Full Transcript: Michael Sippey, CPO of Medium on the Product Love Podcast

Published Apr 22, 2020

Michael Sippey, the CPO of Medium and one of the web’s first bloggers, chatted with us about user experiences and developing impactful hypotheses. Read the full transcript of what he had to say.

Eric Boduch: Awesome. Well, we’ll go over some product today. I am here with Michael Sippey, who’s the CPO of Medium. Why don’t we kick this off, Michael, by having you give us a little overview of your background.

Michael Sippey: Yeah, sure. Yeah, as you said, I’m the CPO at Medium. I have a great team of product managers as well as the design team and our user happiness team and our product science team is in my org. So I work with really great people every day. And I’m hiring so if you’re out there and you’re interested, hit me up. I’ve had an interesting career since the early nineties. As my friend Gibson Biddle has said, we’re both old as dirt. But I started in the early nineties at Advent Software, which is an enterprise software company essentially doing product marketing type stuff. And then moved into product management, and joked that one of my first jobs was actually literally shipping software. We put floppy discs and CD ROMs into boxes and shipped them to users, shipped them to customers.

Michael Sippey: Kind of evolved from that. I went to business school, worked in web 1.0 at an internet consulting company, doing a lot of really interesting fun projects there. Helped to start an email services firm actually that I was focused on large consumer internet brands. And then went to Six Apart which is a blogging platform provider. We made type pad and movable type and a product called Vox before Vox became a website. And then a platform called Live Journal and I ran product there for about six or seven years. We sold that company to Video Egg. Became an online media company called Say Media. I stayed there for a little while. Then it went to Twitter and I ran product at Twitter for a couple of years.

Michael Sippey: And then I had a startup. I left Twitter, I took some time off, then I started a company called Talk Show. We were building a social media app and then a podcast discovery service. And then while we are in Beta with the second one, the company was acquired by Medium. And then I joined here. So had a roundabout way of going from enterprise and some consulting in there to consumer internet and loving what I’m doing now.

Eric Boduch: Awesome. I mean that’s quite a breadth of experiences. Pretty cool story. You mentioned Gib, I just interviewed I think a month or two ago. It was great.

Michael Sippey: Love Gib.

Eric Boduch: The podcast will be coming out before this one I’m sure, but not quite yet, as it turns out. I’ve read too that you were one of the first bloggers, right? Is that true? Did I hear that right?

Michael Sippey: That is true. And it’s something that I apologize for all the time. But yeah, so I started writing online in 1995. really fell in love with the web in the very early days. I started actually in ’93, ’94 with an email newsletter that I was sending to basically anybody that I knew that had an email address back then. And so when the web came along, I fell in love with the web and decided I needed to learn some HTML. And if you need to learn HTML, you need to have something that goes on the web. So I started publishing my writing at a site called Stating The Obvious. It’s actually all still there at And then basically was one of the first people to actually start doing daily link blogging. And yeah, so basically back then there were only a couple dozen of us that were doing blogging at the time. We were linking to each other and learning from each other and talking to each other all the time. And it was a pretty small community in that we always …

Michael Sippey: It’s funny, because back then one of the early pioneers of blogging was Dave Weiner, who’s still at it. And Dave would basically say, “Yeah, eventually there’ll be a billion bloggers on the planet.” And it turns out that there actually are probably more than going a billion bloggers on the planet. And most of them use Facebook, essentially doing a lot of the same things that we were doing back then, which is sharing links and sharing things that happened in our lives. And now it’s just all happening on this massive platform.

Eric Boduch: Yeah, I mean it’s amazing how things have changed and evolved over the past decade. Talk to me a little bit more about that. How have you seen social media and social media platforms transform in the past decade? And how do you think it’s changed the landscape of tech?

Michael Sippey: I think that, well obviously things have exploded. Back when I started working on these products, and I started advising, it was a blog or actually I first met Ev Williams back in ’99, 2000, we were all very mission-driven. And I remember at the time bloggers’ tagline was push-button publishing for the people. And the idea was to help enable anyone to be able to put their words and ideas and thoughts online. And I think that mission, a lot of us were very, very mission-driven.

