The Jocelyn Miller Hypothesis: Growth is Uncomfortable

Jocelyn Miller tells us about working in product at places like Google and Amazon vs Zazzle and what role fun should play in our work.

The Jocelyn Miller Hypothesis: Growth is Uncomfortable

Jocelyn Miller helps professionals in product, tech, & design to create their dream careers. She uses her background as a leader at Amazon and Google to help her clients make substantial increases in compensation, increase their impact as leaders, and ultimately do this with work-life balance.

In this episode of the Product Science Podcast, we cover the difference between working in product at places like Google and Amazon versus smaller companies like Zazzle, what role fun should play in our work, and how Jocelyn helps clients find more fulfillment in their careers.

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Questions We Explore in This Episode

How did Jocelyn get into Product Management? How did getting technical chops under her belt help her on her journey? What did she work on as an engineer at Amazon? How did she work with the UI and the data to improve the experience? What used to happen when a person misspelled a word in their search query? Was product management at Amazon focused on the group you were in or the function of product? What was it like having so much responsibility at such a young age?

What was it like working on Google Health? What happened with Google Health? What surprised Jocelyn along the way? What was it like interacting with Marissa Mayer while at Google? How deeply did they look at the customer journey? How did looking at that help them uncover who their initial customers were? How did she decide to move on from working on Google Health?

What was it like working in ads at Google when they had just bought DoubleClick? What was it like integrating the new company into Google? What was it like working in adtech in the late 2000s and early 2010s? What is the Lumascape?

What was it like working as Director of Product at Zazzle, an e-commerce company? What’s it like working with someone with whom you are ridiculously aligned? How big was zazzle when Jocelyn joined? What size company does Jocelyn most enjoy working at? How important was the work of product in a business the size of Zazzle? How did that compare to working at Google and Amazon?

What role should fun play in your career? How important is it to bond with your coworkers both in and outside of the workplace? How does taking on challenges in games help you take on challenges at work? Is it better to have a professional leader or a fun leader? What does the Star Trek approach to management look like? What has COVID-19 taught us about leadership?

How does Jocelyn help her coaching clients to put themselves out there and value themselves and their work? What types of clients does Jocelyn work with? How can you decide when it’s time to move on from a job? What does Reid Hoffman teach in The Alliance about having a tour of duty? How does life stage impact what matters to you in your career? Can you really have it all? How do you achieve work-life balance? How do you make sure that you keep growing? What advice does Jocelyn have for aspiring product leaders?

Quotes from this episode

If you're feeling frustrated, overwhelmed, annoyed by your current situation get that expert guidance so that you don't burn another 10 years on it.
Growth fundamentally is super uncomfortable and it's totally worthwhile.
One of the big things is bringing about an increased level of intentionality to career choices, where it's a true understanding and appreciation for the value that this opportunity is providing for all areas of your life.


Holly: Hi, and welcome to The Product Science podcast, where we're helping startup founders and product leaders build high growth products, teams, and companies through real conversations with the people who have tried it and aren't afraid to share lessons learned from their failures along the way. I'm your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.

This week on The Product Science podcast, I'm really excited to talk with Jocelyn Miller. Jocelyn helps professionals in product tech and design to create their dream careers. She uses her background as the leader at Amazon and Google to help her clients make substantial increases in compensation, increase their impact as leaders, and ultimately do this with work-life balance. Welcome, Jocelyn.

Jocelyn: Thank you, Holly. Thanks for having me.

Holly: I'm so excited to talk with you today.

Jocelyn: Yeah, same.

Holly: So, I love to get started by hearing a bit about people's journeys into product. So why don't you tell me a little bit about your story?

Jocelyn: Absolutely. Well, it's interesting because I studied a lot of things in college, and that included cognitive science because I was really interested in how people worked, but then I really loved the zero and oneness of computer science and the clarity with everything that was there. So, I ended up doubling in both of those with a little pre-med along the way. But I always talk about that as people and machines, and that got me interviewing with a bunch of tech companies early on. I had an internship in Seattle and it was funny because partly I didn't do anything on the west coast because I was east coast raised and my mom was like, "You can't go to the west coast. They have earthquakes." I don't know, it was a whole thing and-

Holly: That's so funny. I was east coast raised and I also did not consider going to the west coast, but it also was just because it was just very far.

