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Jim Kalbach on Jobs to Be Done

Jim Kalbach is the chief evangelist at MURAL, a leading provider of online visual collaboration software. He’s the author of Designing Web Navigation (O’Reilly, 2007), Mapping Experiences (O’Reilly, 2016), and his latest, The Jobs to Be Done Playbook (Rosenfeld, 2020). In this conversation, we dive into Jobs to Be Done, how it relates to design, and how jobs can create an “out of body experience” for organizations.

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Udhaya Kumar Padmanabhan on India

Udhaya Kumar Padmanabhan, or UKP, is a Global Strategic Design Director at Designit, an international strategic design consultancy. He is based in Bangalore, and in this conversation we talk about challenges and opportunities for information systems in the Indian market.

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Sarah Barrett on Architectural Scale

Sarah Barrett is a principal IA Manager at Microsoft. She’s been writing compellingly about information architecture in Medium, and in this conversation, we focus on her most recent posts, which deal with how architectural scale affects our perception of information environments.

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Sophia Prater on Object Oriented UX

Sophia Prater is a UX design consultant and chief evangelist of object oriented UX, a methodology that helps teams tackle complex design challenges. In this conversation, we discuss OOUX and how it differs from other methodologies.

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Alla Weinberg on Work Culture

Alla Weinberg helps teams and organizations improve the quality of relationships at work. She has a background in design, but now calls herself a ‘work relationship expert.’ In this conversation, we discuss her new book, A Culture of Safety, and how teams can create environments that allow people to do their best work together.

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Jeff Sussna on Customer Value Charting

Jeff Sussna is a consultant and author specialized in helping organizations deliver software more effectively. This is Jeff’s second appearance on the show. In this conversation, he tells us about Customer Value Charting, a visual tool that helps teams balance strategy and agility.

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Kat Vellos on Friendship

Kat Vellos uses her background in experience design to empower people to learn, grow, and thrive. She’s written two books on adult friendship, We Should Get Together and Connected from Afar. In this conversation, we discuss the importance and challenges of making friends, especially during this time of ‘social distancing.’

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Jorge: Kat, welcome to the show.

Kat: Hi, Jorge! Thanks for having me on the show.

Jorge: I’m very excited to have you here with us. For folks who might not know you, would you mind please, introducing yourself?

About Kat

Kat: Yes. So, hello everyone! I’m Kat. In my current day-to-day life nowadays, I am an experience designer, author and speaker, as well as a facilitator, but my background involves two paths that have blended quite seamlessly into one. The first path is my path as a designer: I got my degree in graphic design and worked in a variety of design roles, ranging from editorial, news journalism, all the way up to tech and digital devices and UX design and product design.

And then the other path was the part of my career that involved working directly in communities as a facilitator, community builder, and program director of empowerment programs, particularly for marginalized youth and marginalized communities. Both of those paths blended together in a way when I found user experience design. This was back in about 2014 or so, and I’ve been doing a variety of experience design projects and roles at different companies. And now I work for myself and the focus of my work right now is really blending those two paths and sets of skills together around helping people cultivate more meaningful connection in their lives.

Why friendship?

Jorge: You’ve written two books, We Should Get Together and Connected from Afar, which are about friendship. And I’m wondering what brought you to the subject?

Kat: Yeah, so for starters, a little bit about me is I am an introvert. I also moved quite a bit as a kid. So, I had the experience of sometimes belonging, but most of the time not quite belonging wherever I was, because I was always from someplace else. And I think that really imprinted me with a real understanding of what it feels like to not have the connection that you want. And then later on, when I found it in high school and college and got my friend groups and got that sense of belonging, I was just like, “Oh, this is beautiful. I never want to let this go.” And throughout my adult life I never really had a hard time making friends. I loved being in a community.

But when I moved to the Bay area, it was the first time in my life — despite multiple states, a couple different cities moving — I had a hard time forming ongoing, lasting friendships. And just dozens upon dozens upon dozens of people I met said that they had the same problem. And I got really curious about that as a user experience designer. I know there may be some UX designers listening right now; I don’t know about you, but when I see that a lot of people are having a certain problem, like completing a certain task, or getting success at something, I get really curious about why that is, and I can’t help but think about how we can improve a process to make it easier and more enjoyable for people. And so, just quite naturally, I got fascinated with the subject of connection in adulthood. Particularly around forming and maintaining friendships as life goes on. And I did a variety of… I can go further into depth, but I did a whole variety of experiments and explorations into that and ultimately ended up writing this book about it. I did not know at the beginning, when I started investigating the topic, that I was going to write a book. But it became quite clear that a book was urging to get out of me.

Jorge: People have been making friends for a long time. And I’m wondering, why now? Why do we need a book on this subject? It’s almost like an instruction manual, right? Why do we need one for friend-making now?