Michael Sippey: And when I joined Six Apart in 2004 the mix of the combination of products of mobile type and type pad, and then we acquired Live Journal, was essentially let’s go bring these tools to presumer users, teenagers with Live Journal, and then publishing companies with mobile type. And I think that we were firm believers in the power of the technology. And I think that that served us well and being an evangelist industry and wanting to go have more people. Essentially the thinking at the time was more people doing this as better. And so as many folks as you can get on these platforms and sharing in important. And that ethos basically became what was driving Twitter and then it was Facebook and Instagram and Flicker before it. And essentially more people sharing is better.

Michael Sippey: And I think that made mistakes along the way. And I mean the good news is that now these tools are widely available. The bad news is that now these tools are widely available and used in ways that I think we didn’t anticipate at the time. And so you have all sorts of bad things that have happened around abuse and around both abuse and both on a personal level and a systemic level that now we’re cleaning up from. And so it’s one of those things where I feel that the products are unbelievably powerful and can be used and both good and bad ways. And I think that we didn’t spend enough time thinking about ways that those tools could be used for bad, actually. And so that’s something that I think about a lot.

Eric Boduch: Yeah. I think one of the great things about tech, and having been in tech, you mentioned people being old as dirt. I’m one of those people. I remember gold discs and all of that back in the day. But we all often look at problems and opportunities with wide-eyed enthusiasm. And we’re thinking about all the great things that can be done and not necessarily focused on how the power of the platforms we’re creating can be abused. So I can see it’s good in that looking at it with that wide-eyed enthusiasm, we open up a lot of new opportunities and create things without creating unnecessary restraints. But then you do also create things of huge reach and then you have to go back and reassess the bad impacts on society. Right?

Michael Sippey: Yeah. Yeah. It’s funny, I was chatting with some friends the other night at dinner, and it was a structured conversation dinner party. And one of the questions was, if you could go back 10 years, what advice would you give yourself or would you give companies like Twitter or Facebook or YouTube around how you could avoid what happened. And I think that there’s a lot of inherent, as you say, wide-eyed enthusiasm and creativity about how the platforms can be used and the use cases for them.

Michael Sippey: There’s a discipline that other industries have used for a long time, which is scenario planning and essentially employing really creative both writers, researchers, writers, and creative thinkers to not only outline the positive scenarios, which is something that I think that a bunch of us were really good at, but also the negative scenarios.

Michael Sippey: And so there’s a long history of Shell, for example, using scenario planning to help understand the future of the oil business. And I think that if I were to go back 10 years, one of the pieces of advice I give myself is spent a lot more time doing scenario planning around how things could go horribly wrong.

Michael Sippey: There’s actually a really good article that was published on Medium the last week or so about companies now employing sci-fi writers to write potential future scenarios. And I think that one of the things that you want to make sure you’re doing in that type of planning is to think about the potential worst-case scenario of how things could go horribly wrong so that you can think about now backup then, what would you do to the product and the system that you’re building a little bit differently.

Eric Boduch: Hey there’s a little tapping I think on your side. I don’t know.

Michael Sippey: Sorry about that.

Eric Boduch: Yeah, no problem.

Michael Sippey: I have a bad habit. I play with my AirPods case.

Eric Boduch: I do the same thing. Usually, that’s in my pocket.

Michael Sippey: That’s my AirPods case. I’m going to put it down.

Eric Boduch: Okay. I do the same thing. And it’s funny because some people’s phones will be like, “AirPods. Do you want to connect?” And I’m like, “Whoops.”

Michael Sippey: Right, right. Sorry about that.

Eric Boduch: Yeah. It’s no problem. We should be able to edit it all out. I just want to make it easier. And I wasn’t sure what it was at first, but that makes a lot of sense. And it’s funny that I do the same thing.

Michael Sippey: It’s funny that you can actually pick it up. It’s super small really.

