things.” Which left me thinking, you know, I think you need to really empathize with where everyone is sitting relative to you. 

PF Yeah. True. 

GT Yeah. 

[6:50]

RZ But then ten minutes later, I said, “To hell with that! I’m the President of Postlight.” [All laugh.]

PF Well this is—this is [Rich and Gina continue laughing] an actual paradox of leadership, right? Which is [Rich coughs] that a) every leader is a bottleneck. 

GT Yes. 

PF They’re perceived by the people on the ground as a bottleneck [yes]. It doesn’t matter if you’re inspirational or not. Everybody knows that if they come to you—

RZ Mm hmm. 

PF—it’s gonna slow everything down. And if you get involved it can actually create a failure state and no one knows how to tell you that. And so then you have to, like, set up, you know, these sort of buy in moments. 

RZ I’ve had people tell me they needed a thing. I’ve failed to get the thing to them. Time will pass. It will pop up into the essentially scrambled guacamole that is my brain and remind me of how I owed someone something 48 hours ago, and I’ll walk up to them really embarrassed actually—

GT Yeah. 

RZ Not embarrassed. I am the President of the company but not feeling good. Being completely sincere: not feeling good. And you know what they would say to me? They would say, “I could tell you were really busy.” And I felt even worse when they said that to me.

PF Yeah. 

GT Interesting. 

PF Cuz you were really busy on, like, YouTube. 

RZ I watch some YouTube once in a while. 

PF Same level of type—

RZ No, but that’s no excuse! That’s no excuse because they asked me for a thing and I actually take pride in the fact that I’m gonna get you the thing. I’ll never do that to a prospect. I’ll tell ya that. Never slip on a prospect. And no, I’m not screwing around. I had other things. 

GT You had other things. And people can see it. We’ve got an open floor plan. You can see if we’re rushing around and dealing with a fire or getting a proposal out or—

[8:17]

PF Yeah but people give us a lot of—

GT Leeway. Well cuz you’re the bosses, right? 

RZ I know but that’s not fair. 

PF It’s not just not fair, it actually—

GT Fair?!? It is what it is. 

RZ It is reality. I think that’s the—it is the dynamic that’s in place, right? 

PF Here’s where it’s—

RZ “I’m not gonna go yell at the boss cuz he told me he’d get me the thing by 5 o’clock.” 

PF But here’s where it’s a failure, right? Which is that we are, as the owners and managers of the business, really motivated to get rid of bottlenecks and get clarity, and to move things along. And so, like, people are protecting us but the reality is we’d rather be bothered, so that we can unlock whatever’s going on. And it’s just really tough to manage because also, I need the protection. If I had to manage my own calendar fully, I would be about a third less productive. 

GT Right, you need somebody tappin’ you on the shoulder, “Hey, remember this?” 

PF Yup. 

RZ I mean we’re not at that level but there are those executive assistants that are like superheroes. 

GT Watching your calendar; putting your lunch in front of you; and getting—arranging the call and being like, “Oh, actually they’re running ten minutes late.” “I’ll call on the Lift.” 

RZ [Crosstalking] There’s a binder that’s handed to you for that meeting. 

GT Yeah, being like, “Yeah, there’s a stain in your shirt. Here’s the clean one.” 

RZ Mm hmm. Yeah. 

GT Yeah, yeah, the really good EAs are doing that. 

[9:22]

RZ We’re not that. 

PF Well they’re essentially product managers where you’re the product. 

GT [Laughs] Exactly. 

RZ No, that’s right, that’s right, that’s a real thing. And also they will tell you. Their success in failure is based on actually catching you off your game. That’s actually what they do. But someone who is on the ground—we’re outside the reporting structure. It’s silly to look at an org chart and put us at the top of it. That’s not real. That’s actually not what’s in place. What’s in place is an org structure that makes sense: designers, lead designers, directors of design—because they’re talking to each other, they’re communicating; they’re collaborating; they’re educating each other. And then there’s us who are a little alien but every so often they have to come out of the structure and ask us for a thing. And I think we have to be more sensitive—and I think leaders can learn from this—to understand that they’re not gonna go much further than that. They’re not gonna [right] go and jam this into your priority list. 

PF Yeah. 

