It is always a negotiation. This week Paul and Rich discuss how to be a good manager and leader of people. We compare past experiences we’ve had as managers at our worst and best selves, and what we’ve learned from them (Tip: Do not passive aggressively go in!). We discuss the importance of building a culture of speed and execution from the beginning and how to foster conversation around timelines and scope. Paul and Rich also give tips on how to push back on a manager’s demands, in the right way.
Rich Ziade Hello? Hello ooooh wahhh ooooh. I can’t hear myself at all now [low pitched tapping, music fades in, plays alone for 18 seconds, ramps down].
Paul Ford Ok, Rich, you got something to tell me.
RZ So, Paul, we’re gonna share more wisdom.
PF I like wisdom.
RZ And this wisdom is pretty universal . . . Management’s hard.
RZ Management and managing people . . . and exerting [music fades out] your influence on people is very hard.
RZ And there’s a particular shortcut—there’s two ways to do it, right? And this—I think we’re almost stepping out of technology here but technology is a great playground to talk this through. There’s two ways to get to the right thing. If you are a manager, or a leader of any sort, you are thinking about things at a certain altitude by virtue of being where you’re at, and then you make some calls. But ideally you’re not making every call, otherwise it wouldn’t function, right? You have people. You have a team. And they’re making calls. But every so often you need to make a call. And that call has reasons behind it. Look, there are people who are jerks, who just like to exert power, and flex their muscles, and show that they can tell you what to do. Brush those aside. If you’re one of those people, stop listening to this podcast. But if you are someone that’s thought it through, that is thinking about the strategy and how to distill the strategy down into actual decisions and moving them along: you’ve got one of two choices. One: you can sit down [mm hmm], share your rational, talk through how to get there, and build consensus to then take that and let that drive some sort of a plan [ok] of some sort. Ok?
RZ That’s one way. Another way is to not bother really sharing the rational, you hope that people can kind of connect the dots. And you say, “I want the thing. [Mm hmm] And I want it next Wednesday.”
PF Mm hmm.
RZ Now, we live in interesting times, Paul. Consensus and discussion and dialogue around decisions are really important. But as a leader, right? Sometimes you actually wanna apply a little pressure [mm hmm] and that can be really scary.
PF Is this an intervention?
RZ No, it’s not an intervention.
PF Ok, just checking.
RZ Yeah, and applying that pressure means a few things, right? It means, first off, there’s less dialogue, actually. There’s a little less back and forth and you’re—you are probably the person—look, the world’s changing pretty fast but you’re probably the person’s that’s gonna do the review and maybe determine a bonus.
RZ That’s real.
RZ Like that’s—You can call it power or influence but it is—it is real, right?
PF I think just call it power. It’s power.
RZ It’s power.
RZ So there’s less dialogue there—
PF And what it is it’s backed by money. It’s partly backed by authority, but literally it’s backed by money.
RZ It’s backed by money, right?
RZ Now, there are certain people out there who are able to do that and the people who work for them just want to see them succeed, they just have a particular personality and a particular approach that’s like: “Look, if this is gonna help you, I wanna help you.” Like it’s not even ass-kissing, it’s not even for the bonus, they’re just connected to that leader. That, to me, is a leader I envy. There are very few of them but they do exist and sometimes they actually exert force that way. They actually [mm hmm] put pressure but don’t create anxiety or resentment. It’s like, “Of course, of course we’re gonna do this. We’ll do this for you. Of course we’ll do this for you.” And—
PF Very few.
RZ Very few. Very few.
PF And you know what? The world knows what to do with them.
RZ What does it do with them?
PF Meaning that you don’t just sit around and hope one of those shows up, like everybody’s for the look out for them.
RZ Oh. Yeah, yeah, yeah. There are not many of them.
PF Yeah, you can’t hire them, they’re hard to find. Like they’re just—we’re talking like a very small number of people in leadership or power roles.
PF I felt that actually the last president we had had a lot of that going.
