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What’s the purpose of Email today? This week Paul and Rich sit down to discuss the monster that email has become. Email has transitioned away from a place to have conversation and become a function that eventually moves to another platform (usually Slack). So what is email’s real purpose? Do all meaningful conversations need to happen face-to-face? Can we collectively put an end to the eight-paragraph email? We answer these questions and share the top 5 worst email subject lines (Hint: “You have a minute?” is up there!)

Transcript

Rich Ziade . . . You know what’s a terrible feeling? Not a terrible feeling, it’s actually not terrible, it’s just weird. 

Paul Ford Yeah, I have like a list of about 500 of these. 

RZ Yeah, that’s a different podcast. 

PF No, no, like—

RZ Yeah, that’s called Track—

PF Track PWAL. 

RZ [Chuckling] Track PWAL. 

PF Track Ford [music plays for 17 seconds, ramps down]. So Rich, we had a piece of work—Somebody called us to ask us if we could work on a project together, last week. 

RZ Ok. 

PF And this person is working for a big organization but they didn’t wanna spend a lot of money, like they wanted to spend kinda not [music fades out] not enough money. 

RZ My favorite kind of email. 

PF And! The reality is not only did they not wanna spend a lot of money but this is like a two person project. They didn’t need Postlight, they needed to just like let the person on the phone find a freelancer and solve it. 

RZ Ok, so they shouldn’t spend a lot of money. 

PF They shouldn’t. Really. And that’s what we told them. 

RZ Sometimes we get the ones that don’t wanna spend any money but it’s a really big thing. 

PF No, I was like, “Look, this is a—this is a couple of months of work for two people. This should not be a big ticket and you should—” 

RZ “Go somewhere that’s more right sized.” 

PF Not even—just get a freelancer. And this person went, “That’s exactly right but they’ll never listen to me.” Long story short: I said, “Look, lemme do you favor here. I’m gonna send you an email. And the email’s gonna tell you, ‘Look, all you need is one person here, don’t hire us. It’s time for you to just own this and get it done, and I’m sorry that you’re getting pressure from above but I would advocate pretty strongly for this solution.’” Et cetera, et cetera. And I sent that email. Why did I send that email? 

[1:46]

RZ Why? 

PF So that he could forward it to the people who were giving him heat. 

RZ You helped him right it. 

PF Exactly! He’s gonna forward that over. No, no, I didn’t help him write it. He’s gonna say, “Here’s the outside person who says we don’t need to spend all this money and time and even engage an agency. You know who’s telling me that? An agency.” 

RZ Right. 

PF I’m giving him a little bit of ammunition. 

RZ Mm hmm. 

PF Now here’s the key, this is I think an important lesson for everybody, this is something I learned only through pain. Every email is ammunition. 

RZ The forward. 

PF God. It’s dangerous. Email is a dangerous game. We play with fire everyday when we send emails. 

RZ Yeah, yeah. 

PF How long’s your typical email? 

RZ [Sighs] A sentence or two. 

PF Yeah. “It’d be great to talk sometime.” 

RZ Yeah. 

PF “Here’s the deck that you talked about.” 

[2:29]

RZ If I’m saying a lot of words in an email, I don’t feel good. I don’t feel like I have control over taking you to where I need to take you. 

PF Here are good emails to send: “Statement of work attached. Let me know if you have any thoughts.” 

RZ “Looking forward to chatting.” 

PF “This sounds like a project that we’d love to do. Can we get a call?” 

RZ Yep. 

PF Those are good emails. 

RZ You’re driving out of email. 

PF Mm hmm!

RZ Is what you’re doing. You’re going to other places, right? 

PF Let me tell you some bad emails. “Dear Karl, some late night thoughts.” 

RZ Ugh! The late Sunday long thing. It’s almost—it’s obviously cathartic, it’s meaningful to people, but man, when you get those eight paragraphs. 

PF Oh yeah, the late night eight paragraphs. 

RZ They’re never about everything you’re doing good. They’re always about everything you’re doing wrong. 

PF Or! Someone’s had a vision. 

RZ Oof. 

PF Those are dangerous too. You get the like, “This is what I’d like to do—” And then—you know, it’s tricky . . . there’s no greater fan of the written word than myself. 

RZ You’re Paul Ford. 

PF I like writing paragraphs; I like sequences of paragraphs, but if you’re gonna send me like your big idea and ask me to get roped into it and you send me 22 paragraphs of text. 

RZ Yeah. 

[3:38]

PF It’s a lot. 

RZ I mean, you’re not gonna make it out of the gate. 

PF Every now and then somebody’s like, “I really do need to do a brain dump here.” And I’m like, “Sure, let’s do it. Let’s go.” But for the most part, you gotta be pretty careful about what you write down. See, I think you’re even more paranoid than I am cuz you’re a lawyer. Lawyers never write anything down. 

RZ We like the phone calls [both laugh]. 

PF Well, you know why? Because—and it’s not just that. Let’s say email was useful for something. You don’t wanna start sending the signal that you’re doing something sneaky when you ask for the phone call. 

RZ Yeah. Yeah, yeah, yeah. 

PF It’s better to just be like, “We’re gonna move documents around with email.” 

