Julia Austin on the Making of a Great PM – Lessons from Harvard Business School, Digital Ocean, VMWare & Akamai

On this episode of #Build, board advisor and Senior Lecturer at Harvard Business School, Julia Austin, shares her point of view on what makes a truly great product manager. How does she know? Well years of experience spent as CTO at Digital Ocean and VP of Engineering at VMWare and Akamai.

Julia also opens up about her time as a lecturer at Harvard Business School and experience serving as a board advisor to startups including Drift, Wistia, Help Scout, ZappRx and others.

You can get #Build on Apple PodcastsSoundCloudSpotifyStitcher or wherever you get your podcasts. Or listen to the full audio version below 👇

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Maggie and Julia on Twitter @maggiecrowley and @austinfish.

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In This Episode

0:09 – Maggie introduces Julia Austin

0:40 – Introduction of the two big topics of today’s show: 1. What is a great product manager, 2. How one builds a carrier in production management

0:57 – Julia shares how she went from production itself to teaching about it

4:23 – Product manager is not a cool CEO position, but it turns ideas into made products and can be very gratifying

5:48 – The process of idea to realization in project management that she teaches in Julia’s class

8:32 – By taking a product management class one can walk through and gain knowledge about the whole process

9:05 – Kinds of people customarily being most successful in product management

16:29 – Julia explains what a ‘typical’ product manager looks like

20:24 – You don’t have to build the most fancy things all the time

21:57 – Sometimes you have to take scary risks

23:20 – What makes a great PM is someone who says ‘I know this is the right thing to do,’ and can make the call

23:28 – Julia shares advice on how one can get their first PM job

26:46 – Advice on how to evaluate the next carrier steps as a PM, and whether to go / remain in a big or a start-up company

35:32 – Julia shares some final pieces of advice

37:21 – Be willing to take risks

38:03 – Don’t be focused on titles, but on what you will actually do

Full Transcript

Maggie Crowley: Welcome to Build today. I have an incredible guest that I’m so excited to have here. She’s a mentor and advisor here at Drift and a personal inspiration. This is Julie Austin. She is, these days, a senior lecturer at Harvard Business School. She’s an advisor or board member on what feels like every startup in Boston, including Drift, Wistia, Zap RX, Help Scout, and many others, and was previously the CTO at Digital Ocean, a VP at VMware, VP of engineering Alkami, and I lost count of all the other things that you had on your career. So welcome to Seeking Wisdom.

Julia Austin: Thank you. It’s good to be here.

Maggie: Yeah. Excited we could finally make this happen. So I have two big topics I want to get through today. First, what is a good PM? What makes a good PM? How do you become a good PM? And then second, how do you build a career in product? Because you’re teaching students how to be PMs right now, but first I want to understand, how did you go and why did you go from this career in engineering teaching product?

Julia: Yeah, sure. Great question. So obviously, leading engineering teams and working with engineering teams, you’re always interacting with product people all the time. I would say early in my career, a lot of my roles that were not engineering, like release manager at Alkami in the early days, were really product type roles. Figuring out requirements, talking to customers a lot and understanding their needs, trying to translate technical things back to the business as far as what it took to get things done was always in my blood. So it’s always something I’ve done.

When I was CTO at Digital Ocean, I was running engineering product and marketing by the way, which I think is actually something that’s kind of important and cool and something I always wanted to do because I always felt like marketing was an integral part of what we were doing with product. Everything from knowing when you’re shipping things to how it’s being positioned in why you’re positioning it that way. And so having marketing under a product or with product and engineering in the same room every day actually worked quite well.

Maggie: Was that because your customer was so technical or do you think that model would work elsewhere too?

Julia: Yeah, I know. I think the model would work elsewhere as well. At the end of the day, if an organization is built well, it doesn’t matter who reports to whom. I have a very strong philosophy about that and moving people around just to make things work better isn’t always the answer. But in this particular case, and I think it would work anywhere. I don’t think it’s just in a very technical product. Having marketing or product marketers very close to product. Again, you build empathy just like we build empathy with our users or our target customers, building empathy with the engineering and product team and understanding what’s coming, what sort of the root is, really can make all the difference.

Maggie: Right. So then how did you get that role as a teacher?

Julia: So my entire career, as you said, it’s sort of long, but it’s always been one of those right time, right place kind of things. And so at HBS, I had just left VMware. I was at VMware for eight years, had an incredible run there, super fun. Got to see the company grow from 800 people to 15,000 people and about $800 million in revenue to $6 billion in revenue is a pretty nutty ride. It was great, but I really wanted to get back to early stage companies again. So I was doing that for a few years here in Boston and had a great network and somebody asked me if I would do a guest lecture spot at HBS.

It was for the product class that I teach now, and in that class, I had a lot of fun. I really deeply appreciated that Harvard was investing in teaching MBA students product because there aren’t enough programs out there doing that and really exposing students to not just what is a product manager and how does product add value to business, but we learn by doing. So we’re actually building product to learn how to be product managers.