Kat: Right. So, it’s not that people, like, aren’t making friends right now, or that they haven’t been doing that for a long time. But one of the things that has also been happening concurrently in our society is that there is a loneliness epidemic. The first instance of that phrase that I could find in U.S. journalism at least, was around the 1980s. And since that time, it has slowly been getting worse. Or not even slowly, but kind of quickly! Around the time of my original research into this, around 2018, approximately half of people in the United States were reporting that they felt lonely on a somewhat to regular basis. And by 2020, when my book came out, that number had already climbed to around 61%. So, it’s not that people don’t want friends or that they don’t want to make friends or that there’s nobody making friends, but it’s that loneliness is climbing. And my hypothesis is that the cure for that is healthy friendships and healthy communities. And for some reason there is a need for more support and more resources that will help people do that within the demands of our modern world.

Types of friendships

Jorge: You mentioned healthy friendships and the book offers what I think of as a taxonomy of different types of friendships. You speak of meaningful friendships as one type. And I’m just wondering if you could tell us a bit about different types of friendships.

Kat: Yeah. So, part of the qualitative research that I did in researching the book was spending a lot of time interviewing people about their experiences of connection in both friendship and community, which are a bit different. And also doing a survey and asking people to define in their own words, you know, what is friendship to you? And out of that, a few different categories of friendship emerged. And so, I’ll give you a few examples, and this is directly from interviewee quotes and survey respondents that I think really, really hit the nail on the head here.

So, the first is our category of acquaintances. And acquaintances might be someone that you know some basic details about, you can have small talk with them, you maybe have met them in person a couple of times, but you wouldn’t go out of your way to reach out to them. And there’s no real deep, emotional connection. And then next would be like, a friend category, like a casual friend. And this is someone that you feel happy around. You don’t have to try too hard to have a conversation with them. You probably know a bit about each other’s life circumstances, but maybe you don’t see each other as often as you’d like, or it just doesn’t go super deep when you connect. It’s just casual and friendly and li ght, but not on the deep, deep heart level.

And then there’s that close friend level or best friend level. And this would be someone whose wellbeing I care deeply about and who I feel confident I can depend on. Someone else said, “someone who accepts me completely for who I am, and I can tell my problems to, without feeling ashamed.” It can also be someone who, let’s see… someone said, “someone who knows my secrets, fears, and who tells me what I need to hear, even if I don’t like it.” And then last is my favorite, which is someone who is integrated into my life. That’s really when they start to get into the… almost the category of chosen family, at that point.

Hydroponic friendships

Jorge: There’s a metaphor in the book, a gardening metaphor. You speak of cultivating friendship. And I was drawn to the phrase, “hydroponic friendships.” What’s that about?

Kat: Right. So, I am a plant person. I have been studying plants for a while. I really love spending time in the garden, and anytime I’m in nature is where I’m also sourcing a lot of metaphors about life. And as I looked at what were the challenges people were having with friendship, as well as what were the opportunities and how could we create more closeness, I was drawn to the metaphor of hydroponics and gardening because — for those who may be unfamiliar with it, although I think maybe a lot of people have heard of it — it’s where you grow plants in highly nutritious water instead of soil. And at the time when, you know, the grandfather of hydroponics proposed this idea, he was laughed at by his community. They were like, “you’re crazy. You can’t grow plants without soil. This will never work!” But he did prove that by adding the nutrients plants need to grow to the water, they could thrive. And in fact, sometimes do better than they do in the soil.

And this metaphor came to mind because one of the trends I was hearing a lot in the challenges people were having with friendship is that they felt like they didn’t have enough time. They were like, “Oh, I’m so busy. Everybody’s so busy.” And busy-ness is one of the four main blockers or barriers to close friendship that I talk about it in the book. And as a facilitator, one thing that I’ve seen over and over again when I’ve hosted camps and retreats and workshops, and all kinds of events is that when people have the opportunity to come together in a shared intention and a space that is designed to allow them to develop closeness and to share vulnerably and to build trust, they can bond much, much more quickly than they can just out in the wild world. And so hydroponic friendship is my hypothesis that in the absence of abundant time, your friendships can grow much more quickly if they are immersed in quality connection that involves vulnerability, self-disclosure, empathetic listening, and you experience these things in some kind of concentrated form. So that is the theory of hydroponic friendship.

Jorge: So, if I might reflect that back to you, it sounds like it has to do with creating the — I’m going to use the word environmental — the environmental conditions to allow friendships to blossom. Is that fair?

Kat: Yes. That’s a really beautiful paraphrase, reframing of it. Yeah! I like that too.

Jorge: I’m wondering, as someone who… I don’t think of myself as someone who has trouble making new friends, but I can relate to the framing you spoke of earlier of the challenge of moving, for example, to a new city where you don’t know anyone, and everyone is so busy. I’m assuming that hydroponic friendship starts… by necessity, must start in the kind of lower rungs of the taxonomy we were talking about earlier. My expectation is that you would first start as acquaintances, and then move to… you ascend to a higher level, right?

Kat: Yes, generally. Although there are some cases where people meet and there’s like an instant friendship attraction. It’s almost like friendship at first sight! Or like, love at first sight, but for platonic friendship. Where two people really can be quite magnetized to each other very quickly. And in that case, it’s almost like they’ve leaped from acquaintances straight into like, “Oh my gosh, I want to be friends with you!” and then the other person’s like, “I really want to be friends with you too!” And it’s like right there, they’ve got a great spark to like really initiate a friendship that may grow into a deeper close connection as time goes, because they’ve got this like huge burst of momentum and mutual enthusiasm right at the get-go.

