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25 Years in the Life of a PM

with Steven Jones of project44
Nov 22, 2017
Back to Podcasts
25 Years in the Life of a PM | 100 PM
25 Years in the Life of a PM | 100 PM

Steven: My name is Steven Jones. I had a product here at a company called project44 in Chicago, downtown Chicago.

Suzanne: Welcome, Steven Jones. I definitely want to get to project44 because I'm very curious to know how the world of freight APIs might be interesting to all of our product managers and prospective product managers listening. I want to start with something that for me feels more important in front of that. I did the necessary digging about knowing that you were going to be on the show, and I understand that you've been very active here in the Chicago PM community in particular. Working individually with PMs, you've written a lot of resources for product managers. In that sense, I feel that we have a bit of a shared mission, which is to help bring actionable advice so people can succeed in product management. Can you share with us why you're doing that? Why you're spending all your time working with PMs?

Steven: It does seem like a lot of time, but sure, I'll do that. I've been living in Chicago off and on for almost 20 years, and I am just impressed with how many smart people we have in the city. Even if you just limit it to what the product community is here, it's remarkable how, despite having so many successful product managers, people at all levels of experience, that it's not as connected as you think it would be. Meeting one product manager for coffee and hearing them talk about a friend they work with or a colleague they learn from and wanting to meet that person, I realized there isn't a tight network here, as it could be, as tight as it could be.

I don't know that I would say it was my mission, but everywhere I go I'm listening for opportunities to make introductions to other people. What I've learned, sort of unexpectedly, is that people are finding it rewarding to hear stories from other product people, even if they're not in the same industry, even if they're not at the same skill level. Just to know that there are other people out there struggling with some of the same problems, and a lot of times learning that there's more problems that they didn't even know about.

I think I've heard on a number of your shows, people trying, struggling to define the world. What do we do? How different is it from company to company? The more I'm connecting product people, especially in Chicago with other folks that are also practicing this, I think the stronger our community is getting.

Suzanne: Are you going out of your way to find people and introduce yourself to them? Are they finding you? How are these connections actually being made?

Steven: I get asked that a lot. It's not a plan of mine. I don't have a checklist of product people I need to meet. It certainly didn't start off that way. I think I was searching for people who could teach me or give me ideas of things I didn't understand. I will admit, even after 10, 15 years of this, there's great swaths of this role that I need lots more help on, so, I'm always eager to find people who are smarter than me. It has become a habit of trying to meet new people every week and then figuring out if there's an opportunity in that discussion to connect them with other people or through them find more product people. It has become maybe a mission of sorts. I do get credit for knowing a lot of product people in Chicago, but I am not a matchmaker, I'm not a social person by nature. It is my own quest to learn as much as I can from people and the joy of watching them get connected.

Suzanne: Are there, from the conversations you've been having, any themes that have emerged as being ... it seems like no matter where you work, no matter what your experience, everyone is struggling with 'X' or 'Y'?

Steven: The overall theme is that nobody's completely confident they know what they're doing, or if they've been doing it a while, they might get comfortable in certain areas. I can put a road map together, I can take an idea that sounds fuzzy and validate it and get it to the point where it becomes stories and a back log. But, then that same person might break down when it's time to deliver that to a customer. How do I work with a marketing team to get it out to the market? How do I price it? When you think about the range of things we're supposed to be good at, the theme that most people have is I'm insecure about the parts of this job that I still haven't come across, haven't been asked to do, don't know where to turn for resources. Usually, you can break through that initial air of confidence and find out that they're all struggling just like me to learn more and to get better.

Suzanne: What are the areas, I mean, you've been doing this a long time. It's very humble how you're framing it, but you have multiple pages of scrolling type of resume. Somebody else might look at that and say, "How can this guy be sitting here saying there's things he doesn't know? He's done a lot.” What are the areas that you think are still, for you, rough edges?

Steven: You want me to openly admit what I'm not good at?

Suzanne: Yes, and know that this is going to be on the internet forever.

Steven: Yeah. That's fine. I'm not ashamed. There are parts of market research that I'm intimidated by, that I'm not good at. When I meet folks that have been formally trained or know how to do that, I'm very impressed. One of the things that I obsess about is when I hear an idea, I quickly want to know as much as I can about the problem, who has that problem, and how big of a problem that is. That third question haunts me, because I don't know great techniques for solving that quickly. I would say working next to a wonderful UX resource in my past company made me realize how little I know about user research and design and the scope of that. In many ways, that's a more mature discipline than product management. That's another area that I will reach for experts.

I don't think I have the native skills to be a good designer. Pricing is easy if you continue to build products in the same kind of domain. We were talking about B to B products or just B to C, I kind of have a sense for how B to B products are sold and how those buying decisions are made. I couldn't tell you the first thing about how to price B to C products. All across the life cycle, I'm getting better collecting stories, collecting examples, but nowhere near where I want to be. I need ten more years.

Suzanne: Ten more years and then I'm out of here. Then, I'm going to a beach. That last point you made about how different managing a B to C experience is necessarily than B to B, I think speaks into another one of our big themes here on this show, which is the 'It depends' theme. The nature of the role will depend significantly on who the end customers are for sure, what is the vertical, what is the scale of the company. Most of the experiences in your career history, as you've said, are B to B. Did you choose that intentionally? I'm trying to imagine that there was a moment when you could have gone down one path or another and you said, "No, I choose business products."

