 I'm joined by Chris Lee. Chris is a product manager at Dropbox and has led a product team in his previous jobs and also worked at Apple as a project manager. Welcome, Chris. Hi. Thanks a lot for having me. Yeah, so tell us a little more about Dropbox. It's a huge product and application, so I'm sure most of the audience knows. But for anyone that might not know, can you tell us a little bit more about Dropbox, the product that you guys offer and the specific product that you work on? Sure. So Dropbox is essentially a cloud storage system, but the way we like to talk about is what we're building is the home for all of your most important stuff. So it's a way for you to safely and securely store your most important files, your most important photos, all in the cloud, in the Dropbox cloud, and have that accessible with you wherever you go on whatever platform you're on. Whether it's when you're in front of your desktop computer, on your phone, on your iPad, on your tablet, through the web, wherever you are, it's always there with you. And you can always know that it's safe and secure. The product that I work on specifically is I work on all of Dropbox's photos products. And there's a lot of photos integration throughout all of Dropbox. For example, on the website, we have a tab for photos. In the mobile apps, there's also a photos tab as well, where you can browse all the photos that you have in Dropbox. What we launched earlier this year, though, was Carousel, which is kind of our next evolution of the photos tab. And this is a way for you to view on your mobile device all of the photos that you have in Dropbox, as well as all the photos that you have locally on your device. And it's a great way to keep all that, you know, backed up, safe and secure in Dropbox. We automatically organize all of your photos for you. So, you know, when you look through it, you can see the breakdown by places, by events. It's a much richer gallery experience. You know, we try to make it a lot more engaging for you to relive all of these memories. We do some cool things around with face detection to highlight and blow up the photos that have people in them. These are the people that you really care about the most, like your friends and family. And then we also do some cool things around sharing. So, obviously, you can share with, you know, Facebook, Twitter, email, SMS, what have you. But you can also share using Carousel, which is extra special, because since all these photos are up in Dropbox, we can share 100 photos as quickly as we can share 10 photos. So, if you were to try to share like 100 photos using email or SMS, you're going to have to wait for each one to upload one after another after another. But with Carousel, they just upload, they're just shared instantly because they're already backed up to Dropbox. Yeah, that sounds like, you know, a huge project and almost can be a product of its own, you know, image sharing. And it's kind of a problem that a lot of startups and companies have to try to solve. And I'm a big fan of the way that you guys have done it. But what about, let's actually want to take a step back to like what you were doing before product management and what drove you towards a career in product management? Sure. So I was a engineer by training at UC San Diego. And, you know, throughout my senior year there, I got to work on a project where I sort of took on that project product management role. And I realized that, hey, I like this kind of work a lot more than, you know, the hardcore engineering. I really liked working across multiple teams. I really liked, you know, trying to spend a lot more time thinking about what's the vision for this product, where are we going and how are we going to get there versus the actual implementation of each individual piece of it. So that's kind of what led me down this path. And I was very fortunate to get a project management role at Apple right after graduating. And there I worked as a project manager for Mac OS X, spent four years shipping three different releases. And that was, you know, kind of my dream job. My team was a six person team that managed the entire release process for this 800 person project. It was at the time the largest project at Apple. So it was really a great opportunity to work extremely cross functionally with every, every engineering team across the entire operating system, lots of other external teams as well, like marketing support, operations, developer relations, what have you. So that was a really cool experience. After that, though, I, you know, I was spent a few years there and sort of got the hang of what I was doing and always wanted to always had an interest in business, but never really got a chance to pursue that in undergrad. So I went to business school at Wharton while I was there. I co founded a startup with another classmate of mine and worked on that for about a year and a half in a role that was both a combination of product and engineering. This is a meteor that's that's meteor. Yeah. So after after working on that for about a year and a half, I joined Dropbox. Actually, there's a brief stint in there where I was working with a startup called like bright doing product work. And then after like bright, that's when I ended up at Dropbox. In what, you know, since that since you started your own company and you mentioned that you're really attracted to the world of product manager, because you could kind of design and craft division and direction of products in the company. Do you what product management skills do you think that are important when you are starting your own company? What kind of skills did you really find that was very similar to what you were doing in a product management role? Tons and tons of those skills are