Maggie: That’s awesome.

Julia: Yeah, so I started off as just a guest and then I was invited to be an entrepreneur in residence or executive in residence at HBS. And I did that for a semester and I kept kind of nudging my way into this class because I just thought this class was great. And eventually, the professor who started the course, Tom Eisenmann, said, “Hey, do you want to teach this class?” And it was one of those, and I think we all suffer from this, imposter syndrome moments where it’s like, “Why do you want me to teach this class?”

But to Tom’s credit he said, “You’ve built products before, you’ve worked for product managers most of your career. You should be doing this.” And so it was a big leap of faith in me and it was a big shift for me in terms of my career to do it, but it ended up being amazing because, again, it’s not just standing in front of a group of students and talking at them. They all build a demo-able product at the end of the course. It’s pretty awesome.

Maggie: Yeah. I’m still kicking myself for not taking it.

Julia: You should’ve taken it.

Maggie: I know. I don’t know how, what I was doing. So then what does that class look like? How do you frame what a PM is for those new MBAs who are coming in? Because I know having gone through the HBS experience, I can imagine many students were coming in and saying, “I don’t want to be an investment banker anymore, but what’s the other cool job that can be product? Because I’m going to be the CEO of the product and I’m going to be in charge.” So how do you actually frame it for them?

Julia: So it’s funny. One of the very first things I say at the beginning of the course is, “The product manager is not the CEO.”

Maggie: It’s not that glamorous.

Julia: It can be the most gratifying thing you ever do in your career, it can be the worst thing you’ve ever done. And a lot of it is down to who you are as a person. Herding cats, you’re the janitor, you’re the going and making the coffee, you’re the voice of the customer, you’re everything. We try to get that out of the way at the very beginning, like this is not like the cool CEO job you always wanted. It can be very, very hard, but again, very, very gratifying.

So the things that I’m trying to solve for them in the course is there’s sort of three audiences that I’m working with in the class. We have 50 students. The person who wants to be a product manager at a mature company, the person who wants to be a product manager at a startup, early stage company, and then a person who’s an entrepreneur who’s going to start a company. And a person starting a company is the first product manager, typically.

One of your co-founders, if you have co-founders, is usually the product person. Somebody else may be the sales or marketing person. Typically, not everybody, but typically. So I’m dealing with all three of those audiences in my class. And so what I’m trying to get to to them is understand everything from the real tactical stuff of how do you go and do discovery and understand what the real unmet needs of your target are to the brass tacks of implementation and okay, how do you take those and distill those down to an MVP and actually build it?

We do some fun things. Right now, we’re in the midst of lo fi testing. So all of my students right now are out in the field imagining if there was a product, how it would interact by actually execution. So I’ll give you an example from a team last year who was building a product around strangers staying in hotel rooms together. So Think Airbnb meets Couchsurfing meets youth hostel kind of thing.

But the idea is, I want to stay a nice hotel room. I don’t want to stay in a crappy hotel room and I also don’t want to stay in some random Airbnb. So if I could find a mutually cool human to share a room with, I’d feel better and we could split the cost of a $300 room and have all the amenities that come with being in a hotel. Right? How do you do that?

So before you get into the app and actually building the app, my students got a couple of strangers on Craigslist to share hotel rooms together, which sounds crazy.

Maggie: Super creepy. Did it work?

Julia: It did work, and what they learned though, and this is what I try to instill in my students, is simple things I hadn’t thought of like having some kind of legal indemnification thing for the parties participating but also for the students who were running it to sign. And they were really scrappy so they found somebody over at the I-lab at Harvard to help them write a quick agreement for everyone to sign.

How the hotel cared about these people doing this in the room. Did they care? Didn’t they care? How do you handle things like the person who shared the room with depleted the minibar and then you got stuck paying for it. Credit card trans, everything. So by going through the whole process, which I make a requirement in the course, they probably would have built the wrong software had they not done that for-

Maggie: [crosstalk 00:07:38] End-to-end experience?

Julia: Right, yeah. And they identified a bunch of things and saying, “These are areas of friction, these are things that we should maybe put off and not be in the MVP versus these are things that have to be in the MVP.” So a lot of what I’m trying to instill in the students early is, the time investment upfront will eventually save you time down the road and you’re more likely to build the right product for your MVP and beyond, right?

So that’s a big thing that I bring into the course and again, whether you’re an entrepreneur or you’re going to be a product manager at a big company, you need to know how to do that. You need to know how to imagine what it will look like, how it will flow, what types of things you might run into, what’s fluff versus what’s critical, before you go and ask all your engineers to spin up and build something.