Steven: I think it may have come from having started when I was an engineer at a large consulting company. I was thrilled to be part of a large organization. It just so happened that that consulting company's customers were large enterprises. I grew up learning about large-scale problems, not individual user problems. I've tried to create products on my own for individuals, actually for other product managers, and I failed. I should know this space pretty well. I do know the pain, I underestimated the market and how much money people had to spend on products. I spent 10, almost 15 years, writing software and loving it, for large organizations. Big insurance companies, banks and whatever. That may just be where I grew up. I learned software at that scale.

I talk to folks here in Chicago that work for B to C companies and when they describe how fast they can move. They have meetings on Monday, they pick a metric they want to change, they write some stories, they implement it, deploy it, test it, and then review it the next week. That's insane. That can happen at a B to B enterprise company, but it's rare, and it's largely because you've got other forces that don't let you move that quickly.

That's maybe just where I came from. That's my background.

Suzanne: Do you think there is … we talked about this on the show a few episodes back, this idea of the low-hanging fruit of problems having already been solved. We're living in this interesting time where if you look at the advancement of technology through one lens, it looks like, look at all these advancements we've made. I can get somebody to bring my groceries to me, I can get somebody to drive me around wherever I go, and then the reverse of that is, that's how far we've come. All we've managed to do is accelerate certain things that were never really a huge, huge problem. Business problems or problems at scale, they can't be solved necessarily overnight. For some of the reasons you say around infrastructure, but I think because they're complicated in a different way.

Steven: The more people that are involved in a process, the harder I think it's going to be to solve. You mentioned delivering groceries or a meal or an Uber-type service. The number of people that have to be connected and agreeing on what's going to happen there is relatively small.

If you're talking about, you were mentioning earlier a company that makes office furniture, and all the people that are going to be involved in getting that furniture from the warehouse to a store where it's going to be sold. The logistics, the truck drivers, the people that load the truck, the bigger that problem is, the more steps involved in that flow.

I think that gets to your point about some of these problems can't be quickly audited. You need to think about optimizing an entire process. If multiple companies are involved, so, in our world, we talk about shipping, freight let's call it, from one side of the country to another, that can actually end up on many different kinds of vehicles. It could be several companies. A truck picks it up and puts it on a train, and then it goes to a dock and gets on a ship and it moves somewhere else, so there's many companies involved. That kind of problem takes a little more time. We can take advantage of some of the smaller optimizations you're referring to, but I think, thinking broadly across an entire supply chain, that's not something they can solve quickly.

Suzanne: In the case of transportation, we're also talking about decades and decades of not just people involved, but processes that, whether or not they were the right process, came to be the standard and undoing that. Since we're there anyway, let's talk a little about project44 . You've been here just a few months.

Steven: Six months.

Suzanne: Is it a new company?

Steven: About two and a half years old. It was exactly what I was looking for. It matched what my needs were at the time, which was a tech start-up, B to B focused in Chicago, which is my hometown, and having had no product leadership at all. It was smart folks from the domain and very smart engineers writing software, but not thinking about it in terms of product. What they recognized to their credit is that if we're going to be good at this long-term, we need to start thinking about how we build a repeatable products, products that solve a greater set of needs across a larger market, and deliver them reliably. It was a perfect opportunity for me.

What really sold me when I came in was this description of how this works right now. Even if you just look inside the United States, it's crazy how old and cumbersome and expensive and time-consuming the process of moving your office chairs from L.A. to Chicago is, and it happens thousands of times every day. Our CEO likes to talk about, everything you wear today, everything you ate for breakfast, came on a truck, at some point was on a truck. It's everywhere, and when you work for a company like this, suddenly those eighteen-wheelers on the road start to make sense. All those buildings I see on the train when I go home, I see warehouses and palettes and bay doors and all that. I'm like, oh, that's what's happening.

It's all around us and we just don't pay a lot of attention to it, but it's everywhere and it's happening millions of times a day. It's all being done with phone calls and FTP sites and this antiquated technology I thought we have moved beyond. When I came here, I thought, wonderful opportunity to hone my product skills and see if I am as smart as I think I am. It turns out I'm not. Also, to apply things that I've seen work in other industries to an industry that's desperate for some innovation.

Suzanne: Is there any significant meaning behind project44? It just sounds like a cool top-secret, I don't even know what you're doing.

Steven: Almost like a codename.

Suzanne: Yeah. For a company that's actually going to emerge as “butterfly.”

Butterfly might be a little soft for transportation.

Steven: It's a great story. I'll give you the brief version. Most people know about the historic Route 66. The nostalgia wrapped around that talks about the era it was built in and why people used it. It turns out that it didn't anticipate eighteen-wheelers. It didn't anticipate self-driving cars and all this, so, it's a wonderful national treasure, but it desperately needed to be updated. When they came up with plans for modernizing and almost replicating the old historic Route 66, the name of that project was project44. It's a lot of parallels between what we're trying to do, going into that same industry and modernizing what is essentially a legacy approach to shipping and freight.

