Molding Leadership Within Tech with Adam Zimman

Episode Summary

This week Corey is joined by Adam Zimman, a self proclaimed “public servant” of the tech world, to talk about often unspoken about aspects of the industry—at least on the technolgoy side of the house. Adam is here to discuss leadership, product marketing, and go to market strategies. Adam’s role as a strategic advisor has carried him from large scale organizations to the small, and it has helped him shape a stark awareness of the role of people within a company. Adam goes into how his background has shaped his perspectives on leadership and management. He also offers the importance of providing the right professional mold for someone to provide challenges to management structures within an organization. Adam also discusses how the ability to challenge managers can be valuable and helpful. Adam teases out the differences between leadership and management, and how the former should reinforce the success of others. Tune in for Adam’s valuable insight!

Episode Show Notes & Transcript

About Adam
Adam Zimman is a start-up Advisor providing guidance on leadership, platform architecture, product marketing, and GTM strategy. He has over 20 years of experience working in a variety of roles from software engineering to technical sales. He has worked in both enterprise and consumer companies such as VMware, EMC, GitHub, and LaunchDarkly. Adam is driven by a passion for inclusive leadership and solving problems with technology. As an Advisor he works with a number of startups and nonprofits. His perspective on life has been shaped by a background in Physics and Visual Art, an ongoing adventure as a husband and father, and a childhood career as a fire juggler.


Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

This episode is sponsored in part by our friends at VMware. Let’s be honest—the past year has been far from easy. Due to, well, everything. It caused us to rush cloud migrations and digital transformation, which of course means long hours refactoring your apps, surprises on your cloud bill, misconfigurations and headache for everyone trying manage disparate and fractured cloud environments. VMware has an answer for this. With VMware multi-cloud solutions, organizations have the choice, speed, and control to migrate and optimize
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Corey: This episode is sponsored in part by our friends at Jellyfish. So, you’re sitting in front of your office chair, bleary eyed, parked in front of a powerpoint and—oh my sweet feathery Jesus its the night before the board meeting, because of course it is! As you slot that crappy screenshot of traffic light colored excel tables into your deck, or sift through endless spreadsheets looking for just the right data set, have you ever wondered, why is it that sales and marketing get all this shiny, awesome analytics and inside tools? Whereas, engineering basically gets left with the dregs. Well, the founders of Jellyfish certainly did. That’s why they created the Jellyfish Engineering Management Platform, but don’t you dare call it JEMP! Designed to make it simple to analyze your engineering organization, Jellyfish ingests signals from your tech stack. Including JIRA, Git, and collaborative tools. Yes, depressing to think of those things as your tech stack but this is 2021. They use that to create a model that accurately reflects just how the breakdown of engineering work aligns with your wider business objectives. In other words, it translates from code into spreadsheet. When you have to explain what you’re doing from an engineering perspective to people whose primary IDE is Microsoft Powerpoint, consider Jellyfish. Thats and tell them Corey sent you! Watch for the wince, thats my favorite part.

Corey: Welcome to Screaming in the Cloud. I’m Cloud Economist Corey Quinn, and periodically I like to talk to people about different aspects of the industry. One that I think is interesting that doesn’t get spoken about a lot directly is the idea of leadership. My guest today is Adam Zimman, who’s a startup advisor providing guidance on—as mentioned—leadership, platform architecture, Product Marketing, and GTM 
Strategy—GTM, of course, standing for go-to-market. Who goes to market? That’s right, little piggies. Adam, thank you for joining me.

Adam: Thank you, Corey. It’s a pleasure to be here.

Corey: I imagine that you usually don’t advise your clients to call their GTM execs, little piggies?

Adam: Well, I mean, I guess it depends. You know, if you’re actually a bacon manufacturer then that might be actually a reasonable thing to do.

Corey: Yeah, that’s a level of investment in the product that you usually don’t see in most environments, but we take what we can get. So, snark and cynicism aside, what is it you do?

