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Smiles Northwest always invests in the latest technology, has their own in-office dental lab, and are constantly training their team in the newest advancements in dentistry. Visit smilesnw.com and book an appointment today. Hey guys, today we're talking about making transitions and pivots in your career. Joining us is Michael Chen.

Michael, how are you doing? - Doing well, Tim. Hey, it's good to see you. - Good to see you. So Michael, you and I met when we worked at LinkedIn in LinkedIn Learning. It is essentially a startup at the time, right? It was a new business, they had acquired LinkedIn Learning, or lynda.com, and now they do this big thing.

And you were a product marketing manager at the time, but where you started in career and where you've actually gone from there are totally different. So can you tell us a little bit about maybe what you're doing now, and then maybe start from the beginning, like what was your life journey?

- Absolutely. So today I'm on the product team. I'm a product manager and I work at Asana. But my journey starts actually even before LinkedIn, Tim. When we first met, I had just come out of business school. And prior to business school, I was actually a consultant in the brand strategy world.

So a few transitions from brand to product marketing, stint in head of marketing, and then now I'm a product manager. So a lot of different places that have overlapped. - So can you tell us the very beginning, 'cause I know that you started in consulting, and I've always wondered, is it the right move for early career folks, right?

Is it intense? And why did you choose to start off with consulting? - Yeah, consulting, I would absolutely agree with you there. I think consulting is a really good place to learn. It's great for early career. It's great for a lot of people coming out of graduate school because you get to just learn and see from so many different industries, clients, businesses, and also just work with a lot of different types of people.

So not only do you get to learn the job and the hard skills and the soft skills of being a business or strategy expert, you also learn how to work with just a lot of different people, personalities, and learn how to manage upward and downward. So absolutely, it's a really good place to start.

- Is it considered high stakes? 'Cause obviously as a consultant, you're working for a firm. They're entrusting you to go out there and build these relationships, right? So if you're describing that as early career, like you may not have the business savvy or communication skills to pull it off, right?

And so is it truly a safe place for the early career people to start, or what was your experience? - Yeah, it's a really good point. I think because you are early career and coming out of business school, a ton of consultants as well, and I wouldn't call them necessarily early career, but it is a new foray into a space where you have to be the expert in the industry or the client that you're working for, right?

High stakes, but I think what you get out of consulting is you build the ability to learn as fast as possible, because at some point you do have to become the expert of that field. You'll see kind of this theme as we talk about my different roles and careers, but consulting is a really good place where you figure out a learn from your own research, but also from the people that you are surrounded by.

If you don't know something, there is probably someone that is around you who has gone through that industry, that type of project, whatever it may be for me right now, the engineers that are around me and the team to help me with the technical components, there's someone that you can learn from.

And I think consulting is a place where you can just really figure out how to learn as fast as possible and then become that expert in your space. - And how long were you a consultant for? - For about four and a half years. - Does that feel like the right amount of time to transition to client side or?

- Yeah, it's a great question. I have a lot of great friends who are career consultants. They have gone from the associate into the partner track, right? They've spent over a decade, two decades in consulting. Four years I think is a good amount of time. It was a good amount of time for me to have seen a lot of different types of projects and industries.

And it was the right amount of time for me to say, I think I know exactly, I've learned exactly what I've wanted to learn. And I now wanna go to business school because I am tired of being the expert in some things and actually wanna learn and absorb other parts of businesses that I may not have seen in brand and strategy consulting.

So I would say four years is a good amount of time, especially if you're coming out of undergrad for the first time. And then that number can vary depending on what your objective is, what you're trying to get to and learn from it. - I would totally agree with that.

It kind of mirrors my own experience. I didn't dive into consulting world, but I worked at like a digital agency, which operated very similarly, right? We're all billable. And I agree, you're exposed, in my world, it was like digital marketing. And so you're exposed to everyone doing the work from development to design or whatnot.

And to your point, seeing all the different industries, 'cause they are so different, right? How you treat a B2B client versus B2C, the approach is very, very different 'cause their audience is so varied. And you're right, it's a perfect ground for just to learn and expose everything, whether it's directly or indirectly.

So I agree with you. For anyone who's starting their career, I would highly recommend engaging a agency or consulting to get your feet wet so you can discover what you want. So, all right, so you got that four and a half years into consulting, you decided you needed to do business school.

What were you hoping to get out of that? And did you walk out with this, like, did you achieve what you set out to do or did it kind of evolved as you went through school? - Yeah, absolutely. A little bit of both, right? And I think business school is this first pivot point for a lot of people.