Jocelyn: Yeah. I think that was what her campaign was against was distance. So I had this internship in Seattle, ended up loving it there so talked with Amazon, Microsoft, Google, all the big ones. Got an offer from Amazon ... actually got a bunch of offers, but it was interesting because I had offers for engineering and product, and at that point I remember Microsoft was like, "You like people too much. You need to do product things or you're going to want to talk to people. I was like, "That's interesting." But I felt like I wanted to know more about the technology at that point in my career. So, I was seeking an engineering offer at that point and I remember talking to folks at Amazon and I was like, "I don't know. I don't know that I can really code eight hours a day," and they laughed.

And they were like, "By the time we were here for three months, you'll wish you were coding more because there are so many meetings to decide what we're doing." But at any rate, I was pretty convinced early on that it was just a matter of time before I went into product, but that I wanted more technical chops under my belt. So, I got that and I made that transition at Amazon after maybe a year and a half and then went to Google as an engineer first, because I was like, "Well, let me just see how they're doing engineering."

And, and then after a year, year and a half, switched back into product again and then just never turned back. Just kept doing products.

Holly: Wow. I love how early on you realized that. I feel like I don't hear that very often. People are usually like, "Well I did this, this, and this and then I realized I was really doing product." That's so fascinating that you came across it so quickly.

Jocelyn: Yeah. I mean, it's so funny that you see that because at the time, clearly in my 22, 23 year old self who's like "I should be running this place." I don't know if you went through the highly heuristic phase that I definitely went through, but I remember when you're like, "Oh, it went so fast," at the time I felt like this is taking forever. This transition took nine months. What? But, in the relative scheme of things, that's true.

Holly: Yeah, that's so funny. Tell me more about starting with Amazon. What sort of things did you work on there?

Jocelyn: So I worked a lot on personalization. That's what really initially drew me to Amazon was the personalization team. I worked on it as an engineer and a product manager, and what I loved about all of that is we were using data to get people exactly what they wanted as quickly as possible. And, it was really powerful. I mean, it still is but especially at that point, they were the front runner in all of this. They already had some powerful algorithms, and then we could basically ... One thing I really loved about that work too, is there was a marrying between the UI and the data so you really wanted to figure out how do I best display it? How do I best come up with the best algorithms for what we're showcasing and where? And, we used that stuff all over the place.

We used it to bandaid Search because at that point, Search was pretty young days. We did work on even ... Right now, we take for granted that when you misspell something, it'll auto-correct it. It's a very seamless experience generally, but back then we were asking the questions of, "Okay, well if they mistype it, first off, how do we figure out what the actual search query was supposed to be. Two, do we assume that and then show them results for that query? Do we just show them crap?" That was what by default happening without these decisions. Or, do we have a couple of states depending on how confident we are?

I really loved being at that intersection of the information and the data as well as the user experience. That was a really fun place to play in.

Holly: Yeah, that sounds really fun. So can you set the time for us? What was the timeframe of you working there?

Jocelyn: That was '03 to '07 that we were doing that work, and actually it was funny because we actually also did some work on a very early AWS as well. We created a web service for personalization, but at the time, we decided not to go public with it because it was deemed too much of a secret sauce and we didn't want to expose it. So, we used it internally. A bunch of the ad system that's in Amazon is using that service. I think at what point they exposed it externally, too. Yeah, it's wild times. Wild rides.

Holly: Okay, so what was it like to work on the product team at Amazon?

Jocelyn: Well, it's funny. When you say the product team at Amazon, I want to really say it was the personalization team at Amazon. That's how that ran back there, which was very focused on the group as opposed to the function. And that's partly because we were set up as two teams at that point. You'd have one technical product and program manager, regular manager and some engineers sometimes embedded QA or UX, sometimes shared. It was super fun. And honestly, though, it's funny because a lot of people, they'll come to me and they'll be like, "Oh, what did you prefer, Amazon or Google? Or, this one or that one?" And, it's always rooted in them trying to understand what they should do for themselves.

I always stress, look, I loved my experience at Amazon but it was a very unique time and place, and place in my life and career. So for me, having a huge amount of responsibility at such a young age was exactly what I was after and I learned a ton as a result. But me, with two kids later, I don't know that I would necessarily choose that at this moment, but it was really fabulous.

