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24 / How to Overcome Barriers to Innovation

Hosted by Sean Flaherty & Paul Gebel




Jake Knapp

Designer, Author, Person

Jake Knapp is the author of Make Time and the New York Times best-seller, Sprint.

Jake spent 10 years at Google and Google Ventures, where he created the Design Sprint. He has since coached teams like Slack, Uber, 23andMe, LEGO, and The New York Times on the method.

Previously, Jake helped build products like Gmail, Google Hangouts, and Microsoft Encarta. He is currently among the world’s tallest designers.


Product people chase innovation. Sometimes we grow frustrated by how much time it takes “to get there” and how many barriers to innovation stand in our way. We’ve been led to believe that sprinting as fast as we can toward innovation will help us catch that lightning in a bottle, all the while failing to consider that innovation is a long game. Jake Knapp, author of Sprint, provides a refreshing perspective on today’s episode of the Product Momentum Podcast.

Imagine the irony, says Jake, who joins Sean and Paul for a conversation about innovation. The goal of the design sprint is not to help us move faster – at least not in the short term. It’s to get us to slow down. To pause, even for just a few days, by breaking down barriers to innovation and making time for one thing that really matters.

Here are three key takeaways from our conversation with Jake Knapp:

  • Be aware of the defaults in life that rob your attention, energy, and time.
  • Ask yourself: “what keeps me up at night?” And then listen closely for the answer.
  • Innovation is authentic and different and unique. It is the product of clarity in your mind and harmony in your heart.

Paul [00:00:00] Hey everybody, today we are excited to be joined by Jake Knapp. Jake spent 10 years at Google and Google Ventures where he created the design sprint process. He’s written two books, Sprint and Make Time. He’s coached teams in places like Slack, Lego, IDEO, and NASA on design strategy and time management. He is a now professor at M.I.T. and Harvard, and he is very tall.

Paul [00:00:23] Jake, your relationship with us goes back a couple months at a conference and it’s been great to make a connection with you through that, and you know, this conversation this morning. I’ve been excited all week looking forward to this. Going back into the archives a bit, I watched your Breakfast Club interview with Jason Fried and your pre-roll jitters for that are exactly how I feel right now. One of my nerd heroes on the line.

Sean [00:00:51] Nerd hero, that’s a new one for you Paul.

Paul [00:00:54] So it’s great to have you with this, Jake. Thanks for joining us.

Jake [00:00:57] My absolute pleasure. Absolute pleasure. And well, I’m honored to be mentioned in the same breath with Jason Fried. So, yeah, thanks for having me.

Paul [00:01:08] So just to jump right in, you’ve got a lot going on. You’ve been busy. You recently released a book, Make Time. Well I guess it’s not so recent anymore, but you did release a companion app.

Jake [00:01:18] It depends on how you count a decade, but it was within the last two years.

Paul [00:01:23] Recent enough.

Jake [00:01:26] Recent enough.

Paul [00:01:26] You’ve got an app. Is it considered out of beta now or are you still in beta?

Jake [00:01:30] It’s in beta. The consultors are doing an awesome job with it, for sure. But, you know, you just think, “oh, we’ll just make an app, like that’ll be that’ll be no big deal.” And it’s a big deal. There’s a lot to do to make an app work. It’s funny when you’re working on bugs again, it’s been a long time since I’ve built software.

Paul [00:01:47] You should know better, right?

Jake [00:01:49] I should know better.

Paul [00:01:50] So tell us a little bit about how that process is going? I mean, you’re kind of eating your own dog food at this point.

Jake [00:01:54] Yeah, well, it has been a sort of a trickle process, the app has been. I worked with my friends at AJ&Smart. You were mentioning Product Breakfast Club, which we now just call Jake and Jonathan. That’s my podcast.

Paul [00:02:08] Which our pre-roll does not hold a candle to.

Jake [00:02:12] This is much more professional. So anyway, AJ&Smart, the agency run by my friend Jonathan, who’s the co-host on the podcast, they did the design work for the app working with me a bit. I mean, I’m a designer, so I definitely chimed in, but they handled all of that. And then these folks at an agency called Sidekick, who are a dev shop, sort of volunteered to do the coding. And the thing is, that process has kind of been a side project for everyone involved, and definitely including me, for a while. And then the Sidekick folks really like stepped it up and were like, “let’s get this thing done,” over the last couple of months. My coauthor John Zeratsky was like, “alright let’s get this thing done,” and he jumped in, because I’m, you know, I get distracted. I’m good at starting things sometimes. And so, yeah, they’ve been going back and forth, back and forth, and we’re putting out a course for Make Time called the Highlight Course. We’re just piloting it and they’re trying to get it ready so that folks who are in the course can use the app. But anyway, to develop software, you know how it goes. Everything seems like, “yeah, that’ll be no big deal.” And I talk about it all the time. I mean, if people have ever heard me talk about building products, in the abstract, I talk about how foolish we all are.

Paul [00:03:25] It’s like three lines of code.

Jake [00:03:27] “Yeah, this will be done next week.” And, you know, then cut to a year later. And I joke about it and then you put me in that situation and I do the exact same thing. So anyway, good, stuff; good people all around putting up with me. It’s good stuff.

Sean [00:03:41] Awesome.

Paul [00:03:42] Did you do a design sprint for the app?

Jake [00:03:44] Yes. Yeah, we did do a design sprint. It was cool. I was the decider.