very relevant. I think one of the most important skills is just being able to hit the ground running. Product management is a role that differs across companies and even across teams within companies. So you're never going to have a perfect job description of exactly what you should and shouldn't be doing every single day. So I think one of the most important skills is being adaptable and being able to figure out like where can I have the most impact right now for this product and for this team. So I think a lot of that is driven by being very empathetic, being a very strong listener and being very observant of where you can be most effective, where does this where does this team most need you? Because I think the best mark of success for a product manager is a product and team that's operating most effectively and successfully. It's really the team and the product that you're supporting. What does the day to day look like at Dropbox? Once you get into the office at the end of the day, what do you spend your time doing? Well, kind of like what I was just saying, there really is no day to day and that's a big part of why I think the role is so exciting. Some days are spent more on like the vision and planning process for what are we trying to build here? Who are we building it for? What is our roadmap for the coming months? Sometimes it's focusing purely on execution in terms of what is this feature that we're building? Why are we building it? How does it work? What are the interactions? Have we user tested this? How are we going to iterate on it? How are we going to A-B test this? How are we going to launch this? How are we going to tell the story of this feature to our users so that it's something that they really value and understand? Other days it's working externally to the team with groups like product marketing, with legal, with PR on a bunch of various issues. There's a lot of time spent looking internally trying to figure out how can we improve the processes for this team? How can we make this team move faster? It's every day is a new adventure. I agree and I think that with that the fact that you are involved in so many things and things are just changing all the time it's going to get frustrating at times. What would you say is the most frustrating part about being a product manager? The most frustrating part about being a product manager I'd say it's the best and the worst part as well. As the product manager you're kind of the DRI at the end of the day, the directly responsible individual. There's a lot on your shoulders which is really awesome because you can have a ton of impact but at the same time there's a lot of pressure because you're juggling 100 different things all at the same time serving as sort of a hub for communication across your team and sometimes it just feels like you might be getting stretched a little thin. Right yeah because again there's so many things to work on and one thing that I found is that if you can kind of create the tools and processes in place it really helps you stay organized and you'll do your job better. What tools do you use on a day-to-day basis to help you do your job? We're big users of Google Docs and that's a great way to collaborate on feature specs that you're working on sort of plan out schedules. We have used Asana in the past for task management although that's something we're using a little less of these days. HipChat is something that we're using right now for team communication that's been particularly useful for very active projects where there's just lots of discussion back and forth and sometimes email is just a little too cluttered and a little too slow. GChat for communication as well sometimes with more casual stuff and yeah I mean we try to keep our tools pretty basic and not have too much overhead so we're not we're not really adding new tools every single week. Yeah sometimes you're having too many tools can kind of get you to waste your time you know on on the tools rather than moving things forward. What about like things like wire framing creating mock-ups is that something that you are responsible for or do you work with a designer to create those? We have incredible product designers who sort of live and breathe by that. I'll jump in there occasionally when it's you know really helpful for me to do that but most of the time it's most effective for the designers to work on that. On the product design side, Sketch is a really really awesome tool you know we used to be very big users of the Adobe suite but we found that Sketch just allows us to be a little faster it's a little easier to use. So we use that for static mock-ups for interactive mock-ups we're also using a tool called Framer.js which is a JavaScript framework that allows you to build interactive prototypes that's been really really helpful for you know validating how how features really feel when you play with it versus trying to build it in code first which is sounds easy but is a lot of time consuming it is really time consuming. Yeah it's definitely costly to make those changes with code rather than you know something like like what you guys are doing and do you bring these kind of interactive mock-ups to to users and do any kind of usability testing or I guess how do you interact with with users on a day-to-day basis? So when we are building features where we do want a lot more user feedback we we do have a user research team that will help bring actual users birth potential users and actual users into the office so that we can test paper prototypes with them or interactive prototypes or actual code prototypes just sort of depends on what stage of the project we're on. Okay gotcha and one of the I think you touched on this earlier about empathy and communication are really