Early career, even mid career, do I make the investment and spend all of this money to go to business school? And for me, that decision was even greater because I did my undergrad in business. So the question was, is this going to be repetitive and duplicative to what I've already picked up?

Or is it going to be a really great stepping stone to advance my career? And the answer has turned out to be the latter. It's really good. So I went into business school initially with the thought of, hey, I want to transition away from being the consultant where my deliverables were mostly PowerPoints strategy and being removed from the actual execution and operation of the work, to learning how to take those ideas and bringing it to life, right?

I have always been more of a creative hands-on person and delivering strategy is fun, but I wanted to be more involved in how it comes to life. So I went to business school hoping to make that transition. I actually wrote my business school essay around working in ed tech.

So education tech, right? That was initially what I wanted to go into. LinkedIn Learning, Tim, as you kind of alluded to, was the realization of that in a slightly different space, more of the enterprise benefits space. But it was really, I went into business school wanting to learn about what are the other parts of business that would be incredibly important to actually get my hands on those operational pieces.

So I was in marketing and brand. Can I learn the operations pieces, the finance pieces, and other areas of business that would make me full and well-rounded enough? And then try to see if I can get into the industry. And tech was, of course, and still is a very hot industry.

LinkedIn, LinkedIn Learning became the culmination of not only the skill sets, the industry, but also the subject matter that I wanted to get into. So I kind of checked all the boxes there. - Yeah, I'm wondering, you know, when you're in business school and you're exploring all these various functions within an organization and by industry, for me that usually screams like a executive type aspiration where like you need to have enough experience in all these areas to be a C-level executive, right?

'Cause you need to have experience. Is that kind of your end goal coming out of that? Or was it a little more near term where, you know, it allowed you to kind of distinguish, you know, marketing out of all these things is the track you want to start. Like, how do you make the decision between like applying what you just said to product side right out of the gate versus marketing or even anything else?

- Yeah, the great thing about business school is that people come from all different walks of life, all different industries and backgrounds. The reason why people go to business school after a few years of working is because you want to collect that type of actual work, experience and knowledge, so that you can feed off of your classmates, teach them.

And the great thing is you can go in with one thing that you think you're going to come out with. You can think that you want to be the marketing executive because that was your former job, but from the exposure, the classmates, the classes, the types of projects you do, that may start shifting and forming your experience into what you actually want to do.

So to answer your question, I went in with a little bit more of the near term, the kind of three to five years. I want to come out working in this space a little bit closer to product, with of course the long-term aspiration of getting to that executive level, but leaving the door open as to exactly what type of role that is and how I get there.

We talked about consulting in a sec, right? Or a little bit earlier. A lot of business school MBAs come out as consultants because we are still exploring exactly what that shape looks like. And not only is consulting good for early career, a lot of people pick it up because we joke, you probably don't know exactly what you want to do even after business school.

And it's another way to help understand yourself and what you're passionate about. - Is there advice you would give to someone who's currently going through business school right now? And there's like one thing they should do or focus on to make sure they arrive at an end state where they can actually do something about it?

Like what piece of advice would you give them? - Yeah, I would say business school is one of the only times in your life where you can take protected risks. So try the thing that you didn't think you would be interested in, or that you didn't think would match whatever it is that you're thinking, your personality, the thing that you want to do, because you are in this two year timeframe where it doesn't actually affect your performance reviews.

The trials and tribulations you go through with your classmates are relationship building and bonding events. I would say take those experiential type classes where you get to go out into the field, into the industry. Try something like venture capital. We had a VC class where I'm a marketer, taking a VC class.

Didn't know what I was doing, but because you were in this protected environment of business school, you were there to learn, you were there to observe, and hopefully that can help shape this two year journey of what you want to exit with. - All right, so you decide. Product marketing is for you.

- I'm the marketing. - For you. Prior to going to LinkedIn, what was your impression of what that job was about? - Yeah. - And then what was it really about when you started at LinkedIn? Was it, did it meet all your expectations? Was it a little different than expected?

Walk us through that a little bit. - Yeah, so product marketing was not a job or a term that was on my radar when I was going to business school. Actually working in consulting and specifically brand strategy consulting, the tech industry, of course I'm a consumer of tech, but thinking about what it means to work at one of these companies was also not really on my radar.

A lot of these come through explorations, case studies, competitions we do in business school. So your question of what is product marketing, was it exactly what I was thinking? I think the answer is actually, yes, it is much closer to what I had been doing than what peers or the industry or even people interviewing me would have suggested, right?