Adam: Ultimately, I look for ways in which I can add value. And I’ve had the privilege in my career to be exposed to a lot of amazing companies, and I look for ways to be able to take the lessons that I’ve learned, mainly through mistakes and failure, and be able to translate those into success for others.

Corey: Most recently, you were at LaunchDarkly for a while, taking a number of different VP roles. While you were there we spoke, back in 2017, briefly while you were in that environment. And in fact, my first guest on the show was one of the folks on your team, Heidi Waterhouse, who has been back at least once since then, and hopefully more than that. But it’s been an interesting ride there. Before that you were at places like GitHub—or JIF-ub as I insist on pronouncing it—EMC-slash-VMware—where does one start and the other stop? Hard to say, it’s sort of a giant corporate shell game—but you’ve spent a lot of time in large companies and small ones as well, and now you’re effectively hanging out your shingle as a strategic advisor.

Adam: This is true. I mean, I think that one of the things that I’ve found is that doesn’t really matter what size of company you’re at; you’re going to find new and interesting challenges, and you really don’t have to look that hard. And so one of the things that I found consistently, and I would say that this was most pointedly phrased for me by Emily Freeman in the context of, “DevOps is this amazing thing of people, process, and technology. And the reality is, is the only one that’s complicated is the people.” And oddly enough, small companies, you still got people; big companies, you still got people. So, therein lies some of the challenges.

Corey: And people are inherently non-deterministic; you never know what you’re going to get by applying the same input, even to the same person just separated out by time. It’s a challenge, and the problem that I see across the industry is that very often, you’ll have a team of engineers and you’ll pick the best and brightest one of those engineers, and, “Congratulations, you manage the team now.” Now, management’s inherently orthogonal skill, and what you’ve simultaneously done is gotten rid of a great engineer and introduced a terrible manager. And that’s through no fault of this person’s own. But when I started managing teams, I got surprisingly far by just doing the exact opposite of all the stuff that my previous terrible bosses have done.

And that works really well right up until it doesn’t in a variety of probably fairly easily predictable ways. And the challenge that I’m seeing is that there is no book on how to do these things. If you want to climb an engineering ladder, great; there’s a bunch of very qualified people who will tell you how to go from wherever you are technically, to where you want to go, and what you have to demonstrate, and what you have to do. Leadership is squishy, in that sense. At least it always has been to me.

Adam: The interesting part that I would challenge you a little bit on is that there are thousands of interesting books on leadership, even smaller subsection on management specifically. I think one of the challenges there is that they’re not well circulated within tech as an industry. I think that there are a few that people come back to, like Andy Grove’s book on his experience building Intel. There are a lot of books out there that have done a lot for talking about how to manage people and how to think about what are the specific tactical things that you do. It’s having one-on-ones, it’s having meetings with clear agendas, it’s being able to look for ways to set expectations with your organization.

I think one of the challenges that I see pretty consistently, is the fact that that effort to be able to go out and find that information or to learn those skills is something that is put on to, as you said, this individual who is coming to management through punishment. They’ve been extraordinarily successful and now you will punish them by putting them in a role where they can no longer do all the things that they enjoyed, that made them successful. And I think that you see time and time again, where organizations put people in these roles, but they don’t do anything to either prepare them for it or do anything to continue that notion of professional development or training for those individuals once they’re in those roles.

Corey: There are a lot of books out there for any discipline under the sun; some are good, some are terrible, most are somewhere in the middle of the road law of averages winds up working out. I think a key difference, on some level, is I can take to Twitter, or a forum, or something like that, and complain about software; the computer isn’t doing the thing I think the computer should be doing. And that’s great. I can’t very well go and complain about managerial issues while actively having a team and not find myself no longer having managerial issues, if you catch my meaning. It’s hard to find communities around this stuff.