RZ I’m not sure what’s happened with me and email. I’ve—I wanna just talk to you. I think Slack’s changed things a lot. I think chat, you know, async chat has changed things a lot. I think that’s—actually pretty fundamentally, in fact I don’t think we notice it yet. You know, collaboration tools like Slack have relegated email to document . . . to me. It’s more, like that’s really it’s purpose. 

PF You know what does work? The list of questions that somebody can reply to. 

RZ Mm. Answers in line. 

PF Yeah. That’s still a format that really works. 

RZ Maybe we should rename Track Changes to Answers in Line. 

PF [With Rich] Answers in Line.

RZ Hmm. 

PF Answers in line is good. That’s a good format. Like, “Hey, I got three questoins for you, here you are, I’ve set it up for you. All you have to do is hit one button and reply.” 

[4:56]

RZ Let me ask you this. 

PF Ask me anything you want! 

RZ Be the recipient. When you receive that long email, how do you react? 

PF You know, frankly, in 2019, it depends. If I know it’s coming or like if somebody sent me a really long email that was the night before a meeting and they were like, “Hey, I wanted to a brain dump before our call.” 

RZ Ok. 

PF Fine! 

RZ Important meeting? 

PF Good call, like long-term relationship building kinda thing for the firm. 

RZ Ok. That’s not a bad thing, it shows motivation and—

PF They were also very much like, “I don’t know if you’ll have time to read this, I just wanna get it all out.” [Yeah] Actually that context, I’m like, “Let’s get in there. Let’s figure out what the hell’s going on.” And you know what I did with that email? I turned it into a PDF, I loaded it into my iPad, and I scribbled all over it. I put notes and screenshots. 

RZ Interesting. 

PF Because it was a way to react that was sort of highly visual and playful and thoughtful and it was engaging for me. I was having fun doing it [yeah, yeah]. It’s for a future project and I sent back the PDF and I’m like, “Here is my reaction,” and a lot of my reactions were like, “Sounds great but this’ll be really expensive and might be a bad idea.” You know just like—

RZ How did they react to that? 

PF Everybody’s an adult. I’m not gonna tell somebody to just throw money down after a bunch of crazy ideas. 

RZ Yeah, yeah. I find the most effective people don’t write long emails. 

[6:12]

PF Well that’s a thing, right? We’ve talked about this on the show before where Jeff Bezos just famously just replies with a question mark. 

RZ Yeah but that’s a shit move. 

PF [Chuckles] Well that’s the shortest possible email. 

RZ Yeah, yeah. 

PF The forward is the shortest possible email. 

RZ The forward?

PF Yeah. 

RZ It is truly the most—

PF You’ve said nothing. You’ve just forwarded that bad boy. 

RZ I’m guilty of these, ok. These are the emails . . . I have a fatal management style. Fatal. No. Wrong word. I have a fatal management tactic and that is catching your ass flatfooted. It’s terrible. It’s an awful—I almost—there’s a part of me that slightly enjoys it. And [slightly] I’ll forward an email that is raising a question around some sort of time urgency, and I’ll forward it to the poeple who should’ve gotten back to that person and I will say in the email, above the forward, “Where are we with this?” 

PF Mm [music fades in]. 

RZ It is not a good email. 

PF No. 

RZ That’s not a good email. What are you doing doing that? [Music ramps up, plays alone for ten seconds, fades out]. 

PF Hey, Rich. 

RZ Yes, Paul. 

PF You know how we talk about how people are just great at this company and how much we love our employees and how much people are gonna enjoy working with them? 

[7:34]

RZ And how much our employees love us. 

PF [Chuckles] That’s exactly right. You know, it’s time to stop just letting you and me speak for this company. 

RZ I don’t disagree with that at all. 

PF Let’s get to know some people at Postlight. So you know who you’re gonna be working with when you hire us. 

RZ I think this is a great idea. 

PF Let’s call it it’s time for, ready? It’s time for—

RZ Go. 

PF “Hello Postlight.” 

RZ Oooh! 

PF “Hello Postlight.” 

RZ You know, we say hello, you know, “Contact us, you got questions, you got thoughts, send us an email at [email protected],” and there’s no faces to that. Like it’s not a real thing but there are people behind that hello, right? 

PF Let’s talk to—

RZ Let’s talk to some of those people. 


PF Let’s talk to someone from our product management team. Can you please state your name for the record. 

Peter Croce My name is Peter Croce [pronounced CRO-CHAY]  and I am a Senior Product Manager here at Postlight. 

PF Welcome. 

RZ Welcome, Peter. 

PF Peter, where are you from? 

[8:30]

PC I’m from Deland, Florida. 

PF Oh my goodness, what happens down there? 

PC Gosh. A lotta—a lotta sittin’ in the backwoods drinkin’ beers. 

PF Ok, ok. 

RZ That sounds like a ripe environment [Peter laughs] for the production of Product Managers.

PF Did you go to college? 

PC Yeah, I went to the University of Florida. 

PF And what did you study? 

PC Psychology and criminology. 

PF Perfect setup for product [all laughing] managing. What’s a Product Manager do at Postlight? 