I think the thing you'll see by transitioning different career role themes is that there is a lot more overlap. So product marketing as how I think about it, especially in enterprise B2B as LinkedIn is, is this intersection between the sales and the go-to-market side and then the R&D and the product side.

The product marketer sits in between that Venn diagram and tries to take the information, the needs, the pain points from our actual customers, our sales team, feeds it into product, what we call inbound product marketing. How can we give them the right information to help sequence and stack the roadmap correctly so that the products that come out are actually meeting those customer needs and that folks actually wanna buy it.

So that's the outbound side, doing the messaging, positioning, go-to-market for those products. You asked about LinkedIn and LinkedIn, absolutely. It was a great place to see that come to life, right? LinkedIn has a very, very strong sales side, has a very strong R&D side. And to be able to sit in the middle was a really good opportunity to not only learn from both of those sides, but to figure out what's the best way to put those two together.

Traditionally, product or R&D and sales don't talk with each other as much. And at LinkedIn, what we try to do and what we try to carve out in this, you mentioned we were kind of a startup environment in LinkedIn. How can we make product marketing, how can we be marketing that center that can bridge the information that flows between development and go-to-market?

- What would you say is your high point at an experience like LinkedIn versus a low point, right? Or was it pretty, relatively steady for you in that experience? - Yeah, Tim, you must remember when we were at LinkedIn, we were, as you mentioned actually in the beginning, trying to transition the acquired company, Linda, into the brand new LinkedIn Learning.

That came with a lot of excitement, which was how can we take all of the good that was Linda and make it even better with a new platform? But at the same time, how do we make sure that customers who are so used to and loved linda.com don't hate the new thing because no one likes change?

So in answering your question, I think the most challenging part, let me start with that, is maintaining that customer love from one thing to the next. Change is always hard. And if there are any LinkedIn folks watching this recording, we did that migration project. And that migration project was incredibly difficult because it is more about risk reduction at first before you can go make people love this brand new thing.

Change is hard. Whenever someone changes anything in your favorite product, whether it's the color of a button to how the entire thing runs, I'm sure most people have this visceral, like, "I hate this. "Why did you change the thing I love?" Feeling first. And then as you start using it, you start seeing why the people who made those decisions love it.

So making sure the customers actually would continue to be customers was probably one of the most challenging things. And then the parts that I love the most was perhaps interacting with all the different types of people with the sales team and seeing what they're talking about and forming relationships with them to make the product better and forming a relationship with the product team.

And then, of course, getting to talk to customers ourselves directly and getting their opinions and inputs. I think that aggregation is what makes you feel a lot closer to the work you're doing. And honestly, the thing I was looking for coming out of consulting. - Yeah, you know, I remember that migration project.

That was tough, man. (laughing) - Two plus years. - Yeah, that was rough. And I've always appreciated your approach specifically 'cause I know how stressful it is. And you managed to still put on a really friendly demeanor. Like, you really powered through it. And I think the team benefited from that.

And naturally, when I discovered that you were thinking about leaving, like, it hit me hard, man. But I'm more interested. It's like, as you're going through that, what were you learning about yourself? Whether it's about your own capability or desired rooms to grow that made you even think about exploring something else?

'Cause LinkedIn as a company is known for having great culture, right? And if you have the desire to grow, like, you can make a lot of it. And so I would have thought that you'd be the typical person who would go up really high within LinkedIn. So all that came as a shock to me.

So like, what did you learn about yourself and what kind of led you to start thinking about maybe pursuing a different option? - Yeah, absolutely. LinkedIn is fantastic. It's a fantastic company. The people are great. I remember one of our values is relationships matter, right? And the fact that we are talking here seven years later means that relationships really do matter.

We built them and we've kept them. Some of my closest friends are from LinkedIn and we still keep in touch today. So the thinking that I had was, what did I learn at LinkedIn? What was I good at and wanted to double down on? And what did I not see in my role that I wanted to explore elsewhere?

I think the thing that I've started seeing and observing about product marketing as a function is that each company defines product marketing, the role, the responsibility, and how you're measured for success very differently. I mentioned a little bit outbound product marketing. So the more go-to-market side where you're doing the messaging, the positioning, and then the inbound product marketing, which is more about feature development, working with the R&D side.

I have always gravitated a little bit more to the inbound side. Now, I picked product marketing as a career because I was very good at the outbound side. It was a lot of what I did in my brand consulting role, figuring out how to take something, put the right narrative and story around it, and take it to market for customers that resonate with them, right?