Paul [00:03:48] That’s got to be a change.

Jake [00:03:49] Yeah. Well, I mean, you know, I always like to act like the decider, but I’m usually just trying to convince someone else. And in this case, I was on the West Coast. The agency’s in Berlin and Sidekick’s in London. But anyway, they would do all of the Sprint stuff overnight and then share the results with me on Real Time Board, which is now called Miro. I mean, companies have changed names since we started. Yeah, it was so fun to see, right, because I was just like drop in to the whiteboard, basically. The AJ&Smart folks are great. They’d have like, “here’s the key questions you need to answer.” But yeah, I got to use the design sprints, although in this case it didn’t speed up our development process. But we did test it, you know, we tested it on target customers and made sure that we were delivering. We think.

Sean [00:04:33] Neat. I think when you spoke in Rochester, you talked about this concept of the defaults, which I thought probably the powerful part of your talk, and challenging the defaults, which is kind of where the design sprint came from, right. Like why do we have to go through this whole long process to find out whether or not this thing’s really gonna work? So Make Time is about challenging a default, right? So let’s talk about that little bit.

Jake [00:04:57] Yeah. So when I talk about defaults, like this, normally we talk about defaults like the settings on our phones and our apps or software, and default settings like that exist in life too, and they definitely exist in the workplace. So this is something that I started to notice a bit at Google when I first created the design sprints. Like the way that we normally go about doing things doesn’t always make sense. And there’s this moment in the beginning of a project when maybe you can take control of a lot of those factors for a short period of time. That’s a design sprint. You try to sort of re-engineer the defaults you want by taking one week of time and creating a checklist for it. And Make Time is more about looking at day-to-day life and figuring out what defaults exist. And there are some that exist for almost everybody.

Jake [00:05:49] A lot of it comes from the products that exist. It’s amazing technology that we have and, you know, having email accessible at all times means “I can be communicated with at all times and there might always be something new there, I’m going to check that all the time.” And with social media, of course, people talk about this all the time, but the news, you know, just like wanting to stay on top of the news, that’s sort of a default setting. “I should be on top of the news; I should be a responsible person,” and there are all kinds of these defaults. The default setting that I’m sitting in for most of the day because I work at a computer, you know, all these things tend to rob us of attention and rob us of energy.

Jake [00:06:28] So Make Time, it’s basically a cookbook of tactics you might try to change those defaults so that you’re optimizing for paying attention to one thing that you care a lot about each day, just making sure there’s one thing going on that you spend some time focusing on giving your full attention, being present for. What we’ve been trying to figure out there is something that’s less prescriptive than a design sprint because I’ll have different defaults than my coauthor, John, and then you all, and we’ll have different things that’ll work for each of us depending on who we are and what we like. And also just people are different. So it’s a bit of a different process. But that’s sort of what we’re doing with the course now is figuring out, how do you really take people from like a book, which definitely works for some people. Some people will take a book and figure out how to apply that into their lives. And how do you help more and more people with habit change? Because habit change is so hard. So we’re trying to do that with a course where it’s live and you have sort of a cohort of people that are going through, and we hope that that’ll help. The app is another method. And I found the app to be actually super powerful, even though it’s super simple, but like just to get a reminder.

Paul [00:07:44] Just that block on your calendar.

Jake [00:07:44] Yeah, totally, it’s huge. So, yeah, we’re trying to change defaults in the workplace, in day-to-day life, and, man, some of these things are hard, but I think it’s worthwhile because it’s our human lives.

Paul [00:08:01] I mean, we spend more time with their coworkers and with our work than we do with our families a lot of time. You know, we treat this work as like separate from real life but it’s where we spend most of our lives, unfortunately, or fortunately. You know, I was rereading the book over the holidays trying to find some inspiration for my New Year’s resolutions. In the past couple months since December and now going on two months, three of them have actually stuck for me. Just a quick plug for a couple tactics.

Jake [00:08:28] Yeah, cool.

Paul [00:08:28] I’ve changed my email footer. I’ve said, “if it’s important, text me.” I’m not drinking coffee after noon. I’ve got a stash of camomile tea in my bag now.

Jake [00:08:37] Oh, nice.

Paul [00:08:38] I’m modulating my caffeine. And honestly, I didn’t realize how much of a news junkie I’d become, like every morning on the way to work, it was podcast after podcast, stress about things I can’t change, and I’ve just started switching it up. I’ve been using an app called Blinkist just to power through a couple books in my backlog that I’ve been putting off. Just those changes, I’ve definitely noticed a change in, I wouldn’t say it’s changed my life, but you know, I guess it could say it’s changed my life a little bit just in terms of the awareness. I think it’s just taking the pause to say, I used to have this default of drinking six cups of coffee a day, and now I’m still drinking something hot. It’s still, you know, solving that…

Jake [00:09:16] Yeah.

Paul [00:09:17] …Job to be done. I need something, a mental pause in my typing to grab a cup that’s next to me. It doesn’t matter what’s in it. Take that how you will.

Paul [00:09:28] I think this is driving at a question. The overall sense is, you know, this book Make Time, the whole concept of Sprint, the tactics that are enclosed in it and sort of prescribed as more of a formula in Sprint, but more of a loose collection of things in Make Time. The thing that I’ve been wanting to ask, and this is probably a poorly formed question, but I’m going to ask it anyway. The tactics and the strategy and the intersection there, would you consider yourself to be someone who’s a strategist who’s good at tactics or a tactician who’s aware of strategy?