Adam: I think that you’re right. And I think that this is one of those things where not only that, but I think that we also in tech have predominantly taken a very hierarchical structure to the way that we think about management and leadership, to the sense where oftentimes, it is not only discouraged but downright forbidden for an individual contributor to challenge their manager if they want to continue to have gainful employment. And I think that this is a cultural thing that, you know, it’s funny; I know that you recently did an episode with John Allspaw and were talking about incident remediation. And I think that one of the things that I’ve always tried to do as a manager, as a leader, is think about opportunities for being able to do that type of incident response, for people. If you have a person that leaves, whether that is forced attrition, whether that is voluntary attrition, whether that is something that you wanted to happen, something that you didn’t want to happen, what are you doing from a perspective of kind of a post-incident assessment to learn from that? And I think that the next level that is, how do you do it so that you actually, in some way, incorporate that for the individual that’s actually leaving. Because ideally, they’re learning from that experience, as well.

Corey: Back when I was a generally terrible employee, I decided at some point, I was tired of dealing with computer problems and wanted to deal with people problems instead. Now, let’s be clear, I found a path to do that in a very different direction than I expected at the time, but at the time, it was, “Great. I’m going to go ahead and become a manager of a team.” And I talked to a number of folks about all right, what is the path to go from decent technical engineer—I was a senior SRE type at most of these places—into management. And not just talking to people at the companies I was at, but talking to people in the larger community, and every engineering manager who I respected and talked to about, 
it always seemed like they got this lucky break at just the right time and that made them a manager for the first time.

And once you have a track record of having managed people, then you’re in. You can go back and forth between IC and management roles. But, “Well, you’ve never managed people before, so we’re not going to take a chance on you to manage people.” The way that I did it, honestly, was I—a few times—I wound up joining startups where I was effectively the only ops person; we suddenly started scaling and having fun problems, and well, I did negotiate for that director title, so all right, I have teams now. I was more of a team lead than most things, in some cases.

But it led to a really pretty interesting evolution in how I approach these things. I find now that the right answer is for me not to manage people at all because what I fundamentally do here at The Duckbill Group is basically become the loud, obnoxious center of attention. And I think that what managers need to do is showcase their people instead. And those two things, at least in my view, are opposed. And it’s very challenging to do both of them, let alone well. For me at least, I tend to back away from the management side of things almost entirely and abdicate the 
role. Which is great. People self-manage, right?

Adam: Well, I mean, I think that there are individuals who definitely will take—have the ability to self-organize and self-manage to a degree. I think that the challenge that you run into is, as the organization scales, as the nature of their role tends to change with that scaling organization, it becomes more challenging for them to navigate through those changes. A great example would be, I have had the pleasure and the privilege a number of times in my career of managing extraordinarily senior individuals; these are individuals who, to your point, don’t need a whole lot of care and feeding. But what they do sometimes need is they need someone who is able to be in rooms that they’re not in, whether that’s from a higher-level leadership meeting understanding larger organizational goals, or they need someone that’s going to check them; they need someone that they can trust, someone that they can bounce their ideas off of to know is this something that’s going to be perceived value or something that’s going to actually take me in the wrong direction, or somebody that’s, kind of like, paying attention to the work product that they’re doing and giving them some coaching, whether that’s cheerleading or whether that’s connecting of saying, “Hey, there’s also this other person you should talk to.” Those types of things are really valuable for those individuals who are, to your point, a little bit more self-sufficient.