Or, as you mentioned, this may also grow at a little bit of a slower pace from someone who just starts as acquaintances that you feel fond about, but maybe not quite at that friendship-at-first-sight feeling.

Making friends online

Jorge: When you say friendship at first sight, I can think of friendships in my life where that has happened, where I’ve met the other person and I thought, “this is somebody who, I feel some kind of simpatico with, and would like to get to know better.” And whenever that’s happened, it’s been in a physical environment where I am with that person. We might be sharing a meal with other people or we might be in a social situation, or it might be a work situation, for example. But it’s always been in physical environments. And I’m wondering, given that we’ve just celebrated a year of lockdown here due to the pandemic, the degree to which our socially distant way of being affects our ability to spark at these potential friendships as we would in physical spaces.

Kat: It certainly does affect it, but it’s not a complete impediment because humans are incredibly adaptable creatures. And we’ve seen this in the ways that people have… you know, after an initial moment at the beginning of lockdowns of like, “Oh my gosh, what are we going to do? The world is ending! The sky is falling!” Very quickly, we adapted. Because that’s what we do! You know, with substitution for what we could do before we find ways to create some semblance of that in the current moment. And one of the things that has been really gratifying and exciting to see is that even though we are generally meeting virtually to do our meetings and our events and our get-togethers and everything right now, I have absolutely seen people have that sense of spark.

Even in some of the workshops and talks I’ve given where… a direct quote from the chat one time I saw that just warmed my heart. Someone wrote in the chat, “Oh my gosh. I already want to be friends with some of the people who just shared in the main room!” Like on the big group screen, where people were obviously sharing something personal about their life, and we’re all talking about friendship together and how people feel and right away, as people get a sense of who this other person is, what they value, what their personality is. There can be that same sense of spark and that same sense of not just curiosity, but a desire to get to know that person and to build something in friendship with them.

Jorge: And do you know what happened? Did they follow up on that?

Kat: I don’t know. I usually… at that moment, I’m like, “Hey, if there is someone you want to talk to like trade contact information, don’t just let the call end and let it slip away!” A lot of people hold themselves back from creating the friendships they want, because they’re scared to initiate. And so, I often say if you are open to friendship, don’t be ashamed to say, like, “I really loved getting to meet you all. I would love to connect again. Here’s my email!” Do that because most people don’t do it. And the ones who do are likely to have greater success. Because again, they, don’t just… it’s not ephemeral. The call doesn’t just end and then everyone’s back to just being alone in their apartments. They have some way to reconnect again.

Jorge: I’ve been part of a few virtual cocktail hours during pandemic time. And the way they usually manifest is as Zoom meetings primarily, where you get this all-up view where you see everyone’s thumbnails of everyone’s video feed on the screen at the same time. And the quality of the conversation is very different than in a physical cocktail party or environment, right? Like, you’re not able to as easily break off into little groups and catch up with folks. And it sounds to me from what you’re describing here that the times you’ve seen it happen, this kind of serendipitous meeting of someone else, it’s happening in an environment that has been consciously structured to enable that. Is that true?

Kat: Absolutely.

Environments for friendship

Jorge: Could you describe to us what that looks like?

Kat: It all comes down to intention. It all comes down to envisioning before you even begin, what is the outcome that you want for people to have and similar to what we talked about earlier, what are the environmental conditions that you can create that will allow that outcome to emerge most naturally and seamlessly. So, certainly everybody’s getting tired of Zoom but there’s other tools that are available and there’s other ways to use these tools.

One of the things I’ve done when I’ve had some small groups get together over Zoom is I simply tell people like in real life, we were in a room together, if you were in my living room, you would not be on mute. You would have the freedom to speak at will, and you don’t need my permission to ask to unmute. And I understand that in say an all-hands meeting at a company with a thousand people, do you need people to be on mute, because there’s going to be a lot of background noise. But if you’re getting like a social gathering together or something to connect with other people? Everybody go off mute! Talk when you feel like talking! It’s fine if you bump into each other and someone interrupts somebody else, because guess what? That happens in real life too! It’s okay. It doesn’t have to be awkward because that’s what natural conversation looks like in person as well sometimes. So, I challenge people to really think about the way that you use the tool and make sure that you’re defining how the tool is used and the tool is not defining how you show up. And with that, as I mentioned before, bring intention to how you want people to connect.

One of the things that I do in a community that I run called Connection Club, is providing opportunities for the members to get to build more closeness with each other. And sometimes that needs to happen in a one-on-one conversation. So, I’ll split people off into one-on-ones. Also, in sometimes a small group of three or four. But really keeping in mind, what does it look like when you have a set amount of time, a set prompt, or guiding conversation or guiding question and giving people the amount of space as well as the actual space in a breakout or whatnot, that will allow them to have enough time to go meaningfully into that subject and hear each other and share stories before they then rejoin the rest of the circle.