Jake [00:10:00] Huh, yeah, probably a tactician who’s aware of strategy. I have these big overarching, overarching is… I don’t really know what that means. I have big goals sometimes, right. Like and if I have something that makes it into my crosshairs as a goal… You know, earlier I was talking about how I can be good at starting things, but not necessarily good at finishing things. And that’s true and also not true. I’ll give myself a bit of credit. When something is in the crosshairs, I’m very persistent, but I try to be selective about what I let get into the crosshairs. And the app is a good example of a thing that was not in the crosshairs. It was something that, you know, it’s a nice-to-have thing for everybody who’s working on it, until John decided, “this actually could be really valuable, I’m going to put it in my crosshairs,” right.

Jake [00:10:51] But for me, there’s like, I’m writing a book, or back when I was at a full-time job building products, or when I was developing the design sprint, when something’s in the crosshairs, like, I will run it down over years. And as many of these things meaning the design sprints, this year, 2020, will be the 10th anniversary of the first design sprint ever. I ran that in 2010 at Google and I’m still fired up about perfecting it. When I’m writing a book. That’s a process usually that spreads over the course of years. Maybe, you know, if you actually slice up how long it takes to write it you could condense it into less than a year, but that those are long-term things. However, the way those things happen are tactics. And so I get very into the day-to-day, how do I make this thing happen today? And I’m probably not a person who’s well suited to like direct a team of people or to run a complex business. I run a business with like one employee that’s me, but like, I’m probably not going to be good at those kinds of other strategic things that involve like a lot of strategy. I’m really like a one-item strategy kind of person.

Jake [00:12:01] But the tactics to get there, to me, that’s where it all happens. Like it’s all like, day-to-day, how do we get past this moment when I’m sitting down at the computer and I want to write but I also really want to check the news because, oh man, I’m right there with you. I get so into the news. Or, I’m sitting down to write, but like, I could probably check my e-mail and get a good sense of productivity. These are things that I haven’t conquered. These are like, I need a tactic. I will need a tactic today. It’s 6 a.m. right now as we’re talking in Seattle and I’ll be writing later today, I hope. But I’m going to need to have an array of tactics at my fingertips to keep me actually writing. Yeah. Here’s a poorly formed answer. Actually, I think that was a good question, but my answer was a bit rambly, I guess, really tactician, probably more than strategist, but I do like to have those headlines that I’m going for.

Sean [00:12:53] So first of all, thank you for joining us in Seattle at 6 a.m.

Jake [00:12:56] Sure, my pleasure.

Sean [00:13:00] Appreciate that.

Jake [00:13:01] I always talk a lot, but, you know, whether it’s coherent or not, that’s probably the main factor.

Sean [00:13:06] Your answer led me to a question that we struggle with every single day. So we build software products, obviously, and one of the biggest challenges every product team has is prioritization. How do you figure out what to do next? And even in the context of running a design sprint, choosing, “hey do we design sprint this thing or do we just go ahead and build this feature and experiment with this feature?” Like at what level do you decide that it’s time to pull in a design sprint? I’m sure you’ve been asked that question a million times, but we still struggle with it. How do you figure out, like, what is the priority? What is the thing that you should be approaching first and is there some structure to how you should approach prioritization? What do you think about that?

Jake [00:13:47] Well, I take a really simplistic approach to prioritization, and I don’t know that this is like wise for other people to emulate in their personal lives or in their, you know, in their projects. But I’ll give you my simplistic approach and then maybe we can talk for a quick minute about a more measured, tactful approach. My simplistic approach is to do everything possible to have one big headline and for that headline to come, if possible, from a gut feeling. I am very respectful of people’s gut feeling of what’s most important to them. It can be hard sometimes to tune in to that. There are a lot of things we might feel like we should do or that we’ve sort of made a story for ourselves about what we have to do and to tune into what your heart thinks is right, what you believe to be the right thing to focus on, can be difficult. I know that for me it took many years of building software before I could tune into, “what do I think we ought to do?” Not just, “Which direction is the team headed and what’s my obvious role in what the team is doing,” but like, “what do I actually, as an individual, if I’ve sort of collected some wisdom over time and I’m opinionated, what do I think we ought to do? What’s the thing I should push for?” I think as an individual, if you can tune into that, it can be very powerful for you in a large organization. Maybe you can propose something new. Maybe you can drive for a different way of doing your work, whatever, but often, I think, those come from the heart. I think that when I’ve talked to startup founders and CEOs time and time again, what I always like to ask people was, what’s keeping you awake at night?

Jake [00:15:47] And you know, I’m a designer. I was a design partner at Google Ventures. So if we were having a conversation, me and a founder, it would be about, how can I help them out with design? How can the design team at Google Ventures be of service to them with product design or whatever, hiring, whatever. And sometimes those questions were tactical but the really interesting thing for me was, well, what’s keeping you up at night? Across everything, forget about design for a second, like how are you doing and what’s stressing you out? And the thing that was most on their mind, that was where, if there was going to be a design sprint, that’s where it was going to be. It would be, maybe we can help with that burning thing. And likewise in life, I think sometimes we have things that we were putting off for someday. This is a big theme in Make Time. Projects, or spending time with people, we think, “someday I’ll have the chance to do that more, I’ll spend more time with my kids, or someday I’ll work on that project, someday I’ll take up that musical instrument again, someday I’ll lead a new initiative at work. I’m going to make the time and carve it out just not right now because things are so busy.” Part of the idea with Make Time is to identify what that is in your heart and then create a lane for it where there might not be one.