PC Gosh. A Product Manager sits between business stakeholders and the team and figures out what are the things that we need to make that is gonna make this product a success, and then the Product Manager works with that team to get those things over the finish line and make sure that the product ships, and that’s it’s the right thing. 

PF That’s pretty abstract. What are some of the things that you do? 

PC I work with designers to talk through designs, to help present designs. I work with engineers to write . . . descriptions of what they should make in a program called Jira. 

RZ Boy, do we know Jira! [Peter laughs

PF No, I mean, how do you become a Product Manager? It’s an abstract job. 

PC It is. It’s really funny, I think when you ask people that question they have a wide variety of answers, and I kinda fell backwards into it. I was working somewhere as a software engineer, and they really needed someone to really be a Product Manager but they didn’t know what that was at the time. And the owner was kinda doing everything, it was a similar kind of agency environment. And so I started picking up some of the slack of really deciding what are the things that we need to do, and making sure that those things get over the finish line, and eventually realized, “I think I’m doing product management.” 

[10:08]

RZ I think we’ve had 60 to 70 podcasts on product management cuz it’s just so vague and ambiguous and weird and—but it’s moving shit along. A good Product Manager moves the thing along. There’s forward momentum, the effort moves along without people feeling like their getting pulled. That makes a great Product Manager. Unlike my style which is, “Lemme grab this big clump of hair! On the top of your head.” [All laughing

PF You’re style is definitely rearward momentum. Like—“Ahhh! What’s behind me?!? I can’t stop moving!!” 

RZ And I’m gonna endorse Peter here for a sec. Peter has that quality. He doesn’t—I’ve never heard him really feel like he’s gonna bring stress and anxiety to move the thing along. He knows when things aren’t looking great but mindset, attitude, I think is a big part of—Good product managers would do that without raising the temperature, I really respect. And I think Peter has that quality. I mean you could feel the calming effect of just talking to him right now. 

PF You know when things are going well, work happens almost as a side effect. You’re just like oh, you’re having coffee, and you’re talking, and somebody’s like, “Oh, lemme get that done.” And then suddenly it’s all just happening. And that’s [yeah]—yeah everybody wants to keep everybody else happy—

RZ Stuff does get blocked though! I mean, Peter, let me ask you that question. Like when stuff does get blocked, what’s the first thing that comes to your mind in terms of how to move it along? Cuz obviously there’s, you know, a pound on the table but that’s not your style. 

PC Yeah. I think it all depends on what the blocker is. Oftentimes, with product management, you’re figuring out confusion. Where’s there ambiguity? And oftentimes things are blocked cuz people don’t know how to move forward. So—

RZ Right. It’s not resistance. It’s just uncertainty. 

PC Yeah. Yeah. We often don’t work with people who are gonna dig in their heels and say, “No. That’s a great idea but I’m just not gonna make it.” We work with a lot of great people who are excited about making great things, but there’s so many possibilities in product and in technology. 

RZ Sure. 

[11:53]

PC It could be anything. 

PF What do you wish our clients knew? Like, when you walk into that meeting and you’re like, “Oh God, if only.” Is there anything? I think Peter just takes it as it comes [Peter laughs]. 

RZ I think Peter’s like, “You know what? You’re a putz! But you know what? You’ve got a nice attitude, so we’re gonna figure this out.” 

PF Could I answer—

RZ Peter is—I mean, yeah, God bless, I mean he’s able to do that. I think the ambiguity bit is real. I don’t view it as ambiguity. I view it as . . . I don’t wanna say it [laughs]. 

PF Well here’s what I see, right? 

RZ I get frustrated more easily! I think you can—Product managers don’t get to do the thing. Like the person that fails on it is the person who’s like, “Get outta the way, gimme the keyboard. I’ll do it,” right? Product managers don’t get to do that. 

PC Yeah. 

RZ They’re not allowed. They’re watching everyone else move it along and you’re hoping it all just moves along in this orchestrated way. I mean that’s why product managerment can be very frustrating. Like, you know. 

PC Yeah, I would say along those lines there’s two things that have helped me a lot. I took an improv class, actually. That was extremely helpful because one of the biggest things in improv is listening. 

RZ Yeah. 

PC So it’s not just slapstick, it’s not just saying something out—but it’s listening to what’s going on in the scene and responding with something that’s appropriate and really funny. 

RZ Interesting. 

PC But—

PF Have other people in the company taken improv? 

RZ Yeah, maybe we should—

PC [Laughing] I think so, actually. I think our director—

[13:10]

PF Should we like a [others laughing]—an improv evening at Postlight? 

RZ Professional development. 

PC We should, we should. 

PF Alright, so take an improv class to become a product manager. 

PC Yeah, along with the improv, if there’s other things people are thinking about to get into it. One other thing, sounds out there, is actually meditation. Is actually trying to sit and think and watch your thoughts, really. That’s all it is is just sitting and watching your thoughts. Because I think a lot of times in product management, the initial reaction might be to react. Your initial thought might be, “I wanna react here.” But if you pause and you think about it there’s probably a solution that’s gonna be a win-win for everyone that you’re not thinking about straight away. 

RZ Oof! 