Holly: Yeah, that makes so much sense and resonates so much with my own decisions and experiences. So you went from Amazon to Google, so what did you do at Google?

Jocelyn: So I started on a spectacular failure of a product, which was Google Health, which had all the ambition and it was the opposite in certain ways. It was wrong place, wrong time because we were trying to build a PHR, which is a personal health record. So, really empowering people with their health, which is something that I still strongly believe in and I feel like that was a nod back to the pre-med days that I had where I'm like, "Well, I want people to be healthy and happy and be able to live those long lives." I know that we can use technology to facilitate that in a very powerful way.

That particular incarnation of that product did not end up being the amazing splash that we had initially hoped, but that was okay as well. It was a great learning. And, I ended up from there, I decided to go to the core so I went to product in the ad space there and then into search.

Holly: So, I'm curious while you were working on Google Health, what were some of the things that were surprises along the way?

Jocelyn: Yeah, that's an awesome question. So I think probably the biggest surprise was it was about maybe a month into me having started, and I remember Marisa sat us all down because she was the overseer of that area at that point. And she basically sat everyone down and was like, "Why the F hasn't this thing launched? What are you all doing?" And I'm like, "I've been here a month. I don't even know who these people are. I don't know what we're doing." It could have even been a couple of weeks. It was such a wild thing. So it was like getting your ass handed to you and you're like, "I don't even ... I don't even know. I'm not even quite sure what we were building. I've just gone through the nuclear training and I don't quite know what you all are doing."

So, that was wild. And then I think shortly thereafter, I think a VP was either fired, let go, whatever. It was a wild ride and mess and yeah, that was certainly a surprise.

Holly: Yeah, that sounds like a surprise. So how long had the team been working on it?

Jocelyn: I think it may have been about a year and a half or two, something in that range is what it seemed like at the time.

Holly: Were there any surprises that you found about what happened when it hit the customer's hands?

Jocelyn: There were things that surprised certain people, but not me because I felt that we hadn't really gone into who's the customer. What is that journey? So, I feel like there were surprises were the team and some of the other members of the team were surprised, but I was not especially surprised because earlier on I was indicating as I was getting to know what they had done up to that point and what the plans were, that it felt like it was a very engineering-focused solution as opposed to working backwards from customer needs. So, I wasn't really shocked that it didn't fly off like hot cakes.

At that point, I recall one of the concerns that I had highlighted early was that at that point, this predates EMR being mandated for the health providers. So, there was a question of how much of people's data even was going to be accessible easily within this tool?

And I remember I pursued with one of our PMs ... because remember I'm an engineer at that point ... I pursued with one of the PMs trying out some services to get your data converted into EMR format so that you could see it. And, I remember my doctor had to fax first off, but faxed over an inch and a half of papers or something, all this data that I had collated into one spot. And, three records from all of that got translated into the EMR via the service, and I'm like, "Okay, this is ridiculous. This isn't working."

Holly: Sounds like something that you could see would be frustrating. What did you guys do with that situation?

Jocelyn: Well, so it was interesting. The other interesting and somewhat surprising part of it, because again since it wasn't user led or focused in that regard or customer focused, really, there were some outcomes that weren't predicted because they weren't really looked for. The user segment that seemed to use this most were caretakers, so folks who had ... It could be either an official caretaker role or the middle, what we often call that sandwich generation where they've got kids and parents, and they're mostly trying to manage the health of the parents. And, this was a way for them to track what was going on with the parents.

So, that was a segment that was then explored, and luckily there was more UX focus brought into it and customer driven focus. Again, the thing didn't take over the world but it had some interesting time supporting that segment.

Holly: So did you do products for Google health before you moved into the ads?

Jocelyn: So it was funny, it was actually ironically, despite the challenges, it was a very product heavy org. There were actually a number of product managers. I basically created a proposal for what they could do, but was like, "Okay, so I'm out. Here's my product two cents. Also, there's too many cooks in this kitchen already. I'm going to go cook somewhere else."

Holly: Oh, that's really smart. You were just like, "I'm going to tell you what I see here and I'm going to move on."

Jocelyn: Mm-hmm (affirmative). And that was just the right thing at that point.