key skills to have as a product manager you know for someone that's let's say just starting out as a product manager do you have like a number one tip that you you would like to give them if they are you know working with developers or working with project managers or you know anybody that they would interact with on a day-to-day basis? Sure I think empathy is one thing that is you know as I mentioned before I think it's really really crucial especially as you're starting out and as you're starting to get a feel for the team what does the team value what are your users value and just sort of adapt your adapt your approach accordingly you know I it's really easy to sort of get cut off from your customers from your users and as the product manager you your job is to be the voice of the user so you know if if you're not talking to your users on a very very regular basis then who is so I think though those are probably two of the most important things to keep in mind as a as a product manager. Gotcha yeah in some product manager roles especially I think at smaller companies and maybe not so applicable at a large company like Dropbox is that's the product manager sometimes responsible for the marketing as well or at least is a big inputs for the marketing team are you do you take on that role too the product marketing aspect? So we have a product marketing manager that I work very very closely with he's amazing at helping to brainstorm ideas on new ways to reach our users on the stories that we can tell and we very much collaborate on telling those stories and making sure that they're accurate making sure that they're compelling and just getting them launched right alongside the product itself so that you know when we invest all this work to put something out there we can make sure that that actually reaches our users and resonates with users too. Can you give an example of what you what you mean by like a story is that like an actual story of a user using the application or what do you mean by that? So when you create a feature you can there's there's a lot of different ways to talk about that feature you can talk about what it is what are the exact features how does it work which will help people understand how to actually use it but I think a more compelling way to talk about that feature is why someone will want to use it how it's going to improve their life how it's going to solve a problem or make their life so much better and I think that's that's the story that I think is really the most compelling because that's what's going to resonate with people when you can when you can tell people why not just what. Right yeah tell them about the benefits not just come out and say that the features because most people just want to know like how would this improve my life or how does this affect my life if you are interviewing someone to join your product management team what is something that they could either you know bring to the interview or have on their resume that would blow you away that would make them stand out from the pack? I think the most effective product managers the ones that have startup experience specifically who started a company before because that's really the closest you're essentially a product manager when you're starting a brand new company and you're doing it without any support with just usually without a lot of data and you're just grinding it out doing whatever it takes to ship that product and make it successful so that's the piece that stands out the most I think that's the one that most closely mirrors what role what the role is like as a product manager many of the pms that we have here Dropbox do come from that startup background if you haven't found in a company yourself and at least having worked at a very early stage company is also very helpful because it gives you at a small company you're basically doing everything and anything and you sort of get a certain degree of that same experience of just what it takes to launch a new product what it's like to iterate what it's like to not be successful in the day one but to iterate to the point where you do become successful yeah yeah I think when you say some when you say that it sounds like it could do a good sign to some some listeners are thinking like wow man I got to start my own company you know to get to get a job do you mean like a startup that is actually like you know fully funded and actually has you know a lot of users or maybe even revenue and on that end of the spectrum or do you even mean do you even include things like folks that have started projects on the side you know while they're working another job is that also kind of attractive to a company that is hiring looking for a product manager someone that's just like you know has side projects it's it's a spectrum I think on one end of the spectrum people that have started a company like actually from the ground up and made that successful that's that's going to be the most attractive thing on a resume if you have if you haven't done that if you've just worked at quote unquote corporate job and but have some side projects on the side yeah that's that's definitely going to look better than someone who doesn't because it shows that you are it shows that you're proactive and you're going to go out there and make something happen gotcha thanks so much Chris I think that that's you know a ton of actionable tips running by out there that's just starting their first product management gig or is looking to jump into to that kind of career path so folks want to kind of follow up with you or learn more about what you're doing what where can they reach you what kind of where can the where can they find you online they can find me on twitter lee underscore lee le underscore chris