Eric Boduch: So talk to me a little bit about one thing you just mentioned, and I was actually gonna ask you that same question. What would you do if you could go back? What would you do differently? And it’s great that you asked yourself it. Makes it even easier, but what advice would you give people today? Are people doing enough right now? Nevermind going back to like …

Michael Sippey: You know, it’s funny, I don’t know. I’m sure that there is a lot of introspection and deeper thought happening at the big platforms right now, Twitter, Facebook, YouTube, etc. One of the things that I have on the practical advice for product managers is we write product briefs all the time, and we use an adapted form of the opportunity assessment that Marty Cagan writes about in his book Inspired. And one of the questions that we’ve added to our template, and we do this, I’m not going to say that we do this reliably all the time or that we do it well all the time because we’re still getting better at this. But I asked the PM’s to essentially add a question, which is what could go wrong?

Michael Sippey: And essentially it’s a variant of the question, how might this fail? And I think that essentially having … as product people, as people that build, you’re naturally optimistic people. You have an idea of something that you want to see in the world, and you collaborate with engineers and designers and researchers and sometimes salespeople and marketers to put that product in the world because you want to see change and you want things to be better. And I think it’s the responsibility of the team to also be thinking about how this might fail, and not just fail from a metrics perspective or from a business perspective, but how might this failure users. And I think building that muscle just is a requirement now, especially in digital product management. Really thinking about what negative impact could the feature that you’re building or the product that you’re building have on users as well as your business.

Eric Boduch: I think that’s great. And you were VP of product at Twitter like you mentioned. That had to be lots of interesting experiences like this. You want to tell us a little bit about that? I feel like, as you mentioned before we kicked this off, I feel like there needs to be a part two now. There’s so much we can dig into here. I just had one with Bob Moesta that was just published, and I think there’s going to be a part two on skills people need to innovate. I feel like I might be hitting you up in a few months for part two. But having said that what’s the brief of what it was like being VP of product at Twitter, because it created its own medium, right?

Michael Sippey: Yeah. I was there at a really interesting time. There was a joke in the industry that essentially the role is similar to the role in Harry Potter, the professor of the dark arts or the drummer in Spinal Tap, which is a recurring cast of characters, a rotating cast of characters, not so much recurring. And so I was there from the beginning of 2012 to beginning of 2014, which was a very exciting time for Twitter. And I feel very lucky to have worked on a product that I love and with a set of really fantastic engineers, product managers, and designers and executives. I was there at a really great time and a really, really exciting time in the company’s history.

Michael Sippey: While I was there on the core product, we brought photos to the product. We brought much more in-depth conversations to the product. We really shifted everything about our development process to be mobile-first. We grew the product design team pretty dramatically. The company was growing really dramatically at the time. And then, in addition, we did some things that were really fun and strategic for the company. We bought Vine. We bought a company called Crashlytics, which turned into a fabric. It’s now owned by Google. There are a lot of really fun, exciting things that we were doing. And I got to work with great people on it.

Michael Sippey: We were scaling the service like crazy. We were getting past the fail whale days, which was great. From my perspective, I didn’t really have to deal very much with the fail whale. But we were essentially on the path to going public. And so we were focused on user growth and user acquisition and activation and retention. And so those were exciting times. It was good.

Eric Boduch: Awesome.

Michael Sippey: There are mistakes along the way. You can read all about them. And it was also a time of hard decisions. I was part of the team and wrote the blog post that I’m curtailed the use of the Twitter API and changed the nature of the Twitter API. It was also mistakes we made

Michael Sippey: About, and then quickly reverted about how the block behavior worked on Twitter. So there are lots of learnings along the way.

Eric Boduch: Yeah, so sticking to one thing and I don’t, like you mentioned, we could probably spend a few hours just talking about your experiences at Twitter. But could you take us through the thought process around the pros and cons of the API decision? I think that was very interesting at the time.

Michael Sippey: Yeah, I have to go back and really start to inhabit myself from 2012. But I’ll tell you at the time, the company, before I had even had joined had already signaled to the developer market that building, that Twitter was essentially had acquired Tweety and was gonna build its own clients. And that the goal of Twitter building its own clients and own apps, especially in the burgeoning App Store, was to essentially control the user experience and have better control over the user experience.