Holly: So what was it like working on Google ads?

Jocelyn: It was interesting. So, that was as Google had bought DoubleClick, so I was working on DoubleClick and really trying to figure out ... That was a fascinating situation. In a sense, I think it was that experience that ended up teeing me up for doing corporate training and change management later because we had this whole culture coming into Google, and a whole set of technology, and it had been this market leader for display advertising. And yet, the tech was ready to fall over. It was totally maxed, need the be brought into Google servers. Millions of dollars is going through the ad server, so it needs to continue to do so.

We often would talk about it with the analogy of it's like you're changing the engine mid-flight and hope that everything goes really well.

Holly: Okay, I'm curious too, because I also worked in ad tech in my career. What was the timeframe for that?

Jocelyn: Great question. I think it would've been around '08, '09 to '10 or '11. Somewhere in there.

Holly: Okay, yeah. So a couple years before I got into ad tech. I can imagine because I remember when I joined MediaMath they're technology was only two years old when I joined, and it was already being rewritten in a new tech stack. It needed that care because everything changed in ad tech so quickly.

Jocelyn: Yeah, it's funny. I feel like that name sounds familiar. It's just funny. I remember there was this visual of-

Holly: Oh, the LUMAscape?

Jocelyn: Yep. It was showcasing all the different ad tech things because there's the publishers side, the advertiser side, the agency side, and it just had this smattering of things. Even the categories of stuff, there were a lot of categories and then within it, so many different players.

Holly: Yeah, even knowing what all those categories were, there was the demand side platform and the supply side platform, and of course everything was an acronym, like the DSP and the SSP. It was just one of those industries.

Jocelyn: Well, yeah and at that point there were so many words for this automated backfill or whatever. There was like how do you do the automated targeting so that you're really utilizing and maximizing ad spend, ad buy? All of it. So yeah, it was a crazy time, and in a sense I'm sure has continued as such.

Holly: It's one of those things I always think is fascinating because there's so much technology involved in that split second before you load a page on the internet and just figuring out which ads are going to show up where and how they figured that out, it's mind boggling.

Jocelyn: Totally.

Holly: So how long did you ... you did that for a couple of years?

Jocelyn: Yep. I think that was a couple of years, and then Search for a couple of years. I mean, I'm sure my maths a little bit off here. It feels like so long ago. And then, I went and became director of product at Zazzle doing custom eCommerce at that point.

Holly: Oh, okay. Cool. What was it like being at Zazzle?

Jocelyn: Super fun. So it was funny, one of the co-founders who was CPO at Zazzle, I remember very viscerally when we had our first conversation, because we were so in alignment from moment one. It was to this point where it's almost like, "Are you punking me? Or, how do you know this?" We were finishing each other's sentences immediately. That was just an amazing experience.

And it was funny, we had enough overlap of values, vision, way that we approached things that we knew if one of us was in a meeting or a room, we're covered. And at the same time, we were different enough that we complimented each other on what we were bringing to the table. It was really an awesome experience.

Holly: Yeah. That sounds like a dream.

Jocelyn: Yeah, it really was amazing.

Holly: For any of our listeners who don't know, what is Zazzle?

Jocelyn: Yeah, so Zazzle is a custom goods eCommerce company. So basically, where you want to put does designs on anything, that's one of the core products that they have, where you can get all this swag stuff. Now you can get more advanced custom goods, so custom leather purses, custom stuffed animals, custom ... different kinds of things, which was an add-on that we did at that point where it wasn't just putting designs on things, but being able to configure even more.

Holly: I remember them being pretty early to the market of "Well, I want just this one single design printed on this one tee-shirt."

Jocelyn: Yeah, because there was the whole minimum order quantities. You have to get a special silk screen early, early.

Holly: That sounds really fun, and it must have been a big change for you since you'd come from these big companies. How big was Zazzle when you joined?

Jocelyn: I think it was around 100, and when I left it was around maybe 300.

Holly: That's fun. I love being at companies at that stage of the couple of hundreds.

Jocelyn: And that was exactly what I was after at that point. I wanted to really have the product and the revenue on the line. I wanted to have that level of impact where what we did was materially important to the business.

Holly: What was something that stood out to you about that experience after having come from the large enterprise.