Jorge: That’s interesting, finding a way of adapting the tools so that it more closely mirrors the way that we’re used to interacting in these social situations. One thing that I was wondering as I was reading the book — and it has to do with this issue that we’re talking about here — this idea that we can be more intentional about how we make friends. And you spoke of the loneliness epidemic that is happening, and your case in particular, when you moved to the Bay area. And when one does a move like that, especially in the stage of life when one is working a lot of the time, and one’s peers are also in that situation, it becomes harder to find the time, space, et cetera, for these kinds of serendipitous encounters to happen.

A more intentional approach to friend-making

And I’m just going to try to summarize the way that I understood it from the book, is that our transactional… kind of highly transactional way of being has somehow impaired our ability to make and maintain meaningful friendships, especially in adulthood. And the thing that I was struggling with, and which I wanted to get your perspective on, is how we might regain this ability without turning friend-making into yet another thing to check off our to-do lists, you know? It’s almost like we’re… it might feel like we’re trying to do to friendship what we’re doing to these other aspects of our lives. And I’m just wondering if that’s a thing or how we might do it so that it feels more integrated with who we are as people.

Kat: Yeah. I mean, the first thing I would say there is, don’t treat it like a to-do list item, you know? Because if it feels like a checkbox to you, it’s likely going to feel like a checkbox to the other person and nobody likes to feel like that. So, I would suggest checking in with one’s intention and really clarifying for yourself, is your intention just to say like, “all right, I did my like one hour of friendship time this week, I’m done.” Or is your intention to actually listen and connect and commune with another person? How do you want the other person to feel when that time is done? How can you show up as who you really are, in the open-endedness of getting together in a conversation or an activity or whatever may happen… because there is a certain open-endedness to this?

You spoke to serendipity and spontaneity, and this is actually quite beneficial for friendship. One of the interesting pieces of research I include the book came from a report in the Washington Post that found that people were happier when they didn’t assign their free time activities to a specific time slot in their calendar, and instead opted to do some of them spontaneously or in a non-specific window of time. One of the things they had people do was get ice cream with a friend. And some people were assigned to an exact day and time in advance. And they had that in their calendar like a lot of busy adults do. And other people didn’t. They had it in this window and it was going to just happen spontaneously within that frame. And the people who had a more spontaneous ice cream with their friend reported enjoying it more and having more fun with their friend. So, things tend to feel less fun when they’re scheduled. And so, adopting rough scheduling as opposed to strict scheduling is something that can lead to greater happiness in your own life and can also lead to greater feelings of spontaneity and play and enjoyment in your friendships as well.

Jorge: I’m hearing two things and I love both of them. One is that there might be an inverse relation between the degree to which you structure these activities and the degree to which they add value to your life. And the other is that when you approach it, the intention matters, and it’s not just about you somehow eradicating your own feelings of loneliness, but also providing the same for the other, right? So that you keep the other person’s benefit front and center.

Kat: And the more you immerse yourself in what is actually happening in that time that you’re connecting with the other person, the more likely you are to feel the benefit. You know, when you’re spending time sharing stories with a friend say, focus on their story, focus on them. Get curious. Ask follow-up questions and have that be the focus of your attention, rather than halfway listening and halfway being in your own head. Like, “do I feel less lonely right now? Do I feel less awkward right now?” Get out of that mental evaluation mode and get really immersed and real curious and interested in the other person. And that’s actually when somebody feels heard. That’s actually when somebody feels more connected is when you’re really present and holding space with each other.

Jorge: That’s wonderful. Thank you for stating it like that.

Kat: And two really, really small follow-up tips I want to give on that is that it’s okay to tell a friend at the beginning of a conversation, like, “Ooh, I’m feeling really scrambled right now. I’ve had a really frazzled day, but I’m going to try to get present with you. I just want to acknowledge them feeling off right now.” And let the other person know. Because if they pick up on it, they’ll probably wonder why.

And the other thing around scheduling too, is it doesn’t require both people to agree to do something in a spontaneous way. I was going to have a phone call with a friend, and she was like, “what day and time should we do?” And I said, “I’m trying to schedule fewer things in my life, but here’s some windows. And if you want to schedule it in your calendar, it’s fine with me, but you can call me spontaneously within any of those windows. That’s fine for me.” So, I get to get the benefit I want, which is, “Hey, a spontaneous call from my friend!” And they get to get the benefits they want, which is like, “Oh, I have to put it at this time at this day.”

Jorge: That’s great, and again, that makes me think back to your work as an experience designer in that it’s trying to give the other person the experience that is ideal to them while allowing you to also get the one that is ideal to you.

Kat: Yes!

Closing

Jorge: So that’s great Kat, and that strikes me as a good place for us to wrap up the conversation. Where can folks follow up with you? Because I feel like there are the books, but there’s more to it than that, no?