Suzanne: This word start-up is another one of these confusing terms because I don't think we have a universally aligned definition of what it means. Sometimes people think it relates to how young a company is or how many employees are there. You consider project44 to be a start-up. What constitutes a start-up in your opinion?

Steven: Great question. I have heard that on some of your other shows. It's certainly easy to call it a company that's still figuring out its way. It hasn't really found its rhythm. Operating in start-up mode might be a way I would describe a company versus a stage.

We are very much still figuring it out here. There seems to be endless opportunities, so part of this early phase for us is figuring out what we're good at, what we can solve, bring solutions to a market, sell them, support them. In many ways, we're still guessing. We're trying to make smarter and smarter guesses. I would say that's a characteristic of a start-up. It has less to me to do with the size of your revenue or your employee base or your customer base, but if you're still fundamentally looking around for the right opportunities and trying to get good at solving those, I would call you a start-up.

Steven: Which is why in some big companies, there are start-up type initiatives. We're going to go try out something in a new market we've never done before. Amazon is a great example of someone's who's constantly exploring, in very much a start-up mode, new ideas.

Suzanne: That's absolutely right, sometimes. Sometimes they're guilty of not doing that when they need to be because I think for some of the reasons you described, you become big, you become cumbersome, maybe things are working. You forget to be thinking about how they may not work or how that next young competitor, disrupter that's waiting to prey, to bite at your ankles, so to speak.

Steven: I'll tell you, the start-up thing touches a nerve for me. When I talk to a lot of product people and ask them, "Where do you want to go? What's your next opportunity look like?" The start-up world always sounds intriguing. I think people have this idea that it's glamorous. When I interview for any position if I'm working in a start-up, I spend an inordinate amount of time verifying that they understand what that life is going to be like. When you're in start-up mode, it is not calm, it is not predictable. I think there are certain people that thrive in that sort of environment where I may not know week-to-week exactly what I'm going to be doing. Our needs are going to change. The resource mix is going to change. You need to be sure that if you're thinking about being in a start-up that you're not just looking at all the fun-sounding things that come out.

Suzanne: All the ping-pong?

Steven: We have ping-pong. We have beer. We have all the stuff that, the fun part, but there's a whole nother side to this. There's a reason why not many people are in this kind of company. Whether they're risk-averse or whether they get burned out. If you're thinking about going into a start-up, especially as a product person, understand that it's going to be a lot more chaotic, frenetic, than you might expect. Then, multiply that again.

Suzanne: I would echo that for sure. I think the media has done a good job of presenting a specific type of narrative and that's the Mark Zuckerberg narrative, that's the Instagram $2 billion acquisition narrative. That narrative is troublesome because it's the edge case. It's the absolute edge case. Most of the time it's just a lot of people trying and a lot of people not getting there. This other new thing that's emerging, which is confusing raising money effectively with building a business successfully. I think, not to say it's not challenging to raise VC money, because of course it is, but raising rounds and rounds of capital for a business that you're never actually able to turn into a business isn't the same thing as turning something into a business that sustains itself.

Steven: I like that distinction. I have certainly worked for companies where you could almost say our goals for the quarter or for the year were to get to that next round of funding, which is foreign. That's not a problem you hire product people for, I would say. That seems short-sighted, but just artificial. I agree with you. Let's find a problem that we want to be good at solving. Let's make sure we get to that market and be successful and make those customers happy. Those are the goals for product people. Not I want to be a part of a company that has raised $30 million.

Suzanne: This is not the first time here at project44 that you have been in start-up mode. As you said earlier, you came from enterprise. You came from big companies, big problems, big solutions. At what point in your career did you make that change and was there a catalyzing incident?

Steven: Is this the how I became a product manager question?

Suzanne: This is, the specific question is when did you discover that you liked being in start-up mode versus being in predictable risk-averse, large-scale mode?

Steven: That is a good question. It does dovetail with my start as a product manager. I was on big projects. I loved solving problems with code. Then, I became attracted to larger problems, ones that I couldn't solve on my own, and then realizing I needed other resources, not just engineering resources but design resources and other things. I think leaving those big consulting companies, a group of us spun off, as people always do and started our own consulting company, which was scary. We ran that for five years and finally sold that, which is a wonderful way, if your first start-up is that successful, you're going to be hooked forever. That's a curse.

What I noticed was that as we continued doing more consulting-type work is I wasn't happy just building that solution for one customer. I would always come back and try to change something and try to figure out if there's a way to re-apply that. Can we take it to the very next customer? I was fascinated. This was back in the 90's when I’ll be doing a design started taking way off, frame works, design patterns. There was so much thought into being able to reproduce solutions. That really appealed to me. I had this idea. I wanted to solve big problems, bigger than I could do on my own. There was this new way of thinking about solving problems iteratively and incrementally, which fits in right where we are right now with lean and agile.

Then the other big thing was I didn't just want to write the software, deliver it. I wanted to go end-to-end. I wanted to figure out how we could market it. I wanted to figure out how we could sell it to other customers. All of that ended up leading me down a path of product management. I was probably five years down that path before I realized what I was doing. I just thought I was the engineer who also liked to write documentation and give marketing presentations and go out and try to sell stuff. It didn't really fit with the typical engineering.