Paul [00:17:01] I love that question, what’s keeping you up at night? It’s actually going back to a previous life of mine as a financial advisor. That’s often how I’d kick off a conversation with a prospect or a client. Anybody can build an app, anybody can put a budget together, anybody can do these business processes and if you ask very business-oriented questions, you get very business-oriented answers. But if you ask, “what’s keeping you up at night?” you get a much more human approach to problem solving and prioritization. I think that’s brilliant.

Jake [00:17:31] I think that it is also worth touching on that promised second part of the question, which is the tactical way to approach it, because sometimes it is not clear in your heart or it is not clear what’s the thing that’s keeping you up at night. But you do have competing priorities and you do have to figure out what is the most important. We used to run a process when I was at Google Ventures that we called the Opportunity Sprint. Actually, me and John Zeratsky, again, my coauthor on Make Time and coauthor on Sprint, we’re working on, and this is something that’s sort of like on the back burner, like the app was for a while. So we’re sweating for the eye of Sauron of one of us to turn its attention onto this post. But basically the Opportunity Sprint is a, maybe like a one day process where you are in just the stage before a design sprint. You might have a few different opportunities that you’re aware of and you are going to put a little more detail behind them, lay out a bit of detail about your criteria for making a decision. Which metrics might we care about, which factors might be important to us? Like does feasibility matter to our decision or is it actually the potential audience size, or is it the…? You know, whatever. You go through a process of thinking about the factors that are most important of detailing out the potential opportunities of having people sign up to say, I’ll flesh out that opportunity, I’m going to put some detail behind it, and similarly to how we sketch in a design sprint, you sort of fill out a template, put in a bit more detail, and then we evaluate the detailed, somewhat detailed proposals for these different features as sort of headlines. And then just use it two-by-two matrix, you know, taking the, “what do we think are the top two factors and let’s plot these out on a two-by-two matrix and…” I- two-by-two matrix raising the right thing? Anyway, it doesn’t matter. You know, it’s typically like impact versus feasibility. But sometimes those aren’t the right factors.

Sean [00:19:26] The Eisenhower matrix.

Jake [00:19:27] Right, right. And you know, that is super clarifying. Those are pretty obvious kind of consultant things to do. But man, that can be very clarifying. And a similar exercise for an individual, I think, is just to write a list, and we talk about this in Make Time, write a list of every project that you have in mind and include projects at work and include the responsibilities that you have in your life, and include things like checking email, you know, staying up to date on email, or staying up to date on social media. Or, you know, staying up to date on the news, anything that’s like a job that you might have. You might list out five things or 10 or 20. I always list out, when I do this, be a dad. It’s a project, you know, and things that you hope to get to but you can’t get to right now. List those out. Write a long list in no particular order and then go back across that list and try to stack rank by importance. Just write, you know, which one is number one for you. And if you can just make that decision, that decision is really hard. But if you can write a column with your desired prioritization of those things, and if you can write a second column with your actual prioritization, how do you actually spend your time? That’s super interesting to see where the gaps are.

Sean [00:20:37] That’s what the defaults are.

Jake [00:20:38] That’s where the defaults are, totally. Yeah. And sometimes those gaps are there for very good reason. There might be a, you know, something going on right now that causes it to be impossible for me to work on my number one thing. This past year, we’ve had some family health stuff going on. I have been meaning to work on this new book and it has been so hard and it’s been a source of agony for me, to feel like, “gosh I’m not getting to that thing, but why is that?” At any rate, identifying that there was a gap there helped me realize the appropriate top priority for me right now. It was, you know, dealing with the health stuff. And if you can identify where, “OK, there was like a disconnect in my head between what I thought should be the top priority and what actually has to be the top priority.” If I acknowledge that and embrace that the top priority is this other thing, that’s a huge relief that unlocks energy for me and allows me to say, “I’m going to try to do my best work right now, being present, being helpful, you know, being sort of a system to my family.” And that’s a relief. So I think that by whatever means you do it, if it’s as simple as what’s keeping you up at night, what’s in your heart? If it’s following a process with a team or as an individual to detail out the available projects and then somehow score them, understanding prioritization sort of becomes then the route of doing anything else tactically to make it happen.

Sean [00:22:07] And we say that where you spent your time, where your past behaviors lied, that betrays what your actual priorities are, right.

Jake [00:22:14] Yeah.

Sean [00:22:14] Prioritizing in the future is difficult. It’s challenging because you don’t know, even in the context of a software product, if you choose to build one feature over another, you don’t really know which one was more valuable until you actually deploy it and see the result. You’re guessing.

Jake [00:22:29] Right.

Sean [00:22:30] You can test things and you can experiment with some things, but you still don’t really know until you put it in the wild.

Paul [00:22:35] Yeah, you can ask a customer how much they’re willing to pay and they can tell you a thousand, they could tell you fifty, but until they actually slap the money down…

Sean [00:22:42] …You don’t really know.

Jake [00:22:44] And you know the things that, there are some things where our past efforts show our priorities in a helpful way.

Sean [00:22:53] Sure.