Jocelyn: Well, so it was funny because Amazon is definitely talked about as large enterprise now, but when I was there, it wasn't really that big, and certainly the way it ran, it also was not. In the sense that it already ran super entrepreneurial, it was whatever you see ... It's not that turf wars wouldn't happen in all the environments at some level that I've been in, but one of the things I always find interesting is that in companies where your really resource constrained, things look very different.

At Amazon, we never had enough resources and we were always trying to do bigger and better things, so there was this element of okay, you see an opportunity, just go do it. You see a problem, just go fix it. I always joked when Google had all these trainings and all of this process when I came in, and I found that really fascinating but I mentioned to one of my former coworkers, I was like, "When we were Amazon, I had a really good sense of how all of it worked."

And I'm like, "But, I didn't attend any classes. So, how did I know how this all worked?" And, she joked back, she was like, "Yeah, because it was always breaking so you had to learn about all the different parts because you're on this conference call and it's like, all right, why is everything down? Let's figure out who it is."

And partly, it was because I did delve into all these different areas. Also, at that point, most of the folks who were working there, we weren't Seattle natives or anything. We were new grads out of college, living like people or trying to, where we were all independent and hung out a lot. So, you just learned a lot about how all of that worked really easily.

But that's that more entrepreneurial small company type environment where you're just in the thick of it. In a way, when I went to Zazzle, I felt like it was more a returning to that in a sense, of returning to that place where you're playing board games together after dinner at work, and you're learning about each other's lives and you're, in the meantime, talking through the search algorithms and what you could do to change those up to make an even better outcome.

Holly: You make it sound like a lot of fun.

Jocelyn: Well, I had a lot of fun.

Holly: Yeah, that's awesome. I guess that just makes me curious since I know you talk a lot about dream careers, what role do you think fun should play in your career?

Jocelyn: Funny, because I was actually talking with a client about this, because she was putting it into some of the work that we were doing, the word and concept of fun was coming up and she was like, "Oh, but it doesn't sound so professional." And I'm like, "Well, hold up here." It's like, "Well, wait a minute. Who do y'all want to work with? Do you want to work with or lead or be under a leader, or lead as someone who's very stern and strict and everything's like a big deal? Or, is screaming in everyone like, 'Hey, why isn't this done?' Or, is freaking out every moment and saying, 'Oh my God, oh my God, the sky is falling."

"Or, do you want to have someone ..." This is where you need to get into balance of course, but have someone where, "Hey, let's have a good time." Let's enjoy ourselves because frankly the level of creativity and innovation we want to be having in these companies and in these teams and in these careers, frankly, I don't even think it can happen without fun. Meaning the fluidity of innovation is only going to happen in a fun environment. It doesn't mean that there isn't also seriousness, but ...

All right, so this is going to sound so silly, but okay. For those of you who aren't into it, it's cool, but I love Star Trek TNG.

Holly: Oh, me too. Yes. My cat is named Janeway because I love all the Star Treks. I have a signed poster of The Next Generation crew on my living room wall, so you found the right person to talk to.

Jocelyn: Oh my God, love it. Nice, nice. I love it. I love it. I just absolutely adore it, and at Amazon, my boss and I would joke. We're like, "Star Trek is great management training. It's great management style. It's a great management approach." But now one of the things ... So, when I love something, I really look into all of the details. One of the things I found fascinating was that the writers, especially for TNG, had an explicit approach that they were using where they said, "Look, this isn't about drama between characters, like so many shows are. The drama is coming from the external, as in life has enough challenges. There will be enough aliens that show up. There were be enough threats that show up, things that didn't go your way that will show up. Nebula's, whatever. Stuff that happens that you're going to have to figure it out and deal with that instead of focusing on melodrama between characters, just have that be the focus.

And so, that is what I always think about here where it's let's not create a problem in between individuals that are just unnecessary and are taking away energy and distracting. Let's have that be fun and let the market be the challenging thing. I mean, if COVID has taught us nothing, I think it has taught us that we don't control everything. We can't predict everything. Everything doesn't always go the way that you were hoping or planning, and so let us rally together against this crazy situation that has shown up as opposed to arguing over things that are trivialities in comparison.

Holly: Absolutely. Very well said. I love it. So do you find that your clients are generally people who are looking for that fun and that bonding together against the external force?