RZ People wanted to see him do well [yeah] and he worked for his—towards his mission, even though sometimes they didn’t know exactly why a certain call got made, they’re gonna go execute on it.
PF And they—they might not even agree. They’re just like, “Ok, it’s his agenda and I’m here to help.”
RZ I think that’s right and I think he has that rare quality actually where—
PF And he had the presidency. It’s a good combination.
RZ It’s a good combination to have both of those things. That’s right.
PF Well you compare him to the new president where the narrative—even from the people in the Whitehouse—is like, “I am serving the presidency. I have really mixed feelings about this guy.”
PF It’s just—that’s a story everybody knows—
PF Mm hmm.
PF But they’re like, “I’m gonna serve—I’m gonna serve the mission.”
RZ That’s right. That’s right. So as a leader, it’s tricky, right? I mean, you—you actually sometimes just need the thing. And the other bit of this, and this is where kinda technology comes in, is sometimes you know exactly or generally pretty accurately what it’s gonna take to get the thing. Technologists—the analogy I love to use is the prescription. You ever see a prescription?
RZ You can’t read it.
PF Mm hmm.
RZ In essence, there is a wall between you and really understanding the depths and the complexities around a thing.
PF Mm hmm.
RZ When I was like 25 [mm hmm] I took nine months off from the job I had—26—and learned a program just enough—my goal was just enough so that when someone gave me an estimate I could understand how they got there. Or I could push back. I just didn’t wanna get bullshit. Essentially.
RZ Ok? So—
PF You’re good at estimation.
RZ Thank you.
PF It’s actually one of your—I mean like that’s probably the number one thing I’ve learned from you, like in terms of running this business day to day.
RZ Thank you.
PF It’s how to safely estimate an engagement.
RZ I wish it was a more compelling thing to get a compliment over but estimation is pretty high—
PF It’s the number one risk to our business.
RZ [Laughs boisterously] That’s fair!
PF No, bad estimation could sink us in a minute.
RZ Yes, it can. So, you’re a manager; you know the thing takes three weeks. You just got a six week quote [mm hmm] and you know it can just get done with two resources but five have been put on it. What do you do?
PF At my best or my worst?
RZ Oooh. There’s your title for the podcast [laughs].
PF Right. So first of all, I mean, lemme just counter a little bit. When I—when I used to think about what it would be like to manage [yeah], I imagined like a 1970s South American Republic where they had that—they were going all cyber and they would have these like control chairs and like the Minister of Economics would sit there and he’d go [Rich chuckling], “We need to increase granular to 22 percent.” And he would type something into like [Rich laughs] a—
RZ That’s management?
PF—a telegram, right? And it would go out and it would be, you know, [mimics sound of telegram being sent:]da da da da da da da da.
RZ It didn’t work out that way.
PF That’s what I thought. That was my fantasy. And actually and I think it was partly my fantasy cuz . . . even though I’ve been up and down and as an employee, I was really up and down. I was always a pretty good lieutenant. You’d be like, “Paul, I need to execute on these five things.” And I would say, “I appreciate that clarity. Chick, chick, chick.” I like to put it all in a spreadsheet with a lot of boxes. [Right] So I thought that’s what I wanted. And I thought that that’s what would be real. It’s not like that. It’s not as simple as herding cats, either. It’s not like any of those metaphors [no] but you’re always caught between, “Do I mentor this person and give them a model of thinking that they can apply or do I tell them what I need to get done and assume that they will figure it out later?”
RZ Whether they do or not you get your thing.
PF Hopefully, hopefully.
RZ You’re saying, “I need the thing done. I need the box by Friday, or whatever.”
PF Now, one of the tools—Ok, you get that timeframe. You get the four weeks. I’ve seen you do it; I’ve seen you react to it. My reaction is much—sometimes, if I’m being passive aggressive and at my worst, I say, “I’m gonna help.”
RZ You go in.
PF If I go in—they won’t let me go in.