Michael Sippey: And so that message had been telegraphed prior to my joining the company. The decision that we were making when I joined was, at the time, the API, there were two key things about the API that you need to understand. One is that developers could use the API without actually logging in, so there were whole swaths of the API that you could access without actually using OI, or to access the API. So that was, we had a whole bunch of people that were using the API, and we didn’t even know who they were, so it was difficult to actually either monitor or police that activity in folks using lots and lots of …

Eric Boduch: Yeah, right?

Michael Sippey: Yeah, exactly, right approved use. So the first, one of the big things we did was actually require if you were going to use the API, that you had to authenticate and let us know who you were. The second thing we did is we added rate limits on particular endpoints in the API in order to start to shape its use. And the guidelines that we put in place and the rate limits we put in place were essentially reflections of strategy that we had already started to signal to the market, which was really don’t build clients.

Michael Sippey: And Twitter’s had a kind of long history of having, had a long history at the time of having people building third party applications. The really interesting thing is that the Twitter API really mimicked the web experience, and so you could really get true, any true user experience or new innovation in how people use Twitter from third-party clients. And so we were seeing a lot of the same, basically, the same UX people were building the same UXes the core Twitter experience. And so we essentially as Twitter, wanted the ability to integrate on that user experience with, and so we needed that flexibility of how to do that without being beholden to kind of third party applications.

Michael Sippey: And so we telegraphed really strongly, I did in a very long, very, very long blog post, probably way too long, blog post that kind of explained what our thinking was and then just essentially did that through mechanisms with rate limiting. The other thing that we did at the same time was, at roughly the same time, is launch a whole bunch of new tools for third parties to have much more to publish much more expressively inside Twitter. So we, at the same time, launched Twitter cards, which allow publishers and net developers to include content that is embedded inside tweets. You know, video and link previews and things like that, in order to make their experience publishing on Twitter better.

Michael Sippey: I think we could’ve done a much better job of communicating that. I think there’s a whole bunch of things we could’ve learned. Looking in hindsight, but I think that looking back, I still think it was the right decision and I think that it basically was like paved the way for Twitter to essentially grow its business and to make decisions about to have a lot more degrees of freedom around what it could do actually in the applications themselves.

Eric Boduch: So that brings up some interesting things to talk about, right? I think we can say that it seems, and seems is probably much too light of a word, but it seems that tech is becoming a space that is more and more politicized. Given your experience, both at Twitter and now at Medium, which are both social platforms where users have and are given the freedom to express their thoughts, what’s your perspective on how tech as a medium is becoming politicized?

Michael Sippey: So I think it comes back to like with the thing we were talking about before, which is it’s we’ve created these platforms for people to share. And where you see more kind of radical politicization and content to the extremes is on the platforms where you have both kind of large reach and essentially the thing I kind of talk about is speed, which is you can have fast a post, fast to get shared and redistributed with kind of fast reaction from users. And so it basically, especially on Facebook and Twitter, you have those platforms are optimized for that, right, which is really easy to share. It’s designed to essentially elicit very fast emotional reactions from the readers.

Michael Sippey: And so when that happens, you have essentially it’s no surprise that you have folks that essentially do polarization, and there are all sorts of conversational dynamics and features that inside each of those platforms that kind of either amplify or not the spread of either political means and ideas that are designed to piss people off. So, and I think that both of them, and probably Twitter, Facebook, and YouTube, to some extent, have grappled over the past two, three, four years with the policies that they implement on how they are managing the conversational health of their platforms.

Michael Sippey: At Medium, we have a slightly different approach, and I think that the long-form nature of Medium generally makes it slower, and we have really invested over the past year in a very different approach for content recommendations that doesn’t give folks that are essentially writing core quality content reach. So, we’ve invested a lot in both content quality scoring and machine learning, as well as content curation cues, so that stories that we recommend to users in their home page and their personal lives, to email digests and recirculation at the bottom of an article and our topic pages are all stories that have been vetted by a team of curators.