RZ They’re just gonna ask you once. Probably not bring it up again. And that’ll be that. You know what I’ve seen people do? I’ve seen people say, “Could you just go over to Rich—” They’ll go over to someone else like another partner, and say, “Can you tell Rich that I need that thing?” 

GT Well, I mean also because you, as the leader of the company, are also the ultimate customer of their work. So if you were the blocker, that person isn’t going to get [laughs] dinged. If you were the blocker, you know? The other interesting thing—you know, I’ve been in Postlight for four years and I started and I’ve kind of moved up a few levels, right? So I was closer to an individual contributor when I started and now I’m closer to you all now. And it’s really interesting just to see how at the higher level your tools are different and your view on what’s going on in the company is different; some of your prioritization is different. And so, like, it’s interesting, you know, we’ve had other tools similar to Basecamp: Clockwise and Paper and things kind of come up from the ground up and people start to use them and I’ve had this eyeroll-y, like, “Ugh, like that’s just not for me. I’m not doin’ the work on the ground, so those aren’t the tools that I use.” So I’m not in that system, so I’m not prioritizing those things. I completely, you know, empathize with you all being like, “You know, this just doesn’t work for us. This isn’t how we work.” 

PF It’s not just that, too, I mean our view of the world, foundationally—I sort of knew this about executive work but I didn’t fully internalize it until we had this role which is that it’s all about risk management as opposed to getting something done. So everyone in the company has to get stuff done. 

[11:26]

GT Yes! That’s a very big shift. And one that I am still making. 

PF Well here’s why, it’s because all the things that actually gave you a sense of productivity and meaning in your work: “I got it done. It was very close to the deadline. It was really high quality. I presented to the people. They gave me some feedback and I was complete. I went home on the weekend; I felt, ‘Boy, did I do a good job.’” 20 years of my life. Now I’m doing this—it’s more like, “That looks good but that client has some ups and downs and I’m worried that they’re gonna reject it, at which point we’re gonna slip on two or three other things. I don’t wanna demoralize the employee by giving them feedback about something that’s out of their control but we do need to manage the situation. Who can I talk to? Because I can’t get directly involved. I can only move things around through influence.” 

GT Yes! 

PF “Because I can actually see a weird fireball. Then again, I might be worried about absolutely nothing. Maybe I should just shut up and let it happen and see what happens because I don’t think it’ll blow up that relationship.” So repeat that 60-70,000 times a day and that is running the company. 

GT Yup. 

PF And you’re experiencing this more and more. Rich has been doing it for ten years longer than I have, and that means that my tools don’t really matter that much anymore. Frankly. Like I make lists; I have to keep things in my head; I look through the cards in the CRM to know about, you know, sales leads I need to keep on top of. I don’t care too much anymore. And I love my tools. 

RZ Good leadership translates stress to tasks. If you are a good leader, you are not passing down that anxiety and that stress but instead what you’re doing is you’re delegating and holding people accountable to things that they can pr—Look: I make more money than most of the people here at Postlight but there’s a barter there. I worry about the existential threat to Postlight—

GT Mm hmm. 

RZ All the time. We’ve come to an agreement and that is I’m gonna do my job really well. I’m gonna play my role really well. You worry about the big thing and you can keep—I’ve had—we’ve had partners here tell us, “I don’t want what you have, in fact. This is my line. I want no more than this. I wanna do good work; I wanna build a great team; I do not wanna worry about whether this thing is gonna burst into flames or not.” They just don’t want that stress in their lives. 

PF Let’s be clear because—

[13:34]

GT That’s a particular personality and capability and desire—That’s a thing. 

RZ It is. 

PF So I spent a lot of time understanding that barter in my life and I used to think, like, “Give me the pain, lemme see how I do.” I mean I will say, anybody listening to this who’s in the company or outside, who wants to stress. . .talk to us! 

RZ [Laughs and Gina joins] There’s an opening! 

PF Yeah, no, there’s more money for more stress. 

RZ For horrible, dystopian job description—

PF If you can take just a little bit of this pain away, I will compensate you [others laugh]. 