Maggie: Yeah, I think that kind of problem solving is useful for any job because I just feel like being able to understand what you’re trying to accomplish and exactly what it would take to get there without even having to do anything really for it yet is probably useful for everyone when-

Julia: I totally agree. So to that point, actually, it goes back to your original question about why take a product management class and what are you trying to solve for? Students in my class often realize a few things. Sometimes they realize I’m actually a product marketer. So I am really happy that I understand where product managers do because now I know how I will work with those people. For an entrepreneur, they may say, “Okay, today this is me, but at some point I’m going to hire these people. Now I know what they’re supposed to go do.” Really helpful, right? So live it, go through it, walk through the paces, and then you’ll have a better sense whether you’re going to do that job or not, what is that job?

Maggie: What kinds of people have you seen be most successful as PMs?

Julia: Yeah, there’s a couple of characteristics I think that make a good or great PM. One is a really strong EQ, which is somebody who has strong emotional intelligence who can context switch very quickly from working with someone who’s very technical and nerdy and enjoys that, by the way. They have to like working with those types of people, but then can switch contexts right away and say, “Okay, now I’m gonna go talk to the CEO and tell them why they can’t get their favorite feature in the next sprint or whatever it is.”

So they have to be pretty strong willed but also have empathy for all the different players. So I think that’s really, really important for a PM. I think being comfortable with a nonlinear process is another thing that I see over and over again. The people who don’t enjoy it are ones that really are more comfortable in a role where I know if I just follow the recipe, what should happen on the other side, that oftentimes there’s ambiguity. Priorities change depending on the size and nature of the business. You have fuel to roll with that and actually enjoy it.

So the ones that I see that do the best are the ones that say, “Okay, this is what we thought we were building and then we tested it and we realized this isn’t what we’re building. So now we’re going to build this instead and that’s fun.” Versus the, “This is so frustrating. We keep changing our minds.” That’s not a good-

Maggie: We talk about that here sometimes as almost as no ego because I think that when you are sort of obsessed with your process and you have that linear thing and it’s like, okay, these are the five steps I’m going to go through, and then I know exactly what’s gonna happen at the end of it. And if that changes and you get frustrated and you take it personally, then it just can drive you absolutely crazy.

Julia: That’s right. And so it’s someone who can kind of cut through the noise who isn’t in it for them to win, they’re in it for getting to the right thing, ultimately the customer’s right thing, who even have a deeper appreciation for if you’re in a B2B market, customer’s customer. So if you’re building a product, say a sales product for example, it’s not just the salesperson who’s using the product, but ultimately their customer, and that was the experience for them.

So if you’re a strong product manager, you’re thinking all the way through and then the other thing you’re thinking about is your company all the way through. So I’m building a product. I’ll use a great example of Bevy, which is one of the companies I’m an investor and advisor in. And so they build water machines.

Maggie: We have one.

Julia: You have one. Yeah, I noticed that. Everywhere I go there’s a Bevy. Anyway, they’re thinking about everything from you as a customer who goes and fills up a water bottle, but they’re also thinking about the people who service and install the machines and what’s their user experience? So they are sort of a customer as well.

And then as they’re selling through whether it’s maintenance, upsell, they’re thinking about the back side of the business and how is the business handling the customer? What am I building in a product and how will that be supported? How would that be priced? How would that be marketed? So a product manager is thinking about not just customer and customer’s customer, but also we as business, how we’re building this product, how are we going to service it?

Maggie: Right. So it’s not just the product itself, it’s the product in context with the business, the people, all aspects of what they’re doing.

Julia: Right. So another example I’ll give you, when I was at Digital Ocean and I did a walking tour with our customers and spent a lot of time out in SF and New York talking to customers using our product, most customers were using some form of multi-cloud, so not just Digital Ocean but other cloud providers. And what I kept hearing over and over again as a theme was billing and that the other products they were using had really bad billing systems.

And it was really hard to figure out what they were paying for and who was using … If they’re a VP of engineering with lots of managers working for them who are using and consuming cloud product, they couldn’t understand who was using what. It was a mess. I came back as sort of the CTO but with owning product and went to my product managers and said, “We will not suck at billing, and from the website to the bill, our product will be amazing.”

So it wasn’t just spinning up a droplet, which was our virtual machine, and having a great user experience at low cost for an end user. It was also, and when they get the bill, they’re going to love us still. So great product managers are thinking all the way through the life cycle and they’re thinking about support, and how is it to support the product, and how easy is it to make a change on the fly if it’s not going to bother engineering? And they’re thinking about all of the things, not just, is it a pretty UI?

Maggie: Okay. So they need strong EQ, they need to be comfortable with ambiguity and nonlinear processes. They have to be able to think all the way through the full life cycle. That’s the three things?

Julia: I think that’s the primary things.

Maggie: Can you teach people how to have a better EQ or is that just out of the box?

Julia: Yeah, so that’s a good question. No, the answer is you can’t teach it. A lot of it, I believe, my own beliefs, is you can get better at certain things that you’re falling short on. If you’re not an extrovert but your job requires you to talk to customers, you may figure out ways through coaching and others to get more comfortable talking to customers. If you’re a linear thinker and ambiguity is just not in your blood, it’s really hard to change that.