Michael Sippey: And that actually gives essentially removes the incentives, a lot of the incentives for folks to kind of write really the type of political content that you see on other platforms. I’m not saying that it doesn’t exist, saying that it doesn’t get amplified the way that it would on a Twitter or a Facebook. The other piece is we’ve taken an approach with our rules, we made a change earlier this year where we changed our rules so that, even late 2017. Anyway, we made a change to our rules so that we take into account behavior off of Medium so that if we see you essentially toeing the line on Medium but you’re doing things that would break our rules off of Medium, then we’ll make decisions that we can remove you from the platform.

Michael Sippey: We think that we’re doing things both from a recommendations perspective and a rules perspective to make sure that we’re spreading ideas that matter and helping people understand the world more deeply. And, I think the nature of the product is very different from what’s happening in kind of the faster mediums of Facebook and Twitter.

Eric Boduch: Cool, so as much as I’d like to talk about Twitter, Medium, Six Apart, and Live Journal for a few more hours, let’s save that for another day, and let’s talk a little about skillsets for product managers. You’ve talked in the past, and you’ve written about the concept of setting up the hypothesis. Why do you find that that’s really important for PMs and how do you talk to them about setting up and testing effective hypotheses?

Michael Sippey: All right, here we go, I love this stuff. This is really fun, okay. So, basically, I have this point of view that essentially all product management, and even like all companies are just tests of hypotheses, right? Which is based, if you go back to the scientific method stuff that you learned in like eighth grade, which is you observe somethings about the world, right? You look at the world and you see things, and then you have a theory that says, “If I do X, it will lead to change Y.” Right?

Michael Sippey: So, that’s your core hypothesis. If we do X, it will lead to change Y. This will happen. And then what you do as a scientist is you go test that hypothesis, right? So, if you’re a consumer Internet company, you have different tools available to you than if you’re an enterprise software company, you have different tools available to you. But generally, you’re going and testing a hypothesis, and so I talk a lot with PMs and work with my PMs on like let’s make sure that you have both strong hypotheses that are kind of logically consistent, that you have data that backs them up, and that you’re bold in your hypothesis testing, right?

Michael Sippey: And let me talk about both of those two things. So one is like what is a strong hypothesis? Well you actually, A, you actually have one. You have a theory of change. If I do X, it will lead to Y. And what I really try to work with PMs that I work with on is like, let’s make sure that we understand that theory of change, which is do we know? Let’s say we’re gonna change a feature on a particular surface, and we want a user to do something different. So do we know how many people visit that surface? Do we know if we change this particular action, do we have any data that says like this is an actual problem for them, that if we change it, it’ll make them better. Like if they actually change their behavior, what downstream impact will it have?

Michael Sippey: So if I do X, will it lead to Y. Show me the math, even if it’s like back of the envelope, lightweight spreadsheet math that shows if they do X, it will lead to Y, and that Y will lead to some business outcome that’s good for us. So, is the change in Y big enough for it actually matter? And that gets to the second piece, which is like old hypotheses, which is it’s very easy to think like, all right, I am blessed. We have a great testing infrastructure at Medium. We can run A/B tests on a bunch of different surfaces. We have all sorts of tools that will test for a statistical significance about whether a change has happened, et cetera.

Michael Sippey: But unless you can actually make a case that if we do X and it leads to Y, and it will lead to business outcome Z, you need to have a hypothesis that’s bold enough that the users are gonna notice. It will actually drive enough change so that it’s worth our development time to actually go do it. So, we just spent a lot of time thinking about what are the problems we need to go solve? And what’s our hypothesis for how we can go solve that problem? And because generally, like, we’re all just product scientists, essentially doing tests about we observe something in the world, we have an idea, we go test whether that idea turns into a hypothesis and we go test whether that hypothesis is true.

Eric Boduch: That’s fun.

Michael Sippey: Fun.

Eric Boduch: Yeah, it is fun.

Michael Sippey: Yeah.

Eric Boduch: And I think the more PMs and product managers think about it that way, the better. Can you take us through an actual example, like talk to me about the hypothesis, how you tested it, maybe even talk about it one that, I imagine, there are common mistakes people make when they set up tests? Maybe touch on that and talk to me about the outcome? Is that reasonable?