Corey: On some level, I ran into this trap a lot, and having over drinks conversations with a bunch of people who went on similar paths, it’s blindingly obvious that it’s a dumb move in hindsight, but an awful lot of us did it, where we’re sitting there as engineers with the belief of, “Ah, if I can make my manager—or beyond, several skip-levels up—look incredibly foolish in the middle of a large meeting, they will inherently see the value of what I have to say and will thus elevate me to management.” As it turns out, they elevate you to customer because you’re not working there anymore, in many cases. And when I talk to people about this, it usually has that lightbulb coming on moment of as soon as you hear it, of course, it is blindingly obvious that you aren’t going to sarcastically obnoxious your way into being management. Instead, the path there—in hindsight, also blindly obvious—is act as if: act managerial; help to effectively carry on your manager’s message to the rest of the team, and when you have reservations or whatnot, talk to them in private rather than calling them out. And it’s the obvious stuff of who gets promoted to management? Well, the people that look managerial. And that is what that looks like, in many respects.

Adam: And this is one of the reasons why, when I talk about management I like to separate the notion of management from leadership. Because I think that anyone can be a leader. You don’t actually have to be the administrative manager of an individual to be a leader to them.

Corey: I saw a great poster once when I was younger. “Leaders are like eagles. We don’t have either of them here.”

Adam: [sigh]. Yeah, yeah. Ugh. I do miss good motivational posters.

Corey: Oh, yeah.

Adam: You know, I think that there’s some truth to it. I think that finding people who are genuinely invested in being able to enable the success of others—which is how I define leadership—is challenging. I think that, especially in rather capitalistic-type industry like we’re in, there is a lot of measurement of people’s success by their own personal achievements and by their ability to beat their own drum. And I think that it’s something that is, frankly, a failing of our industry, where we don’t do a better job of encouraging folks, and rewarding folks that actually look out for others and enable the success of others. Because I think that’s something that is—ultimately you think about how you build strong teams, and it’s not about getting a bunch of individuals who can do amazing things individually. It’s about getting individuals who are capable of working together and being able to do more than they would be able to if they were simply working individually.

Corey: Do you ever find that people are chasing management in many respects because they think that it’s something very different than what it is, and then find themselves in situations where well, I’m the dog that caught the car that I was chasing and only now do I realize that I have no idea how to drive the thing?

Adam: Oh, absolutely. So, this is something that has been interesting me a lot recently, in the sense that I think we as an industry also do a very poor job of measuring management, measuring leadership. We give a lot of power to managers through performance reviews to measure their individual contributors, but there are very few companies who actually efficiently do things like 360 reviews, which has always confused me because I think that implies that you’re getting feedback from all around you, as opposed to what you really want is you want feedback pointed back at you, which would be 180. But maybe that’s just—

Corey: Let’s be clear, that was also pioneered by the German [Wehrmacht 00:13:48] in World War II, which is yeah, basically how some people I’ve worked with do tend to manage.

Adam: Yeah. I think that if we can think about how do we measure the success of a manager, is it simply a function of the output of their team, or are there other efficiency metrics that you should be looking at? Very obvious one is how efficient is a manager from a perspective of the utilization of their resources? And when I think about that, I think about are they actually able to effectively hire? Are they able to effectively retain the people that they hire?

What does it look like for the people on their organization from a promotion perspective in terms of skill growth? Do they become more valuable over time? Those are ways in which we can think about how we measure the manager, potentially, directly. And then there’s indirect things like what’s the qualitative aspect of those individuals that work for them? Are they people who are enjoying the work that they’re doing?

Are they motivated to continue to work towards the company’s vision and mission, to be able to actually make their manager look good, but also make the company successful?

Corey: A challenge, too, because I’ve seen this myself is, all right, you’re not elevated to manager. Congratulations. It’s not really a promotion. It’s a lateral move. However, a lot of companies don’t treat it that way.

They don’t compensate it that way, et cetera. And oh, okay, management, it turns out is not for me. There’s no real good way to say, “I’m going back to being an IC,” especially at the same company, without it being perceived by many—rightly or wrongly—as a demotion or a failure.

