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The world of software and technology has never been so employed. From product designers to product managers to engineers, the need for finding new talent abounds. But what about retaining existing talent? Postlight’s dear friend and returning guest, Tim Meaney, joins Rich and Paul to offer his tips for making your best talent want to stay.

Transcript

Rich Ziade Mmmmodern.

Paul Ford [Joins Rich halfway through the word] Mmmodern, meaning like a—

RZ You mean like really uncomfortable chairs? 

PF Or like a cool flapper in the twenties?

Tim Meaney [Chuckles] Yes. 

PF [Sings high-pitched] “All I do the whole night through”—Oh I’m sorry.

[Intro music plays for 12 seconds, ramps down]

PF Hey, Rich! Guess who’s here! 

RZ This guy’s leading the pack. In terms of—

PF Yeah, yeah, friends of the show. Friend of the show.

RZ—return visits. I think this is number four. 

PF Mmm. Old friend, Tim Meaney, podcaster par excellence. Tim, welcome back to Postlight Podcast. 

RZ I wanna—before we get started [music fades out completely] I wanna pitch some of our best podcasts ever, actually were with Tim. The one about just the greatest software ever. 

PF That was—That was about 200 years ago. 

RZ It was—it’s really, really good. Look it up, I forget what the title is, you’ll find it. Just search Tim Meaney Postlight Podcast. It’s really good. I think we ended we ended up with Excel being the greatest piece of software ever but—

TM Still undisputed. 

RZ Still—[chuckles] It’s still leading the way. 

PF No, I mean it is though, actually, Excel runs the world. 

RZ VR Excel, no? 

PF Oof! 

RZ When you’re inside the cell. Ooh. 

[1:08]

PF You know they’ve done it. You know there’s a research lab at Microsoft where one day they came in, they’re like, “Shut it down.” [Laughs, Tim laughs] 3D Excel! We’re gonna be able to like—instead of sheets having to tab, you can actually fly through them.

RZ Rotate them.

PF You could fly through the spreadsheet. That’s—

TM What is Microsoft’s metaverse strategy for Excel? I wonder. 

RZ Don’t do it, Tim!

PF Well, there’s two things. One is that—that is essentially all the fun of playing flight simulator is doing a spreadsheet in 3D. So there’s that. They also have Minecraft. So, you know, you’re building things with blocks, that’s not a far reach to building things with cells. 

RZ Yup. 

TM Fair. 

RZ But! That’s not why we’re here. 

PF That’s not what this podcast is about. 

RZ Tim sent us a message, he said, “I’ve got an idea for a podcast.” 

PF Once you’ve been on the podcast a lot, you can actually say like, “Look, I could do a little better than one, you—I have some ideas for you.” 

RZ So we’re gonna talk about—

PF The metaverse! 

RZ No. We’re gonna talk about talent and retaining talent and keeping talent. 

PF Mmm! Talent. 

RZ The world right now is extremely employed. 

PF Yeah our world is super double extra employed. 

RZ Super double extra employed. Designers. When I say designers I mean: product designers, UX, UI designers, product managers—

[2:17]

PF Feeling designers, there’s beverage designers, really there’s designers everywhere now. 

RZ Engineers of all flavors—

PF Of course. 

RZ—are in extremely high demand. 

PF Love them too. 

RZ Postlight is an amazing place to work. And please come work at Postlight if you wanna work at an amazing place and learn from great people. 

PF Looks good. 

TM Are you hiring? 

RZ We are hiring across the board. 

PF Across the board. 

TM Hmm. 

RZ And we are hiring everybody. And, if you wanna surround yourself with like, just immensely talented people that are gonna help you grow, you should come work at Postlight. 

PF You know what else you should do is if you know anybody where you’re like, “That person would actually be happy there.” Tell us, we’ll reach out to them. 

RZ Yes. And who doesn’t want Paul “Flippin’” Ford reaching out? 

PF I don’t know if I was the one who was gonna do the reaching out? I thought maybe the recruiter that works here might do it. 

RZ Ok, fine. 

PF But I’m glad to be CC’d. 

RZ Paul—

[3:03]

TIM See this conversation is actually representative. Everybody likes talking about recruiting new talent. But I wanna talk about retaining existing talent. 

PF Ahhh! 

RZ Mmmmm! 

TM See that? 

RZ I wanna tee this up for you—

PF Wait, hold on, what’s talent? Can someone define it for me? Rich, you go and then Tim.

RZ What’s talent

PF What is talent? Yeah, oh everybody’s a talent expert! What the hell is it? You’re like—

RZ Look, you ask the head coach of a football team what talent is and if you ask the CEO of a consulting firm what talent is they’re gonna give different answers. 

PF I’ll tell ya—I have one definition for talent but Tim, what’s your definition for talent? 

TM People who work well with an existing team. We’re a team sport. 

PF Ok. 

TM So they’re bringing a particular skill that works well with an existing team.