GT No but it’s true though. Taking uncertainty and ambiguity and stress and risk and turning it into a plan and here are the next steps and this is what you’re going to do. And having—shielding the folks underneath you from the stress but giving them, you know, solid next steps—

RZ That’s a great leader. 

GT That’s—that’s the job and it’s—

RZ The worst leader is the one that unleashes it on their people. 

GT Yeah. 

RZ Not in stress but in power; in fear; and—

PF Oh the worst I ever saw was a person who stood in front of a room of 50 people and went, “If we don’t get this, I will get fired.” 

GT What. 

RZ How is that gonna inspire anyone?!? And this can translate into how you are as a human being. Some people let it out on their people. 

GT Yeah. 

[14:42]

RZ And then when they go home they let it out on their family [laughs] and so that’s real. 

GT Yeah

PF Yeah. 

RZ And that’s hard because I’d like to think that my stress is compostable. Because otherwise if you bury it’s a horrible thing—it turns into acid reflux or something. 

GT Yeah. 

RZ You know, you try to do other things that are gonna let that energy out. So it’s just sort of—

PF I’ve seen you bury your stress. It lasts about ten to 15 minutes and then—

GT And then what happens? 

PF And then the explosion occurs. “You’re right, I’m just gonna take this at comes. I’m tired of freaking out about everything. I’m just gonna just calm down [Rich laughing] and let this play out.” Tick. Tick. Tick. “What the hell are they doin’?!? What are they doin’?!?” [Others laugh boisterously]

GT And then you have the conversation like, “Why are we doing this way? This doesn’t make any sense.” And you’re like, “Uh oh.” 

PF It’s actually real. Like, the—I’ve learned this over and over, right? Like, for me to be successful. . .here and with other people, I can’t just let what’s in my brain come out. I have to, literally, I mean, and I think this is the weird side effect—and if you talk to other people who lead companies this happens—you say the same damn thing over and over and over again. You never stop saying it. And then every year or so you kinda change the script. You go like, “Ok, you know what? I learned that that’s not working over here. I’ve been saying, ‘This is the process we should follow’,” And we literally just did it this year. We introduced a new acronym for how we should think about engagements and—

RZ Framing our thinking in a big way. 

[16:05]

PF Yeah. I would reboot and restart my thinking and come up with new processes—and I’m not kidding—on like a daily basis. Right? That’s how my life used to go and if I do that now and I do that with Rich—

RZ It’s chaos. 

PF It’s absolute chaos for everybody. So yearly or quarterly—and that’s where those time frames come out of, right? Is that that’s a reasonable amount of time to ask people to learn to work and think in new ways to be more effective. And coming up with that it’s so strange to sit in a room, and think for a month and a half about an acronym and how we’re gonna communicate it. 

RZ It is and I can tell there’s still a lot of people who are still processing it. 

GT Definitely. 

RZ Even to this day. They’re still not really fully getting what it is because people look at anything like that. Through the lens of the metrics of their own success. Always. They’re wondering, “How did I do on this score? They’re scoring me differently now. What is this new measurement tool that they’re using?” And that’s normal, like that’s not selfish at all. That’s just people thinking professionally, “How am I—” 

GT “How do I succeed at my job?” 

PF This is—

RZ “How do I succeed at my job?”

PF I’ll tell ya—this has been hard for me as a writer because as a former journalist any confusion was bad. So you craft all the confusion away. People have to get the point of the story or you’ve failed. Whereas in this environment, it’s utterly fine for them to go, “What’s this bullshit?!?” For like a week or so and then go like, “Oh, I guess this is real. Eh, it’s not so bad.” Because it’s their lives, not just them reading that freaking article but. . .boy, did that take me a while to learn. 

RZ What does this mean for me? 

PF Yeah. 


GT Yeah. 

RZ Is the immediate reaction to just about anything you put in front of—You know, there’s—There is the aspirational sort of, you know, “We’re gonna make the world a better place. We’re gonna get rid of paper towels,” or whatever it may be and that’s meaningful and people can latch onto that. We are the other extreme of that. We are an agency. We are for hire. We do frame ourselves in the context of a mission, around our craft, and doing good work, and—

GT Quality work. 

[17:57]

RZ Your quality work. But, it’s hard. It’s hard. Because people still are thinking about their trip to the Pacific. 