Michael Sippey: Yeah, let me think about one that … Yeah, I’ll give you an example.

Michael Sippey: So Medium is a subscription business. We run, what in the media business is called a metered paywall. So we allow users to view a set number of stories every month for free before they hit the paywall and we ask them to subscribe. And it’s this paywall mechanic that actually drives our business, right? We had a hypothesis that, right now that meter is set at three stories per month. We observed a whole bunch of data that essentially where people, how many people read one metered story, two metered stories, three metered stories every month, we know how many people actually try to read four metered stories, five metered stories, six metered stories while they’re actually metered out.

Michael Sippey: And we have a bunch of support requests and anecdotal data about the meter actually, people being worried about reading all of their, reading too many stories and getting metered out. And they just worry about their reading behavior. So based on the things that we observe, we had a hypothesis that said, “Okay, if we increase the meter limit, we will have a potential X percent decrease in conversion to subscriber, but it will be offset by an increase in engagement from users who decide to read more.” And if you have that increase in engaged users that decide to read more, over time we would see, like, if we increase that limit to five, we would see over time that those users would stick around longer and be more engaged and eventually convert to members.

Michael Sippey: So it’s a pretty big, that’s our hypothesis. We decided to be bold. Well, we tested both a five-story limit and a seven-story limit because we really wanted to understand the shape of that supply-demand curve, if you will. And what, kind of, essentially like price elasticity as for reading metered stories. So we ran that experiment and we ran it for an entire month of the cycle because our meter resets on the first of every month. And we ran that test for the entire month, and essentially learned that we should stick with three.

Michael Sippey: So this is where it’s like, I love being a product scientist because sometimes you actually learn things that like, “You know what? We should stick with what we have, and we should try a different approach.” And what we learned is that we wouldn’t have as much of an increase in engagement from five and seven to offset the change in conversion. And so instead, and basically we did some user research and looking at the user experience and basically learn that we needed a change. That experience in different parts of the funnel, in order to get the benefits of increased user engagement. And so at the end of the month, we knew that’s kind of two, we had a hypothesis that it wouldn’t work kind of two weeks in.

Michael Sippey: Somebody really did it, but we ran it for the full month in order to get the full cycle’s worth of data. And now its basically let us like, okay, we learned that, it led us to a new hypothesis that we’ll test in Q1 around in a different … in a personalized meter behavior. We learned a ton about tradeoffs of user engagement versus inversion rates using those different emitters.

Eric Boduch: Yeah, that’s very interesting, and I think it’s interesting you had a little comment about people would ration themselves like, I don’t want to read the first week, because then there’ll be something I want to read, and I’m not going to be able to it, because it’s worthy. I think there was a Seinfeld about being worthy, I won’t exactly mention, but that’s something whether you’re worthy or not back in the day. It was pretty funny. So the same thing with reading medials. Is this article worthy or not of one of my readings?

Michael Sippey: Right.

Eric Boduch: That’s pretty cool. Talk to me about common mistakes you see. What do you see people make as a common mistake when they set up a test?

Michael Sippey: One of the common mistakes you see is that basically … sometimes it’s about setting up a test, sometimes it’s just bad having that product hypothesis, which is that people fall in love with the solution, and then they’ll back into a problem in order to support the solution. I’ll give you an example of a thing we’re building right now. One of the things that we … we have a whole set of topic organization inside Medium, so every story that we commission or that we syndicate, or that we carry into recommendations, gets added into a primary topic and a bunch of secondary topics, and a medium that helps with story discovery and framing for a reader and understanding this is a story about technology, or this is a story about self, or this is a story about relationships. And it dates and further discovery … those topics, and on desktop web, you have many, many, many, many, many more pixels to essentially place those topics, and express those topics, and help people discover those topics, etc. On mobile, things are more constrained.