Jake [00:22:53] Like the illness thing, right. Or, you know, someone might say, “well I’ve been spending a lot of time managing my team and that’s preventing me from being an individual contributor on this project or leaving this new project.” Well, maybe your team needs that right now. By looking at that and examining it, you might uncover that. But a lot of times when it comes to teams working together on building software, building products, or when it comes to an individual trying to get things done, there are common places we spend a lot of time that almost never reflect what we actually believe to be important. One of those is email and I am guilty of contributing to this. I mean, I worked on the G-mail team for many years. I love email. Email is a sink.

Sean [00:23:36] But it’s your fault.

Jake [00:23:37] It’s my fault. It is my fault. Yeah, I did want to make it better. I worked on a feature when I was at Gmail called Priority Inbox.

Sean [00:23:45] Please tell me you’re not one that came up with a little badge.

Jake [00:23:47] Oh, like the unread count. No, no, no, no. Those are, that’s horrible. No, we tried to sort your email into what was important and not important. And our metric was actually trying to reduce the amount of time people spent using email.

Sean [00:24:01] Oh, I love that. It’s great.

Jake [00:24:02] However, I don’t think we were ambitious enough at that time. At the time, it seemed like this could be like a really big deal, and it was helpful, but it turns down the dial, you know, like a half a degree. And the reality is that email is a big challenge, but we’re still using the same email structures and even the most sophisticated email app out there, even Superhuman, is still a tool for making you react as fast as possible to other people’s priorities. We do this in our personal lives. We do this in our work lives. It eats up tons of our attention. And there are things like that that are shocking. If you look at how teams usually spend their weeks, how many stand-ups and recurring meetings and one-on-ones, bouncing and changing context, we do. And how difficult it will be, if you ask a team who has identified their top priority, to spend one week focused on that top priority. It’s like pulling teeth to do that. It’s crazy. We can always make time for email; we can always make time for recurring meetings, but it’s almost impossible for us to make time, especially long stretches of focused time, especially as a team, for the most important thing that we’re doing. And that is an astonishing truth and yet I totally know why it’s the case, but it’s very hard and it’s very hard in our personal lives to make time for the thing that is the most important to us.

Jake [00:25:19] The easy path is to continue reacting and it’s hard. You know, you talked about changing your signature in your email to say, “if it’s urgent, text me and I can get back to you.” We have to reset our own expectations for ourselves first and then make like an outward indication of that, like an outward commitment, to raising our reaction time. “I’m going to be slower. Our team is going to be slower. We’re not going to be up to date on all hundred features we’re working on. We’re going to be super up to date on the one that’s the most important.” And we have to make first sort of an inner decision about what’s important and then we have to make an inner decision about changing what our reaction is going to look like and then we have to, to the outside world, say, “OK, I’m prioritizing this one thing, everything else is going to suffer.”

Paul [00:26:05] I’m loving this conversation. I think this concept of emotional intelligence and self-awareness I think is super important. Most of our audience is dialing in because they’re product designers, product developers, product managers. They’re product people. So taking this concept of awareness and expectations, if you’re talking to a fledgling product manager, say, two or three years in the role, looking around at some of the industries in a state of, of I would say it’s in a state of flux. Scrum is becoming more and more standard. Agile is being accepted by the Fortune 500s, Fortune 100s, almost across the board. Everyone knows that this stuff is good. What are you looking at over the horizon as what’s coming up next from a business perspective? Where can a product manager focus their time to learn, get sharp, and get ahead of the curve.

Jake [00:26:54] Well, this is going to sound incredibly self-serving, but it’s what I believe and it is also about the only thing you can count on me to know about, which is design sprints. If you are in a world where Scrum or Agile is the way your team operates, those systems are definitely acknowledged to be really good right now. And that’s good but it’s also super dangerous because what those methodologies are, they are ways to build a super-fast development engine. OK, well I mean, that just sounds good.

Sean [00:27:27] Just going to throw it out there.

Jake [00:27:28] What could be possibly wrong with that?

Sean [00:27:30] New default.

Jake [00:27:31] Yeah. It’s a new default right. The new default is we move fast now. Whatever you want to build, we can build it fast. So let’s get going. And when I’ve been on teams who use Agile or you know, worked with startups, whatever kind of size company is using Agile, you see the same problem. The engineering team is this cranking machine and they are hungry for stuff to build and they start to build things before there’s a plan. And you’ll see this again and again and again. It is impossible for the product team and the design team to stay ahead of the engineering team. This is not well structured or well built into Agile, or if it is, I haven’t seen the teams that are running this in a super thoughtful way. We just don’t see it. You see these engineering teams take off and become these monsters. It’s like a steam engine. It’s like, “well, we’ve got to shovel something into this steam engine to keep it going.” They’re hungry for what to build next. And quite often what happens is that the engineering team starts building before what they’re building has been thought through. And then we’re committed to this thing we’ve already invested in, you know, even though it’s a sunk cost, oh we started building this other thing, even if we start to learn we’re not on the right track, even if we haven’t done a thorough sort of process to think through the design…

Jake [00:28:51] And I’ve often seen teams where the engineers, they become sequestered into the Agile process and they’re no longer a part of the consideration of, what should we build? So it’s an irony that I am so squeamish about Agile and Scrum, because the process I’m talking about, it’s called a design sprint, and the word sprint is shared across the two. In fact, people often hear me talking about sprints and they’re like, “oh, I know what that is.” And of course, what I’m talking about with a design sprint is that we’re going to all pause. I want the engineering lead, I want her or him in the room and in the design sprint participating and figuring out we’re going to do, but what we have to agree that we’re gonna run some kinds of experiments before we commit to building. Because building is a huge commitment and even if we’re doing it fast, it’s, I mean, I probably don’t have to convince you guys. It’s a huge commitment. So I think that’s the challenge. If you’re getting a team there can be this big process of, “let’s get up and running and let’s start doing Scrum or Agile, let’s get super, super efficient.” That’s great to get efficient. But you have to have a toolset to make sure you’re building the right thing or you’re just moving really fast in the wrong direction. Or as my colleague Daniel Burke at Google Ventures often says, a lot of teams who are running Agile, they’re driving a really fast car from one ditch to another ditch, back and forth, back and forth. And the design sprint can be a way to give you some GPS so you sort of know which way to head.