Adam: This question of, like, motivation to people, why do they want to go into management? I think that oftentimes this is misplaced. A lot of times the number one motivation that I’ve heard has nothing to do with wanting to actually help people or solve people problems, as you said earlier; it has to do with I want a bigger paycheck, I want more seniority, I want more responsibility, and therefore the only path available to me is management. In fact, many career ladders at organizations require an individual contributor to go to a management position before they can become a principal or a staff-level engineer, which is nonsense. First of all, why would you torture the individual to do something that is so completely and utterly outside of where their interests are? Secondly, why would you just decimate your lower-level individual contributors, your newer individual contributors by having someone who is completely non-inclined towards management be responsible for them? Oh.

Corey: Oh, yeah. Used to be your peer; now they manage you, and great. I think people underestimate exactly how broad the blast radius of a manager is.

Adam: Yeah. Talk to anyone, and they’ll be more than happy to tell you the worst manager that they’ve ever had. At the same time, they’ll also probably be able to tell you the best manager they’ve ever had.

Corey: Oh, yeah. I called both of those out—only one the one of those by name, by the way—in conference talks that I’ve had because it’s—yeah, you can probably guess which one I would call out and which one I would not name publicly—yeah—

Adam: It depends on the conference, I guess. But yeah.

Corey: Oh, yeah, absolutely. If it was you-know-what-your-problem-is con, yeah, it went super well.

Adam: [laugh].

Corey: It was fun. And management, especially in the current era is getting interesting, as we’re seeing the heating up of the market in a bunch of different ways. And I understand, to be clear, that Twitter is not a perfect microcosm of the industry, but there’s a recurring theme that I’m seeing among a number of engineering types that seemed to get—and again, I don’t want to get letters for this, so if I misstate it, audience, please go ahead and be kind—but there seems to be a certain thread running through engineering communities that the purpose of a company is to provide a utopian work environment for its staff. Now, as someone who runs a company myself, yeah, I absolutely want to provide the kind of working environment I wish I’d had in a bunch of different environments. And that’s not going to work for everyone, but that’s okay.

But fundamentally we’re here to make money, and ideally, enough monies that we can keep the lights on. And that does mean that, however, we want to treat our staff that has to be subordinate to can we continue as a going concern? So yeah, it turns out, we can’t—sustainably—outbid Netflix on every hire that we make and we aren’t able to wind up having three catered meals a day as a full remote company delivered to everyone’s house. Now, I’d like to, in a world where money flows like water, but it doesn’t. For better or worse, there are constraints, and constraints shape us.

But there’s a thread that I’m starting to see of… I hesitate to call it entitlement, but it trends slightly toward the direction of folks who are in tech, and in some ways seem very far removed from business realities—now, let’s be clear in the FAANG world, yeah, it’s pretty attenuated. And in startup land where well, we’re the VC backed, so we’re losing money by the billion but we’re making it up in volume. Great. That is not necessarily what I’m talking about here. I’m seeing a thread where, oh, engineers are clearly the smartest people in any company, which means that every other department should defer to them. I disagree with that position.

Adam: I want to follow that thread a little bit with regards to engineers. So, I’ve worked as a software developer—

Corey: My condolences.

Adam: Yeah. I’ve worked as a technical salesperson. I’ve had the opportunity to work in pretty much every department with the exceptions of HR and finance. So, that has been part of my career of jack of all trades, master of none, but it has given me some interesting insights in terms of the value that different organizations, different individuals, bring to a company. And I think that—one of the things that I will say is that for the longest time, in large organizations, especially non-tech industry organizations, the engineer or the developer was at the same expectations or the role as someone in the janitorial staff.

It was basically, “You’re part of the plumbing. You just do the things so that the tech just works, and we’re going to have the other business folks that are more responsible for actually making decisions that are going to make our business money.” The quintessential example is someone like Kraft Foods or someone like John Deere, right, where you’re building tractors; for the longest time, the guy who ran the website wasn’t going to be the guy who was going to make or break John Deere’s quarterly earnings. Now, you’ve got tractors that literally are more computers than they are mechanical devices and so you suddenly have this change in dynamic with regards to the importance of that developer. But I think that something that’s interesting, also, is that those other people who worked at the company didn’t go away.