Suzanne: I'm glad you say that, because I wanted to ask. I think we have a number of folks in our audience who sit today in what I describe product management adjacent roles. Whether that's as was your case, a developer or whether that's somebody in marketing or somebody on the user experience design team and for whatever reason are feeling that call. I shouldn't say for whatever reason, we know what the reason is, but they are feeling that call toward the more strategic or more holistic center.

One of the biggest challenges of going out on your own, maybe you discovered this, you said it was hard, is now you have to sell. You can't just be an engineer. If you're going to have your own consultancy, you have to be the engineer that provides the solution and you have to be in whole or in part committed to the pointy end of the business, which would have been foreign to you. When you are somebody with a specific domain set, how easy is it to burst into the world where you have other responsibilities, even if the desire is there? Or how not easy is it?

Steven: If I take it from someone who is becoming familiar with what product people do, so your point about being in an adjacent role. A lot of UX designers, a lot of people from marketing find their way into product engineering for sure. The strangest story I heard was an airline pilot. I met a product manager and said what did you do before this. He used to fly commercial airplanes. I'd never heard that path. I've heard lawyers become product managers.

I think if you're becoming familiar with the role, you can certainly expand to fill some of what a product person is meant to do. You can start upstream and think harder about defining the problem that you ultimately want to solve and bringing that product. Then, there's downstream stuff that you can, as was mentioned before, what I'm not particularly good at is all the work it takes to deliver that product and put it in the hands of the customer you intended to and charge what you intended to and support them.

You can expand to fill up any subset of that world, but be prepared to field questions and be asked to do the entire thing. I think the more this role becomes popularized, the bigger the expectations seem to be about what you should be able to do. I'll get an idea from my CEO one morning, and implicit in that is what is it going to take to sell 10,000 of these. The path to go from an idea to that with 10,000 people using this product. That's vast. It can be intimidating. I think what I hear from people breaking into this position is, it seems like you're the boss. You get to make decisions. Where I'm at over in design or as an engineer or QA or marketing, I don't get to make decisions. I participate, I contribute, but I don't make decisions. You seem to be making decisions.. I don't know if this is the right place to argue that or not, but I think the expectation is that you are going to make a range of decisions that will get you from an idea, a light bulb, all the way to a huge customer base.

Suzanne: It sounds from your answer like a lot of this informs the very problem that we started this conversation with, which is the increasing sense of inadequacy that practicing product managers feel because the expectations of the role are changing or aren't realistic or aren't clearly defined. It prompts me to ask you this question, which also relates to your starting here at project44. When does a company, operating in start-up mode, need a product manager? If that's not a universal answer, how can you know if you're a founder that's listening, how can you know what are the signs of needing that specific type of person?

Steven: I think it's fair to say most tech software start-ups, this is the area I'm most familiar with, tend to delay hiring full-time product personnel. I'm having a debate with a CTO friend of mine who says that maybe the CTO title will become less valuable and that start-ups will be a business person and a product person, if they're not the same person.

The key though, and this is something that just came up recently, I just blurted it out without trying to make it sound like a mantra, but if you're selling what you're building and not building what you're selling, then you're in great shape. That's what you should be aiming for. Again, it sounds like I read it off a box, but I think early on, companies are desperate to get any customers they can, any revenue they can, to show some progress. Maybe they're going after that raise and they want to show, hey, we're on to something here. But, if you're selling something and then scrambling to build it, you clearly need help from someone who's more product-focused, because that's not going to scale. You're going to end up with, I say to people, what's worse than not selling anything is maybe selling one.

Because now you're stuck. If you sense that, hey, we just keep scrambling to do whatever our sales team promises customers, you're not going to be around that long, unless you're in consulting. If you want to build a product company, you need to switch that to a, let's go figure out something that's important enough to spend the energy on building, and then prove that we can sell it.

Suzanne: I can speak candidly when I say consulting has its trade-offs for sure, in that the dream of product defying or at least being able to package a solution into a repeatable type of sale is typically a dream just at that. Unless you end up building, then you're 37signals and you build base camp, and you're like there's our business, we're SaaS.

To go back to this point that you make about selling in advance and this ties again to the pointy end of the business and the challenge that comes with that, I think so many people misunderstand the challenge and the importance of acquiring customers or having a plan and some proof of your ability to do it, and not unlike when I say someone quits and goes and starts their own consultancy, it's like building a product isn't without its challenges, but it's not actually the hard part.

Steven: No.

Suzanne: It's building a product that people want, and I love that you say selling it more than once. Why don't people take this more seriously, seemingly?

Steven: I think it's a combination of they underestimate how hard it is for salespeople. As much as we like to get angry at what sales do, they have a hard job of convincing people that are at some stage of a buying process, if they're even qualified to buy. Convincing someone to part with money is hard. People mostly underestimate that. If you've never done it before, then you probably have unrealistic expectations of what it's going to take. I always listen out for young entrepreneurs or first-time entrepreneurs who already have their first five customers lined up, but they’re folks that they've known. It's their friends, it's their colleagues or they're turning around and selling something to the business they've just quit. That's not the same. You should really think about, how do you get that next ten. How do you get that first 100 customers. If you don't have a plan for executing that you feel supremely confident in, you're going to struggle.

Suzanne: I always say if you want to be told you're the most beautiful person in the world, you ask your parents. That's a different kind of validation than the validation we're seeking in product.