Michael Sippey: There’s been a thing floating around, like we should change our default search tab experience to enable more topic browsing because people can’t find topics, and they can’t what it is, and so the team fell in love with its own idea, essentially came down this path of let’s go build some wireframes around this topic browsing experience. Really, that became … the problem is we don’t have the topic browse experience. That’s not really the problem. The problem is that readers aren’t discovering topics well enough. We go through a product review process here, and really one of the things that we did is in product review, is back up and say, is this really the best way to solve the problem, and so we spend a bunch of time thinking about other ways that you could solve this problem.

Michael Sippey: And we have some things in development essentially that are simpler and easier and faster that will help us and help readers discover topics faster on services where they’re already exploring on the home screen, story pages, etc that don’t require an entirely new service to … so there’s often this … you get an idea in your head for a product feature, and I’ve 100% been guilty of this in past, and will 100% be guilty of this in the future, of let’s go build this thing, and you fall in love with the idea, and you fall in love with a feature, and you forget that, hey, there’s probably an easier way to go solve the problem that you initially started out with.

Eric Boduch: Yeah, I think it’s interesting. I was interviewing Ryan Singer a little while back, and we talked about the what’s and the when’s, like what were you trying to accomplish, when were you trying to accomplish this? What were you doing getting better understanding what the customer was trying to do, as opposed to pushing a feature you think is a solution to their problems, may not be in any case, or maybe total … 

Michael Sippey: And again, it gets to the thing we were talking about before, we’re all just generally optimists. We love to build things, it’s fun, building new things is fun. You have to be the hard nose, do we really need to build this? Is there a simpler way or easier way to go solve this problem?

Eric Boduch: Yeah, yeah, and is it really solving the customer’s problem? 

Michael Sippey: Exactly. Exactly.

Eric Boduch: Quick time shot. Do we have five minutes, 10 minutes, 15 minutes? I’m just trying to gauge how many of these things …

Michael Sippey: Can we go 10 minutes more?

Eric Boduch: Yeah, that’s perfect. And I probably will hit you up again to see if we can do part two at some point in the future. I’ll owe you for this one. This has been amazingly good content. You’ve had a wealth of experience because it’s really fun. I would love to talk at some point about how you came at this from writing. That’s very interesting. But maybe I’ll save that one for next time. Talk to me about the future. What upcoming trends do you see in product management?

Michael Sippey: Oh man. Let’s see. I think there’s something really interesting happening, so on the product side, and related to product management just in the consumer textbase. There’s something really interesting happening in the broad category of connected devices. We were talking earlier about AirPods. AirPods are pretty much my favorite new product in the past year or so, couple of years, however long it’s been. Because they’re really, really simple and really, really sophisticated. They’re like an iceberg product, where the new Xes, there’s this case that charges. You stick the things in your ears, they turn on, and you can enjoy the world. That’s fine. Enjoy music, it can join to your phone calls, you can do whatever. But the product decisions that go into each one of those things, how’s the case, where’s the battery, how long do the things last? All the double-tap things through Siri, all of that, they’re essentially like these little tiny computers in your ears. All of the decisions that go into those things that make the user experience, the things that the consumer actually touches and feels, incredibly simple. There are tons of tons of sophisticated product decisions that go into that product.

Michael Sippey: The voice things, like all the stuff that’s happening, with Google Home and Alexa, are super challenging from a product perspective. Because discovery on those devices is really, really difficult. How do you find new skills? How do you get access to the consumer? It’s like the channels if you thought distributing things through Facebook is hard, it’s like 100 times harder to get anything popular on Google Home or on Alexa. That’s really interesting to me. Additionally, related to that is essentially all of this news acts that’s going into glanceable UI, and basically what it’s going to push us to do is really focus on the end user and the consumer in their context, whether it’s in their home, or whether it’s in their car, or whether they’re fumbling around and sticking little white things in their ears to really understand their motivation, what they’re trying to get out of that product, how they use it, what other things they’re distracted by, and really the successful products from the successful peons that figure this out, will find the best way to put the user at the center of that experience, and not their product or their content at the center of that experience.

Michael Sippey: That’s just super, super hard. That is a really, really hard product and design challenge. All of those products are going to create all sorts of really interesting product and design challenges for people, and so if I were starting out in my career, I’d be thinking a lot about how do I get deeper customer and consumer insight, and how do I think about essentially competing experiences fading into the background, and how do you become a great product manager for those types of experiences.