PF Yeah, that’s not one for you. 

PC I do ten minutes every morning. 

RZ Is that it for the whole day? 

PC Yeah, that’s often it. If I can get more, I’ll do it but ten minutes once a day. 

RZ You’re a pretty centered dude and in ten minutes—

PF Since I’ve had my kids, my mantra is, “Get your socks on.” Say that for ten minutes a day which used to be like, “Ohhhm.” But no, no, no. “Get your socks on. Get your socks on.” And then if I don’t find peace through that, I’m coming to work and working with you. [Rich laughs] This is very sensible, right? [Yeah] Like organize your thoughts. What do you—

RZ This is the closer, Paul? 

PF This is my closer. 

RZ Alright. 

PF In order to do your job, what are some of the things that you like to read, look at, think about? Like what are some resources that you go back to? 

[14:24]

PC So Wait But Why is definitely something that I read a lot. 

PF What is that? 

PC Wait But Why is a website, waitbutwhy.com, and it’s a blog where Tim Urban writes longform posts about topics that are—require a lot of attention to really understand fully and deeply. So, for instance, he’s talked about energy, as a large topic [sure], let’s write 40,000 words on energy. How does that all fit together in the world. And how this ties back to product management, I think, is really understanding things in depth and being able to articulate them . . . in a way that’s concise and understandable. 

PF So the whole system, you’re interested in the whole system. 

PC Yeah, yeah. That’s a great way to put it. The whole system. 

PF If you wanna have a little product management thinking in your life: Wait But Why, like the singularity—like all these sort of big [Peter laughs], heady topics, he likes to go in deep. 

PC Yeah, just plug your brain right in and it’ll all be easier. 

PF Alright, great. Peter, thank you for coming on Track Changes. 

RZ Thanks, Peter, for our very first Track Changes Postlight guest. 

PF That’s right. Hello, Postlight. 

RZ That brings to a conclusion our very first “Hello Postlight.” 

PF And goodbye, Peter [Peter chuckles]. 

RZ And if you’d like to talk to Peter or anyone else at Postlight, email us at . . .

PF [email protected]! [Music fades in]

RZ There you go [music plays alone for six seconds, ramps down]. I opened my email [music fades out] from a month ago and I was in the middle of whatever was passing under my shitty nose [mm hmm] a month ago [mm hmm] and it was weird. It was weird because it was about five different things that I had decided in my crappy little brain were the most important things to deal with. 

PF Mm hmm. 

[16:07]

RZ And if you had told me, “Rich, what were the five most important you think you should deal with?” 

PF It wouldn’t even be on the list. 

RZ It wouldn’t be on the list. 

PF Yeah. 

RZ It was just whatever was in front of me. And it makes you think that all you’re really trying to do is just move the five different colored marbles down an inch a day. 

PF That’s it. 

RZ That’s all you’re trying to do, right? 

PF Yeah. 

RZ Email has lost its lustre because of other tools that are out there. And other ways of gaining access to people. 

PF Well, let’s be real though: that’s great, that’s a wonderful point but email is still the way that every stupid thing moves along. 

RZ Oh, I agree with you! I agree with you but the idea of composing an email . . . is—

PF Oh, and like getting—“Hey Guys, here’s 12 things that we need to do in order to achieve this success.” It’s impossible. 

RZ Vision update or—it’s not. You’re done. First of all, people are like, “Why is that longer than a tweet?” So there’s problem one: the brain has been conditioned to not deal with that kind of like—

PF Also, you’re really supposed to use project management software now. You’re not supposed—Every now and then if I’m working with an external party or there’s something that’s really specific to a group of people, I will write and I’ll be like, “John” (bold) will take this on Tuesday, Jane—[stammers] I will assign things via email [yeah, yeah] but it’s not the way you do it anymore. You create tasks that are then distributed to them via Basecamp or another—or Asana. 

[17:31]

RZ I mean it could run down the list; there’s a lot of these nowadays. 

PF And somehow I don’t think it creates more accountability but it definitely looks like data. 

RZ Well, it looks you inventoried [mm hmm] what you need. 

PF “I got a plan now!” 

RZ Yeah, “I got a plan now,” right, exactly. Now, my—your hopes and dreams are you don’t have to do that. We make this distinction around what we call coin-operated people and people who are just sort of self-propelled. And you don’t need to give them the 12 checkboxes and then you check on how many got checked off, they just sort of come out of ‘em. Some people bust their asses. And I’ve seen people mature from a . . . coin-operated mindset which is like, “Give me the 12 things, I’m gonna do those 12 really well for you.” 

PF Let’s be clear: everyone starts their career coin-operated. 

RZ Everyone. Of course. 

PF You go in, you’re like—

RZ You’re satisfying somebody above you, right? 

PF Yeah, “I need you to tell me what to do so that I can do it.” 

RZ Yeah, “Sit down, I’m gonna tell you these seven things, ready? Go do them. Come back and tell me how it’s going. And if you get blocked, come let me know.” 

PF Mm hmm. 

RZ Then there are the others like—

PF Well then you have to tell ‘em what blocked is. I mean really like people need to learn. 

RZ Yeah. 

PF Yeah. 