PF Here’s my definition of talent: people who are obsessed with a specific form, and they need things to go into form and if they don’t see that happen, they get really anxious. 

TM Can we combine our two? 

PF No, they have to resolve it, right? So, to me, talent is a form of anxiety. Like, “If I don’t get that right—” 

RZ If you don’t realize the thing in your mind. 

PF I need the touchdown. I need to get the Powerpoint done. 

RZ Determined. Motivated. Driven. 

[4:07]

PF Yeah. So like you look at—you know, does Martin Scorsese seem like a really happy guy to you? 

TM I wouldn’t say happy

RZ Very jittery. 

PF Yeah. Martin Scorsese [very antsy] he’s gotta get that movie—he has got to digitally deage Robert De Niro. He has to do it now. 

RZ Yeah. 

PF That to me is talent. Ok, so you’ve got—

TM Can you make that a team sport though? 

PF Well if the team has a collective sense of form and supports each other in resolving that anxiety, that’s very healthy cuz then you can say, “I get it. I don’t want you to stay up tonight. I want you to go home and get some rest because we’re gonna do this together tomorrow.” 

RZ But great leaders know how to bring that outta their people. Like great coaches do that. 

PF Yeah. 

RZ They don’t have it anymore. Their knees are bad and they’re not athletes anymore. But they have an amazing ability to draw the best work out of those people. 

PF But with—in the least pathological way possible. [Tim chuckles] Right, like, they’re like—You—or I’ve seen us do this. Like, “I know you can’t finish this unless you stay up tonight. That’s fine. Sleep in tomorrow.”

RZ That is talent in and of itself, right? People who get people to work—Tim has this skill, by the way. It’s a skill that I don’t have. I’m a little more direct and rude but Tim motivates people to want to all collectively succeed. 

PF I think that’s true. On the floor. I do it at a very meta level, people like to kinda come closer and see what I’m up to. You do it by force [laughs]. 

RZ Well, no, no. I wouldn’t say force! 

PF No. Gentle. The force of a hurricane. 

[5:29]

RZ When I’m looking at the output, [yeah] like the human beings in the room kind of melt away and I can’t help but comment on the output. 

PF They just become a large blob of human beings. 

RZ We’re not gonna—We’re not gonna share how to hire. We’re not gonna do that. 

PF No. 

RZ How to market on LinkedIn. 

PF That’s our secret. We’re not gonna tell anybody that. 

RZ We don’t have the big buffet—the Google buffet here at Postlight. Tim, by the way, to give us a little bit of background—is a product and technology leader at a very big company. Should we share the name? 

TM Sure, of course! 

RZ SageSure. 

TM SageSure, yeah. Favorite client. 

PF Favorite client at Postlight. 

RZ Favorite client at Postlight. Tim is an old friend even before SageSure. 

PF I do love SageSure. 

RZ Wonderful. 

PF We should just point that out: like there are clients and there are clients. And SageSure is like a deep and loving relationship between a vendor and its client. 

RZ Well they’re an innovator in their industry too. 

PF Yeah, I know, that is true. 

RZ So there is that. 

PF People are rarely excited by insurance but SageSure is the exciting kind of insurance. 

[6:19]

RZ And they’re also forward-looking, I mean, Tim, how many people are in your team? 

TM 50. 

PF Insurance has to be—50 people [whistles in amazement]. 

RZ Mix of—

TM Product, strategy, design, engineering, QA, QA engineering. 

RZ Ok. Alright so—

TM Creation of digital products. The whole—

PF Alright, alright. So let’s retain them. 

RZ Well, I mean, let’s talk about what SageSure does, [Paul laughing] just real quick. 

PF Alright. 


RZ I mean, it’s not trying to save the world. It’s not a fun entertainment company. It’s—

PF Well, SageSure is—it’s insurance. That’s it. That’s all I got [chuckles]. 

TM [Chuckles] We sell homeowners’ insurance. 

RZ Ok. 

TM People need homeowners’ insurance so they can go live their lives. 

RZ Ok, so which renders Tim, frankly, an expert. And I don’t mean that as a jab to SageSure. Like, there are a lot of industries where people can go work anywhere right now. How do you retain those people? 

PF Well, wait, and actually we should point out what they really do, like we’re being—like, what is the digital product in this world? It is—I mean, on a very, very abstract level: a complex set of forms and interactions that allow people to assess the risks with a given property and then make a decision about how that insurance is—You know, what should be the rate. 

TM All the pricing that goes into it. 

PF Yeah. 

[7:30]

TM Then, once you sell insurance, all the service that goes into it, self-service, claims

PG Geographic information systems, expert systems, there’s actually a lot of very, very deep technology that goes into making any insurance decision on your behalf. And so that is what you’re building. It’s a pretty big stack. 

TM Yup. 

RZ Share your thoughts. What are some good, tangible tips for people to retain talent? 

TM Ok. I have some notes here. I’m gonna distill it—I’m gonna work back to front. 