Jocelyn: Yeah, that's a great question. There's a variety of ways in which clients initially show up. They might show up where they're burnt out. They might show up where they're just really frustrated for whatever reason. Maybe they haven't been promoted fast enough or being recognized at the level that they think they should be, or they've ... I don't work exclusively with women, but heavily with women, having been a woman leader myself, and could be they just found out that they're being compensated tens of thousands dollars less than some male counterpart in a comparable role, and it's like, "Hey, what the heck's going on? What do I need to be doing here?"

It could be anything from that to just I don't feel right. I'm questioning whether I've got my clear North star, whether I'm going in the right direction, or I want to have a family, I want to spend time with the family I have, or start a family and I don't feel set up to do that. So it could be any of those things, and sometimes it's like, "Hey, I'm moving along, I'm cruising along, but I want to have even more of an edge. I want to know that I'm maximizing my impact, my value, my experience here in the world."

So any of those things, but when you say are they already anticipating and asking for this combination, I think for many of them when shown that that's an option, they want to do it. But, often when they're showing up, there's just a lot of question of is that really possible? Can I really do that? I just wanted things to suck less right now.

Holly: Yeah, that totally makes sense. So tell me a little more about how you work with your clients. What does that journey look like once they start working with you?

Jocelyn: So, we have a few different ways that we work with folks. We have programs oriented towards how to create your dream job, and sometimes that's creating, designing it. Sometimes it's finding it and finding that match, but we have a whole journey and process that folks can go through. And it's funny because sometimes I've even come to learn over time that sometimes going through that process leads you back to where you are, but in a new way. I've had clients who literally have put in their notice saying, "I'm out of here. It's toxic. I don't want to do this anymore," and used our program and our system to lead them back, but to a different place. So it would be, in this case a recent example where a client ended up meeting with a different manager who put together a position that actually was put together independently of her that exactly matched what we had come up with using our process for what would suit her best.

And, it was this moment of, "Well, gosh, he's saying exactly what I want," and not that he even knew. It was just like it was coming together in a very natural and organic way. And that was really wild because actually she was going to be done on that Friday. They're having this conversation on a Wednesday. He's like, "Can I just keep you on payroll, keep getting you benefits and would you allow me the time to make you this offer if I do that?"

Holly: Wow, that's incredible.

Jocelyn: Totally. And he convinced HR to set that up. And so, she ended up with I think a month in between her old position and her new just getting paid staying, and then he made the offer, and we talked through it and it was like, "Yeah, this makes sense. This absolutely works." And, it was funny, I asked her, I was like, "If I had said to you when we had our first call that you would stay at this place, that you would be happy about it, what would you have said?" She was like, "I would've hung up the phone. I would've just ..."

Holly: Yeah, that's awesome. Have you had situations where it was more of a struggle and people I imagine did have to leave and go to a new place to find what they wanted?

Jocelyn: Yeah, though I don't ... So I will say, I don't necessarily think going to a new place has to be a struggle or a challenge, meaning it's funny, I often talk about, as you go through that journey, it's really about finding your next position. So, one thing that I really loved from the book, The Alliance by Reid Hoffman ... and I don't know if you've read it and if you haven't, I really find it to be great.

Holly: I'll have to check it out.

Jocelyn: Yeah, totally. So one of the things he talks about is having a tour of duty. He has this notion of when you're setting up your next position, whether it's in your current place or another, having this notion of over the next 18 to 24 months, what is the main thing that each of you are after? Both you as the job seeker, the leader and the company? And then having at the end of that period, an evaluation. How did it go? Are we on track? What's the next tour of duty with the next thing in store?

So, in a lot of ways, I recommend that approach really having a regular evaluation of okay, great, are we good? Are we on track? Is this feeling like the right thing? Or, should we look at what it will be better suited now. Because I feel like even my own journey, in addition to my clients, has been a great example of I have loved every step of the way, but that doesn't mean I would make that same decision for where I am now today in this place in my life.

Holly: Yeah. That resonates really strongly with me right now because I've stumbled across an opportunity to work at a high growth startup that's in that stage where people are working crazy hours, and that's a thing that I did in my past, but it's not a thing I want to be doing right now. I've counseled other people that they should take that opportunity, but it's not always the right choice at this point in your life and there are times when you say, "Okay, at one point this was good and now it's not."