PF Because it’s really clear about what the transaction is here which is you come level up your career and you get paid a salary and you can either lock into the culture and stay or you can maybe one day you might go do some—Like, it’s understood what an agency is. When you go work for do-gooder organizations, it’s some of the most viscous politics imaginable. 

RZ Yeah, yeah. 

GT Yeah. 

PF Because there isn’t that like—

RZ [Crosstalking] It’s unbelievable. We witness it. It’s unbelievable. 

PF What I—What I have learned over the last couple of years, right? Is that that’s the healthiest, most normal thing: just always predict it and factor it in. Have an answer for it. What’s it mean for me? Well, let me tell ya. And—Like, that can be a slide in the deck. 

RZ Yeah. 

PF And don’t fight it. It’s not a bad thing at all. It’s totally—it’s a job. 

RZ Back to the intranet [Gina laughs]. Leaders don’t want intranets. Do you know what leaders want? Because intranets are communication tools, leaders don’t want that. Leaders want to be terminal. They want a dashboard. A dashboard is—if it’s a good one—an objective representation of various metrics of success or failure that they can stare at. And there are rarely humans on a dashboard. It’s usually metrics around—

PF Revenue. 

RZ Revenue; units sold; marketing spent and how effectively is that translating into clicks; et cetera, et cetera, et cetera, et cetera.

[19:20]

PF [Crosstalking] Right, cuz if we set up the process, we can’t then get involved in the process. 

RZ All we can do is hope to gain insights in the vulnerabilities of the system. 

PF Basecamp is about—

GT See the risks on the horizon before they’re upon us. Before it’s blowing up in our faces. 

PF So Basecamp is about process. It’s about getting things done, and often in a recurring way or as a group. 

GT Yeah, I mean, I think the impetus of the intranet conversation was like, “We use all these different tools; new ones happen here and there; how does anybody go to one place and know, ‘Where do I go to know what the next company event is,’ or, ‘Where do I file my expenses?’” Right? I get that and that’s a communication tool for people. It’s empowering people who work here, right? Which is also like a big—

RZ Absolutely. Absolutely. 

GT—you know, part of the job of leaders. Their dashboard. . .to get stuff done, without having to ask or check with someone, and what you’re talking about is the leadership dashboard of, “How do I see those risks, you know, on the horizon?” That’s actually something that shouldn’t necessarily [correct] be exposed to everyone if part of your leadership style is to shield the floor from anxiety and just do great work now because that’s gonna bring us great work later. 

RZ Yup. I’m not sure if there’s anything worse than a leader descending in altitude, like 50,000 feet, joining an email thread, and applying their very particular lens, and imposing themselves on the work at that point. It’s almost like an audit. You’re just saying, “You know what? I gotta be able to spot check.” It’s like when they go and they ask for every thousandth packaged cookie box off the assembly line. I just gotta see one. “I get that sales are going good. You gotta get me a box of cookies. Every 50,000th is gonna go into my mouth.” 

GT “Give me a cookie. Why does this taste like cardboard?” 

PF Right, right. 

RZ Exactly. I get that. Because there’s no dashboard that’s really gonna let you do a better job than just spot checking what’s going on at any given point in time. 

[21:06]

PF Well, in—in our world, right? The equivalent of the 50,000 cookies is looking at work about a month ahead. Reviewing the plan when there’s enough time to give feedback on engineering and design. If I see it the night before all I can do is say, “Good job,” and clap like a seal. 

RZ We’ve been talking about what’s good, what’s bad, and communication and whatnot. Did you guys read this article about this woman executive—

PF You can just say, “Executive.” 

GT You could just say, “Executive.” 

RZ I’m sorry. 

GT That’s alright. 

RZ I don’t know her name. Jen Comber [Stephanie Korey] or something? 

GT Hmm. 

PF No, I don’t know her name. 

RZ It’s the Away bag. 

GT The Away luggage CEO. 

PF Oh, the Away person, yeah. 

RZ For those that don’t know about this, Away is a very fast growing startup—I don’t even know if they’re a startup anymore. They sell travel bags, like the roller bags that have like a little charger in ‘em and—

GT Luxury hard bag luggage. 

RZ Hard bag luggage. 