PF [Whispering deeply] Tim wrote a book, everybody. It’s—he’s written notes in a Field Notes.

TM When I—When I get to the punchline, this is—you started to go in a certain area which is like, well, what is the content of people’s work? Why are people passionate about what they’re working on? When they’re working in an insurance company that’s not why you retain somebody. They’re not staying there because they’re deeply—

RZ They’re not passionate about homeowners’ insurance. 

TM They’re passionate about how they work with other people. 

RZ Ok. 

TM The group of people there working to realize something. 

PF Now wait, hold on, we negotiate with this a lot because a [sic] agency is a mercenary organization. Deep down. Fundamentally people come to us, they say, “We’re gonna give you money. We heard you have some really talented people,” and we go ahead and we deliver the services and hopefully everybody feels ok about that. But ultimately, we don’t—we have a mission in terms of like, we’re gonna develop careers, develop craft, a lot of people come into an agency for a while and they really level up their career. So we’re very proud of that. We’re proud of that community, proud of the culture. We don’t really have a mission. And you’re telling—like when I look at you, I’m like, “Well, at least they—they ship the insurance.” But you’re telling me people don’t lock into that necessarily as much as the community. 

TM People locked into the content of their work. That’s not what keeps them there. When you talk about retention. 

RZ What keeps them? 

[9:08] 

TM I think it boils down to four things. People in technology—

PF [Whispering deeply] He’s reading from his notebook. 

TM—[chuckles] want to be connected; want to have agency; want to feel like they’re growing; and it has to be in a modern environment. 

PF Ok, so let’s go through all four. Number one was—

TM Connected. 

PF Connected to what? 

TM Connected to their teammates; connected to what they’re working on; connected to their manager. Engaged in the work. 

PF Ok, so—

RZ Collectively. 

TM Yes. 

PF So that means that if I look over to the person—I mean it’s not a cubicle anymore next to me, or even an office next to me—if I look over to that person and they’re going like, [Starts with a strained whisper] “Oh my god, thank GOD it is Thursday afternoon, so I only have to pretend for two hours tomorrow and then I can go to the lake house.” 

TM There’s probably plenty of jobs where that can lead to retention. 

PF Mm hmm. 

TM But in product development, in engineering, that’s not one of them. 

PF Well, you’re not gonna get good results out of them. 

TM You’re not gonna get good results and they’re gonna leave. 

PF Ok. 

RZ How are people gonna stay connected in this new distributed work environment? 

[10:04]

PF Well, and—and be the manager, how do you assess connection and encourage connection? 

TM This is a very important topic.

PF Kinda softballing here, [Tim laughs] let’s be honest. You know, you’re a friend of the firm. 

TM I mean there’s some basic things, right? Like, you have to have a relationship. If we’re looking at this from somebody who’s managing other people, you have to have a fundamental relationship with the people who work for you. And that relationship has to be real. You cannot fake a relationship. And a relationship is two-sided: it’s listening, it’s acting, it’s respecting them. I think listening and caring for somebody and acting—those are things that you cannot fake. Go through each one of them. To listen to somebody, you cannot fake that. To care for them, you cannot fake that. And then that has to result in action. You have to be seen as someone’s manager who’s actually listening and taking action on what are the frictions in the work environment. Why are people frustrated? Why are people being slowed down? 

RZ You have to pay attention to those things. 

TM You have to listen and listen, literally, and pay attention would be like observation. Yes! You have to be deeply aware of those things [right] and not only viewed as the person who’s clearing a path on all those things [yeah] but is actively closing the loop with people. 

PF Be it red flags, alarm bells go off, regarding connection when somebody says or does—

TM Nothing. [Chuckles] If they’re saying or doing nothing, if they’re not coming to you in a skip level or you’re in a meeting and observing them and their video is not on in Zoom. 

RZ Detached. 

TM And you just see—

RZ Detached. 

TM—that they’re not connected.

PF They’ve disconnected. Occam’s Razor: they don’t appear to be connected, they’re probably disconnected.

TM Yeah. 

RZ You know what’s profound about this bit is that it’s actually amplified down the chain. What I mean by that is if I as an executive have four managers, and I just exert enormous pressure on them to deliver, a lot of their attention is upward to me. Satisfying me. And they can’t help but deflect that anxiety out to their people. 

PF Yup. 

[12:06]

RZ Because now their own stability and place is on shaky ground and when you have that, some leaders are able to absorb all of it and keep calm—

PF Oh, the worst scene in the world, I was in a meeting once, a woman stood up and said to 50 people, “If we don’t get this done, I’m gonna get fired.” 

RZ Yeah, like that’s not helping anybody! 

PF Ooh! And it tells you—it didn’t tell you, “Let’s rally around her and help her.” She ended up having a beautiful career and doing incredibly well for herself actually but what it tells you is, “Get to the exits as quickly as possible.” 

TM What was the word for that? Like, psychological safety, right? 