They’re still there; they’re still important. In fact, they’re still oftentimes making the buying decisions on behalf of the developers. The developers aren’t the ones that are making those choices. And so you need to figure out, how do you actually make the technology choices and the technology outcomes accessible to individuals that are in roles that were, historically, had nothing to do with tech.

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Corey: I’ve always been a big believer in the idea that if you’re going to transition into a new field, be it into tech, out of tech, et cetera, great. In almost every case, you should find ways to do that laterally. I think that this idea that, oh, you’re going to go ahead and just start over with an entry-level job after you’ve been in a field for five years—no. Find the position that’s halfway between where you are and where you think you want to go next and start getting exposure there. In time, it’s those niches that add value that distinguish you from other folks.

It turns out that they don’t generally want to hire someone in almost any role that comes from Central Casting, where it’s alright, give me a 
standard MBA with the following pedigree and drop them in as my new executive, whatever. No. They want to see things like industry experience; they want to see things that distinguish folks, and having experience in industries that are not traditionally, purely what this role is, is super helpful in a lot of different ways. What I do pretty clearly blends finance and tech; that goes reasonably well. Increasingly it starts to blend media, which is something I don’t pretend to understand. But here we are, he said into the microphone.

Adam: Yeah. Well, as long as you’re not starting the next Fox News, I’m fine with that.

Corey: No, no. Generally not.

Adam: Okay, fair enough. But I think that you’re right. This is one of the things where, trailing back, we’ve throughout this conversation to the notion of leadership, this is something that I found extraordinarily rewarding and empowering that I’ve done with individuals that I’ve brought into new organizations, either through initial conversations during an interview process, or during, as part of their onboarding, is I sit down, and I actually talk to them about what are their plans? What are their expectations? What are their goals, not only for the next 30, 60, 90 days in this role that we’re talking about but what are they thinking about from a perspective of what do they want to do in the next year? In the next three years? Five years? Ten years? What are those checkpoints of what do you want to do in this role? What do you want to do at this company? What do you want to do with your career? Like, where do you see it headed?

And it doesn’t mean that you’re writing this in stone, or that I’m going to hold you to it, but I think that one of those things that’s really empowering for a leader is to be able to help those individuals find those connective threads that tie one position to the next and help them get there. If they’re somebody who is saying, “Hey, look, I’m currently a developer, but I really wish that I could give more talks.” Okay, well, that’s great for me to know. Let’s put you on some projects that maybe actually would result in great content for a talk that you could give at a conference. And then we’ll figure out, how do we work with the marketing department to be able to help you bring that to fruition?

There’s a lot of ways to be able to leverage this experience that you have as a leader, as a manager, to an individual who’s coming up in their career and saying, “Hey, look. This is how some more ancillary things are connected.” And being able to bring those back to them.

Corey: I really wish, on some level, that there was a more defined path toward a lot of these things, where the stuff is explained to folks. So often, I had terrible managers that, in hindsight, weren’t that terrible. Because I didn’t understand where the role started and stopped, I tended to view the role of the manager is there to protect the team. The end. And be our advocate in the organization, and get us the thing that we want, and what do we want? Comfy chairs.

And it turns out that isn’t ever how it really works. If I had to define management, it would basically be, balancing competing priorities more than it is almost anything else. And counterintuitively, the higher you rise in an organization, the more responsibility you have, and the less you can actually directly do. Everything you do drives influence. And that’s it. That’s how it distills down.

Adam: You talk about the engineer that wants to move into management role because that’s how they see their career progressing. This is a close corollary to the engineer that wants to move into a product management role because they want to have greater oversight into the decisions that are being made about what’s getting built. And what you come to realize, for any engineer who successfully made that transition, is it’s really complicated and difficult to be able to have that mental switch take place between this is how I’m going to build it versus this is the priority of what needs to get built next. And all too often you see engineers that land in product management roles that are dictating how something should be built, and suddenly the engineers are just like, “No, I have no respect for you. Because that’s not your job.”