GT Former Warby Parker folks, have lots of experience in retail, kind of the Instagram bag. 

RZ Yeah, and more—

GT Luggage. 

RZ—mail order driven and connecting with millenials, et cetera, et cetera. So this woman is the CEO, I believe she was and now is again. 

PF Was. 

[22:09]

RZ And just an absolute lunatic. Just this overwhelming personality that just would insult, put pressure on you in an undo way, ask you to stay late, which you can ask people to stay late. You need the help. But would just take an absolute shit on you if you didn’t. Just nightmare—

GT Her employees would hear her typing and could tell by the rate of how hard and fast she was typing how bad the Slack message was gonna be and they had like a total transparency policy in Slack where every single channel was public and DMs were forbidden, so everyone got upbraided [Paul and Rich crosstalking] publicly by her.

PF To be clear—where—where was this article published? I think it was—was it Buzzfeed? 

GT It was The Verge. 

RZ The Verge. 

GT And it was a while ago. 

PF So a little while ago an article came out—we’re not talking out of school here—if you read the article, the actual messages from this person were pretty intense and it was kind of a lot to put on your call center staff. 

GT It was a lot. Yes. 

PF Right? Like it’s—these weren’t execs who were sitting next to her who were like, “Ok, here we go. I’m gonna take my two by four to the head.” 

GT Right, these on the ground customer service folks who were dealing with a cue of customers.

PF So it was so kind of toxic that it became a big story. 

RZ And I wanna go back to what I said before which is a good leader translates stress to tasks. She didn’t bother with the translation, she just literally poured her stress—

GT She just funnelled it. 

RZ Poured her anxiety right onto people in a toxic and unhealthy way and in a way that wasn’t gonna scale. I bet this isn’t a bad person. I bet it’s a really smart person. And I bet this is not a bad or evil person. You know, when you tell a story like this, this is someone who is gonna make a lot of money or is making a lot of money [clears throat]. 

[23:43]

GT Very driven, very ambitious. 

RZ Type A. 

GT On top of it. Detail oriented. 

RZ But if you don’t know how to translate that in a way that people want to do it for you, rather than out of fear or just like, “Oh God, here we go again.” 

PF Well they’re gonna call The Verge and share screenshots of Slack messages. 

GT Yeah.

RZ They’re gonna burn out; they’re gonna make more mistakes. I am not the polar opposite of this. Just to clarify. I try to be self aware but I envy leaders who whisper to their group and everyone busts their asses—

GT Lines up and busts their asses cuz they want to. 

RZ And they want to for the leader’s sake and for their own and they feel connected. That’s the hard part. 

PF There’s always a sense of the stick well behind that carrot though. You know, people are—sometimes people are motivated by love but I don’t know if I’ve ever met anybody—it might be you really like and respect them but you’re really afraid to let them down or to be met with their disapproval. Like it just is what it is.

RZ But that’s ok, right? There’s disapproval and there’s respect. What are you looking for in the end? You’re bustin’ your butt because bonus time—when bonus time comes, they’re gonna say, “You know, he busted his but.” So you get a better bonus. I mean what motivates people? You like your work environment; you like to support your co-workers; and you wanna make more money and get promoted. Like we’re allowed to say that in 2020. You know, in many environments where people speak more idealistically, ultimately money is very meaningful because it’s freedom for people. And that’s ok! That’s totally normal. That’s ok to be driven by that. As long as there is respect in the environment and there’s opportunity that’s given, right? 

PF And fairly given. That’s a big—a lot of people what people are upset about in the world right now is the opportunity fairly distributed. 

[25:20]

GT Compensation’s obviously a very big part of it. But there’s also just like status amongst your peers. I’ve worked with execs who I admired so much and I wanted to gain their trust so I could get closer to them to learn more, like that also can be a motivator for a leader or for someone who wants to do better and be a leader. It is tough though. There’s ruling by love and there’s ruling by fear and both of those things come with their difficulties. 

PF Well, neither one’s ideal. 

GT Neither one is ideal. 

PF It’s an unholy—

GT Or a combination of those things. 