Eric Boduch: I think that’s a great thing to think about in upcoming trends. I see that a lot. You see the world changing, I have three or four Alexas in my home. I think that’s going to become more and more prominent. The experiences people have, and how designers and product managers think about them, it’s a different way of thinking about things. I think you get ahead of.

Michael Sippey: You need to think about also, back to our earlier thing of what could go wrong, doing some scenario planning around what’s the absolute worst thing that could happen with an Alexa device. Your private conversations or things that happen in your bedroom are recorded and shared on the internet. That would be pretty bad. So you have to think about how do you actually build trust with the consumer of putting that type of device into your home. There’s fun stuff in there.

Eric Boduch: Yeah, there’s lots of bad scenarios. Someone hacks into them and has access, and can speak through them, right? There are all kinds of potentially horrible scenarios there that you want to avoid. You mentioned the AirPods, I’m a huge fan of them, I wish they stayed in my ear a little better, but I feel like I have a … I have an abnormal ear opening. I have no idea. They stay in, but not when I work out. Favorite product. Is that it, or is there another one that’s your favorite product?

Michael Sippey: That’s probably my favorite product over the past couple of years. Because it’s something that … you didn’t actually think that you had this problem that it would solve, and it really solved this problem well. Yeah, that’s probably my favorite. It’s probably my favorite.

Eric Boduch: Yeah, I know. I bought it for a very different reason than I think I love it today. I bought it because I’m a destroyer of headphone cords. Within two months, I can pretty much destroy a headphone cord. I don’t know how I do it so effectively. They continue to break, the sound gets bad, it doesn’t matter if they’re cheap or expensive, I try to take care of the expensive ones at least. I still break them, so it’s like AirPods, there’s no cord to break, so they’ll last, and they have, but now just everything else about them I like even more. It’s an amazing product.

Michael Sippey: It’s such a boring product for me to take, but it’s so good.

Eric Boduch: It is. It’s changed a lot of things for me too. They’ll hold hands free, you don’t touch any cords, spend a lot more time having conversations while doing other things, whether it’s driving, or walking the dog, or all that. It’s the whole process simple, music simple, there are some little things I would love, like my car … it slips it onto the Bluetooth. I was like, if I have my AirPods in my ear, I really want the phone calls coming to my ear. It doesn’t seem to make up its mind, but I love, love, love that product. The other thing, you’re an avid book reader, so what’s a book you always recommend?

Michael Sippey: Well, do you want business or fiction?

Eric Boduch: Let’s have one of both. Let’s have a fiction one, and a business one.

Michael Sippey: All right. Let me think. For product managers, I love Martha Higgins’s book because it’s full of practical advice. So inspired early products that customers love. It’s just full of really practical advice and templates and things when you go do. There’s another great book that I recommend to peons and designers as well by Erica Hall, called Just Enough Research, which is practical advice on how to actually talk to users and do, as she says, just enough research. So it’s not like the in-depth guide that’s like the, here’s the on the ground, practical advice on how to make sure that you’re bringing users and customers into the conversation of when you’re building products without going way too deep. It’s a very, very good book. So I recommend those two. On the fiction side, I read a lot of fiction. I can tell you I think the best book I read this year was called Asymmetry, by Lisa Halliday. It’s a really outstanding novel that has two very different, seemingly disconnected stories in part one and part two, that have the same theme and really make you think about asymmetry in political relationships and personal relationships and economic relationships. It’s an incredible novel. Merely fantastic.

Eric Boduch: Awesome. I read a lot of fiction myself, that’s one I haven’t read. I’ll have to check it out. One final question for you, at least for today. Three words to describe yourself.

Michael Sippey: God, oh man. This is on your list and I didn’t even … I should have prepped. Let’s see. Three words to describe myself. Enthusiastic and … I would say enthusiastic, reflective, and silly. How about that?

Eric Boduch: I like it.

Michael Sippey: Every once in a while.

Eric Boduch: That’s great. Thank you for your time today, this has been awesome.