RZ Eventually, not everyone—by the way, you could have a perfectly coin-operated—I’m implying is a negative thing. Like really good coin-operated people are incredibly important. The most glorified of coin-operated roles is what I call the Chief of Staff. 

PF Mm hmm. 

[18:48]

RZ Now the Chief of Staff is apparently in the corporate world. Did you know this? 

PF Yeah, this is a new thing, everybody’s got a Chief of Staff now. 

RZ Everybody’s got a Chief of Staff now but it’s actually not coin-operated anymore [mm hmm], it’s like . . . “Tell me what you think we should do about marketing,” and that Chief of Staff is like dealing with—blocking all the politics and all the bullshit. 

PF The idea is that like the CEO will set a strategy, or the President. 

RZ Yeah. 

PF And the Chief of Staff will execute the strategy like on the ground. 

RZ Correct. 

PF “Let me get these people together,” and so instead of you having to meet with your VPs and listen to their little VP problems—

RZ He’s a proxy! 

PF Chief of Staff will do it and the little like, [nasally] “I wanna have a promotion to C-level,” [correct] not your problem anymore, that’s the Chief of Staff’s problem. 

RZ Correct, correct. 

PF Yeah, corporate world is [laughing] ridiculous. 

RZ That’s just ridiculous. 

PF Yeah, I mean why not just—Yeah, anyway but Chief of Staff does allow you to avoid yet more human relationships, so you can focus on golf, swimming . . .

RZ [Laughs] Remodelling the kitchen. 

PF Mm hmm. All [Rich chuckles] the priorities of the CEO. 

RZ Yeah. 

[19:44]

PF I’m doing this job incorrectly apparently. 

RZ Yeah. 

PF I have a sort of ancillary point here, too, you used to be able to say, “Let’s do a thing,” and you used to want to deliver clarity . . . what I notice with email now and with most of my corporate communication is . . . you just don’t wanna say anything. [Stammers] Recently I needed to introduce somebody. Somebody was like, “Hey, can you help me find a leader?” And I was like, “Yeah, I know just the person.” . . . And the key thing is not to say—I hit the person on DM and I was just like, “Should I tell ‘em what it is?” And I was like, “Nah.” You just wanna throw a little bait into the water. You’re like, “Hey, I got a really interesting role for you. I don’t know if you’re looking but I think it’d be something you’d love.” 

RZ Interesting, so you didn’t share the details. 

PF [Chuckles] No, no details. Cuz then they make a decision. You just gotta get ‘em into the light. And then like get ‘em—just see if they’ll nibble at all. 

RZ Ok. And if—

PF And if they nibble, then you open up—

RZ “Sure, I’m curious, what’s going on?” And then where do you go? 

PF Well, you’re kinda setting it up for the other person to tell the story, right? 

RZ Yeah, yeah. 

PF Right, like, I don’t wanna . . . There’s two things goin’ on: one is I wanna just like . . . see if I can catch ‘em and bring ‘em in and back this introduction; the other is I don’t wanna in the position of selling a role or making—or pushing someone in a direction, whether it’s right for them or not. I want them to meet the other party and have a conversation. But I’m noting more and more—Also, you and I talk about a lot when people write in with sales questions, we don’t say too much in reply . . . 

RZ No, no. 

PF We’re just—we move towards that phone call. We want the—

RZ Always. 

[21:16]

PF We want the chance to tell a story and create a human sorta warm interaction so they know who they’ll be dealing with. 

RZ Ah this is Sales 101. If they’re in town [mm hmm], if they’re not far, you see ‘em in person. In person—I stand behind this. You’re doubling your likelihood of landing a deal . . . if you can meet the people in person. 

PF Are you gonna fly across the country or not? 

RZ Yeah. And sometimes—Look, you’re not some Joe Shmoe and it’s not your primary job, you have other responsibilities at Postlight. And you couldn’t do it. 

PF That was a tough one. That was a like—

RZ You did a video call which is sort of an inbetween call but it’s kinda shitty. 

PF I will say I didn’t have—If I had had a strong urge—not a strong urge but a strong indication that we could get close but I really had a sense that there was already a favorite. 

RZ No need to explain the reasoning behind it but there’s no doubt [oh!] you’d be in a better place if you could—Look, there are salespeople—

PF Oh it’s good to be in the room. I tortured myself. 

RZ They fly out to loiter outside. They fly out—

PF You’ve done it. I’ve done it. 

RZ I’ve done it. I’m like, “I’m gonna be in San Francisco.” 

PF You’re not gonna be San Francisco. 

RZ I’m not gonna be anywhere! I’m going to Brooklyn [yeah], I’m going home! 

PF But if they’re like, “Oh, I’d love to see you. Come by for coffee.” 

RZ You just fly out. 

PF Get on the plane. 

RZ You sit there in the hotel like a lonely human being. 

[22:28]

PF That’s true enterprise sales. We don’t do much of that. We’ve done that once or twice. 

RZ We don’t do much of that. 

PF You don’t, honestly—

RZ I guess what we’re getting at is . . . email’s not for about getting engagement anymore. It’s not about engagement and building—

PF It is, maybe with old friends and you throw a picture of the kids in. But not, even if they’re like work friends but—

RZ Do you know what gets me excited when I’m talking to a prospect? 