RZ It’s always a combination. That was a wonderfully juicy story that had an extreme example of someone that, who knows, right? Maybe 90% of the time you’ve got a totally brilliant, pleasant person to work with, but you’ve got cut and paste evidence [yeah] of this nightmare scenario, right? That should never get to that. I know I can be tough at work but I’m also aware of it. Sometimes I ask people to hear me out, like if I need to talk to person X, I’ll speak to person Y for a while about it and sort of let it out a little bit before I speak to person X, just to sort of let some steam out. That’s normal. We’re human. I mean this is—

GT Yes. 

RZ—part of it but disrespect and threat—I mean bullying, she was a bully. 

GT She said she looked at those transcripts and felt embarrassed about things that she had said. 

RZ Right. 


GT I mean certainly her failure was the way that she spoke to her staff. But there’s also this bigger thing of as the CEO of the company, she didn’t have the training in place and she didn’t have the staff in place that she needed to accomplish her goals. And that feels like a bigger failure. Why does she have to ask her—

RZ She failed to scale. 

GT—to work the entire holiday? Because she hadn’t hired the folks that she needed to hire to get—You know, it’s all related. 

[26:54]

RZ She was late to the game. She was reactive rather than getting ahead of it and—

GT Their victims of their own success. The company’s doing really well, the brand was great, and they had more inbound that they were equipped to handle!

RZ Right. 

PF I gotta say, too, I think if it had been a dude, he would just be an asshole boss. 

GT  It’s true. It was a juicier story because it was like—

PF A young woman. 

GT A young woman. 

RZ I think, look, this is—this podcast is entitled, “Intranets and How to Treat Each Other as Human [laughing] Beings.” 

PF Yeah, that’s right. Ok, how—[stammers, Rich and Gina laughingI mean we always try to leave with, you know, good marketing clues for people. 

RZ I think we’ve given a lot of leadership advice this podcast. I don’t know—

PF That’s right, so what is our big—You know what? Career growth. What’s your big advice for people who wanna move towards leadership? What do they need to do? 

RZ I would love to hear Gina’s response to that question because what we’ve watched with Gina is someone that went from senior but you know kind of amongst the group right to the top of Postlight. So, what have you learned? 

GT Learned so much here. I’ve been in school here. How about we said that—Postlight’s the biggest company that I’ve ever worked for, right? 

RZ Right. 

GT I’ve either founded my own companies or worked at pretty small [yeah] startups. I mean Gawker got really super big but I was really kind of only in charge of Lifehacker. So, I mean, this is literally the first company that had an HR person that I’ve worked at. So I wanted to learn. I came in with a sense of sort of humility and wanting to learn and I came in and tried to do a good job at my job and then see where else I could help. . .without threatening anyone too much [laugh]. 

PF Mm hmm. 

[28:18]

GT And then I helped where I could and when I couldn’t I said, “Can I sit in and listen? And can I ask some dumb questoins?” I mean you two, in particular, and everyone who listens to the podcast knows this, are very willing to share what you know and talk about what you think and share your opinions and both of you, actually, are naturally teachers. So that worked to my advantage cuz I could say, “Hey Rich, how does sales work here anyway? What does sales look like?” I didn’t have any aspirations, necessarily, to get into sales but I wanted to understand more. 

RZ You wanted to see how the machine worked. 

GT I did! I did. 

RZ You said it. I remember you saying, “I wanna see how this machine works.” 

GT Yeah cuz I was getting allocated to a client project and I was writing code every day, all day, but I was kind of like, “How does a bill become a law? What happened before that? You know, how did that—” 

PF Well you were seeing growth around you too. 

GT Yes. My whole career growth path has been driven purely by my own sort of curiosity and desire to just sort of help out where I could help out. I’ve stepped on some toes. I’ve made folks feel threatened or wonder what I was doing there. But that’s happened. 

RZ Gina, there is no ladder. It’s just [Gina laughing] other people’s bodies. 

GT That’s true. 

PF Yeah. 

RZ One sentence response—

PF Living bodies. 

RZ [Laughing] What’s the—that’s even worse. 

PF Yeah. 

RZ You’re like knocking the wind out of ‘em. 

PF I know, I know. 

[29:30]

RZ One sentence, one piece of advice you’d give to someone who wants to elevate into leadership. 