RZ Oh, no. You’re not supposed to go in.
PF No, everybody—
RZ What are you doin’ in there?
PF That’s real bad.
RZ You’re not supposed to go in.
RZ We’re talkin’ about code. You’re in [laughing] and you’re committing code, not good.
PF That’s me at my worst. At my worst, I’m like, “Well if it’s gonna take that long and I really want it, I better pull up my sleeves, show everybody that I’m on the floor with them.”
RZ That’s the equivalent of a baseball manager putting on a mitt and saying, “I’ll do third base. We gotta get this going.”
PF Absolute destruction.
PF And it is passive aggressive, at best, and I suck at it. And it’s a terrible thing to do.
RZ Don’t do that. Here’s a don’t [laughing] in this wisdom.
PF No, don’t. The right way to do that is to say, “That is too long for what we need to get done, it would be hard to justify the project and we need to cut scope or else find other efficiencies and speed.” And the way you actually make that work is you—I think we’ve done this here to a degree: you build a culture of speed and execution. Like that’s where you start.
PF You start two years ago, or three years ago, and you say, “Speed is a virtue here and being able to do things quickly and make mistakes and move fast is a virtue.”
RZ “And iterate.”
PF That’s right [yeah]. Now, does that land? No, not as much as it needs to. You know? It doesn’t get there 100 percent of the time. 60 percent of the time, yes. And what you need is a culture—you need a culture—that’s the thing, that’s the kernel that everybody has to understand . . . that when they come to you and say, “Four to six weeks,” and you say, “Actually it needs to be three.” That that is not a ridiculous, dangerous career destroying request.
RZ [Sighs] Yes.
PF And that you know what reality really looks like. That if they come back and say, “Nope! Damnit. I did everything I could, I cannot squeeze this any further,” I am going to back down.
PF If they truly have done the work, show it to me and say, “I just don’t think [music fades in] you’re gonna be able to get that in that amount of time,” I’m gonna back down [music plays alone for seven seconds, ramps down].
RZ We have a lot of fans [music fades out] that listen to this podcast.
PF Thousands of people listen to this podcast.
RZ Which is really great. Which is really great but you know what? They don’t see our faces.
PF No, [chuckles] and that’s why it’s a successful podcast.
RZ But! We also like doing it in front of people and sharing the experience and actually—
PF We like doing the podcast.
RZ [Chuckles] We like doing the podcast in front of people.
PF Thank you.
RZ Opening it up to questions, having a little more dialogue, and then talking to people afterwards. Do you know how we are able to pull that off?
PF We have an office at 101 5th Avenue.
RZ In New York City.
PF That’s right.
RZ And on April 11th at 6pm you’re welcome to join us. We’re having a little live recording of Track Changes. Right in the office of Postlight.
PF We’re gonna talk about business. So come by.
RZ It’ll go off the rails. Don’t worry.
PF Yeah, don’t worry, and then there’ll be some drinks and [music fades in] [and food] and some hanging out.
RZ Ok, so visit postlight.com/events [music plays alone for seven seconds, ramps down]. You know some—one of the things I love to do? If I can.
PF Of course.
RZ Sometimes we tie [music fades out] deliverables around this thing that we can’t control.
PF Events are really good, right?
RZ Events are great, right?
PF “We’re having a party in May.”
RZ April 11th I gotta show somethin’. Now what happened like [stammers] let’s like dive into that for a second, what happened there? There’s this external force that has nothing to do with any of the personalities in the room that has just landed and hit us on the head [chuckles].
PF Well this is because we don’t have that magical type of personality that everybody is desperate to please or—
RZ That one we started this show with?
PF Yeah [laughs].
RZ [Laughing] Neither of us are that person [no, so it’s just like—] so we’re trying to get by.
PF They want our approval, you know, but they—nobody wants—nobody’s like, “I will move heaven and earth to get just the merest hint of a smile on Rich Ziade’s face.” No one has ever said—
RZ Oh! Let’s back it up a little bit.