Paul [00:30:17] So I actually had the honor to facilitate a design sprint just last week for one of our clients.

Jake [00:30:22] Oh cool.

Paul [00:30:23] And we spent a ton of time, about two or three weeks actually, just recruiting the right people to get the right mix in the room. There were a couple of people who had the right title, but just getting that chemistry right. And we were fortunate enough to have a very thoughtful architect, engineer in the room who was open to design thinking, design sprint thinking, and he was able to really contribute some things that we just would not have thought of in a room full of just designers or just product people. And having that insight to, “this is the optimized design, this is the business case for the product and here is the realistic approach from an engineer’s perspective.” And that moment, I will say I’ve been a part of, I guess nine or 10 design sprints at this point and I’ve facilitated two and it’s always around afternoon Wednesday where this switch flips where it all seems lost and you reach up to one of the how might we’s or you find one of the mockups and it’s like, you haven’t talked about this since this morning, and you plug it into the storyboard and it’s like all the lights come on. It’s like, “how did we not see this, it was right in front of us?” That kind of magic doesn’t happen unless you have the right people in the room and you have optimists and optimists with their hat on backwards, you know, the right chemistry of the people on the team as well. I think building the right team is critically important. Just having the right skills is not going to cut it. Yes, you have to have people here who have empathy for not just the users, but also for one another on the team.

Jake [00:31:55] Totally. Yeah. And there’s so many good things that happen when you get into a room and spend the time working alone, also. Like making decisions alone and coming up with our own opinionated solutions, but also seeing what the other people think and having options and having healthy disagreements and a healthy competition between those solutions. When I worked at Google, it was rare when I was there, and this is 2007 to 2012 when I worked at Google proper before going to Google Ventures, but it was rare when I was on product teams for the teams to use Agile or Scrum. There were a couple, but it wasn’t very common in the company. That’s a big part of the reason why I called this process design sprint because inside Google, sprint to engineers meant fast, but it didn’t necessarily mean anything specific.

Jake [00:32:44] Anyway, the teams, there were huge engineering teams. When I got there, there must’ve been about 50 designers in the whole company and typically you’d have one designer or maybe two or three working on a whole product area. You know, there were three of us who were the designers for G-mail, you know, working with two product managers. And then you’d have like a hundred and fifty, two hundred engineers. It’s like a hundred to 1 ratio designer/PM to engineer. And so they’re cranking through stuff no matter what. And the way that we would get things done, and actually this was the same when I worked at Microsoft before, was that usually my responsibility was to go off and figure out, what are we building? And I would design it and hand it off to them as fast as possible because they were raring to go. Then later, and this happened on multiple occasions at Google, this happened to me at Microsoft, and I’ve seen this happen in many companies. Somebody’s job, like it was mine, was to go off and come up with a plan and then come back. “Yeah, sure, we did a pretty good job, like it’s a logical proposal for the product should work.” The engineers start building it. “Good, we’re unblocked, now we’re cranking.” And sometime later, weeks later, months later, whatever, an engineer comes to my desk and she says, you know, I’m working on this part, and did you ever think about having it work like this instead? And shows me like a different way that it could have been designed that’s better. And I’m like, why didn’t I ask you when I was off by myself coming up with a solution. It took a while before I was willing to like like maybe say that out loud. At first you’re just like, “no, no, my way is the right way,” you know?

Jake [00:34:15] But like the truth is, when people would later on propose other ways, like “couldn’t it have worked this way?” Or we’d be doing V2 and they would propose another way, I’d be like, “why didn’t I ask them in the first place? Why couldn’t I have seen these different paths in the beginning when I had to make the decision?” And that’s like one of the big themes in the design sprint is that if we don’t see those other paths, if you don’t have different people working on it, you just get locked into the one path of the one person who sort of, we think should be in charge of doing this. And that’s okay but it’s very limiting. And it’s so nuts when you think about how many people and how many human days of a limited human life will be spent executing any project. I mean, you look at where it comes from, like, it’s crazy that we’re in such a rush to start building that we don’t take the time to say, let’s have a competition and figure out what’s the best way to do this.

Sean [00:35:07] Alright so I want to just quickly pull on that concept, Paul, you brought it up, like having that focused time in the room and creating an open awareness around the problem set. The problems that we’re solving today are not single facto problems. They require lots of different minds. That’s the reality and I think the design sprint process helps us kind of get a shared open awareness around what’s important, create some serious customer empathy, and in short order, helps us to solve problems. I think it was Daniel Goleman that came up with that term in his book Focus about this concept of open awareness.

Jake [00:35:40] I’m not familiar with it. Can you tell me, like so open awareness, yeah, what does it mean?