And likewise, in a management role, oftentimes people view that as an opportunity for them to make all the choices, make all the decisions, and suddenly lose sight of the fact that they used to be on the other side of that outcome themselves, and were disappointed when they weren’t included in some way, shape or form, or their priorities weren’t taken into consideration.

Corey: As you look at your own career, what is the worst job experience you’ve ever had? Or the worst job you’ve ever had? Or the worst boss you’ve ever had? That’s always a good one to do.

Adam: [laugh].

Corey: Pick a superlative and not the good kind. Hit me.

Adam: Yeah, no, I mean, look, I think that probably the worst… experience that I ever had with a manager, with a boss, was actually when I was first a software developer. And my manager would occasionally just come up behind me and just stand and watch me code. And we’re not talking about peer programming, where it was just like, we’re working together. No, it was, literally would come up, stand behind me on my shoulder, and just stand there. Not saying anything; just watching me write Java code. And that was probably the most disconcerting 
experience that I’ve ever had in a job ever. I lasted about six months and then I was just like, “I need to move on to something else.”

Corey: It turns out one of my failure modes was that I was great for the first three months in new ops roles because things were invariably a fire, and—

Adam: [laugh].

Corey: —I know how to solve those things. And then it becomes a maintenance role, and I’m bad at that. For longest time, I thought I was just a crap employee. And I am, but for different reasons. Instead, though, for me, it turned into a, I need to find the thing that I’m good at and embrace that. And I have to say, it was not being, basically, a cloud comedian on Twitter where my primary means of communication is shitposting. But you know, here we are, and this is how we’ve gotten there.

Adam: I mean, know your strengths, man. Know your strengths.

Corey: Yeah, lean into it. I mean, you went to college in Maine; you know what it’s like there. It’s dark and cold nine months out of the year, so all we do is sit inside and develop personality disorders. And well, here we are.

Adam: Well, hey, I mean, I took a break from tech after that first job in software development and I actually went back and worked for a guy that I met while I was in school, and I worked for him, he was a general contractor. So, I have an appreciation for Maine winters in a way that I never gained as a privileged college student, when I was actually digging snow out of ditches to be able to pour concrete at six in the morning and then later in the day, I got to go up and use 80-pound weight shingles to reshingle the roof in 20-degree weather. So, it was an eye-opening experience. But I’ll tell you, I learned pretty much everything that I know about how to build infrastructure from that eight months that I spent doing everything from framing, ditch-digging, to electrical, and plumbing, and roofing.

Corey: Kind of fun how often is that we wind up trying other things. And this is part of it, too. As much fun as it is to complain about various jobs and whatnot that we have, let’s be very clear here for a minute that I’m not dealing with hot tar, being paid seven bucks an hour. There are advantages to the [unintelligible 00:28:08] jobs I have.

Adam: I mean, that was a number of years ago, but I still got ten bucks an hour.

Corey: My first job at the University of Maine call center working in tech, in those days, I think I was being paid something like $5.35 an hour. To answer phones, which again, not that hard of a job. I made a lot more money a couple years later when I moved to construction. Yeah, I wouldn’t recommend any of those things for me these days, but it was instructive.

Adam: But at the same time, I would argue that you also have benefited from those experiences in the way that you approach the things that you do now. And I think that’s one of the things that I’ve tried to bring forward in my career is look for those opportunities to make those 
connections, and understand the value of those experiences, and be able to help to enable other people because I’ve had those experiences.

Corey: To me at least, the answer is to turn whatever you’ve done or whatever happened to you into some form of empathy. The idea of well, I had to struggle coming up, so you should, too. Let’s instead focus on making it better for people who follow us. Send the elevator back down, 
as it were.