PF Right. 

TM It’s like this is an environment, you used the word anxiety. 

PF Yeah. 

TM Right? When you’re talking about retention—

RZ Ok. 

TM You’ve gotta clear that path. 

RZ So, as a leader, as a manager, create connection, listen to your people—

TM Observe a lack of connection. 

RZ Observe a lack of connection. So listen when there’s silence, reach out, and whatnot. Ok, number two. 

PF Yeah, number two. 

TM Agency. 

[12:59]

PF Agency. Well, we’re at an agency. 

RZ We are an agency and, you know, we’re—

TM Different kind of agency!

PF hello@postlight.com! Right, so agency, meaning—


RZ Reach out! [Chuckles]

PF—that a human needs the ability to have control and agency over their environment? What do you mean? 

TM Environment, path, career, I like the sports analogy from a moment ago. 

RZ Yeah? 

TM Right? You’re a GM and you’re looking to bring in a pitcher. There are more openings for pitchers than there are really good left-handed relievers, right? Same thing hiring really strong tech talent. 

PF Sorry to 80% of our audience. That’s just like—[everyone laughs].

TM There is more tech employment available than there is left-handed base throwers, right? 

PF Sure! Sure, sure, sure. 

TM So why are you a worthy place for them to work? You should probably start by asking yourself that. 

PF Yeah, but this is tricky cuz the other incredibly fatal thing is for you to get into a customer service mode with your own employees.

TM Ok. 

PF That’s very dangerous, cuz then you’re like, “Ok, what can I do to make you happy?” And they realize at a certain point: “Actually, my job will never make me happy, I should just go somewhere else.” Like, I mean—

[14:03]

RZ This—I think this just goes back to the word relationship which I think is how you’re gonna wrap all of this up. 

TM Yup. 

RZ In that setting, customer service is not a relationship. Customer service is transactional, right? 

TM Yup.

PF It’s one way. And cuz what happens with that dynamic is you’re basically saying, “Look, I need to keep my job and what do you need in order to leave me alone?” 

TM Well, let’s talk about agency. Like a strong frontend engineer, how would you give them agency over what they’re doing? The tooling that they work with. 

PF Let them get their tools, let them—Maybe they don’t get to pick their framework but they get to like, “At least we’re gonna get to the newest versions, like we’re gonna get—”

TM A team’s process. 

PF Uh, yes, that’s right. 

TM Letting a team have some agency over how they work together. 

PF And so less mandatory standups, more just casual conversation on Slack. 

RZ This is a great point, someone—

TM A career path: what’s next for me and how do I get there? Give me agency over it, not you telling me I’m being promoted, but you telling me what I need to do and have agency over what path looks like. 


PF Here’s—here’s what it looks like, yeah. “So if I do those things, odds are I will get to go forward in my career.” 

RZ This is proven out at Postlight because we don’t have endless control over the kind of tools and environments we work within. Some of the worst engagements we’ve had are the ones that are—where the team has been forced into a very onerous, overbearing, like button-down environment, where they have to use certain tools, they’re Citrix-ing into—

TM Sure. 

RZ—desktops, it’s a bad scene. SageSure, by contrast, has been truly a partnership because we have always come to the table with very modern, very forward-looking technologies. And SageSure has never said, “Mmn, nah, nah, nah, nah. You—”

[15:36]

PF To be clear, we don’t show up with something where we’re like, “Seven people use this, they’re all in the Ukraine but—” 

RZ No, we make a case. 

PF Yeah. 

RZ Sage—Look, there are smart teams at SageSure who are going to assess the risks around the technology choices but some of the most satisfying work that was done at Postlight is for SageSure, homeowners’ insurance software, because of the trust and the sort of autonomy that’s been given to the shop versus like, “Here is the compliance manual you must adhere to and there it goes.” 

TM I can give people agency over things like frameworks and architecture, it doesn’t mean you always have to say yes. 

PF No. 

TM It means people have agency over it, to learn about it, experiment, and make a case for it. 

PF Well and that’s—you can have a conversation you can report back and say like, “Look, that’s just not gonna work—” 

RZ Have the conversation. 

TM Yes. 

PF But it’s an open, transparent conversation. I mean this—this is a funny thing, right? Like insurance is a great client because—like SageSure is a good client and we’ll butter you up and go out for drinks and all that stuff, right? But like, the insurance is sort of in a funny zone where there is a little fluidity around the tools that you use. It’s not like a bank where you’re beholden to absolutely everything being as boring and bad as possible. You get a little bit of an advantage by having better technology yourselves. It has to be fast. It has to do certain things. 

RZ There are people who listen to this podcast at very big companies where they’re like, “I wish I could—I can’t do that. I just can’t do it. I wish I could do more of it.” 

[16:59]

PF You should get into the exciting field of homeowners’ insurance. 

RZ You know what? It’s a new world. It’s harder to keep people. We’re all distributed. We’re working from home. 