On the EQ side though, the only I will say is it still depends on the type of product you’re building and company you work for, so I’ll give an example. I had a student who more of a quiet person and not very extroverted, very strong technical background, undergraduate degree in mechanical engineering, and didn’t sort of from the stereotypical PM side, didn’t really come off as someone who I would say is the typical PM.

Found a fantastic job working for a company that really services people in manufacturing and very technical engineering types, completely credible, can talk the talk with those people. People were building the product on the back end, get it, perfect fit. Right? So is it impossible? No, and I’m not saying he didn’t have a strong EQ, it’s just a different type of-

Maggie: Right and fits better within a certain type of company.

Julia: That’s right. So if you are a very outgoing person, you like to talk to different types of individuals, you are good at translating different types of communication styles into something that’s really concise and easy to understand, it could be a perfect role for you. But I think again, a lot depends on type of company, stage of company, type of product.

Maggie: Yeah. I think one of the things I keep coming back to you more and more recently is that just being able to bring in all those pieces of information and articulate back sort of a well defined problem. If you can do that, pretty much everything else can fall into place, but that is one of the most critical things to be able to do as a PM.

Julia: I agree and I think that it’s not just the conciseness of the problem, but I see great PMs are those who like to say it almost rises up from like, here’s all the noise, but if we look at this, this is the thing. This is what my students have, those moments now where they’re like, “We need this, we need this, we need this,” and I say, “Really? Do you need all of that?”

And they look back and they’re like, but this is the thing they kept talking about over and over again and holding onto that. Then let’s do that and then that will build around that. There’s this fear from some and I think these are the less good PMs, are the ones that we have to throw everything in. Let’s throw everything in. We have engineering dedicated to this, let’s make sure we all get it in because that way we’ve satisfied everybody’s needs.

Maggie: Right, or they’re working through their sort of itemized backlog and it’s like, well it’s on the list, but it’s down there and we can’t do it yet.

Julia: Right. And then you ask the question of, okay, so but it’s been on that backlog now for months. Do you really need it? And the great PMs will ponder or put it forward and say, “Listen, we’ve put it off this long, we don’t need it. Customers are not begging for it. We’re not dying and there’s no impact to revenue. Whatever it is, we’re good.” And they’re comfortable sort of being the voice of that list and saying, “We don’t need it.”

Maggie: Okay. So you mentioned what a typical PM is. How do you think people view, especially with your background in engineering, how do you guys view typical in PMs? What does that person look like? What are the traps we fall into?

Julia: So I had a student who did a semester of reflection last year. That’s one of my favorite quotes, was she said, “After this course, I can now say anytime anybody introduces themselves as a PM to me, I don’t know what they do.” And so I think the answer is a typical PM, again, is very centered around what’s the right thing to build and much more again, the what not the how. So they are respectful. Even if they’re former engineers, they know enough to understand what the engineer is saying, but they’re not stepping on toes and questioning or whatever.

The typical product manager is comfortable floating, is comfortable knowing they’re wearing different hats a lot. The day is context switching and moving around and being comfortable that the world is moving around them sometimes while they’re committing to something. I think that’s an important one to call out, by the way.

Maggie: Yeah. What does that mean?

Julia: So there’s one thing if you’re a PM. So if you say “the day in the life of a PM” at a midsize company could be, and you’re doing this, you can tell me if this is what you do.

Maggie: Every day is a new day.

Julia: If you look at your calendar, you would say day in the life of the PM is I might have a meeting with sales. I might get on a call with a customer or go visit them. I may sit on the support desk and listen to things that are coming in or look at support tickets or things that are telling me what’s going well or not with our product. I’m sitting with engineering, maybe doing a sprint and talking through what we’re going to do in the next sprint and how the current sprint is going in a stand up.

I am going to an executive meeting maybe to report on how we’re doing. Are we making our timelines, are the sprints coming in or whatever. And what I mean by while I’m doing all of that, I’m meeting and checking in, lining and prioritizing and I’m in maybe Jira or Trello or whatever system you use to track everything. There’s lots of other things going on. So more tickets are coming in, people are in Slack dealing with things, and yours are having their conversations. And you have to be okay with that.

Maggie: Yeah, that’s exactly what my day is like. [crosstalk 00:18:38] I don’t know what’s happening, what meeting I’m in, who’s Slacking me.

Julia: Right, exactly. And so that could, again, either be the biggest high in the world. For me I love that stuff.

Maggie: Well, there’s a feeling I think. I don’t know how to describe it. I’m working on how to describe it, but that resonance when you know that it’s the right product, it’s the right time, it’s moving at the right pace, the team is working really well, and it’s sort of all moving in the right direction. And it might feel or look chaotic when you look at a calendar where you look at all the Slack messages that are coming in, but you’re still making progress and you can kind of feel. And I think that to me is what, when I see PMs are doing really well, it’s PMs who are feeling that energy and getting energy from that process.