PF Yes. 

RZ When I’m talking to a prospect—

PF Yes, I do but go ahead. 

RZ—and they say, “I have an idea, do you have a minute for a quick call?” 

PF Yeah. 

RZ When they say that, that means I’ve connected with them in a meaningful way beyond just, “Are you interested in our services?” That person is calling me cuz they wanna talk to me and get my thoughts like right away. They want immediacy, they don’t wanna wait for email responses. 

PF Well, this is the tricky thing you and I have as leadership of the company, right? Which is that we don’t really have jobs. There’s no—no one ever says, “Good job.” 

RZ I’ve said that to you a couple of times, Paul. 

PF It’s not—not really. [Rich laughs boisterously] You know—I flatter you because otherwise you’d just like I gotta keep you calmed down but the reality is like no. No. We don’t really [stammers]—there’s no such thing as, “Good job.” 

RZ No. 

[23:39]

PF And you know sometimes you’d like a little, “Good job.” But what you get is . . . “I am under a position of stress and I need your advice.” 

RZ Yes. 

PF That is the equivalent of, “Good job,” for a leader. 

RZ Yeah, that’s absolutely true because in our business [mm hmm] where we are effectively making available our resources on an ad hoc basis, [that’s right] and you don’t have any contract or anything yet going with the person, it’s like, “Can I bounce something off of you?” 

PF Mm hmm. 

RZ “Do you have a minute?” And it’s a good thing. That’s a very good thing cuz that means the trust level has gotten to a certain place. 

PF “Good job,” is that—it’s “I’d like you to—There’s somebody I know who could really use some advice.” 

RZ Yup. 

PF That is maybe another possibility—like them passing business along, anything like that. “Bad job,” is . . . “We need to talk.” . . . “Bad job”—

RZ Yeah. 

PF “Bad job” increasingly—I’ll tell you what—

RZ On the other side of an engagement. Yeah. 

PF Phone calls are usually pretty good, text messages are usually pretty bad. [Rich laughs boisterously] That’s just reality. 

RZ Not always, not always! 

PF No, I get a lot of—the texts. 

RZ You find yourself in places. I don’t get the texts. 

[24:49]

PF Now, you’re not as on the ground with the ones that I’m—like I’m—

RZ You have some relationships. 

PF I have ones that are very relationship-driven that are a little more granular. You’re a little—you’re on some of the bigger engagements. When they’re granular and things are going wrong, and a text message. When things are going right and there’s an introduction, it’s like, “Let’s do a call, would love to get a drink.” 

RZ Yeah, yeah. 

PF Yeah, I feel it. I feel that. 

RZ So worth noting: I mean email is fading away. 

PF I don’t think it’s fading away—

RZ What the hell is it? 

PF It’s for marketing now. No. 

RZ Do 15-year-olds have emails? 

PF Yeah they do but they use ‘em for like getting newsletters . . .

RZ Interesting. 

PF That’s what we know, right? We know that from—just that’s how—marketing is still done through email. Logins are still done through email. You know, password recovery. Like [yeah] it’s—

RZ Conversations are not. 

PF I don’t think that’s totally true. I think that is the conversational medium of record that’s totally distributed and open. I’ll give you an example, like . . . family plus. I don’t try to—A lot of people have their family on the group chat but like if you’re planning a barbecue, you could be doing it on Facebook, you very well might also be doing it on email. 

RZ Mm. 

PF Because not everybody’s in the same Groups—

RZ Reunion and shit. 

[25:58]

PF Mm or just like, “We’re all gonna get together in the park on Saturday.” 

RZ There’s 20 of us. Yeah, yeah, yeah. 

PF Yeah. 

RZ No, you’re right. 

PF And then what happens, it falls to the group chats—like as like different clusters of people are saying [yeah], “Hey, I’m gonna go over there to the barbecue.” 

RZ Yup. 

PF But the actual coordination takes place via email. So there’s like this function. And the introductory email. A lot of people come in through DM and or like, “Hey, I’d like to talk to Postlight.” But for the most part it comes in as email. There’s like a function to it, right? 

RZ So, Paul, I wanna—I wanna take this towards some guidance we can share. And some advice I think we can share around—

PF Well, first: have an email strategy. Don’t try to have conversations too much. 

RZ In email. 

PF Yeah, don’t put forth agendas; don’t like—

RZ I agree with this. 

PF Don’t try to resolve—don’t try to resolve things through email. 

RZ This gives me hope, dude. I mean essentially what you’re saying is: good management; good interaction; good communication happens in person which nobody talks to anybody anymore. So, now we’re—we are a small company. 

PF Let’s not even say in person, face-to-face. 

RZ It could be over video. That’s true. 

PF Yep. 

[27:06]

RZ It’s just better. It’s better because you wanna interact and you wanna have those—I mean when it comes to sales, it’s the only way you can build trust and to get people to say, “Hmm, I think I could really—I really want these guys with me.” 

PF It’s real. Have we closed one piece of business without meeting the person? 

RZ Mmmm. Yes. 