PF Yeah, everybody got on Zoom, maybe you could just update the recent version of React. Like, it’s ok. Or Java. Get off of Java 8.

RZ We have clients, banks, that refuse to look at Zoom. Pandemic hits, they approved Zoom in like two weeks. 

PF And everybody joked about, like, the pandemic hit and suddenly that digital transformation effort was real after like five years of discussion.

RZ [Laughing] Yeah!

TM Well it’s a competitive environment, so draw it back to that, right? So if you’re trying—

RZ Ask for that lenien—that flexibility. 

TM If you’re trying to hire that hotshot product manager who has agency over their career, and you’re telling them, “Come in where you’re gonna work on this set of tooling and this set of technologies, and you have no voice in it.” Good luck. 

PF Alright, so, agency

TM Agency. 

RZ Connecting. 

PF How can you tell somebody doesn’t have agency? 

TM Well, they’re probably not engaged, they’re [ok] not engaged with their manager. They don’t have a view about what they want next. 

RZ They’re clockin’ in. 

PF The average human in this situation often will get a sense of learned helplessness. 

TM Yeah. 

PF And you actually have to remind them over and over, like, “You have a lot of control here.” 

TM Oh yeah and have—

[18:08]

PF How do you get people to realize they have agency cuz most jobs will try to take agency away from you. 

TM There’s a definite role for effective management here, engineering management and otherwise, as being the other side of that coin. 

PF Telling the story over and over.

TM Not me as hero but throughout the organization, everybody’s manager. 

PF I mean, frankly, the only way you really get this to work is you keep going, “What do you think?” 

TM Well, I was gonna give you pro tip number one from SageSure! 

RZ Love a tip.

TM Which is every six weeks we do something called a How We Work session. Which is an agenda that’s driven by the team. 

PF Ok. 

TM Which is what are we doing that’s dumb? Inefficient, causing friction. It’s an actual forum that’s ongoing and—

PF Rich likes that part. It’s like, Rich’s favorite part. 

TM It’s a forum that people know and respect which is—doesn’t mean I have to cue up and wait but there will be a forum where people want to listen to, “What could we be doing differently here?” 

PF Ok. 

TM Somebody joins the team new. That’s another wonderful moment to pull them aside and say, “You’ve now been here for six weeks and observed how we work, what do you think?”

RZ “What do you think?” 

TM [Chuckles] “What do you think?” What are we doing that’s—

[19:04]

PF Give me—give me an example, it doesn’t have to be specific to your business right? But was it something somebody might say? 

TM We were going through an elaborate Jira ticketing process for every release. 

PF Mmm. 

TM Which was causing a lot of slowdown and friction, and we’ve done away with that. 

PF Mm hmm. 

TM Automated all of the release orchestration to move to CICD, so we no longer slow down and have to create these release tickets. 

PF Ok, so what if somebody says, “I think we should get rid of Jira. We used Shortcut in my last job and it was much better”?

TM I have to be honest, we are very rigorous about what tooling we have to use. If somebody came with a really strong case about why we shouldn’t be using Jira, we’d be open to it. 

PF Ok. 

RZ Have the—Again, back to have the conversation. 

TM Have the conversation. 

RZ Hear them out. 

TM We’ve built a lot of automation and hooks into our corporate infrastructure that starts with Jira and it’s actually quite efficient to just change something in one place and it flows through magically.

PF “So if you learn a little more about our system, you might change your mind, but I’m open to hearing about Shortcut as well.” 

TM Absolutely, [ok] yes. 

RZ Number three! 

PF Dun dun dun dun dun dun [suspensefully].

[20:03]

TM This one, I mean, has to be on there which is growing. Tech talent, engineers, need to be in an environment where they’re growing. Whether that’s in their—their literal job which is taking on new frameworks—

PF Or in buying 12 Raspberry Pis and putting them in the closet. 

TM Well, we’ll get to that, or in learning and development opportunities or in a lab or in all the different ways that people like to be learning and, frankly, when somebody’s working for you, they’re working for you in anticipation of their next job, and that’s ok. You should just kind of recognize that as a leader, that someone’s working for you the 18 months to three years, maybe six. 

RZ Mm. 

PF Yeah. 

TM But they’re gonna go somewhere else and as long as that’s an open conversion that you have with them, that they’re putting things on their resume and learning for their next job and that’s ok. 

PF Mm hmm. 

TM You’ve gotta be on the other side of that for really good tech talent. That’s gotta be ok. That’s a part of the arrangement. 


PF Yup. 

RZ Be careful you don’t—especially you don’t put someone on the ticket backlog where they’re just chewin’ through ‘em and they’re essentially wrestling down technical debt for a living. Like, engineers- 

TM Or if you do need to put somebody in that position for a little while, be aware of it as a leader, talk to them. 

RZ “We need your help here.”

TM Yeah. 

RZ “We need you to chew through these for the next couple of months.” 