Julia: Yeah, totally. And I think that your use of the term energy I think is really important. You have to love that vibe even though sometimes you’re really uncomfortable. You don’t know what’s going on, and you tell me if I’m wrong here, but there’s nothing like talking to a customer and having a customer say, “That thing that you just released, oh my God, changed our lives at work,” or changed my life as a consumer, if you’re a consumer. You just made my day.

A lot of times, and this is, I think for my very first job out of college, my biggest learning was I worked for a very small trade association. We were building product for people who handled their manufacturer’s reps in the electronics industry. And most of my end users were people just logging inventory and tracking sales for electrical products. And I would hear our product people talk about all these fancy new features and things that they were going to give these people and I was on the calls with these people daily.

Part of the job was help desk stuff and I would say, “You know what they want? They just want the product description field to be like from 10 characters to 25.” Imagine electrical wire where everything is the same except for the color is blue or it’s red or whatever and they couldn’t fit that in. And my biggest takeaway, I mean this is decades ago, first job out of college, was you don’t have to build the fancy things all the time. Sometimes it’s the most basic fundamental thing where the user is saying, “You get me.” This is what I do every day and it wasn’t hard to even build. And we forget that.

So great product managers are always balancing that. They’re balancing that we got to do something cool. They’re sort of paying attention to what the competitors are doing if they’re out there, but not being driven by that. That’s the biggest downfall, right? We have to build this because they just built that. Don’t ever do that. Thinking of innovative, cool new things, not always what the customer’s asking for.

When I was at VMware, we kept releasing things that no one had ever asked for, but our intuition was when we build it, they will love it. We were lucky that that happened. If we build it, they will come. Doesn’t always happen, but we were making sure every time we released something we had just the basic fundamental things that were just helping people get through the day and that matters.

And as a PM, when you say like, “We just made them happy because we changed the description field,” which back then that was hard to do, because that’s how old I am, but we also then threw out this fancy cool thing that they just blew their minds. As a PM, when you can nail both of those things, you’re killing it.

Maggie: I think some of my favorite features I’ve ever worked on were teeny tiny little fixes that you could probably classify as quality of life, but they were so frustrating and so annoying and then you fix them and immediately, there’s not a single bug getting filed, just shuts down a whole line of whatever was happening and it just feels so good when you’re like, oh, I finally solved that thing.

Julia: Yeah, and sometimes it’s taking scary risks. Right? When I was at Digital Ocean, there’s a fun story of a particular problem that we’re having with the product. We’d been putting off fixing it for a really long time. We did a bunch of analysis, how many of our customers out of, we had a million customers, were actually dealing with this problem. I think out of a million customers, maybe 20,000 had this thing.

Maggie: That’s a lot.

Julia: It’s a lot, but is it? 20,000 out of about a million customers would be impacted and my guess was maybe about a hundred of those would really care. And it was a big leap of faith, but we did analysis. I had a very heated conversation with the co-founders. I’m like, here’s what my gut tells me. I don’t think we’re going to go out of business if we make this change. I think we should make this change.

We heard from 70 customers out of 20,000. Mostly, they just wanted to understand the change. Why did you do this and how did this impact us? We had already prepared and this is part of the product manager’s job, we had prepared a, here’s what we’ll say if they call, if they email, if they tweet. It’s part of your job and we were ready for it. And all of them were satisfied and it was really not a big deal, but part of being a great product manager is saying, “I have to take a risk because of the bigger scale for the business. This is important for us to do.”

It was a big enough impact that it had to be fixed and we had a plan for how we would deal with it with our customers and we rolled with it. And it’s hard, especially if you’ve got founders yelling at you saying, “We’re going to make this change.” I’m sure that never happens here.

Maggie: No comments on that.

Julia: I think again, what makes a great product manager is someone who says, “I know this is the right thing to do.”

Maggie: And can make the call?

Julia: And can make the call.

Maggie: Yeah.

Julia: That’s right.

Maggie: Okay, so I want to switch gears just a little bit. Now that we know what makes a good PM, how do you get that first PM job? I get that question all the time. And obviously, you’re teaching classes of new PMs. What is your advice to them on how to actually get in the door?

Julia: Right. So the tricky thing about getting a PM job is it’s a catch 22. So I equate it to my daughter wanted to be a barista, but no one would hire her to be a barista. So how do I become a barista-

Maggie: You have to be a barista to become a barista?

Julia: Right. How do I do that? It’s a similar thing where I said, “You got to go find someone who’s willing to give you an apprenticeship and teach you how to make coffee maybe for free, and then at some point, you’ll actually be a barista.” So it’s similar with PM in that I think there’s sort of two avenues.