Sean [00:35:44] In his book Focus, it’s this concept of, like when you have a group of people that has open awareness around a shared goal and they’re all signed up for that goal…

Jake [00:35:52] Yeah.

Sean [00:35:52] …Magical things happen. When you have an open awareness yourself and your mind is tooling on this project, you know, you’re in a weeklong design sprint, there’s no way for you, if you’re passionate about what you’re doing, there’s no way for you to go home and not be thinking about it in the back of your mind. That’s where, you know, you sleep on it and you wake up in the morning and boom, all of a sudden, like Paul, like you said, on Wednesday it was magical. “All of a sudden we all came together and were like why didn’t we try this?”

Paul [00:36:18] Happens every time.

Jake [00:36:19] Yeah.

Sean [00:36:19] You put your brain in that state, I believe that’s the key. And I think that’s what design sprints and that focused week really helped people to do together.

Jake [00:36:27] Right there with you. I have two metaphors that I often think about with this. One is booting up a computer, a really slow computer. I’m old enough to remember booting up computers off of floppy disks and you know, it’s like, “OK, let’s get disk one in there, all right, it’s going to grind away for a while, alright, let’s get disk two,” just like waiting and waiting. And our brains are like that. They’re slow to boot up on things. When it’s complex it takes a while to load the software and that’s the crazy thing about the normal way we work in offices is we’re changing contexts all the time and I don’t get the chance to boot up very far before the meeting’s over and it’s time to go on to the next thing. Even like in this podcast. I’m so much sharper now than I was at the beginning of the hour when we started talking and now it’s almost time to close up. This is like the best, probably the best answers I’ll have all day for you guys and it’s almost time for us to stop. So that boot-up time is slow. And if you can do it over the course of a week and you can get a bunch of people who are running, maybe not the exact same software, but they have the same context. That’s so powerful. It means that the solutions you’re creating on day two of the design sprint, the decisions you’re making on day three are so much higher quality. The understanding you get from the test you run on day five of the sprint. When we all have the same context, we all know exactly what we were testing, what we were trying to answer, man, that’s so powerful and that is so hard to get when we’re running in different directions.

Jake [00:37:54] The other metaphor I use with this in my own work from writing, usually writing is the thing I do that’s the hardest for me to do. And I think about it as like a lake, like when I’m writing I’m in the lake, you know, I can go right up to the lake and dip water out of it. It’s warm and it’s sunny. But as soon as I walk away from it, the temperature starts to drop. And if I’ve been away from that lake for more than a day, especially more than two or three days. Ice, there’s just it’s like a glacier when I come back and I got a chip back in. I can’t just jump back in the lake, like I can’t just start writing again. I have to boot up. And yesterday, as we’re talking, yesterday was like my first day back in on the writing project. I’m entering into this big streak. I’ve set my out-of-office on my email. I’m going to be spending weeks trying to finish drafting this book. But I know the first thing I have to do is spend several days breaking that ice, melting that ice, and I have to be kind of gentle with myself and not judge myself too much by the work that I do those first couple days kind of sucking. It’s going to be hard because my head is not going to be in it in the way you described. I’m not going to be thinking about it all the time even when I’m away, so totally. That is a huge deal and we rarely get the chance to get into that mode at the office. We rarely get the chance to get into that mode in our own personal projects or even in the time we spend with our families. Sometimes you take a vacation with, if you have family and take a vacation, it feels like, my friend Michael says, “you know, we’re all rowing in the same direction when we’re traveling,” because we’re away from things, our heads are all in the same place. It’s powerful, so powerful, but it is too rare in life. So we have to create opportunities for it.

Paul [00:39:38] Yeah. There’s a dozen questions that popped into my head. We’ll have to do part two of this if you’re willing…

Jake [00:39:43] Yeah, totally.

Paul [00:39:43] …Later in the year after a couple of things start to pop on your schedule.

Jake [00:39:47] I’m always free at 6 a.m. as it turns out.

Paul [00:39:51] We won’t do this to you again.

Jake [00:39:51] I’m usually sleeping.

Paul [00:39:51] My last question is a question we ask frequently just to see how people gauge the definition of innovation. So how would you define innovation?

Jake [00:40:05] Yeah. Innovation is like a funny word. Everybody knows that they want it. Everybody wants to be innovative. And I suppose there’s a good reason because I guess the things that we admire, the products we want to buy and the people who we want to be like, they seem to be innovative. I am always sort of striving to just like do a simple thing well and explain it well to other people. It’s really hard. You know, people love to talk about Apple Computer as an example of doing things well. And I think that’s you know, it’s a cliche. But the thing that I admire so much about Apple is what seems to be the harmony between the way they talk about what they’re doing on the outside and talk about what they’re doing on the inside. Like they seem to have a real clarity of what’s most important. If you look at the marketing for the new iPhone, which is arguably the most important product to them, it’s all about the camera. And they made it 100 percent all about the camera. Their marketing is super clear. It’s excellent. They go into great detail about the camera. I cannot look at their marketing page or an advertisement for them without coming away from this impression about the quality of the camera, and I think the same is true on the inside, that’s what they focused their effort on. They talk about privacy. They have a very clear message on the outside and I think that message is clear on the inside. Rarely, and those of us who’ve worked inside big companies will know how hard it is to do that. That doesn’t happen usually there’s not that clarity and we’re scrambling after we’ve already made the thing, usually, to figure out, “what’s our message going to be to the outside world?” And to have that clarity on the inside and on the outside. I always think, again, if I can do that with my own personal projects and in my own personal life, if I could have clarity in my thoughts and in my heart and then translate that clarity to my actions and my messages to other people… That’s simple, but very powerful, very hard to do. And no matter what you do with a clear heart and with clear actions and intentions, I don’t know if it will be innovative, but it will be right and it will be powerful. And in a way, whether it’s new and shiny and different from what other people have seen will fall away because what you do will be powerful and it’ll be from you, from you as a company or from you as an individual, and that will give it an authentic-ness and a different-ness and a uniqueness that’s inherently innovative, I think so anyway, that’s the way I think about it. Yeah.