[21:15]

TM “And then we’re gonna put you on this research project about the future of insurance or we’re gonna do something.” 

PF Go back—I mean you go back to those first two: like it is—the backlog, somebody has to deal with the backlog. But you need—

TM The team has to deal with the backlog. 

PF That’s right and you need a good sense of backlog heroism, right? Like you need a sense of like, “We’re gettin’ it done. It has to get done.”

TM Pro tip number two from SageSure: make it a metric that’s visible to everybody which is a number of items in the backlog that haven’t been touched in six months. 

PF Oof! 

TM And if that number is 62 right now, I guarantee you it’ll be zero three weeks from now. As soon as it’s a number—

RZ It’s surfaced. 

PF I would just delete that backlog [all laughing]. 

TM Well, that’s one way to go from 62 to zero, isn’t it? 

PF That’s what I like to do. Wait, what was the last one? What was the third one? 

TM Third one was growing. 

RZ Give people the room to grow. 

TM “Oh and what conference are you going to go to this year, super awesome tech person number one?” 

PF Ok, like, what if I say like, “Ah, I dunno. I don’t really wanna go to a conference.” 

TM “You really should go to a conference. Or, maybe, if you don’t wanna travel to a conference, maybe you should learn something and in our weekly lunch and learn you should bring it to the group.” 

RZ Share it, yeah. 

TM Yeah, so you don’t have to go to a conference. 

[22:19]

PF Full of pressure there, I can’t just—I can’t just say, “I’m learning all about it.” Yeah no, no. 

TM Learning is about bringing it back to the team also. 

PF Back to the team. Ok. Fair enough. 

TM I think that’s the transaction related to learning. 

PF Yup. 

RZ Number four!

TM Modern. Engineers wanna work in a modern environment. I don’t mean—

PF How about designers? Do they care? 

TM Of course, designers are the perfect example, right? 

PF They love Figma. 

RZ Can I just say the word Sketch? Sketch was like—

PF Four years ago it was like, “Goodbye, Photoshop, welcome to Sketch.” 

RZ “Photoshop’s dead to me. Hello Sketch.” 

TM We were talking about tooling and yes, I agree with that. 

PF What are—

RZ What are you talking about? 

PF What are you talking about, Tim?

TM Uh, everything, like processes [Paul gasps dramatically]. Do designers want to put on their resume that they implemented a design system? Yes, they probably do. 

PF Are you sure? 

TM Is a design system a good thing? Yes. We can talk about why. 

PF Yeah, for the most part, but yeah, sure. 

[23:12]

TM For the most part, so you can connect those two dots. Make it something that is accretive to the organization, implementing a design system: you can move faster with more standard and higher quality. 

PF So this is—this is a foundational difference between the for-hire organization and the large organization cuz you’re able to say, “Hey, we have a lot of other stuff to do, we also have to get that design system done.” 

TM Yes. 

PF That is har—we do that sometimes with internal projects and you try to get people across a variety of projects but a lot of the work we have doesn’t have that ability to level up what you have is instead somebody’s gonna be done in four months. And then they’re gonna move on to the next project where, ideally, we’ll level them up. And so we—we aim for that with people. But you’re saying, and this is most organizations: “Ok, I know you have to do this. I know you wanna do this. Let’s make sure we figure that out.” 

TM And let’s connect it to the strategy of the business. We’re implementing a design system right now, not because it’s cool or so our designers can put it on their resume and interview for the next job—

PF Well, so you have to triage that a little bit as a manager cuz people [yes] will come to you with those ideas because you’ve built this transparent organization. “We need a design system.” We have to be like, “Do we?” 

TM Yes, what’s that? 

RZ That’s the advice is how do you navigate this upward, right? Like—

PF Well and how do you keep from becoming the manager because everyone’s gonna ask you for everything and then, “Ah, Tim’s a good listener,” and then there’s a point where you must wanna say like, “I don’t wanna hear about it anymore.”

TM You just made it about me, about Tim. It’s not about me. 

PF Not about you. 

TM Nobody’s coming to me and saying, “Tim, let’s do a design system.” It’s like, “This year should we as a software leadership team in this business commit to delivering a design system?”

PF Mm. That sounds—sounds really healthy. Sounds good.

TM And if so, why? Why that over the other infinite things we could be doing? 

[24:50]

RZ You’re touching on the why which is tied to the business interest. I mean, let’s pause for a second. We’re a smallish agency, you’re not headcount-wise huge.

TM Yeah.

RZ Your team is 50, we’re 120 now. 

PF Maybe, it’s hard to keep track. Go ahead. 

RZ If I’m at Bank of America. 

TM Yeah. 

PF Little bank. 

RZ And I want to implement some of the things you’re talking about, they make sense to me, everything resonates. Now, I have to go to the management above me. 

TM Mm hmm. 

RZ And make a business case. Now look, retaining people is a business case. 

TM Sure. 

RZ If you do these, less people will quit. 