Steven: Here's the best part. In the last five or ten years, there's been new focus on early validation and without going through all the different techniques, the idea that you can ask the right questions up front and with very little effort, very little investment, figure out if you're on the right path or not, so you don't make that mistake later on when it's expensive to be wrong.

That is an area that fascinates me. I could spend my whole life just doing that, like helping people get from that idea that they think is a million dollar idea to, in most cases I would say nine out of ten, I'll convince them you need to think about it some more. Not that it's a wrong idea, but you haven't thought through this. That journey is so rewarding, and every time that happens, I feel like I hope they appreciate how much time we've just saved them.

The classic example is these guys, they all quit their jobs, they're literally holed up in a basement, and their plan was in six months we're going to release this product and we're going to sell it like crazy. I said, you're giving it six months to even figure out if you have the right idea? What if you're wrong? You're probably going to be wrong. Most people are wrong. That should be a cautionary tale for anyone. If you think that's the way real products are done, successful products. I'll tell you, some people guess right. This company guessed right on a recent product. I was skeptical and wanted to do a lot more thorough assessment and validation to your point, and we guessed right. Sure enough, customers are lining up to buy it, which is phenomenal. Most of the time that doesn't happen.

Suzanne: Exactly. I have a sound bite to describe what you speak about in early validation, which is "Pre-work is free work." Before you take that $50,000 from your parents or your best friend or early draw down on inheritance, you could spend a week and you could save yourself a lot of that heartache, absolutely.

Steven: You bring up another great point. Let's say you could convince somebody that they should spend time doing that. All the time they're going to be biased at how they conduct that experiment. They're going to be looking for the yeses. I mentioned earlier having this wonderful UX research and design person available and learning about bias and learning about how hard it is to do a real test, to do a survey that isn't telling you what you want to hear. There's skill in that, and if you don't do that well, you're just kidding yourself. You're delaying the inevitable. You're going through the motion of what you think is an experiment and it's not.

Suzanne: People hear me talk on this show a lot on my opinion about tools. Tools accelerate good process and they accelerate bad process. And I'm with you, I think asking great questions, first of all it's such a tremendous skill to have for building intimate relationships in life, forget about just succeeding in product management. Imagine a world where you can actually talk less and listen more. Wow. If you say, go out and talk to some people, they'll say to me, well, I have a survey, I did a Google survey or used Typeform. Let me look at your questions. Insane. The questions are bad. The questions are seeking to confirm that which they already know, which isn't going to tell you anything other than what you already know. It doesn't matter that you can press send and blast it out to 1,000 people. All you've just done is accelerated your way towards 1,000 bad insights, and you're not any further ahead.

Steven: The worse case, you believe it, and you rely on that as validation. You'll be so much more disappointed later on, and you will have burned through a lot of extra resources.

Suzanne: You said something that intrigued me. You said recently here at project44, you guessed right and you were skeptical and I like that you owned your skepticism in it. We're talking a lot about the unrealistic narrative that so many people have adopted as the primary use case. We're arguing for … that's edge case, that's the rarely that it happens. That's the don't believe the hype. Is there a right balance of skepticism or pragmatism and gut instinct? How much do we need to go towards scientific method and at what cost of trusting yourself?

Steven: I think I go back to those lessons I learned in the 90's about iterative, incremental development, which now is, you can call it MVP. It's all driven by the same thing. Let's build enough to where we can test an idea, test a hypothesis and evolve from there. If we try to build everything the first time, we'll almost certainly get it wrong.

I am constantly training myself to be more skeptical. I feel like I'm hired in a product role to be the guy who says no. It's so easy to say yes. Everybody want to say yes. If you just came back from a conference or you just heard the latest and greatest thing that's going on out there. If you've got a sales guy that just hopped off a phone with a prospect and he's all excited because it's the biggest deal in the company's history, it's so tempting to want to say yes, let's do that.

In this role, you have to be the one who is skeptical and says, "Prove it." In the case of the sales, I tell the folks all the time, if you want to be good at being a product manager, learn a dozen ways to say no, in a way that doesn't offend people. So, if a salesperson says, “hey, I just got off the phone with somebody, they want this.” I say, that sounds awesome. Let's find five more people that say that. That's a way of saying no, but it's not dismissive. Maybe they do. Maybe they find five more, and guess what, now we're on to something. It's harder with the CEO or some senior level exec who is determined they're right about something.

You have to be skeptical, because here's what it comes down to and I'm developing this as sort of a philosophy or whatever. I feel like what I'm doing, what product people do, is make product investment decisions. If you put that word investment in the middle there, the company is trusting you to decide on how to deploy the resources that we have. If you don't think of it as an investment that's supposed to make returns on it, then I think you're missing a big part of it. You have to be sure. You have to be as sure as you can be. It's a balance.

Suzanne: We talk a lot about product managers don't typically get associated with glory, although I think that's kind of another common myth. What I'm hearing from you is to be a great product manager also means embracing the reputation of, “Ugh, we’ve got to go and ask Steven and he's for sure going to say no, because everything with him is a ‘let's validate it first.’ That's a hypothesis, we can't be sure,” which isn't the most popular reputation.