Julia: One is it might mean you step down a rung from where you were before to be scrappy and say, “I’ll be an associate PM or I will be a program manager in a product management group,” but also be very transparent you’re doing that. You don’t want to get stuck. Right? So it was very fair to say to someone, “Hey, give me a shot. I think I’d be good at this, but I’m happy to be a program manager in your team or an associate PM until I sort of cut my teeth and prove I can be a PM.” So that’s one angle.

Another angle is to take a role in another department that interacts with PMs. So product marketing, or biz dev, or strategy type role where you’re exposed to it, you’re getting to know the PM team, they’re getting to know you. And again, I’m a big believer in full transparency. Hey, I’m a good fit over here, I’m happy to go do this, but my goal is to really get to know that team over there because someday, I’d like to do that. So that’s two avenues that I give people a lot is try to get in that way.

There’s a lot of great bigger companies that have rotational programs where they’re perfectly fine [crosstalk 00:25:11]. Where did you do yours?

Maggie: TripAdvisor.

Julia: Right. So that can be really helpful because you get exposed to all of it and they know they’re teaching you, which is fantastic. So the other thing I talk a lot about is people take for granted what they’ve done that are PM-esque things in their past jobs that they’re not pulling into their resume. So what did you do?

If you were to look at the job description of a PM, what things did you do in your past life that even though your title didn’t say “product manager” you were doing what product managers do? How often did you talk to customers? How often did you work with engineering? You could have been an engineer who was talking to customers and PM all the time. Put that in your resume, pull that out.

Maggie: Or maybe you’re an engineer who had a feature idea and figured out how to get it done.

Julia: Exactly, right, or you did some rapid prototyping of things, or you had a startup on the side, or were helping a friend do their startup and were building things, or helping them figure out what to build. There’s plenty of things I think people don’t think is a big deal for them, why would I put that on my resume, which could be the pivotal point for them on their resume to actually say, “You actually are doing this.”

Selfishly, of course in my class I tell my students, “Don’t you dare put, ‘I took a product management class.’ You should be saying you built a product while you were in school because my students build a product, but not everyone can take my class.”

Maggie: Right, or some of us just should have but didn’t.

Julia: It’s a tricky one. I would say the same thing holds. It’s not like it’s a big unicorn, right? People who are doing sales when they want to break into sales have to start with maybe just inside sales, taking calls, and learning how to follow a script before they get to actually go out in the field and do outside sales or do something else. So everybody starts somewhere.

Maggie: Yeah. Just because you get an MBA and then take a class doesn’t mean that you get to be VP of product somewhere, which is the next question I have.

Julia: Sure.

Maggie: This is one I get all the time and I think one that I even talked to you about at one point in my career, which was, I’ve been a PM for a while, I have an opportunity to go and have a VP title, director title, whatever, startup or a smaller company, or I have this other opportunity to be maybe a group PM or senior PM or something at a bigger company. What’s the way to evaluate those choices?

Julia: Yeah. So there’s no right or wrong answer in terms of which one you should do first. I’ll start there. Big company, small company, each gives you an advantage. Big company, you would get a lot of exposure to mentors and to see best practice, or sometimes you see all the wrong things to do. I tell people that’s nothing wrong with going to work for a bad boss or a company that’s not delivering because you can see what bad looks like, but oftentimes, if you’re going to a big successful company, you’re going to get exposure to things.

You might have a narrower scope, smaller impact, maybe not get to do all the things, maybe have a lower title, but you’ll get to see how the machine runs and you’ll get to see what great looks like so that if you do go to a startup, you know what you’re trying to strive towards. I know what it will look like when we have product market fit and are building new features or whatever.

Going to a startup, I think you have to accept if you took a VP of product role at a startup and you’re right out of school or you don’t have a lot of experience, then you have to accept it’s inflated and that wouldn’t translate. You’re not going to become a VP of product at a big company from there, so put the title aside. Who cares? It’s really what you’re doing.

So if you’re an early stage company, you are doing all the things and you have to be comfortable with that. There is no team to do these things. Sometimes you are the product marketer or the product manager. You might be the designer, you might be support, and you have to be okay with that, even if you have a fancy title. You might not have mentors and best practice in the business that you join. A lot depends on who the founders are.

Here at Drift, you have very senior experienced serial entrepreneurs running the company. So that’s awesome when you can get exposure like that at an early stage company, but it’s unique. It’s really unique. Most early stage companies are first time founders and so you have to be prepared to get mentors, find people to advise you outside the business. So I recommend to anybody who’s taking a PM job for the first time in a startup, go get your network squared away, figure out who you’re going to call upon.

I do that a lot with my students who are in those jobs where we do coffees once a month and just talk about what we’re challenging. We’ve done this. So what’s challenging, what’s hard, how are you learning, where are you getting access to resources? Whatever it is, it’s critical.