PF Your children don’t say that.
RZ There are people here who want to uh . . . what’s the word? . . . Maybe you’re right [both laugh].
PF I mean it’s just not who we are. You gotta admit—I was talking to someone who owns a consulting firm the other day and he just went, “You gotta remember, I’m just terrible at my job.” [Both laugh]
RZ He owns the firm?
PF He just owns—yeah, of course. Of course.
RZ I will say this: I wanna pivot now to the person, we’ve been talking about managers [mm hmm] cuz probably managers listen to the podcast [mm hmm]. I wanna share a piece of advice for the person that has a manager and that is—
PF But wait, before you do that—
PF What do you do?
RZ What do I do?
PF “Hey, Rich, I know you said you need this in three weeks. It’s gonna be six and we need four people because there’s just so many reasons.”
RZ I—and this is probably a flaw, I go into a mode where I just—I signal much less sympathy and I say—
PF I’ve seen—you fold your arms.
RZ “I want the thing. I want it next Friday and that might take—talk to me about what is involved.” And I’m not insane, I’m not unreasonable but I also know very well what it’s gonna take but also, by the way, a lot of it is well meaning. Sometimes it’s like, “Well, we gotta get it to work in Opera.” You know? They’ve just—they’ve already sort of formulated all of these other requirements that have not—that aren’t necessary out of the gate, right?
PF I mean this is what we want people to learn and maybe we should talk about the person on the other side of the table, right? But it really is a negotiation. Like if you firmly believe that anything less than six weeks completely is a risk then you have to come back to me and say, “We gotta cut scope.”
PF And then work on that together. Like, we don’t wanna fail and be humiliated in public.
RZ None of us do. We’re aligned. All of us are aligned in that sense, right?
PF But there’s also 20-some years of experience here at getting things out the door and a set of instincts that eh, we can probably—There’s always gonna be something on the table.
RZ There’s always gonna be something on the table.
PF I have seen projects where you’re gonna put one word on one webpage go for six months. I mean it’s just like—people—software can stretch out a million different ways.
RZ Yeah, and we’re talking right now and there are large organizations and bless their hearts but it takes eight months to do anything.
PF Oh yeah.
RZ I mean just anything.
PF Well, here’s what happens—
RZ And, by the way! We are Postlight at 101 5th Avenue.
PF Come on by.
RZ And if you wanna retain us for eight months straight, we’re down.
PF Mm hmm. Look, because what happens is they go, “Well did we consider internationalization? And did we talk to Sue? And did—” You know?
RZ Some of it’s real like compliance ugly legal shit that just has to get adhered to and whatnot. I will—I will say something about us that I think was a really smart thing that we did which was we took time as a metric of success out of Postlight. Your ability to stay longer—cuz for many agencies if you stay longer, you make more money.
PF Yeah we don’t actually respect that grind very much.
RZ No, we don’t, in fact we try to explain it to prospects that we don’t think it’s the best way to go about it.
PF We see it as a symptom of something going wrong. If I’m here—sometimes I’m here late and it’s—sometimes it’s for work, sometimes it’s not. And if I see someone here at seven or eight pm, something’s wrong.
RZ Well, I think that’s an extreme.
PF Not always but if it’s like over and over.
RZ If it’s a launch, if it’s something—
PF Sure, people have worked on weekends. Like there is stuff that happens but [yeah, yeah] we tend to compensate them for their time, let them take time off. Like we’re pretty careful about keeping the time banked because the absolute focus—Here’s what we don’t do, and this is what a lot of agencies do, you don’t get to wait until the last two weeks and then say, “I’m gonna really put my shoulder down and get this done.”
RZ No, you can’t.
PF Creative firms do that a lot.
PF “Oh, hey—” And what that leads to is a culture of martyrdom. Where people get to show just how much they’re willing to suffer but they don’t suffer for the first month, they suffer for the last week.