And I really wanted to learn more about the inbound side, which is creating, building, ideating about what the different ways of product in the future can come to life. And at LinkedIn, I got to see both sides of it, but I think the thing that I was missing was working a little bit more closely with the product management side.

I wanted to work with them to figure out what features should be coming out, working with design to figure out how the thing should look like. And that was part of my desire to look elsewhere is because I had this vision of what product marketing could be, how to become a successful product marketer.

And when I made the transition out, it's because I got a call to say, "Hey, can you come to this company "to help us define what product marketing could be "and could look like?" And I saw that as an opportunity not to go, not only to go to a new company, work on something very, very exciting.

The company was Slack. But also be able to help define at an earlier stage what product marketing as a function could be. - Yeah, you're calling out something which is really important, which I'm really glad you went through that thought process 'cause a lot of times when you hear people making pivots, they're disgruntled or something.

And so when the opportunity comes to them, they'll grab the opportunity 'cause it's opportunity to parachute out and land somewhere else. And oftentimes it works out, sometimes it doesn't. I can definitely tell you the grass is never greener. It's always gonna be shades of brown, but the patches of green are just in different places.

And for me, I don't know actually if I've ever told you this, Michael, like LinkedIn for me, my role was also really healthy. It was really good. And when I was thinking about where I wanna advance in my career, I wanted to be very intentional about my decisions because leaving a safe space like LinkedIn, it's a tough decision, right?

'Cause there's a lot of stability there at the time. Today, the job market is different. That statement is totally quickly outdated. Like what is stability anymore? But like you, I kind of went through my checklist of what I wanted to do in my career. And while you were, your equivalent is like kind of getting closer to product and kind of getting and influencing that, the roadmap.

For me, my version was, you know, 'cause I'm older than you, although maybe, hopefully I look young. - Can't see, can't see. - Can't see. - I just can't do any of this. - This beard added like five years to my age. I think at that point, for me, I was like, you know what?

I want to not only get back to leading teams, but LinkedIn is known for having such a great culture. And I felt like I was a culture contributor, but I wasn't a culture driver. And so for me, when I was looking at opportunities to leave, that was my very specific lens.

Like I only would wanna go somewhere where I believe that the culture wasn't a place that was open to change, but maybe needed the right catalyst. And so for me, that was how I kind of looked at the next opportunity. And then that became my first director role. But I think I quickly learned that your position in the company doesn't necessarily imply how much influence you have over it with things like culture.

And so that was its whole interesting journey. And I can get to that another time, but again, it was a very intentional decision. I think the takeaway for people here is that, you know, as you're looking at making pivots, have a true, honest conversation with yourself about what you're really looking for.

That allows you to go to interviews with a very specific set of questions that might be eye-opening conversations that the interviewer is not expecting. And that in itself can make you stand out. Cool, so you teased us with Slack. And you kind of talked about the opportunities of presenting yourself there.

Can you tell us a little bit about like, again, expectations meeting reality? Is that what you thought it was? Grass is greener, grass is the same. - Well, so actually, right before I talk about Slack, you said something that really clicked with me, which was going toward an opportunity instead of running away from something that you don't like.

Let's talk about that for a second. And I'll tap into the risk tolerance part because that is a very big barrier even before I decided to go interview somewhere else, right? - Yeah, okay, yeah. - Let's talk about a few things and then let's talk about Slack after. The first one, and I actually would be very curious to how you thought about this as well in your own transitions.

The running toward an opportunity piece is something that I've heard a lot. Don't leave your job because you are fed up with it. You're frustrated because then you've limited your scope and visibility into what the next thing is. You will probably reduce the number of opportunities because you're just trying to get away from something if you're able to, right?

And I say this because not everyone has the ability to not exit or hold on. But if you're able to not run away and see those opportunities that excite you, I think one, it helps you stay longer at the next job. Two, it helps you enjoy it more. But it also helps you succeed in the interview and the actual job more because something drew you in that you want to build more on.

And building something, not just features and products, but building your own skillset, personality, your own journey, and that is just done that much better if you're going toward instead of away. But Tim, how did you think about it and how did you also approach the risk equation? Because LinkedIn is a fantastic company, still is, and it's hard to leave a known for an unknown.

And I'm curious how you decided then, and then let's talk about Slack afterwards. - Yeah, definitely. And actually, there's another experience from earlier in my career where I absolutely ran away from something like you described, and it totally, I flamed out from that decision. For LinkedIn, because I wanted to see if I could shape culture, I had to spend some time thinking about what culture meant to me, right?