Steven: I'm flattered because they do come back over to my desk and they start conversations, I know what you're going to say, but I want to ask you anyway. I don't know, as long as they're still coming over, I feel like we're doing something right. I would prefer having that conversation than them just assuming I sold this, now you've got to go build it. I think those are opportunities to help other people think more broadly about the kind of decisions you want to make, healthy decisions for a company. Another way out, I'll engage someone in conversation like that. If they have a brilliant idea, it's like, let's say we go off and build that. That's going to take X many of our resources to do that. What if there's another great idea right behind that? That we won't be able to do because we've committed to this. Think really carefully about whether this is the right thing to do at this time. Do we have the right skills or should we think through it a little bit more. It's opportunities to help people think about how best to use their scarce resources.

Back to the start-up point, if you don't have 500 people, if you don't have entire divisions you can devote to building something and you're talking about it's going to take three guys the next couple of weeks and that's all they're going to do, you have to think harder about that.

Suzanne: Straight up, my biggest failures in my career have everything to do with not enough focus. I think there is a maturity to that. Especially if you're ambitious and capable. Some people don't have the capacity or they don't have the ambitions that always keeps them focused by default. When you're ambitious and you're capable, you're like, of course we'll do that, and we'll do that, and we'll do that. You get the equivalent of moving a bunch of things across the desk incrementally. It's tremendously easy to start, incredibly difficult to finish and there is a great maturity in saying, maybe I do want that as well, maybe I want all of these things, maybe they are all right. If I finish this one, then I'll grab another one from the top of the list and work on that too. There's a certain amount of trust that's saying, if it's worth doing, get through what you're working on now, and then you can tackle that one. Not be constantly switching around or taking on too much and never finishing anything you start.

Steven: You're bringing me right to another topic that I think is crucial for this, and that is credibility. If you routinely start and never finish, you never follow through, anyone's credibility will suffer, but I think it's harder for a product person. If you're being asked every month to start another initiative and you never get around to delivering anything, it's going to be very hard to motivate a team to work on the next thing. One of the fun things about coming here was I didn't know anyone from this company, I didn't know anything about freight and logistics, so this idea is how quickly can I establish credibility here. They had no previous product person, so I didn't have anyone to measure up to, so that was kind of nice, but they also weren't sure what it was going to look like here. I wasn't sure how product was going to work here.

To your point, taking on things that you know you can finish is going to help you establish credibility. Sometimes that means taking on smaller versions of things. Hey, let me just build a small part of that and then we'll go out and test it, and if that works then we'll move forward. I'm consciously aware of how important it is throughout the organization because of everyone we touch, how important credibility is to build and sustain.

Suzanne: The example that you give raises another consistent challenge I think that PMs face. You said if you're given another assignment, if you're given another initiative, which suggests that there's somebody doling out those initiatives, which means somebody in the organization, usually the CEO or the founder, someone from the executive leadership team or the investors is saying focus on this, focus on this. Let's say I am a mature product manager, let's say I do believe in focus and I do believe in building credibility through finishing, but what I'm actually up against is a stakeholder who is trying to force me away from that mindset. Then, what can I do?

Steven: Force me away. That's a hypothetical that I've never encountered before. Somebody actually forcing to do something. I think about reminding them. Going back to your example, it is sometimes the senior exec sort of strong-arming you into taking on their project, their initiative.

The key to this is reminding them that I'm also getting ideas from sales, I've got a support team that has a customer base that's constantly calling them and suggesting we improve things or fix things. I've got engineers who are never satisfied with the way the product is and always want to change it. These are other sources of inputs.

One of the fun things about roadmapping to me is that there's no shortage of ideas coming in. It's not always to top down executive with the crazy idea they came up with in the shower that morning, it's all this stuff. Finding a way to make everyone feel like they're being listened to, but also completing things so that support doesn't just throw up their hands and go, I had mentioned it to product, but I know they never get around to doing the stuff that I ask. Same with sales.

That opportunity when a new idea comes in to show that it's joining a funnel of other probably good, not as good as your idea, but good ideas, and showing that we're going to have to find a way to balance this thing. It's very easy to drop customers by name or say, hey, we just got off the phone with a customer. That tends to carry some weight. There's usually a revenue associated with that. There's techniques, remember that idea of how do you say no creatively or not yet. That’s one of the better ways to say it.

Suzanne: One of my favorite activities that I run in some of my product classes is just simply a role play about saying no. Everyone comes in and thinks we're going to do something really cool like user experience design or wireframes and actually it's like, okay, you're the volunteer, your role is to really, really argue for something that you want on the roadmap, prioritizing something that you think is important, changing direction. Your role over here is to say no, no matter what they throw at you. It's interesting to collect the data of ourselves I think. One is, am I comfortable asking for things, which is an important part of the role in succeeding in product, and am I comfortable saying no.

Steven: Those are great exercises.

Suzanne: Maybe you can run some here at the office if you want. You can have that.

This topic of commitment, just to change gears here for a moment, even as I heard you speaking about it, I was laughing thinking of this project, 100PM. One hundred product managers, by the way, is a lot of product managers I discovered. I didn't really realize that when we were at like one product manager and two and three. Now that we're sitting up here around 40 or so product managers and we're not even halfway there, I'm like, one hundred is a lot of product managers. Commitment. Be careful what you say yes to. You committed yourself to a project equally, you have an article series called 'A Year In the Life of a PM'. It's 52 weeks of --

Steven: Half as ambitious as yours.