PF It’s so expensive to hire. 

RZ It’s incredibly costly to hire. It’s incredibly costly to lose someone!

PF Yeah, think about like a quarter of a year’s salary, just [makes a blowing sound]. 

TM That’s right. 

RZ Because what you’ll find is, the more—the higher up the chain you go, and the more detached people are from the sea of humans that are actually making it all work, the less sympathy you’re gonna usually find. Right? But a lot of the things you’re proposing here, like design systems, are actually—also happen to be good for the product. 

TM Yes. 

[25:58]

RZ So when you pitch upward, yes, part of it is retaining people: they wanna use modern techniques and tools; they want to feel like their careers are growing, but when you’re pitching upward frame it—

TM Connect it—

RZ—in the business case. 

PF True. 

TM Yeah, don’t misunderstand what I’m saying. I’m not suggesting prioritizing a design system, or go into a continuous delivery because that will help you retain people. 

PF Mm. 

RZ Yeah. 

TM I’m suggesting that those are good things that generally come from the organization up the chain like you’re saying. 

RZ Yes. 


TM And listen to them, and do them—

RZ Yes. 

TM—because they’re good in value creating—

RZ Yes. 

TM And they help you retain. 

RZ That’s right. Look, I think you do have to draw a line when it seems like that’s gonna be something that’s gonna make the team feel warm and fuzzy but is actually drag or bureaucracy or process that’s unnecessary but everybody seems to embrace it cuz they read an article. 

[26:49]

TM A team can filter that out. A good, healthy team will filter that out and say, “You know what, that’s interesting but that’s not—” 

RZ I think that’s the balance you’re striking here. And look, if your leadership can’t empathize with these asks, for the interest of the platform and the people? Then they’re gonna lose. They’re gonna lose this battle. 

PF Alright, lemme throw a curveball which is something—

RZ Oh! Baseball reference. Keep going. 

PF Yeah, it’s all about sports today. “Tim, you seem like a good guy, I’ve enjoyed working with you but it’s time for me to move onto the next thing.” Pause. Counter offer?

TM Depends on where the relationship is at. 

PF Ok. 

TM It depends how much of a surprise that was, or part of a conversation. It depends. There’s no right answer there. 

PF Ok, it’s a tricky one. 

RZ Can I share a piece of advice related to that? 

PF Yeah. 

RZ If you’re finding yourself phrasing it this way: is there anything I can do? Don’t bother. 

PF Yeah. 

RZ If you’re already there saying, “Would you mind helping me out of this ditch you put me in?” Don’t bother. If it’s like, “Is there anything we can do to keep you here?” 

TM If someone comes to me and says, “I really wanna stay here.”

PF Yeah. 

TM “I really love what I’m doing.” 

RZ That’s a different conversation. 

PF No, that’s true, see—

TM “I have this one concern, financial or otherwise,” we haven’t talked about any of that yet which is relevant. Table stakes. You gotta pay people. “Can we talk about that?” That’s a very different framing than sliding an offer across the table and saying—

[28:08]

PF I’ve also seen like—I’ve also seen, “Why don’t you take a leave of absence? Sounds like a lots been going on and if you wanna come back, come back.” And then sometimes people come back. 

TM Yes. 

PF Right, like, there are boun—

TM We’ve done that on my team. 

PF Yeah. 

TM I think another related thought to that: I think you have to have a long term horizon for building a team. So if somebody did come to you and say, “Here’s how I’m thinking, how I’m feeling, and I do need to take a leave of absence,” like viewed over a long enough period of time that could make perfect sense. 

PF Sure. 

TM If you’re always optimizing for next week, next week, it probably won’t. So what’s your time horizon as a leader for this team you’re building? 

RZ Recap: connecting. 

TM People have options in our market.

PF Mm hmm. 

TM So, you, as a leader, should be thinking very actively about why are the people working for me who could have left have not already? And not assume they won’t. And this might be four lenses you might wanna think about. How connected are they and what can you be doing about it?

PF Mm hmm. 

TM How much agency have you given people over how they work together? How modern is your environment? How open to being modern are you? 

RZ Mm hmm. 

[29:09]

TM And are your people growing? 

PF Anything else in that little notebook we should know about? 

TM Oh there’s a lot in this notebook. You riff for a minute lemme see if I have any—Uh, number three: my SageSure pro tip number three—

PF Ok?

TM C’mon you’re supposed to riff! 

PF Oh we’re supposed to riff! 

RZ Oh! Oh! Right, sorry. 

PF So, hey, how about that—what about that metaverse? 

TM [Chuckles] What’s your company culture? What’s culture? That’s a big one at the buzzer I threw at you. Everyone loves that word, what is it? 

RZ No, I will say this—I think, look, Postlight—

TM I don’t mean what is it literally, what is culture of a group? What is it? 

PF What is culture? The sum total of the patterns of interactions between individuals and how much control and power they feel over their own destiny within an organization. 