'Cause again, when you talk about culture, it seems like a very soft thing. LinkedIn was actually the only place I've ever seen where they operationalized it by metric and measured it by success, and it held people accountable at all levels of organization. So for me, I wanted to see if I could replicate that.

And so when I'm looking at other companies that have a certain executive structure, a lot of it was understanding what's my future VP's point of view on culture and what their tolerance was. I also had an aspect where I wanna learn how to grow my abilities to lead larger teams.

And so I had a little checklist. It went really granular from my abilities to mentor, my good as I thought it was. So there was a hypothesis that I had about myself. My ability to take culture, influence my team and develop people was always a passion of mine. Learning how I can shape the future of technology investment was another kind of interest area of mine.

And so when I was interviewing there, I found out that they're still on WordPress. Oh, there's an opportunity to maybe re-platform. So there's a potential there to do something really, really big. I think a lot of it is just other areas to cut my teeth. At LinkedIn, I had budgets, but I never influenced budget, nor was I held accountable to pipeline.

And that's an area that always kind of freaked me out. And so I wanted, without the safety of business school, I wanted to take the risk and expose myself and see if I can do that. And hopefully it would have worked out better than worse. Thankfully, I wasn't exposed for being a fraud.

Thankfully, I did a good job. I mean, those are the kinds of things where like, those are responsibilities that I never had before that enticed me that would have projected myself. How about for you? - Yeah, it's real, right? I mean, you mentioned being a fraud. Imposter syndrome is a very real thing.

- Absolutely. - The fear of not knowing what that next job may look like, whether it's just a new company or taking a completely different role, that risk is probably the biggest barrier for myself. And I'm sure for a lot of folks that we know to even consider making a change.

There was one, learned a lot of great things in business school. There's one professor that said, if you're going into your next job and you feel like you already know how to do 80% of the job, then it's too junior of a role for you. He said something in the percentage, it can of course vary by person, but he's like, you should only know maybe 40% of how to do the job, because you also want to continue growing and learning from that job.

- Wow, that's deep. - Yeah, and again, one of the, it's easier to say than it is to actually do, but imposter syndrome is real for everyone, for all of us, but the spirit of learning and observing how other people around you do it, you will always be surrounded by people who can teach you something.

And to your point about culture, if you're in a company that has that mentality, then you can become the person that you know you can be, that you wanted to be in joining that company and grow your way into it. So taking a risk is obviously hard, that's why it's a risk.

But if you can imagine and foresee yourself in that role, I think that's what can help generate the confidence for you to even consider taking that leap and then actually getting there. - Yeah, that's, oh man, that statement about if you already know 80% of the job is too junior for you, that is fascinating, 'cause talking about risk, there's a piece of it which is like going, staying within a realm of your comfort zone, right, and still advancing your career.

Now, if you're, let's say you do the 40% role where like you're only 40% knowledgeable, but you know enough to be dangerous to cover the other 60, the challenge there is, as you're moving into a senior leadership team, your dependency on your team is then more important. So is the incumbent team positioned in a way to allow you to succeed?

And in today's economy market, it's hard to find the headcount if there's no budget either, right? So like there's so many things you need to take into consideration, like can I get the most out of my team? Are they high-performing? Are there opportunities for improvement or managing out? But if I were to manage out, would I even get the backfill?

If the answer is no, then you need to rethink the whole strategy, right? It's about development or shifting, helping people shift careers. But yeah, that risk piece there is really high for, you know, as you get up the chain for, you know, responsibility. - Yeah, and I'm gonna go on one more tangent, but I think it's relevant.

So this is from a me looking for a job standpoint, right? I've also built teams and hired them. And I think it's a similar type of philosophy and mentality in hiring teams. Of course, it's easier to hire someone who has the title on their resume, because you know that they've done something similar for that job, right?

Less they have to learn, they're probably at that 80% mark threshold, so they can come into the company, figure it out and just start running in the first few weeks. But what I've actually learned and where I've found some of my most successful hires were people who did not have that same job title, but you recognize transferable skills and talent.

If you see someone who has potential and has built a story, and you see that they are capable and eager to learn, that person can grow into something that could be much greater and do make more impact than that person who's been doing it for a little bit, for their past job already, right?

- Yeah, I totally agree. It's like, do they have that proverbial growth mindset, right? Do they have the curiosity to learn? And then for you, it's up to the manager to kind of uncork that a little bit and let it all out, 'cause they may not have had the opportunity to really fully explore.