Suzanne: That's a lot. Can you tell us about that?

Steven: Sure. That was motivated by two things. One is I tend to try to find something every year to challenge myself whether it's speaking on a regular basis, finding opportunities to get up in front of crowds and speak. That's one I constantly need help with.

That particular year that you're referring to, I wanted to get back into writing. I wasn't good at it. I wanted to challenge myself, so what I did is I found a topic that would come up in every conversation. What does a product manager do? What do you guys really do? Even the people I worked with weren't sure. They were at the same company, they'd see me every day. I thought I had just started a new role as a senior product person. I was head of product in this company. I said, I'm just going to document what I do every week. I'll pick a decision I made.

At the beginning, just like you, it sounded glamorous. Hey, this will be fun. It was a lot of work. I forced myself to use a template so that the article series is consistent. You can pick up any one of these and read it independently. The idea was to document once and for all what a year in the life of a product manager could be. My life is going to be different than the person right next to me, but what was fascinating about it as I got about two-thirds of the way through it, was there was not repetition. I didn't have to go back and write about a topic I'd already written about. It was that diverse. The problems, the challenges, the decisions I was making were everything from how do we help a customer who's angry to how do I fend off a crazy idea that's coming from sales, to the one that, a lot of people seemed to like and I wouldn't have guessed it, was the week I took off. Just to recharge, I went out into the woods and just disappeared for a while, but people said, yes, I do the same thing. I need time off to ...

It was an interesting year to chronicle. I'm glad I did it. I won't ever do it again. I don't mean to discourage you from the podcasting, but it's good to challenge yourself. I think that people should expect in this role to challenge themselves, and that's going to come through writing, that's going to come through speaking. You've got to be a good communicator in this role, because so many people are going to be relying on you to explain things. That was a fun, exhausting year. That was a lot more work than I thought it would be.

Suzanne: I've spent some time going through that year of yours in product management and I think there's a tremendous amount of value in it for our listeners. I'll be sure to pull some of that forward, and anybody listening in, if you're part of our newsletter group, you can look for some of that, direct from Steven's journey to your inbox.

Steven: I will tell you I will be very surprised if ten of the titles don't resonate with you. People read these and they're like, yeah, I had the same problem. I didn't do it the same way you did, better, probably. One of the things I'd love to do someday is go back and revisit every one of those decisions five years later and see if they actually were the right ones or not. It was too soon to do on a weekly retrospect. I hope it's helpful. It certainly was therapeutic for me.

Suzanne: In the meantime, for folks who haven't had a chance to read all of that content, we do a little segment here called 'Get the Job, Learn the Job, Love the Job', so would love to try to distill some essence of all of these years of insights that you've collected and are continuing to collect as you've said.

Let's start with getting into product management. What would you tell somebody who is not currently working in the role, but really, really wants to?

Steven: I hire product people, so I'm constantly looking for what makes a good product person and how do you discover that in a very first interview. I would say if you haven't already, go build a product. Nothing is going to help you more than having gone through the entire process. It could be an info product, where you decide I really know a lot about a topic. I'm going to build an ebook and put that out. I talk to people who, for them that's their product. It could be a podcast. It could be something that you end up selling, but if you follow any of those standard frame works or you pick up a book about product management, you're going to find that there's, it's well-charted out here.

Do that, because the very first thing that you should be able to talk about is experience you had in developing a product. What I think someone in a hiring position should be looking for is do you understand how to identify a pain that enough people have. Did you understand how to deliver a solution to address that pain, and what was that experience like for that user. How hard was it for you to deliver that solution.

If you haven't done this before and you're just romanticizing about what product role must be like, you're probably not far enough along. You need to do that. There are opportunities usually in any organization to latch onto something that's already in progress and say, how can I help. No one is going to turn that down. No product person is going to say, no, we've got enough bodies, we don't need anybody else to help out with this.

Find something in your existing organization and come out of that company with some experience, but you can also just do this on the side. Take some time every week and think through how to build a product and bring it to market.

Suzanne: This is a little off-book, but hearing you speak about that you recruit product managers and hire product managers, I think there's a lot of people who face this roadblock. It's, I went out, I took Steven's advice, I took the advice of the folks I listen to on the show, I did a side project, I built a thing. What I can't get around is that bullet in the job description that says, ‘three to five years product management experience.’ I don't know quite what the question is. Maybe it's how can you circumvent that potential roadblock or can you? Maybe it's, is that really a necessary requirement, or do we need to be thinking about changing the dialog with employers. This goes back to setting realistic expectations for what the PM role is. Do you have any perspective on that?

Steven: I tell people if they want to be a product manager and they're being offered an opportunity to take on anything in their current organization that has that word in it, product owner, associate product manager, product designer, something like that, jump on that. Seize that opportunity, because to your point, it sounds silly, but it does make a difference if I don't see product manager on your resume at all, you could be as ambitious as you want to be, but I don't have any evidence that you’ve experienced any part of this role.