Maggie: Yeah. Just being able to talk to someone who’s in the same type of role that you’re in at a different company is amazing because all of a sudden, is this normal, is this not no moral, how are you handling this problem, or do they have a problem you’ve never even heard of before?

Julia: Right, and that’s really important. If you’re a first time PM at a startup for the first time, you don’t know what normal is. It’s really fun for me when I’ve been at startups where sometimes I hear things and I looked at whoever the role is, not even just be able to like, “You know this is normal, right? Like this how it works here. Until you get to the stage, that’s just the way it’s going to be.”

Versus, “What do you mean you’re doing that? That should not be happening here. What dysfunction is going on or where’s the person who does this?” We don’t have that person. I will also figure that out. Right? So I think you’re right. I think finding that cohort of whether it’s peers, mentors, whatever, I think is really important and I think that ability to, I guess a couple things.

One is if you go into an early stage company, it’s both the thrill of we get to just do a bunch of crazy things and it’s like blue sky and I don’t know, and that can be really crazy and who knows what the product’s gonna look like in a year. That can be fun or that can be scary and daunting. Again, it goes back to who you are as a person and what gets you excited.

If you go to a big company, could be very structured, We know exactly where we’re going, We have a roadmap, we know what we need to deliver by the end of the year, could feel secure and really nice. Oh good. I don’t have to worry about that stress. Within the year, we may make a few changes or shifts, but overall I know where we’re going and what we’re trying to do. That could be great and very comforting and it gives you the ability to hone your skills without the stress, but it can feel very slow. It could feel very process heavy. Depends again on who you are.

So I always tell people there’s no right or wrong. Both are fun. I’ve done both. Both are great. It’s just what are you trying to get out of each? The question I get a lot is, what should I do first? So if I’m right out of grad school or college and this is what I want to break into, where should I go? So sadly, I don’t have an answer in terms of this one first. It depends. The way I view it is if you’ve started at a big company, what you’re bringing to a startup can be some structure, some experience, some view of what it looks like at scale, which can be super helpful.

You can also bring in other talented people that you’ve met in your network. There’s a lot of advantages of going big company to small, so starting there. The risk you can run as if you’re in big companies for too long. So I’m at a startup looking at your resume and I see every company you’ve been at for the last 10 years are these massive companies. Then I immediately ask, how are you going to be able to handle the environment of a startup?

Maggie: Right.

Julia: And very few people can. Some people say, “This is amazing.” I was working and really entrepreneurial in my current company. So even though it was a big company, I ran innovation at VMware and we were just cranking out startups all the time. So it was very comfortable for me to go back into startup land, but not everybody can handle that. And definitely on your resume, anything you can call out if you’ve been serial big company to say, “But I’m scrappy and I can do this,” that can be great.

So it’s only a negative, I think, if it’s been a long trajectory where you’ve been only big co most of your career. That would be very hard. But otherwise, one big company but doing entrepreneurial things in a big company can be an advantage. Flip side, if you go to a startup, a big company could look at you and say, “You don’t know how to work at scale, or you don’t know how to deal with process, or you’re going to be impatient, or whatever.”

Maggie: Yeah, or you’re even going to have trouble navigating the sort of subtext of a big company that’s not as obvious as it might be at a startup.

Julia: Right? Politics, lots of other things that you have to deal with. The other side though, is I’ve been at big companies hiring people from startups and say they’re scrappy. They’re not going to expect an entire team to do something. They’re going to do it all themselves. When you come from a big company it’s like, “Oh, I had people who did that.” That would be you at this company. When flip side is, I can hire someone from a startup and say like, “Awesome.” I might have to teach them all the politics and context and process, what have you, but I can just spin them up and let them go and they’re going to do the job of like 10 people because that’s what they’re used to doing.

Maggie: Right.

Julia: So say you’re a big company hiring for a new project that you’re doing at your company. Having a startup person who’s very entrepreneurial, who’s going to be scrappy, could be the best thing you ever did. So if I’m applying for a job from a startup to a traditional PM role in a big company, I would try to pull out the, I can be scrappy, I can work through processes, or call out things if you’ve implemented processes at your startup.

Maggie: Sort of how you help the startup [inaudible 00:33:30].

Julia: That’s right, and I think either works. There’s no right or wrong. Really again, I think it’s the how long you’re in either. I have a friend who’s only been a serial entrepreneur and a product guy at multiple companies, so he started, so he joined who went to a big company, very, very, very big company as a product person because he wanted to see what it would be like. And he lasted three weeks.

Maggie: That’s incredible.

Julia: He’s just like, not for me. Can’t do it.

Maggie: Wow, three weeks.

Julia: Yeah, three weeks.

Maggie: I feel like at a big company, your onboarding isn’t even done.

Julia: Right. [crosstalk 00:34:00] they were having meetings to talk about what meetings to have. He just couldn’t handle it.

Maggie: Yeah, I know. I’ve worked in both and I think I like both, but I definitely felt that I’ve been in a big company for long enough. I want to have that startup experience and I want to have that somewhat more chaotic, more energy, bigger scope opportunity.