Adam: I mean, I think that’s great advice, and I think that it’s something that’s done far too infrequently. One of the things that I’ve noticed is that that aspect, unless somebody has actually been through the experience where somebody has done that for them, it is oftentimes something that is a lot harder for people to see. This goes to your earlier statement around the expectations that maybe are changing, and they’re not such great ways with regards to what people are expecting from companies, what people are expecting from managers. I think that there is a distinct lack of expectation setting that takes place at companies in terms of what is the role of the company, what is the role of an employee, and how can those two come together to still have a positive interaction, but aren’t overstepping on either side? Because that’s really where you get into problems. That’s where all of a sudden you have these companies that are looking to fill the role of, I will take care of all aspects of your life, when in reality that’s not a very healthy relationship for an individual to have with a company.

Corey: So, I want to thank you for coming and speak to me. What are you up to these days, and where can people find you? And why should 
people find you?

Adam: Well, I don’t know that anybody should find me.

Corey: “I hope this email finds you never. I hope you’re free.”

Adam: Yeah, exactly. No, I mean, I would love to find folks that I can add value to and help out. It’s easy enough to find me on Twitter. It’s just @-A-Z-I-M-M-A-N—azimman. And they’re welcome to reach out to me there. My DMs are open—much to my displeasure sometimes—but happy to help people who are looking for help. I’m particularly interested in spending my time with those individuals who maybe are coming from underrepresented backgrounds in tech and looking for ways to be able to either get into tech or to move up within leadership roles in tech.

But I’m spending a lot of my time doing a lot of coaching, doing a lot of advising for small startups, and then also just as a small side project have been working pretty extensively with James Governor and a woman by the name of Kim Harrison on this little thing called Progressive Delivery, which is, as far as we’re concerned, it is the next iteration of the software development lifecycle that we’ve written about and talked about pretty extensively. James and Kim and I are working on a book together to be able to capture all those ideas and bring them and coalesce them for people, to make more consumable. But ultimately, we’re trying to say, “Hey, look. The way that we’ve done things leading up till now, moving from waterfall to agile to continuous delivery into what’s next?” And look at some of the market conditions that have changed. A lot of stuff that you talk about. I think that you would be the first to point out how things have changed since the launch of AWS.

Corey: Oh, yes. It’s more confusing now.

Adam: Oh, way more confusing. And the ways in which people consume cloud-based services has radically changed. And so I think that the way that we are building software and the way that we’re consuming software is something that we need to put some serious thought into. And the players that are—you know, as I spoke about earlier on this talk with you—are different. It’s no longer just your developers that care about your AWS choices or care about the cloud service choices that you’re making.

You’ve got other individuals, whether it’s the finance side you focus on or thinking about it from the perspective of the marketing team, or the HR team that’s thinking about which cloud service HRIS are they going to use. There’s a lot of people that need to be party to those choices that you’re making and how you build out your company stack, as it were. And the Progressive Delivery model looks to take into consideration that changing and evolving group of people.

Corey: And we will, of course, have links to that in the [show notes 00:32:46]. Thank you so much for taking the time to speak with me. I appreciate it.

Adam: Corey, thank you so much for having me. It was a pleasure.

Corey: Adam Zimman, startup advisor, and oh, so much more. I’m Cloud Economist Corey Quinn, and this is Screaming in the Cloud. If you’ve enjoyed this podcast, please leave a five-star review on your podcast platform of choice, whereas if you hated this podcast, please leave a five-star review on your podcast platform of choice, along with a scathing comment telling me why you as an engineer are best suited to be the manager of everything.

Corey: If your AWS bill keeps rising and your blood pressure is doing the same, then you need The Duckbill Group. We help companies fix their AWS bill by making it smaller and less horrifying. The Duckbill Group works for you, not AWS. We tailor recommendations to your business and we get to the point. Visit to get started.

Announcer: This has been a HumblePod production. Stay humble.
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