Kat: Oh, yeah, for sure. So, the books are there. We Should Get Together obviously is about creating better friendships. Connected from Afar gives you 25 weeks of activities to do with a friend from a distance. And if people want to get more from me, I have so much more to give. So, one is subscribe to my newsletter; that’s at weshouldgettogether.com. Every week I send out tips and guidance around how to show up as a better friend and a better community member in your immediate area or in our larger world. And so, advice and resources are always going out about that. I also have an ongoing events list at my website weyoushouldgettogether.com where I always have something coming up. They can join Connection Club, or they can hop into an upcoming workshop or talk that I’m doing. And I also am available if people want me to come and give a talk at their conference or their company or their community organization. That’s also an option as well.

Jorge: And I would advise that folks should not pass up that opportunity, because this is an important subject and one that people need to know more about, especially in these days when folks are spending so much time apart from others. Thank you so much Kat, for being with us on the show and sharing it with us.

Kat: Thank you so much for having me here, Jorge, and this was really quite lovely. It was great to share this with you.

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Matt LeMay on One Page / One Hour

Matt LeMay is a product management consultant and author. He’s a co-founder and partner at Sudden Compass, which helps companies reconnect with their customers and helps teams focus on addressing human needs. He’s the author of Agile for Everybody and Product Management in Practice. In this conversation, Matt shares with us One Page / One Hour, his pledge to make project collaboration more agile.

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Read the transcript

Jorge: Matt, welcome to the show.

Matt: Jorge, thank you so much for having me.

Jorge: Well, I’m very excited to have you here. For folks who might not know you, would you please introduce yourself?

About Matt

Matt: Sure! So, my name is Matt LeMay. I’m a partner at a collective consultancy called Sudden Compass. My career has been kind of all over the place. I was a professional musician in my early twenties and a music writer. I worked in marketing for nonprofits. I accidentally became a product manager and made so many mistakes, mistakes that keep giving in the sense that I am still learning and sharing lessons from the many mistakes I made as a product manager. And now I’m mostly helping teams manage the way they work together to solve problems, which is really, I think, the thread that’s run through everything I’ve done from being a musician and working with my band, to being a product manager and working with developers and designers, to being a coach and consultant and working with cross-functional teams that span marketing and sales and everything else.

Jorge: Well, that makes me super intrigued. What are the connections between managing the work of creating music and product management?

Matt: Yeah, that’s a great question. And it’s kind of the question that got me into product management in the first place. When I was in a band and kind of informally managing the band, a lot of the work I did was managing specialized skills. You know, our bass player was a really good bass player. I didn’t know how to play bass like that, but I knew where we needed to go.

When we worked with mastering engineers and mixing engineers, I didn’t know how to do that work, but I knew what we needed to deliver. It was a lot of managing complex specialized work to achieve some outcome, which spanned both emotional outcomes, creative outcomes — and though they were hardly in the super exciting range — business outcomes as well. We needed to be able to at least break even when we were going on tour in order to have any plausible defensibility to continue going on tour, which was something we really wanted to do. So, a lot of what I learned was about how to motivate and communicate and coordinate specialized work in the service of creating something that nobody could create on their own.

And really that’s a lot of what I was able to bring… when I was doing well as a product manager, what I was able to bring to that experience was… you know, I’ve told people that when I was a musician, convincing four tired people to wake up at six in the morning to drive from Columbus, Ohio to Dayton, Ohio, and play a concert for 10 people and lose money on it, it was a great team motivation challenge. You have to really learn why people are doing what they’re doing. What they’re excited about, how to get people through difficult times, how to get people excited about the work that they’re doing, even when that work isn’t really giving them the kind of external validation that I think we all want. So, in a lot of senses, I think software product management is much easier than being a musician. And in other ways, it’s more challenging.

Jorge: I’m not a musician myself, but I would imagine that musicians also have like their own expression that they want to bring to the project. And somehow balancing the personal needs of the individual with the overall needs of the group must also be a factor, no?

Matt: Yeah, absolutely. I mean, It’s kind of a joke among mixing engineers. But when you’ve got a band in a room and they’re finishing a record, everybody just wants their own instrument to be louder. And at a certain point, if you make all the instruments louder then everything sounds quieter. If you’re not willing to be subtractive, then everything you add actually makes the finished product weaker and less focused and less compelling.

Which I think is very true in product development as well. If everybody has their feature that they want to build, if everybody wants to highlight their own individual contributions, you very quickly get to a point where the thing you’re building no longer makes any sense. Where if you can’t prioritize, if you can’t think systematically and then think structurally about how everybody’s contributions come together to create something new and meaningful, then you wind up with something which is just a collection of features, or a collection of ideas that really don’t coalesce into something interesting or powerful, or that solves a problem.

So, I’ve been on both sides of that one. I’ve been the person saying, “make my instrument louder in the mix!” I’ve been the person doing the mix and trying to manage a band full of of people saying, “make my instrument louder in the mix.” I think both in music creation and in software product management, you really learn to recognize the power of subtraction. That the most meaningful work you can do is often subtractive work, not additive work. That constraints and subtractions and blank spaces are really what define the work that you’re doing more so than features and additions and things that you add in.