Julia: But I think the important thing is, and I hear this a lot, unfortunately, fortunate, I don’t know. A lot of people say they want to go to a startup because they want to make it big and they want to make a lot of money, get equity early.

Maggie: When does that happen? Is it happening yet?

Julia: Well, it can. I’ve done it twice, but that was, again, absolute luck of the timing.

Maggie: I’ve had a couple of people reach out to me and saying, “Oh, I’m evaluating startup role and I’m evaluating my equity grant, and this company is offering me this and I have this over here,” and they haven’t even launched their product yet. And it’s like, which lottery ticket do you like better? I don’t know. How could you possibly evaluate that? I don’t know.

Julia: So that’s part of it too is thinking about when you’re joining a startup as a product manager, your job is really fundamental to whether that business is really going to get product market fit, and it can be the best thing that ever happened to you if money is important to you, but that’s not why you’re there. You’re there because you’re getting to take a blank canvas and actually build something from scratch and feel proud of the work you created. That will happen in a big company too, but in a big company, again, structure, process, fixed salary, equity won’t be worth as much.

Maggie: So we’ve learned what makes a good PM with EQ, and comfort with ambiguity, and being able to understand your place in the life cycle, how to evaluate a startup versus a mature company, how to get your first PM job. But if you could give everyone who’s listening just a couple of pieces of advice, if they’re interested in product, what would you tell them?

Julia: So if you’re interested in product and you haven’t done a product role before, go meet product managers. The wonderful thing is there’s so many great groups now. It’s very trendy, so almost every major city has some kind of people in product group. There’s the mind the product Slack group, which I love, and they have a city by city channel. They have women in product, they have just people who are doing research if you want to talk about research. Plug into that because you’ll get to meet a bunch of people in your city and then go to meetups.

Again, almost every city has some kind of meetup. So get to know product managers and really connect with them and understand what they do. And to your point earlier, hearing what other people are dealing with and what’s common and thematic versus unique to a company will sort of get you primed for what to expect. So I would say do that for sure. Get to know your fellow potential peers and mentors. That other piece is mentors. Find somebody who would help guide you through the process.

Maggie: Find your own Julia.

Julia: Find your own Julia, yes. So find someone who both, not only will be there to introduce you to people when you’re ready to take that job and help give you credibility, but also be there once you’ve taken the job to give you the mentorship and guidance. I think too many people, and this just goes regardless of product, don’t ask for help. They think it’s somehow a weakness to say, “I need a mentor. I need a guide,” or they wait too long. I will tell you I did that in my career. I waited way too long in my career to find mentors and I wish I had done that earlier.

It’s worked out okay, but I still think I look back in places where I think I could have handled something better, done something better. Had I had the right advisors, I probably would have sailed through that a little bit better. So I would say that’s the other key part. So meet your peers, get to know them, get introductions, attend events. There’s plenty of them in every city, and then be willing to take risks. That might mean you’re going to change compensation or title. Almost every job that I have taken in my career, I would step down to step up.

Maggie: Yep.

Julia: True story. So if I look at my resume right now, all of them involve me going into something that gave me either less responsibility or less money or less title, but at the end of the day, I knew I was trying to learn something I hadn’t done before and was willing to take that risk. And it paid off because I knew I could do the job, I just needed to just take the chance and they were willing to take the chance on me.

Maggie: Yeah. I think optimizing for where you’re going to learn the most, to me, has been the best thing I’ve ever done each time I’ve made a choice in my career because I think if you can do that, the success, the titles will follow.

Julia: 100 percent. I’ve seen it, I’ve lived it. I think people who are driven by title, honestly, I get totally turned off if somebody is applying a job and they’re negotiating title with me. And I think, do you care about what you’re gonna actually do? Because that’s what I care about. I’ve seen it, again, personal experience. Every job I’ve taken, I just execute and get it done and I’m having fun and learning. And it sounds like a cliche, but I will not go somewhere unless I’m about to learn something new.

Even being at HBS, even though I’m teaching something I know very well, just being in this environment, learning how to be an educator, working with incredibly talented, smart humans who challenge me every day but in a great way, and they’re teaching me. Just the way they’re learning about how they’re building their products, the different industries they are tapping in the products they’re building. I’m learning every day and I never want that to stop.

Maggie: That’s amazing.

Julia: Yeah.

Maggie: Well, thank you so much for coming. This has been incredible. We learned how to be a PM, how to pick what type of PM role you should take, what matters, which is ask for help, take some risks, and find people who can help you. So thank you for coming on the podcast. Everyone, leave Julia a six-star review. Give her a shout out. I need more six-star reviews. DJ and DC are getting too many of them.

Julia: Right on.

Maggie: Yeah.

Julia: All right.

Maggie: And let me know what you think at maggie@drift.com. Thanks.

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