GT Go in not trying to prove what you know but learn from the person who is ahead of you, aside you, has a different experience from you. Go in with that sense of—

RZ Good advice. 

GT—humility [humility] and openness. “Tell me what you got. Tell me more about what you do.” 

RZ Just a point of pride about Postlight: we didn’t talk about politics, and how people find their way up and wriggle their way through an org by aligning and one of the things I’m proud of at Postlight is that there’s not a lot of it. You can’t buddy-up to leadership to get ahead at Postlight. And unfortunately that’s not how it works in many, many, many places. And that is part of it. The good places actually give you opportunity and support you to grow into leadership. 

PF Well they have to let you advocate for yourself without throwing somebody else under the bus. 

RZ Right. 

PF And that is. . .rare. Something that we’re mindful of and that we’re gonna try to preserve because as we grow it is—people just start to go, “Well, why would you give that to Sally?” 

RZ Yeah, we’re small and we’re growing, so it’s an unfair comparison in many respects. 

PF Oh yeah. 

RZ A place of 20,000 is gonna have what it’s gonna have but that’s real. 

PF I have a pretty simple rule for people who are trying to figure out the next step is just you have to figure out how to stand next to the person who is doing what you wanna do. It’s the simplest thing but it’s like if you wanna be a writer, you have to go be near the other writers, and if you wanna go be—

GT Absolutely. 

PF—an executive leader, you need to go work for an executive leader. There’s no secret knowledge. 

[30:58]

RZ The hard stuff really shows itself fast when you get next to the leadership. Yeah. 

PF Trust me, billionaires are reading the same magazines that you are. 

RZ Yeah. Totally. 

PF Like it’s not—they don’t have like a super secret everything, unless they want it and then they can have that [all laugh]. 

RZ Well, there is that disaster chamber or whatever it’s called. 

PF Oh yeah there’s always one of those. Like, you can get your own apocalyptic fallout shelter. No, no—

RZ They’re all building those. 

PF They all get nice things! They get private jets and you know, extra helpings. You can spend a couple million dollars and get much better information and then that’s kinda it. You know enough! Just go stand next to people so you can learn how it works. 

RZ We’ve been talking about Postlight a lot. . .Paul. 

PF You know we have. We’ve been talking about leadership. This is how you make the products. We talk a lot about engineering, design, and product management but the actual origin of making the products is conversations like this. 

RZ Oof! That’s heavy. 

PF That’s real because our clients aren’t usually engineers, they’re like leaders in the org and—

RZ A lot of strategy, a lot of conversation—

PF They might have been engineers. 

RZ Yup. No, it’s real. 

GT They’re trying to change something about their business and their business is made out of people and they have to communicate those changes and the impetus behind them and what the software—what the role of software is gonna play in them.

RZ We got some really cool, exciting stories, case studies to share in the near future around the work we’ve been doing. Some really cool work’s been happening at Postlight. So we’ll be sharing that soon. We’d love to hear from you! How should they reach out to us, Paul? 

PF Well, let me throw that question over to Gina. She’s leadership. 

GT You should send us an email. . .to hello@postlight.com. 

PF Oh my God, the way you—you make it sound so much nicer. 

RZ Much more pleasant. 

GT  You can also tweet at us. We’re @Postlight now. We dropped the studio [Paul and Rich crosstalking]. We’re like Cher or Madonna. We’re just Postlight. Yes. 

PF Thank you to our friends at Twitter. 

RZ Yes. Thank you Twitter. 

GT Yeah, thank you Twitter. 

PF Hey, Gina, thanks for giving us the truth! I’m ready to lead.

RZ Thank you, Gina. What a great podcast. I’m ready to lead [mm] after this. 

PF We have [laughing]—

RZ Have a great week everybody. 

PF We left a lot out. Let’s be honest.

RZ Yeah, we did, we did. 

PF But we’ll get to it—

RZ It’s part of a series [laughs]. Part one of ten. 

PF This is episode 200 so by about episode 600 we’ll some frickin’ clue what we’re doin’ [Rich laughs] but hello@postlight.com. We kinda do know what we’re doing, we’d love to talk to you. 

RZ Have a great week [music ramps up, plays alone for three seconds, fades out to end].