One Page / One Hour

Jorge: That is a perfect segue to the reason why I wanted to talk with you, which is that I saw something that you built called, “One Page / One Hour.” And I was hoping you could tell us about that.

Matt: Sure. So, One Page / One Hour… I’ll give you the kind of brief backstory. In my coaching work, I spend a lot of time talking to product managers who are torn between two things. Between on the one hand, the work that they believe is going to deliver outcomes for their team, their customers, and their business. And on the other hand, the work that they believe is going to bring them recognition and praise as individuals. And these two things are almost always in some degree of tension with each other. Because in a lot of cases, for product managers, the most meaningful work you can do leaves no trace. That leaves no deliverable. There’s nothing you can point to and say, “I did this.”

Instead, your team’s success is your success. Your team’s work is your work. And for product managers who… many of us tend to be overachievers. Tend to be, you know, people who are very accomplishment and recognition-driven. This creates a real tension. As if you’d make, for example, a beautiful 20 slide deck and present it to company leadership, then you are likely to get praise and recognition.

However, all that time and effort you spent on that beautiful 20 slide deck is likely not going up in the product. It’s not resulting in any value for your customers. And I’ve seen product managers who will, for example, pull visual designers off of product design and have them help them design the deck, and walk out of that presentation, feeling validated and accomplished, even though they’ve just spent tens, if not hundreds of hours on something which doesn’t actually deliver any value to the customer and only marginally delivers value to the business.

So, in my coaching work, I found myself advising a lot of product managers to start really small, make something that is incomplete and messy, bring it to your team and then work together to co-create from there. I brought this experience to Trisha [Wang] and Sonny Bates, our other partner, and they both kind of smirked at me. And I said, “why are you smirking at me? What’s that look?” And they said, “Matt, you are worse about this than anyone we know! You are always showing up — just in our internal meetings -with these beautiful, like 20 page, ‘look at this incredible workshop plan I put together!’ You are the thirstiest person we have ever worked with in terms of wanting feedback and wanting that validation! And it’s funny, but good that you are realizing in your coaching work that that is not the most productive pattern.”

So, I thought about that for a second, and I said, “you are absolutely right. I need to shift this.” Because Trisha is a genius and a powerhouse and I want her to be impressed by the work I’m doing. I want her to be like, “Matt, you’re smart. I feel good about working with you.” So, I realized that if we wanted to change that behavior, we needed to change the incentives. In other words, we needed to create a situation where if I showed up with something too finished and polished and impressive, I would actually get negative feedback, not positive feedback.

So, I wrote up this pledge to my business partners saying I’m willing to forego the sense of individual accomplishment that comes from presenting finished and polished deliverables to my colleagues. I promise that I will spend no more than one page and one hour working on any deliverable — any document — before I bring it to the team. In other words, if I show up with five beautifully formatted pages or a one-page that took me 10 hours to create, I want you to hold me accountable to that. I want you to say, “man, why did you do this? We made a deal. We made a commitment to each other! We all know that if we actually want to deliver value, if we want to do valuable work, we need to collaborate earlier on. You can’t go off onto your own and create this big thing, and then just want us to tell you how great it is!”

So, I did this and massive credit to Tricia who said, “publish this!” Who said, “put this out there. This is not just for you. This is really gonna make a difference.” So, we put together a One Page / One Hour website and we’ve been putting it out there and it’s been just incredible to see folks from so many different organizations, people who I have never spoken to, who so far as I know, have never attended a talk I’ve given, just find this and share it with each other and take this pledge, which now has over a hundred people from over 75 organizations all over the world committed to spending no more than One Page / One Hour on anything before sharing it with their colleagues.

Jorge: That’s really awesome. And it’s… well, proof that it works: it’s how I came to you, right?

Matt: I hope so.

Jorge: I feel totally identified with the problem as you described it. I too am very thirsty for that kind of adulation that comes from making something beautiful — and perhaps overwrought — if I am hearing correctly, the spirit of it. And you’re describing it as a tool to collaborate with your colleagues. I’m wondering, as a consultant, if the boundary for collaboration stops with your team, or if you also extend this to your customers as well? Your clients. Because I’ll just say, like, in my case, I feel most compelled to share the beautiful thing when I’m presenting to the customer, right?

Matt: You know, it’s funny. I used to do a lot of training work in ad agencies. And I would talk to them a lot about how to do paper prototyping in particular, how to do really low fidelity prototyping. And they would all say the same thing, which is, “yeah, this is great, but we could never show this to a client. We can never sketch something on the back of a napkin and show it to a client.” They would say, “why isn’t this finished? Why isn’t this beautiful?” And I kept thinking to myself, I’m also training and coaching a lot of the companies that are your clients… people are pretty capable of understanding if you show them a sketch on the back of a napkin that it’s not intended to be something finished and polished. People are actually much more open to seeing unfinished and to participating in the co-creation of unfinished things than I think we think they’re going to be.