RZ That is why Postlight’s been successful with retaining people. 

PF Yeah, we should point out: we’re pretty good at it. Like, people—agencies, people tend to come and go but they actually—

TM You have a very good and healthy culture. Yes. 

PF—they tend to stay. People tend to stay and I mean it’s a lot of work, frankly. 

RZ I mean, this, the last two years have been the ultimate test, right? 

PF Yeah. 

TM That’s a great point. 

[30:06]

RZ It’s a test that actually tests your ability to trust and empower or mistrust and exert control because you feel, “I can’t see what they’re doing in their dining room, while they’re on the video call, when they’re not on my video call,” and I think one of the things that we’ve always taken pride in, it’s worth saying to the world, on this podcast, cuz the whole world listens to this podcast: we don’t do timesheets at Postlight. 

PF Never. Never one. 

RZ We’ve never done ‘em. That sounds like a flex but what really—what we’re saying is: we don’t want to oversee your minutes and hours and that predates the pandemic. 

PF Yeah. 

RZ And the advice I would give the whole world, during this time is don’t do time sheets. And I don’t mean that literally, I mean it figuratively. Meaning: don’t worry about your people’s time. Trust your people. That autonomy and freedom is going to benefit you longer term. 

PF It is true and that doesn’t mean—

RZ That’s the number one thing—

PF That doesn’t mean you’re not gonna be paranoid. You’re gonna be kinda paranoi—you’re gonna be like, “Is that person doing something?”

RZ If you’re gettin’ gamed, it’s gonna show itself. 

PF Yeah. 

RZ It’s gonna show itself. Don’t worry about it. Really don’t worry about it. Like, it’s gonna show itself. 

TM Especially the kind of talent we’re talking about wanting to retain. 

PF To your point earlier: if they’re not connected to the work and the community, people have options. So. 

RZ This was great! Uh Tim, this is your superpower: instead of like [stodgy tone], “5 Business tips,” you humanized it in a very profound way. 

[31:34]

PF Tim cares about humans as humans in a way—

TM Ready for my close about humans? 

PF Absolutely, in a way that maybe you and I can learn from, Richard. 

RZ What is that supposed to mean? 

PF Oh, we’ll talk about it in drinks. 

RZ Paul, fine. 

TM My final note in my little notebook here—

RZ Uh huh. 

TM—and this is gonna come off as cheesy but I actually really mean it. 

PF Ok. Live. Laugh. 

TM People are gonna work for you for a period of time and then they’re gonna go work somewhere else. And when they come to you when they’re gonna leave, you shake their hand and you say, “Thanks for working together.” Because, guess what? That reputation leaves the room with you. They might come back and work for you. Their friends might. Like, people are gonna leave. Retain them as long as you can, and then when they leave, it’s ok. 

RZ Do you know anything about Lebanese loyalty? At all? [Tim laughing]

PF We’ve been working on this for five years. 

RZ I’m kidding. 

PF No, I know [forces laughter]. 

RZ It’s great advice—it’s [laughs]—again this ties to the overarching theme: these are humans in relationships that are crossing each other and it’s a point of pride. Name the fancy tech company they’ve all graduated out of Postlight and gone to those places. 

PF Oh yeah, we love that [music fades in]. 

TM That reputation follows you around. 

RZ It’s wonderful. 

PF Yeah. 

RZ It does follow you around. 

PF The good agencies are like grad school, right? You’re just like—you come out and you’re like a little bit confused and you’re like, “What’s going on?” And then people are like, “Great, I’d love to talk to you.” 

RZ Yeah. 

TM Be the place somebody wants to come back to. 

PF So, Tim, I love you when you come by and it’s—frankly, this podcast is just an excuse so we can go get a really good cocktail. 

TM Awesome. 

PF So let’s go do that. But it was also very good advice, thank you.

RZ Yes, this was a great—a very unconventional podcast. You and I didn’t complain for 30 minutes and then give advice [chuckles]. 

PF This is actually extremely conventional. This is what we don’t do. 

RZ Oh. 

PF Mostly we just yell. 

RZ This was great. No, I mean, unconventional for us, Paul. 

PF Yeah, yeah, like good and organized. 

RZ Yes, yes, that’s right. 

PF hello@postlight.com

RZ Tim, thank you for doing this. 

TM Yeah. 

RZ Check out our case studies. If you’d like to come work with amazing people, let us know.

PF Or if you’d like to be a client like Tim, you can do that too. 

TM hello@postlight.com

PF Actually, Tim’s been a reference for other clients, so, you know—

RZ Yeah, this is great. 

PF So if you wanna talk to Tim—

RZ [Laughing] Yeah!

TM I’m always happy to do that, to advocate for Postlight. 

PF If you’ve ever received a proposal from us you might’ve seen his picture in the back. 

RZ [Laughs] Have a great week. 

PF Alright, bye everybody. Let’s get that drink. [Music ramps up, ascends and comes to a stop.]