Sean [00:42:35] It was heartfelt. I like that. Thank you. A last question for you: a book or something of educational content that you have been reading or read recently that you’ve been recommending to others? Obviously not your own…

Jake [00:42:51] I’ve been reading a lot of fiction lately, so I should probably start there. Actually, you know what, I’m going to look at the books that are on my desk because they’re a good reflection of, they’re things that I wanted to talk about in my podcast. I put them up here to remind me. In fiction, there’s two books I’ll talk about. One is The Fifth Season by N.K. Jemisin. It’s an excellent sci-fi book. Another book is called There There by Tommy Orange. It’s an excellent novel. I won’t go into detail about those. If you like novels and you want to try something that’s a bit different, either of those are unusual, but excellent books. And I don’t read a lot of nonfiction. I don’t read a lot of business books. I used to, but after writing a couple of business books, I probably need about a decade to sort of recharge my interest in reading business books. I do still read them, but not super often. But my bar as high so I’ll start reading a lot of them and it has to be really good for me to go all the way through. The book that I’ve read that I got all the way through and it transformed the way I thought about the work that I do and the way I talk about my work and my life is The Power of Moments by Chip and Dan Heath. The Power of Moments. It’s excellent and it’s about exactly what you would think from the title. It’s about the power of moments. They sort of define this idea of a moment and how a business can think about the moments that happen for their customers, how to figure out which ones are the most important and how to engineer them so that they’re amazing and it’s a very sticky idea that I find myself thinking about in all kinds of contexts, personal life and work as well.

Sean [00:44:30] That’s a great, great recommendation. So thank you for that.

Paul [00:44:32] Excellent.

Sean [00:44:33] I’m going to close it up about us both being kind of workshop geeks and…

Jake [00:44:37] Yeah, yeah.

Sean [00:44:38] …the conversation of being sticky geeks.

Jake [00:44:40] Yeah, we have that in common and that’s rare. I think a lot of people are happy to write on whatever sticky note you give them and you and me are serious.

Sean [00:44:48] Yeah, exactly. And I think it goes into the concept of moments.

Jake [00:44:51] Yeah, that’s right.

Sean [00:44:52] The little details big difference. Remember these guys I sent you? I’m going to put a picture up for our podcast listeners to view and we’ve engineered around sticky notes and Paul came up with a brilliant concept for the numbering system we use in prioritization and the stickers that we put on the sticky notes. And to pull on that concept of the moments that you create, these workshops, they’re powerful experiences for all of the people that participate in them and thinking about the little details matters.

Jake [00:45:19] Yeah, it really does. It really does. There’s so many things that we want to do. And when you’re in a system where somebody has considered all of those elements, the default becomes to do the right thing. Just as simple as you walk into a conference room and there’s no whiteboard or it’s small and dirty and it sucks and like the pen is half dry with ink. The default then becomes like, “we can’t write on the whiteboard so we’re just going to have to talk our way through it.”.

Sean [00:45:43] I’ve figured out that whiteboards are never enough space.

Jake [00:45:46] Never enough. Yeah, yeah, there’s no situation where you’re like, “God I wish there wasn’t so much whiteboard space in here. It’s really annoying to me.” Never, nobody ever says that.

Sean [00:45:55] The default is the whiteboard. The flip chart is a magical thing because you can take the flip charts and keep drawn on them and you can wallpaper the whole room and just keep going.

Jake [00:46:03] That’s true. That’s true. Although I mean, you know, flip charts have the downside of that you can’t erase. You can’t do fine-tune edits. You got to redraw the whole thing. What we need is like a flip chart whiteboard.

Sean [00:46:15] Oh, erasable flip charts, we’re on to something here.

Jake [00:46:17] Erasable flip charts, yeah. But it’s true. But when you have the right materials and when the materials you have are configured for the task at hand, it’s like having dot stickers that have numbers on them for prioritization. Now the default is, “we’re going to think about prioritization; these things are lying on the table.” You know, like the easy thing to do now becomes when we’ve had a discussion, if we’ve written things on paper, the easy thing to do, “hey, let’s just prioritize these real quick- these dots are here.” If they’re not there, well, somebody has to think of that and then like sort of explain it to everybody else and convince them that we should do it. Defaults are powerful and the materials matter for sure. Office supplies are of paramount importance in life.

Paul [00:47:03] Who would’ve thunk.

Sean [00:47:04] I’m telling you, a geek about that stuff, so… Alright, man, well thank you so much for joining us. This was awesome. We got a lot of great nuggets and insights for our audience here. Super honored, Jake, that you joined us. Can’t wait to see you at the next Product Momentum conference.

Jake [00:47:19] Likewise. My absolute pleasure. Thank you both for having me. Sean and Paul, it was great.

Paul [00:47:25] Thanks Jake.

Jake [00:47:25] Talk to you soon.

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