I would say, again, if there's any way to maneuver in your current organization to be more product-focused, even to the point of a title change, that will unfortunately make a difference. If you haven't done that, it's really tough. What you'd probably end up trying to do is find somebody who knows what you're capable of, and through them, through networking, which is something I believe is a huge part of getting ahead and advancing your career is getting to know and talk to people. Find someone who knows what you're capable of and have them give you a chance.

Suzanne: Probably you've never made any mistakes in the number of years that you've been a product manager, but if you had made a mistake, what do you think that mistake would have been? What are the potential pitfalls of this job that don't get celebrated or talked about as often as they need to?

Steven: I'm sure there's ratios out there of how many projects and products fail, and you're right, you only hear about the ones that succeed. Ten year anniversary of the iPhone, but how many phones didn't make it. I certainly had my fair share of failures.

And I will continue, I expect to continue. What I'm trying to do is measure my progress on how soon I recognize there were failures so that I can stop them or pivot or whatever you want to call it. That's the key for me. You're going to fail. You're going to continue to fail. But if you can get smarter about how soon you recognize you're on a failing path and adjust, the better.

One of my classic failures, and it's right there on that same website is I recognize that while you have all these canvas tools out there to think through an idea before you get too far into it, Marty Kading (?) you mentioned earlier and his opportunity assessment is a lightweight business case. I looked at that idea and thought these are great, but product people need a way to capture that and then present it to the people who are asking the tough questions. I built a tool around that and I thought to myself, I've got a product here, and guess what, I'm selling it to product people. I know them intimately. I made the classic mistake of not thinking about whether those people had budget to buy a tool like this. I'm sure if I gave it away, it would be easy, but I actually wanted to try and sell it as a product. Colossal failure. Colossal failure. People have bought it, but I was way off in my understanding of what my target market, people like me, who loved the tool, by the way. They just don't have any money to spend on stuff like this.

Suzanne: We're late in the conversation to surface such a critical point, but you talked before about “build what you can sell”. This idea of value becomes especially complex when we begin to recognize that there is a difference between what I would use and what I would pay to use. Evernote is a great example of this. So many hundreds of millions of users, but five percent of them are paying. Of those five percent, it takes them almost two years to convert them. So, can I build something, can I get people to use it, can I get people to pay for it. That's hard stuff.

Steven: You just made it easy for me to wrap up a number of things. I remember a great conversation I had with a woman who was offered a product manager position in a company and she was pretty sure she wanted to be one. She had been doing it for a year, and I met with her and she said, "I've been at this for twelve months. I'm not sure if I'm doing it. How do I know if I'm doing it or not?"

Back to what you just said, I didn't really have a good answer, but we came up with this idea of, are you regularly building and shipping your software. She said, "Oh, sure, yeah. We've got that on lockdown. Every two weeks we roll out." Okay. Are customers using your software when you release it? She goes, "They love it. They love our software." Are they paying for it? Are they exchanging something of value? She goes, "Yeah." You're doing it. It doesn't get harder than that. That's how you know.

So I went back to my advice, if you go out and build a product and you've thought through how to build it incrementally and keep iterating on it. If you've thought about how to get it in front of customers so they take it and like it, and you've figured out a way to charge them for it, that's all the proof I need that you know what you're doing.

Suzanne: What do you love about product management, Steven?

Steven: What don't I love? Specifically, what gets me excited about coming in everyday?

Suzanne: What's the single feature or attribute that rises above all of them to say this is why I can't do any other job than the one that I found myself doing?

Steven: It's impossibly hard. I keep coming back to this. I don't think I'll be good at it for another ten years. If this is all I do for ten more years, I might feel, if we meet again and do another podcast, I might feel like I've gotten great at it. It just seems something that's impossible to get great at. When I started coding, I was okay. There were plenty of people that were much better at it, but it was surprisingly easy to be good at coding if you had the right kind of brain or you really dug what software development is all about.

This is much, much harder. It's much harder to be good at the entire range of things you're expected to do. When I first decided this is my new career, I want to do this. I remember doing a lot of reading up front and thinking, crap, this thing is vast. How am I supposed to be good at all of this? I still am overwhelmed by it. I think that's the thing that drives me. In every conversation I have with another product manager, I'm reminded of how much more there is to learn, how much better you could be at it.

Suzanne: I was tempted hearing you say that. Maybe 100PM, where are they now. I'm going to practice focus and the art of saying no.

Last questions for you. Is there a life or work philosophy that tells us about who you are in the world, what you believe in, how you like to govern yourself that you can leave us with?

Steven: I think I would never tell someone to model anything after my career or my behavior or anything like that. I'm reticent to give advice. I think that healthy skepticism, apply it to yourself as well. Just keep checking yourself that you're not as good as you think you are. Don't spend too much time celebrating that last victory, because you're probably going to struggle the very next day. Again, being overwhelmed by this profession. I actually take some comfort in that nobody seems to understand how to explain what we do. This group that I meet with every now and then, we tend to get together and commiserate about how hard this is. You can't really say that at work, and maybe people at home don't really understand what you're going through. It's a very different kind of position than an engineer or marketing type role. Just keep grounded and realize there's always going to be room for improvement. Even if you're ultimately successful, I've started and sold businesses and it's been a wonderful ride, but that doesn't make this job any easier. I start it all over again.

Suzanne: Steven Jones, project44. Thank you so much for being a part of our show.

Steven: Thank you.

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