RZ Yes. Yes. I don’t know that world very well but—
PF I do.
RZ That makes sense to me because it’s a creative process.
PF Well and then they’re like, “Uh I couldn’t get it done,” and then everyone’s there at two in the morning, eating pizza, like getting the deck done. You know one thing that was fun? I used to work at an agency and it was just Tuesday was always late night day. Like it was just—
PF Yeah you would just stay until eight or nine on Tuesday.
RZ Are people just enjoying that though?
PF Well it was just like Tuesday we’re just gonna all hang out and kinda clean up everything.
PF Like just get all the messes out—
RZ That’s not terrible.
PF There is something like at eight o’clock that one proposal or that pitch or that thing that you’re supposed to be working on is somehow less embarrassing cuz you’re just all kinda hanging out and you’re like, “I—I haven’t even started that.” And they’re like, “Yeah, well, you better start it.” And you’re like, “Ok, ok.” [Chuckles] And you’re eating a nice dinner that you got through takeout, like it just somehow takes the temperature down. And then the rest of the nights are your own. Ok. Let’s switch it around: you’re on the other side of the table. You’re mean-spirited, selfish, completely out of touch with reality boss has just said, “I want it in three weeks not six.”
PF What should you do?
RZ The best advice I can give . . . and I’m allowed to give advice now cuz I’m an older gentleman.
PF Mm hmm.
RZ Is . . . pause and think about the motivations of where that pressure—what are the motivations that are creating that pressure? . . . Unless you have someone that’s very sort of paranoid and distrustful and doesn’t believe you’re working hard or is just a jerk, there are motivators. The motivators—I mean I’ll give you an example. There is a potential, follow on project at client X, if we deliver this earlier but in time for a conference they wanna show it at.
PF Or even more so, we need to stay on this cadence because there’s other work coming down the pipe, it’s all gonna start to back up.
RZ What are those motivators? If you pause and think about those motivators, then a) you start to empathize more with why you’re getting that pressure and b) and this is the bigger one, you can actually have dialogue, when you’re talking to your leader or your manager about that pressure, it actually opens up the manager’s thinking to some extent and you know what they start to see? In you? A leader.
PF You know why though? Here’s the key. I can unlock this for people on the other side of the table. You are team slash discipline oriented. You are oriented around being a designer, an engineer, a product manager, a data analyst, a business analyst. The person on the other side of the table making the unreasonable demand . . . is business oriented.
RZ That’s right.
PF They might come from your discipline [yes]. They might have empathy for it but they are reacting not to the goals and needs of the discipline [yes] but to the goals and needs of the business that they have agreed to internalize in exchange for like money and privilege and to have part of their life ruined [that’s right] by the company [that’s right, that’s right] ok? So you’re there going like, “This is not how you do design. This is not what good engineering looks like.”
PF And they’re going, “I get it but there’s probably something in between.”
RZ Yup. You touched on this with different words but what happens with leadership is you’re willing to put aside some of your own personal motivations and allow in the motivations of the organization.
PF Mm hmm!
RZ And that’s—it’s a little weird sound because a motivation, you know, an organization doesn’t have motivations but it very much does. They are very clear actually: survival and thriving and growing are real motivations. And if you’re locked into those and those are the drivers for you then that’s real. This is sounding very like airport management book but man this is the fundamental shit.
PF It’s real because I can’t pay you do be a good, thoughtful engineer unless the work keeps coming in. Now if it’s all compromise, it’s really bad but if it’s compromise sometimes, you should definitely go with it and try to help them get there.
PF Right? But if they’re saying, “Hmm, you’re really good and really talented, I just need some help here.”
PF Do whatever you can because that’s leadership [that’s right]. It’s you stepping out of your discipline and the goals of your own careers and saying, “Let me help you.” Now they’re—and they’re gonna keep that in mind. That comes around.
RZ Yes, absolutely.