Jocelyn: I love it. And along those lines, I think one of the big things that I work with my clients on is bringing about an increased level of intentionality, which I think is exactly what you're exhibiting with what you've said here, where it's a true, full bodied understanding and appreciation for the value that this thing is providing and offering and knowing look, you've already made that transformation. You've already grown in exactly that way. And so, one of the big things I'm doing with folks is helping them get to that next level of leadership and impact in their life where they can have the integration of ... I know we talk about work-life harmony, balance, whatever verbiage you want to put around it, but at the end of the day, I'm a very strong believer in yes, you can have it all. Yes, you can find a way to have a kick-ass career, get paid really well and compensated really well for it, and still have that time and energy at the end of the day to be present with your loved ones and for yourself, grab that spa day, which I'm a huge fan of.

Holly: Yes, I love it. So how do you help people do that?

Jocelyn: We go through that journey. So, whether it's the catapult journey to get you to your dream job and for some people, it's just a leadership up-leveling. We have programs to ignite impact in your leadership space and really understand all of the things ... because one of the things I always find interesting is as people become better individual contributors, they're often either led to management positions ... they'll get promoted into managing in some form or they're really craving it. They're like, "Oh, why am I not a manager yet?"

And in either situation there's this interesting thing where we've all heard the phrase, or maybe even read the book, What Got You Here Isn't Going to Get You There. Damn. Damn, is it true?

Holly: So do you have any success stories that you want to share where you helped somebody find the work-life harmony that they were looking for?

Jocelyn: There are so many really, so I'm trying to think of ... Here, let's try this one out. One person who comes to mind, she is a high up leader today. She's had a huge amount of impact on the company, but she felt like she was getting blocked at a certain level, that she wasn't getting promoted. And, this happens a lot with my clients. For a lot of clients, it's not even about the money or the status per se, but there's this question of am I making forward progress and am I fully appreciated and recognized for what I'm doing?

So, we've been working together on really honing in her leadership skills. And for her in particular ... it's always different as far as what specific thing I'm working on with a client, but for her, there was an element of really tuning into intuition and gut, and trusting herself being a really big theme. So, that is something that we've spent a special time on and as a result, she's now moved into a position where she left me a message ... she's like, "Oh my God. I just wanted to say I feel like I'm exactly in my zone of genius."

She had move don to a new team as their leader. I think she was getting feedback within a week or ... Oh, because this is the other thing. We arranged for her to take a break, for her to take a month off. It was in between positions but she had actually started this new role. And, one of her counterparts a week in, when he hears that she's going to take this month long sabbatical, he's like, "Oh my God, what will we do?" She thought that was so funny, and so did I because it's like you've been there a week and now you're indispensable. That's amazing.

Holly: That's awesome. I love it. Well, are there any other lessons learned that you really like to share with your clients and listeners?

Jocelyn: Some of the things that I've just personally learned over time, and a lot of them might be things that you may have heard before, but it's funny ... I want to make one distinction here between what you have heard versus what you know. And so, I feel like I have made what feels like every mistake so all of this comes from deep empathy and connection with the many mistakes, the insane amount of hubris, I know everything. Things I've learned are like when we come from that know-it-all place, it really impedes progress. It really impedes your ability to grow. And it's so funny, so many clients come to me and they're like, "I want to grow." And it's like, "Okay, great. So we're going to have to change them stuff," and it's like, "I don't want to change anything."

It's like, "Nope, that's not how that works." Growth fundamentally is super uncomfortable and it's totally worthwhile. One of the things I always say is if you think you know something, if you're like, "Oh yeah, yeah, I know it," just because you've heard it, the question is are you living it every day? For example, one of the things that I've absolutely learned is the best investment you can make is in yourself and you should do it just ongoing-ly. The notion that learning stops at school, I've never subscribed to that. I've constantly been in continuous learning and growing environments getting coaching myself.

And here's the thing, what I consistently see for myself, for others, for my clients is by virtue of getting that support, you take decades and turn them into days or months instead of making all of those mistakes yourself. Look, can you make the mistakes yourself and get there? And even with that, I want to say maybe meaning sometimes you just keep making mistakes. I think everyone of us knows someone who you've listened to for years or decades where the problems and the challenges and the complaints have stayed the same for all of that time.