PF Yeah, but even so we did video chat with a large group—

RZ Oh you’re talking about nothing, nothing, nothing—

PF I’m just thinking like we have never closed business without an enormous amount of interaction. I think we did it once with video chat. 

RZ Yes. 

PF After a lot of phone calls, and that was a relatively small project with a personal introduction. Every other piece of business has involved one or more meetings. 

RZ Yes, that’s right. 

PF That’s four years in the future. We live in the future where everybody can video chat, et cetera, et cetera. 

RZ I wanna end this with a warning. I have this terrible—I’ve stopped doing it, just to be clear—I will message random people and say, “Do you have a sec?” 

PF Yeah, you can’t do that. 

RZ I’ve learned you can’t do that. I’ve had people route around to HR and say, “Do you know what he wants to talk about?” 

PF Oh, yeah. 

RZ It’s not good. It’s never lands positively as a request. You have to include the context of what you wanna talk to someone about—

PF [Exhales sharply] I don’t love my very presence giving people the willies. You’re a little more used to it than I am. It’s still hard for me. 

[28:24]

RZ It’s not good! It’s not good and it doesn’t feel good to know that that’s the dynamic. 

PF Cuz the person on the other side is working on a strategy to minimize their risk with their interaction with you [Rich laughing] and sometimes—sometimes you just—

RZ That’s a jab! I just got a jab! 

PF No, sometimes—No, no, you and me! I’m literally like they’re sitting there going like—

RZ To be clear, I don’t—

PF “He likes baseball.” You know? 

RZ I don’t think people are saying, “Oh my God, I’m getting fired.” I think people are saying, “I wanna be ready. I don’t know what’s coming at me.” 

PF There’s that. 

RZ “I wanna be ready.” 

PF I think there are also—Look, every boss in the world has a terrible tendency to ask for what’s on their mind that they see as urgent and blow up your whole weekend or life [Rich laughs wheezily] and we are very mindful of it. We haven’t—

RZ I—I have not blown up many weekends. 

PF No. 

RZ I’m gonna flaunt that fact. 

PF The risk is always greater than zero that—

RZ Yes. Yes. 

PF—that if you talk to someone, you’re gonna blow up their weekend [yes], their world, just something—

RZ Absolutely true. 

[29:20]

PF You’re gonna ask them to go somewhere they don’t wanna go. Well this is the reality we’re all in is that email is no longer a decision making medium. 

RZ It’s not. It’s a nudge—it’s a push-it-along medium. 

PF Yeah, that’s right. 

RZ “Can we get in a room about this?” 

PF Push-it-along is a PITA. It’s a PITA. 

RZ Or a MITA. Yeah. 

PF Yeah. 

RZ Yeah, yeah, yeah. I think that’s what it is. “Where’s the thing?” “Hey, can you just get this signed real quick for me? I gotta get this over with.” 

PF Or, “Let’s get everybody to the barbecue.” 

RZ It’s just a gather—it’s just a move-it-along. 

PF If you are—unless—and, you know, and every now and then, like I literally made, you know, a move to do something kind of symbolic [mm hmm] with email with that one potential client where I was just like, “We’re not the right people for this, you should do this instead.” To give them some evidence. 

RZ And they actually appreciate that, often. 

PF They can use it or not. 

RZ Yes, I wanna end this, Paul, with five subject lines to never use. 

PF Mm! “Just checking in.” 

RZ Don’t use, “Just checking in.” Oh yeah, one sentence reason why not to use it. 

PF Oh, it’s just terror. 

RZ Ok. 

PF It’s never good. It’s always like, “You’re extremely late on this and I’m unbelievably anxious.” 

[30:26]

RZ [Laughs boisterously] It does have anxiety on the other side. 

PF Yeah, and no one is “just checking in” because they think you’re doing well and getting it done. 

RZ Yes, true. Another. I’ll take this one. Uh, “Thoughts.” 

PF “Thoughts” is bad [Rich chuckling]. Oh yeah “Thoughts” is grizzly. 

RZ It’s just not fair. It’s not helpful. “Thoughts.” You got one? 

PF “Need to pick your brain.” 

RZ That’s flattering. 

PF Kind of. [Rich laughs] Kind of. 

RZ Oh man. 

PF “Need to pick your brain” is “I need you to work for free for me for up to 600 hours.” 

RZ [Laughs boisterously] Oh goodness. 

PF “Pick your brain” is always coming from above to below. 

RZ Yeah, yeah. Anyone that is just sort of a one-word description of someone’s emotional state like “Frustrated.” 

PF Mmmm! 

RZ “Subject: Frustrated.” Not good, right? 

PF Yeah, yeah. Or just like, “Measurement difficulties.” You know just sort of like “Analytic challenges.” 

RZ “Challenges.” Challenges as a subject line is tough. 

PF It’s noun plus—“Analytics Challenges.” 

RZ Yeah. 

[31:33]

PF Yeah, you know, you see that and that comes in around 11:40 and you’re like, “Why know what’s happening now?” 

RZ Yeah, yeah. 

PF There are certain ones—That’s one where I now understand how the rest of my day is gonna go. 

RZ Yup. 

PF There was some ambiguity. 

RZ Here it is. 