PF That is leadership. It’s just really—it’s hard to articulate cuz when you are a designer or an engineer or a product manager or something and just starting out what you do is you think, “How do I become the best designer possible? . . . I wanna go to the right conferences; I want people over here to think that I’m really smart; I want my professors back at school to know that I’m doing really great work; and I wanna see myself and my stuff in the public marketplace.”
PF Right? Those are wonderful goals! We encourage them. We want people to like live their lives that way but there’s a point where you go, “I can’t worry about that right now. I have to be in a meeting in about two hours.”
RZ Right, exactly.
PF So that is the big negotiation.
RZ It is, and I see my blind spots as a manager and as a leader. I do. But I also know my strengths and that’s the other bit: a good manager, a good leader, loves to cede control. Loves to cede power because they actually want to fill in those spots. The ones that are like—all they do is think about their territory and their terrain and making sure they get credit for the thing [mm hmm] down the hall, I mean, whatever. They exist. There’s a lot of ‘em. They’re probably—some are listening to this podcast. Whoever you are, you’re probably not that person.
PF You know what though? Let’s be real. We work with—and I’ve worked in the past with tons of NGOs and not-for-profits, right? I mean that’s—the relationship’s there. You go and do a piece of work and you have to then get a grant to continue on that path.
PF That means you have to go before a board or an ultra high net worth individual and say, “Here’s the path that we’re on. Do they wanna fund the low level API or do they wanna fund the beautiful app that millions of people will use?” It’s a trick question. They actually wanna fund both. But the story you have to tell is on their level. They don’t care about the granularity. And you can’t make them care about it. You can only enter into an exchange with them and they say, “You know what? This seems worth it.”
PF And so it’s negotiating that, right? Like a skilled person might actually be very territorial that way like I need to have this conversation and, “No, I don’t need the head of design—or the head of engineering in that conversation,” and so on. So it’s tricky, there are some aspects where a little bit of territoriality and boundary defence and knowing whose talking to who is important.
PF But regardless of whether it’s important or not, it’s human and it’s not going away.
RZ No, it’s not.
PF But you know what, Rich? All this said . . . There’s a really, really, really important thing and it’s actually, I’m gonna counter to everything we just said for one second.
RZ Uh oh.
PF Don’t over promise! Don’t go in there and say, “I can get it for you in two weeks.”
RZ Don’t over promise.
RZ Over deliver.
PF That’s right.
RZ I mean this sounds cheesy and obvious like what we’re saying right now but—
PF That’s ok.
RZ—like pause for a minute. And yeah.
PF Stick to your—you know if you think it’s six weeks, walk in there with six weeks and then say, “I need help shrinking it, I know there’s some urgency.”
PF And they’ll go, “Let me help you. Let’s figure out what can come off the table.” The worst thing to do is just put your feet in and say, “There’s no negotiating.” But [music fades in] the even worstest, worst thing to do is say, “No problem,” and then [chuckles] disappear [Rich chuckles]. You know the other good move for the young employee would be like: “I’m gonna get this for you,” and then goes on vacation. I’ve seen that.
RZ Oh that’s the best one.
PF They forgot to communicate it. It’s just like, “Oh I’m in uh—”
RZ That’s a real thing.
PF Yeah, “I’m in Singapore.”
PF So, anyway, you’re all great, you’re all working hard. Nobody—I’ll tell ya: it’s almost never laziness. It’s always just communication.
RZ And strangely we have none of these problems at Postlight.
PF Everything’s great.
RZ Which means that we’re an incredibly efficient, well-run organization that builds great apps and experiences [laughs].
PF I mean we all have challenges, we just try to keep ‘em in the open and we do meet our ship dates. So whatever we’re doing and as messed up and bad as any given day might be . . . most are pretty good and we hit our ship dates. Alright, Rich, let’s—
RZ If you have thoughts or feedback, this is a weird one but it’s a great topic for us, email@example.com.
PF firstname.lastname@example.org! Bye [music ramps up, plays alone for four seconds, fades out to end].