I actually really enjoy that part of management. - Yeah. - Yeah. - Yeah, it's much easier to teach a hard skill. Actually, you tell me about your roles as well. I feel like it's easier to teach someone how to create a great slide deck or some technical skill than it is to teach someone how to be curious or how to develop good relationships with your sales partner or your design partner.

If you see someone with the soft skill ability who has the potential to learn and build, I think as a manager, as a leader, you can mold and shape that person or that team into a direction that helps them and also helps the company. - Yeah, no, in every individual that I've ever mentored, there is a process that I go through, and it's the first one.

If you're watching this, you've been through this with me, you're probably chuckling right now, 'cause I don't even know what to call this thing. I need to brand it. Basically, it's like understanding what, as a human, what gives you joy, understanding what are your values that you can't negotiate on, and then what the next two to three years looks like.

And the reason why that applies to your conversation and uncovering growth mindset or potential to learn is every individual is different. So as a manager, you need to understand exactly how your team is wired and what makes them happy. 'Cause some people, just getting acknowledgment is joy. Some people don't want an acknowledgment.

And for them, it's something else. And some people, it's more around being around people, whereas other people are around joy from getting a task completed. So understanding how they're wired, then tying into what their core values are. So for me, I'm a very people-oriented, so respect and accountability is really important for me.

When you tie respect and accountability with things that give me joy, and you package into what I wanna do in three to five years, there's a very specific track there I can go on that's tied into hard skills and soft skills. So I typically do that. I think once you start assuming everyone's kinda like you and you get stuck in mentoring as if you're mentoring yourself, then you kind of limit the capability to help people grow at all.

- Yeah, absolutely. And these folks bring in so much, not so much, but like really good ideas that you may have not even thought about. If you as a manager can be learning, I think that's one of the best things because you're expanding your knowledge base. You're expanding your own potential if you have people that you've hired for your team.

- Yeah, absolutely. I am constantly reminding my team to challenge me. And sometimes I'll throw something out there that I'm hoping someone challenges and no one challenges me, I'll call everyone out on it. I'm like, what I just said made no sense. Like, why is everyone nodding their head?

- You're playing games in your head. - I know, it's like four teachers, yeah. But I think that goes to the culture, right? A culture where it's a safe space for people to truly be themselves, to feel empowered, to challenge the status quo. Like, that's what my management style is all about, right?

- Yeah, absolutely. - Cool, so you're at Slack. And so, what did you discover about yourself there? And 'cause I'm assuming from there, was it from there where you eventually went to product side? - No, so I was still in product marketing at Slack. - Okay. - Different level and also just a different scope, right?

So a lot more on the, well, I'll talk about it. I ended up a lot more on the inbound side, but it wasn't an easy journey to get there. - Okay. - So going to Slack, well, the first thing you notice is LinkedIn is what, it was a 15,000 person company or so, even though we were a small group, it's still a massive company.

Slack was about 800 or so people when I joined. And you can feel the energy, momentum, velocity, everything being a little different there. People are a lot scrappier, as we like to say, in the tech world, right? You have to figure out what, how to do the next thing, because that path has not yet been set for you.

I mentioned earlier, one of the reasons I was brought into Slack is to help define what product marketing as a function could be for the company. And I would say it wasn't easy to do that. The team at Slack, so I would say product marketing, the core responsibility is to take a product to market.

You have to market that product. And the inbound side, and this is through a lot of reflection and just talking through and working through a lot of different places, the inbound side is a nice to have. And I believe it's really important because it makes me better at the outbound side.

If I know why we chose to build a product in the way that we did so, the trade-offs that we considered, then I can actually craft the narrative for the market that talks about why the value of the final product is what it is and how it comes together.

But that said, when push comes to shove, you have to be a good outbound go-to-market product marketer to succeed in that job. Side of that is, well, if you're a PM watching this, you're saying, hey, the inbound side is actually my job. I'm the one who should really be deciding how the roadmap is built and sequenced because, well, at the end of the day, it is the product manager's core responsibility to set the product strategy, the roadmap, and figure out how a product comes to life.

And the reason I give that context is as a PMM at Slack, trying to say, hey, every PMM should have that inbound role was first met with a lot of resistance. It felt like stepping on toes, right? Why are you taking this part of my job as opposed to you can help me do my job better and add different perspectives that I may not have considered yet?

Very fair perspective to hold, right? If you are used to doing it one way and someone comes in and says, no, you got to do your job differently, your first reaction is going to be, no, I don't. I already know what I'm doing. And what value are you going to add?