And one thing I’ve found really helpful about One Page / One Hour is especially since it’s one of our calling cards as a consultancy now, it gives us a way to present unfinished, unpolished deliverables to clients that feels purposeful. Where rather than just showing them something and saying, “yeah, here’s what we did. Whatever.” We’re letting them in on this little operational secret of ours. We’re saying, “we have this guiding principle called One Page / One Hour, and we’re going to agree to this with you. So, you’re always going to be in on the ground floor with us. We’re never going to bring something to you, which you’re going to have to feel even remotely guilty about ripping apart.”

We did a One Page / One Hour exercise with a client once where they were 75 pages into an organizational transformation plan. And they had brought us on to help them with this plan. And we said, “tell you what, what if we do a One Page / One Hour pass, just synthesizing this down. You put together all … this big thing. We’re going to just spend One Page / One Hour reading your 75-slide deck, distilling it down and reflecting it back to you.” And they said, “sure, why not?” So, first of all, it’s very hard to read a 75-slide deck in one hour, which already helped them understand that asking everybody in their company to read a 75 slide deck means that you’re asking people for a lot of their time. But we did our best to distill this down, and we presented it back to this leadership group. And they got furious.

They said, “this is not what we intended at all. We don’t want people to take this away. We don’t want people to take that away. You captured this idea, which is totally the opposite of what we wanted.” And we said, “Great. Hey, if this is the best we can come up within one hour, then there’s probably some contradictions in this document you put together. What may have happened is that you have a leadership team, which can’t actually agree on some of these things. So, each person just puts 10 slides in there. Those 10 slides are totally in conflict with each other, but because you can always add more, you haven’t actually identified that conflict. You’ve just worked around it.” And they said, “huh. You’re right. This is really… this is really helpful!” but then something really interesting happened. They started saying, “well, but you know, don’t worry. We don’t have to throw out the work you did. It’s great. We realized….” I said, “I don’t care! I literally spent an hour on this. You know, how long I spent on this!”

How many times have you done an hour of something? If the takeaway from this one hour is that you need to align as a group and work within constraints to actually resolve these conflicts? Then it’s a success, even if we throw it out. So, it’s been really helpful, not just to work in this One Page / One Hour way with clients, but to share with them why and how we’re doing this. To let them in — into this world of One Page / One Hour, so when they receive an unfinished, unpolished deliverable, there’s no chance that they’ll think, “why is this unfinished and unpolished?” They understand that they’ve been inducted into this world of One Page / One Hour and they feel really awesome because they’re seeing this work better for them too, and they’re like, “wow, I get to participate in this in a different way!” So, there’s that meta layer on top of the One Page / One Hour pledge where it’s not just the way of working, but it’s the conversation and the agreement to the way of working that also clears and creates a different kind of space for collaboration, including with clients and customers.

Modes of communication

Jorge: Sounds like a little bit of a jiujitsu move, where you take what is potentially a liability and turn it into an asset, right? And it speaks to this shifting of incentives that you spoke of earlier. I’m wondering what that does to the intensity of communications. Because obviously if you’re spending less time working on the artifact and sharing it more quickly, that speaks to a higher volume of messaging. And is that an issue? How does that get managed here?

Matt: I’m so glad you asked that question because part of the point of One Page / One Hour is to force us out of our comfort zone a little bit. Is to get us having those conversations with other people before we’re sure about the path that we’re taking. Before we’re confident in the deliverable we’re creating. And that is emotionally difficult. It forces people into a very challenging mode of communication. And as I coach more teams through this, I’m just appreciating that much more. That in a sense, One Page / One Hour also forces you to level up your communication skills. It forces you to get more comfortable communicating when you don’t have control.

This has been a big theme in so many of the conversations I’ve been having with teams in the last couple of weeks is: what does it mean to be willing to give up control? When are we truly willing to give up control? When are we willing to let someone else see something we’re working on before we feel confident enough in it that we would do that necessarily of our own accord, if we hadn’t made this commitment to each other? I think that’s really one of the biggest challenges around this, and one of the reasons why it’s so hard to keep up with it is that we do have to be forced into… I think you’re right: a more intense form of communication, a more vulnerable form of communication, a form of communication where we don’t know what the outcome is going to be going into a conversation nor are we trying to convince or persuade or sell people into an outcome. We are genuinely open to things going in an unexpected direction. And the value of that is pretty clear and straightforward. But the challenge of that is something that I think people often underestimate until they find themselves having to do it themselves.

Jorge: One method that I was reminded of when I read about One Page / One Hour is Amazon’s 6-page memo idea. And the main similarity there is that it feels like they both impose constraints on the format in which things are going to be. It time boxes the activity, and also constrains the format in which it’s going to be presented. As I understand the 6-page memo, the idea there is that it’d be shared prior to meeting so that people have an opportunity to review that. And I’m wondering if there are any communication best practices around One Page / One Hour that would be analogous to that.