PF “Analytics Challenges” is going to define the rest of my day. 

RZ I’m gonna end with a horrible one—

PF But notice—but wait, wait! 

RZ And I want you to give me—I want you to think while I say this one. 

PF Ok. 

RZ Of the best subject line you could ever put universally in an email, ok? But I wanna end it with a bad one on my side, ready? “Timing?” [says question mark]

PF Yeah that is a rough one [Rich chuckling]. Notice that all of these are like passive aggressive ripcords getting pulled. 

RZ They’re awful. They’re awful. 

PF The best email is, “Ready to go.” . . .

RZ [Sighs with pleasure] Isn’t that wonderful? 

PF “Ready to go.” “We got there. All the conversation’s over—” 

RZ Oh my goodness! 

[32:19]

PF “Let’s stop emailing.” 

RZ “And go to work.” 

PF The best email is the one that stops the—

RZ “I’m taking you over that hurdle.” 

PF Stops the thread. 

RZ It’s a wonderful day. 

PF “We signed the contract; we got the team; we’re ready to go.” 

RZ Yup. 

PF I love sending that one. 

RZ Yeah. It’s a great—it just has forward momentum. 

PF You know what happens after you send it? 

RZ What? 

PF You set up the Slack. 

RZ “Subject: Snags.”

PF Snags. [Rich laughs] No, you move immediately towards the convers—

RZ Yeah, you move elsewhere. 

PF Yeah, you go, “Ok, we’re done with the formal interaction . . . part of email. Now it’s a conversation.” 

RZ “We live together.” Absolutely. 

PF But then! Richard, what happens? Endless conversation. 

RZ Endless conversation. 

[32:57]

PF Oh God. 

RZ Quick little pitch, Paul, this is related to what we’ve been talking about, not directly, but it’s—

PF This is real, right? Email is that sort of like, “I’m gonna send you the contract,” then the modern consensus is you move to conversation, but then that doesn’t solve it exactly either cuz now there’s no way to get anything done, it’s just everybody saying, “I guess I’ll do it?” 

RZ It’s chatter. It’s chatter. Right? 

PF And then a new system comes in like Jira or whatever. 

RZ To organize and—

PF Yeah or Trello or like, “We’re gonna move the cards along.” 

RZ Yep. 

PF Which actually was giving us a huge amount of anxiety cuz we couldn’t get conversations going across the organization around getting stuff done. 

RZ Yes. Accountability. 

PF Yeah, that’s right. 


RZ Yeah, “We’re gonna start a conversation and when it ends it means we solved the thing.” 

PF Right, so that’s why we built Dash which I mean we’ve talked about on the show before [yes, yes] but that it’s coming out of that email context, I think it’s worth noting, like we built a tool . . . for Slack called Dash that literally, you just go slash Dash. Um. Then the handle—and then the name of the Dash which is like Plan Barbecue. 

RZ Yeah, Decide on Marketing Agency. 

PF That’s right. Perfect example. Doesn’t fit into Trello. Doesn’t fit into—

RZ You’re trying to force people down a funnel, right? Like towards a goal line, right? 

PF Man, then you gotta get in Basecamp and it’s just like those systems get a little exhausting when there’s a million of ‘em going at once. 

[34:19]

RZ Yeah but what’s the end—setting up a Dash, what’s that last piece of it? You have to pick a . . .

PF Deadline. 

RZ That’s the whole point of it. 

PF So three or four people are in that sort of virtual room and then they have to do something. 

RZ “In five days we’re gonna pick that damn marketing agency. And then we’re done.” 

PF So it’s that—taking that responsibility, so it’s interesting, right? Cuz we all started in email. Email was the [yeah]—And then chat took over and seemed like, “Oh now we’re all really together.” 

RZ Yep. 

PF And then we’ve got all these other [music fades in] planning tools but now there’s like 50 of them [yep] for different projects. And it turns out what we really wanted was the—like somewhere between a meeting and a conversation. 

RZ Yes. 

PF So we built that. We’re proud of that. 

RZ It’s free. If you’re using Slack just type Slack dash or dash Postlight and you’ll find it. 

PF How native is this marketing right now? Like we just marketed right in the middle—

RZ Well, it’s annoying cuz not everyone can install it, you have to go to your like Slack Master or whatever he’s called. 

PF [Chuckling and muttering] I don’t—I don’t know—

RZ To do it. 

PF Slack Master Steward. 

RZ Your Slack Admin needs to green light this tool. 

PF Slack Master Steward is here to DJ your [Rich laughs] work day. Anyway, check out—

RZ Check out Dash. Check out all our Lab stuff at postlight.com/labs. 

PF Check us out. 

RZ Check everything. Call us up. 

PF Browse the whole web . . . today! 

RZ Yes [laughs]. 

PF Just hit reload a lot and—

RZ Joking aside: we love all the love we get for this podcast. So give us five stars on iTunes. If you’re so inclined. 

PF Give us six if you can, if you can hack in there. 

RZ Yeah. And reach out and talk to us: hello . . .

PF @postlight.com. 

RZ [email protected] Thank you. Have a great week! [Music plays alone for four seconds, fades out to end.]