And I think it's that last question, what value are you going to add that really helped me break through and form that partnership with the product team, just as we did at LinkedIn Form8 with the sales team that helped me shape this kind of, we'll call it a full stack or both inbound and outbound product marketer.

- Can you give me an example of how you kind of broke through that wall and came to that ultimate realization and alignment with your teams? - Yeah, yeah. It took some time. And I think it took relationship building. It took bringing the right pieces of information such as data that you were able to collect, research that we as marketers tend to do, user experience research or some quantitative research.

And it also took a success story to actually make it come to life. It's hard, it's hard to do. So a few of those things, I think getting to know some of those product managers or the R&D side, what they're looking for, where their gaps, not in terms of what they can do, but in terms of what time they have, how can you help add some value, filling in more sales stories or VOCs, voice of customers, for example, is one.

Building those relationships, giving them that data, how many customers of what size of what revenue are saying they need X versus Y and helping them think through that trade-off decision was really helpful and important. And lastly, not just talking, showing how that partnership can actually make a product better and how the design as well as the go-to-market is better with that kind of embedded PMM was what helped me create that kind of relationship within Slack.

- Yeah, I totally agree. I mean, you're talking about the art of building credibility, right? And I think you're totally right. If you don't spend time in their shoe understanding what they're responsible for and what they're going to be measured by, then naturally they're gonna take a defensive stance, right?

'Cause you're gonna make a decision that could impact their livelihood, their responsibility or scope. But like, yeah, I like how you're data-driven, results-driven approach to kind of help them understand, first of all, that you understand what they're trying to solve for and how you actually add value to that is important.

And I think the better storyteller you are in helping them understand the ultimate vision and how this thing works together is really, really important. More often than not, people are not good storytellers and they come in with a very focused lens and it's not clear why it matters or why you should care, then becomes very confrontational.

And those are the mistakes I made very early on in my career coming in with a lot of passion and a lot of fire and ambition and just bull in a China shop. - Yeah. - You don't want to be that guy. - It's, you said it perfectly, it's the empathy.

It's being in their shoes. I mean, hey, we're talking about what it looks like to transition careers. It's a very similar mentality as building a product for the market, right? You have to know the customer, you have to know what their pains are and you have to know how to make it better and be able to craft that story, that narrative and help them see why your vision, idea, product, anything can make their lives better.

You can't assume that a customer is going to buy your feature of your product. You can't assume that a partner at work will want to work with you. But if you know what it is that they're trying to get to, then I think at the very least carves the path that you can take to get to that destination.

- So with this journey, starting from where we started this conversation, you're moving closer and closer and closer to the customer. You're moving closer and closer and closer to product and roadmap. So was this the juncture where you're like, hey, marketing versus product, was that the decision point or did it happen after Slack?

- Yeah, so that question started maybe even when I applied to business school and went through it. And LinkedIn and Slack were both experiences in building up the marketing background that I had because I was interested in it and because I wasn't yet ready or it felt like too big of a risk to jump from what I've known and have been very good at for the past 10 or so years at this point into what I thought was a completely new field.

To answer your question, I took one more detour before I went into product management. And it was another one of those go-toward experiences where now that I have done product marketing, now that I had done brand and consulting, what could it look like to actually run marketing for a whole company?

And I decided to take that leap, a very, very scary leap, because marketing, as you know, Tim, you do a part of marketing that I would never be able to do, right? And as we know, marketing is so broad from demand generation to web strategy to product marketing, brand strategy, content generation, social, so much happens in marketing.

And to lead a marketing team was super exciting, to be able to build out what you think all of those functions should be able to do and then create the holistic impact of how that story gets told to market. So I took a little detour there trying to learn about everything marketing before I then committed to, I actually am interested in the product and the development side, and made a switch, actually, from being pretty high up in marketing to learning how to become a product manager.

- So that's interesting. So you're kind of starting at the high where you've hit that final, that pinnacle point. How long into that experience did you have the realization? It's like, you know what? This isn't for me. 'Cause it's a very big decision and impacts a lot of people.

So what did that look like for you? - Yeah, it's wild emotions fluctuating up and down, right? So it wasn't easy to come to that realization because of, well, a few things, right? Risk, not only what does it look like to switch jobs, but when you're at a certain point in your career, the opportunity cost of switching is much higher.

And I think that just becomes another dimension in transitioning. I think, so a few things, right? One is the passion. What gives me, what gives you energy to want to do that next thing? What makes you wanna leave something on one day and then pick it right back up the next day?