Matt: That is another great question. It’s funny. To me, the big differentiator between the narrative memo per Amazon and One Page / One Hour? Well, two things. Number one: One Page / One Hour includes that explicit time box. You cannot spend more than an hour. The trap I’ve fallen into with narrative memos as a writer is that I can spend forever writing a page. It’s funny, the program I was in in college had a one-page maximum on all papers. It was sort of a critical theory, very like, post-modern studies kind of program. And a lot of people would take it because all the papers were a maximum of one page. So how hard could it be? It turns out it is really hard, especially when you’re working with really complex ideas. So, for me personally, if I just have a format constraint, I’ll spend way too long trying to make it perfect. So, it’s the duality of the format and the time constraint that I’ve found really helpful for me to not let myself negotiate out of the constraint.

The other thing is that One Page doesn’t need to be one page of text. One page can be one page that you’ve sketched out. It can be one drawing with some text around it. You know, I work with people who are very visual. I’m not a very visual person. But One Page / One Hour can be one page of visuals. It can be one slide. You can use visuals within that format to communicate between people who are more words-oriented and people who are more visuals-oriented.

As to the question of how to share it, the timing of this is perfect. I’ve been using this technique a lot, which I’m planning to write up later today called the “Synchronous Sandwich.” The synchronous sandwich is how I’ve been structuring almost every meeting and activity that I do remotely in particular. And a synchronous sandwich is: an asynchronous pre-read, a synchronous meeting, and an asynchronous follow-up. In other words, you send something through as a pre-read, using a lot of these same concepts. So, you time box how long you expect somebody to take to send the pre-read and how long it will take them to read the pre-read. Then you work through the document or do something synchronously together, and then you send through a follow-up or a revised copy of that deliverable or whatever it is afterwards.

I’ve been really lucky because in a lot of my coaching work, I’ve worked with people who are not afraid to raise questions and challenges. And when I started doing more of this synchronous working through things, some of the people I coached said, “you know, for me personally, I need a little time to think about it before we go into a meeting. I don’t like being on the spot. I don’t like showing up and you’re asking me something I haven’t had a chance to think about until we’re in the meeting together.” So, I found that that synchronous sandwich format gives people who need a little bit of time to process offline, a chance to do so.

You’re really structuring and using that synchronous time well, and then you have a chance to follow up afterwards. A lot of the day-long whiteboard-y type sessions I used to do in person are now three, one and a half hour synchronous sandwiches. We have a chance to pre-read work together, regroup, pre-read, work together, regroup, and… it works really well with One Page / One Hour-style documents so that we can actually work through the document, edit the document together synchronously, and still have a chance to do some of that preparation and pre-reading asynchronously.

Granularity of problems

Jorge: That makes a lot of sense, and this sounds like a really good approach. I love this idea of the synchronous sandwich. It sounds like something that can be applied even to other ways of working, you know, beyond the One Page / One Hour. I’m wondering if there are some types of… I don’t like using the word “problems?” But some types of issues that you’re working around that lend themselves better to the One Page / One Hour approach than others? And I’m wondering specifically about granularity. If there are some… I’ll use the word problems, why not? That are small enough to be dealt with in a One Page / One Hour format versus others that are so huge that maybe you need to pull back too far for it to be useful.

Matt: It’s so it’s so funny because that was how I approached this work at first as well. I was thinking of it for more granular issues One Page / One Hour would be a more accessible and more valuable approach. A year into this, I actually feel the exact opposite way. That the bigger and more strategic and more high-level something is, the more important it is that you take this One Page / One Hour approach and involve more people earlier on.

I’ve been finding myself in a lot of coaching conversations with product managers, hearing people say to me, “we’ve got to put together a strategy for my team. So, I need two weeks to come up with a strategy.” Which is dangerous when you think about it, because if one person goes off for two weeks and crafts this impeccable-seeming team strategy, the team might not feel invested in it. But that person who came up with it is going to feel really invested in it.

So, I’ve been finding for some of these high level, really big picture challenges, One Page / One Hour is actually the best possible approach. I’ve had some coaching conversations where I’ll say to our product manager, “all right, we’ve got a half hour left on the call. Let’s draft our strategy now. Who are we solving for? What problems are we trying to solve? How will we know if we’ve solved them? Great. Bring that to the team and see what they think!” So, the kind of paradox of One Page / One Hour is that the bigger and more difficult to granular-ize a problem seems? The more transformative a One Page / One Hour approach can be, which has genuinely surprised me.

Closing

Jorge: That is so exciting to hear that and intriguing. And I also think that it is a good place for us to wrap the conversation. I definitely want to learn more and I’m expecting that folks listening in want to as well. Where can folks follow up with you?

Matt: Yeah. So onepageonehour.com is the website. We just worked with the fantastic team at Design Stack to revamp the site. So, we now have some templates and resources, some kind of “One Page / One Hour — Getting Started” if you are somebody who is terrified of a blank page, as many of us are. You can see a list of all the people who’ve taken the pledge. You can take the pledge yourself and add your name to the website. I am still — manually, I receive an email every time somebody takes the pledge and I go into our website and add their name and go into MailChimp and add their email address, if they’ve requested so. You can join the mailing list where we communicate with each other and share our own experiences and tips and tricks. So, onepageonehour.com is definitely the place to start.

Jorge: Fantastic. Matt, thank you so much for being with us.

Matt: Thank you so much. This was such a great conversation. I appreciated the questions very much.

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