I will often talk about for myself, and many of my clients, it's like, "I want new problems. I want the problem of how do I scale this team to its next level instead of how do I just manage my to-do list? I want the problem of how do I manage all the incoming funds because now we have to do more tax planning because we're getting paid so much." And so, how do we then estate plan and the kids? That's what I want to help my clients get into instead of just running a hamster wheel and feeling like they're stuck.

Holly: That's awesome. Any particular advice that you like to give to people who are aspiring product leaders?

Jocelyn: I think for aspiring product leaders, there is a question of one, what is your next developmental edge? What is the next place that you need to truly invest in? But relatedly, as you answer that, two, do you really know that that's it? Meaning ... So, one of the things that often comes up is people will come to me and they'll present a problem, even companies. A company who I'm talking to and they're like, "We're having trouble writing user stories and story points," and you're like, "Okay." So, we're thinking if we just had better number estimates at the end of a scrum meeting then all of our company problems go away. Probably not. When people are career switching, they're like, "The thing is I just need my updated resume. Once I have my updated resume, I'll be great." And, it's like, "Okay, so you think your career over the last five years that's stagnated has been stagnating because you don't have a document as a resume that looks perfect and amazing and is getting you there."

So, there's this question of one, what's the next level of development that you truly need? And two, are you sure? Is that actually it? That's really why I recommend getting expert coaching and really investing in that because I've been there. I understand. I understand the inclination to say, "Well, this is the problem." And even for myself, I remember early on in Seattle, as an example, I remember I was in this apartment and I was having trouble organizing all my stuff. And, I remember I got this organizer woman in and I said to her, I was like, "Yeah, for some reason, I can't quite figure out how to get a specific location for everything. I can put things back into a place that it's supposed to live, but I'm having trouble creating places for each of these things to live." And she was like, "Yeah, because there's too much stuff in the space." And, I was like, "Oh, okay. All right."

Holly: It seemed so obvious to her.

Jocelyn: Yeah, because she's an expert in physical organization. And when she said that, you're like, "Oh cool. I will stop this fruitless task of with all the constraints that I have put into this, I will stop trying to ..." That's what causes the hamster wheel experience. That's what causes Sisyphus pushing the rock up the mountain is you have a set of constraints that you don't even realize you have, and you just keep trying to work within them. And that's the whole I keep replaying the same pattern again and again expecting a different outcome. If you even are flirting with that, if you feel like you've been stagnating for a while, recognize this is a signal. If you're feeling frustrated, overwhelmed, annoyed by your current situation or just like a lackadaisical ... You just feel a bit of apathy, a bit of is this all there is?

These are all indicators to say something needs to change, something needs to shift now, and hear it for what it is and know that while it's awesome to have your hypothesis of what it is and think that it's a resume or if only we could estimate scrum points, understand that if you have been in this pattern for months or years, yeah, it's more than that.

So get that expert guidance, get that coaching so that you don't burn another year to 10 on the thing that you're facing, but rather up level yourself now so that you will be able to enjoy that time with the kids, so that you will be able to go to the spa, so that you will be able to travel the world again, or do whatever it is you are into while also feeling like a superhero at work. Because everything that you're doing there is just kick butt, high impact, high powered, and you're having fun while you're doing it.

Holly: Awesome. I love that. All right, well we are about out of time. So how can people find you if they want to learn more about Jocelyn?

Jocelyn: Absolutely. So they can go to www.Jocelyn, J-O-C-E-L-Y-N,

Holly: Awesome. Well, thank you so much. It was such a pleasure to talk to you today, Jocelyn.

Jocelyn: Thank you so much, Holly. This has been such a pleasure and I look forward to more conversations together.

Holly: Yeah, me too.

The Product Science podcast is brought to you by H2R Product Science. We teach startup founders and products leaders how to use the Product Science method to discover the strongest product opportunities and lay the foundations for high growth products, teams and businesses. Learn more at Enjoying this episode? Don't forget to subscribe so you don't miss next week's episode. I also encourage you to visit us at to sign up for more information and resources from me and our guests. If you like the show, a rating and review would be greatly appreciated. Thank you.

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