And for me, so much of my impetus for going to business school, for going into product marketing and tech was to be close to the product. I love designing, working with the R&D side to see and figure out how should your product roadmap and strategy feel. And when you're taking on everything in marketing, well, the product marketing side is such a small sliver.

And depending on the stage of company you're at, your attention may have to be completely, somewhere completely different. Brand building was one of them. Loved it, different than product. And I also needed to generate pipeline, which was quite frankly a skillset that I hadn't built in to product marketing.

And it was that frantic learning and trying to figure out how do you build demand generation program with the marketing ops and systems and technology to feed into it. It was a very exciting and also a very humbling experience for me to know what I could do and was good at, to learn what I didn't know how to do and figure out how to plug those gaps, either through hiring or learning it myself.

And then ultimately that realization of, hey, maybe product was the direction I wanted to go in versus higher up in marketing. - So when you made the leap to product, my fear is always like, okay, getting close to the product means your technical competency has to, the bar just got raised, right?

And so how much would that, coming into, I'm assuming Asana's the next one, how much of that was on-the-job learning versus education or preparedness prior to Asana that from a technology point of view, like how'd you make that leap? Was it a painful transition? What did that look like for you?

- Yeah. So lots of learning, absolutely. By no means that I come in and was able to become a fantastic product manager, but I was able to come in hitting the ground running for a few different reasons. One of which was I know the subject matter very well. Having spent time building our learning platform at LinkedIn, having worked on Slack as a collaboration software, Asana and the workflow space that I work in is very familiar with me.

One of the biggest things that carry in, and we kind of touched upon this theme is knowing your customer. And I had carried in a lot of research and knowledge about what this customer profile looks like, what the market of buying profile looks like that I can bring in actually as a different and new perspective as a PM, as a product manager and carve out a different shape of what it looks like.

That's one part of it. The second, as you mentioned that the technical chops of it, I would say you probably know more than you think you know, right? If you are working at that company, if you are a consumer of technology, you generally know how things may interact with each other and the technical pieces of being a PM is just, well, it's several layers deeper, but knowing how various aspects of the product relate, depend, work with each other, and then figuring out, hey, technically, is this feasible?

Does it cost more to do X versus Y? And just really understanding how the puzzle as a whole fits together is my kind of translation of the technical components, but having good tech partners. So I have a fantastic tech lead on the team and we are always bouncing ideas off of each other and learning from each other.

I always run an idea. Hey, if I have this brand new idea for a feature, let's talk about what it might cost us because we have either never built this thing in the past or we can leverage some existing frameworks and foundations that we can tap into. So I am always learning from my peers to give me enough of that technical knowledge, making me, as we like to say, dangerous enough in these tech conversations to be good at my job.

- So now that you're in seat doing PM, what's maybe the top two things that are always on your mind as a practicing product manager? - Oh yeah, two things on my mind. So I think the first thing is the customer. It's absolutely the customer, but when you say customer, we know that not every customer looks the same.

And actually, quite frankly, the segmentations and the different profiles and the different usage profiles, the buying profiles for enterprise tech are all so different. How do you figure out how to sequence and see and prioritize what is the most important thing to do? One example is voice of customer, right?

These are current customers who have used your product and said, these are the great parts of it. And then these are the pieces that I need you to fix. And that ladder is probably a lot much larger list than the floor. So you got to figure out, okay, when do I build the incremental product improvements versus taking a whole net new idea that you think may help differentiate your product or your company and try to take that kind of a bet and build something big.

So the first thing on my mind is always what does the market, what's the market telling me? What are my customers telling me about what they want next? And then the second part is making decisions at both the micro level of not just, here's the holistic product you're building, but how does every single user story feature stack up and in what order you want to build it in to continuously add value and making sure that the rest of your company, be it the product leadership level or the sales side, get on board and understand, and actually lastly, be able to recite that back to the market.

You need that kind of consistency and support throughout your organization for your holistic product strategy to actually take flight. - Well, I mean, none of that surprises me in terms of like your thoroughness 'cause I've been a long time Asana user. And so knowing like there's someone like you at the helm, you know, like in your respective area leading it, like it all makes sense to me 'cause I know you and I had such a great product experience.

Michael, I just want to thank you for your time here. I would love to have you come back sometime if you want to talk about something else, but this was really enjoyable. - Absolutely, so good to see you, Tim. Great to hear that you're an Asana user and it was really good to connect again in this.

- Cool, thanks, Michael. - Yeah, thanks, Tim. (upbeat music) you