Old music, new music, and our not-so-new fear of technology

I get these weird obsessions sometimes—a thing that starts small in my head until it becomes all-consuming for weeks on end. Maybe you can relate? Anyway, my current obsession is centered around jazz, and how much we can learn from it about technology, how we listen to music, and yes, even design.

If you follow me on Twitter you’ll know that I just finished reading How to Listen to Jazz, a book I thoroughly enjoyed. I shared screen shots of some of my favorite sections from the book here, but suffice to say it is about so much more than jazz, and I highly recommend it not just for music lovers, but for anyone who works in a creative role.

Right on cue, as so often happens on the internet, I came across Ken Norton’s excellent post Please Make Yourself Uncomfortable, about some of the leadership lessons we can learn from great jazz records (especially the all-time best one, Kind of Blue):

Miles, Ella, and Duke were adept at guiding their bands into the optimal anxiety zone, making them restless and opening up a space where they could create masterpieces. Such talent is also needed in product management. So much of what we’ve learned, our instincts, are to do the complete opposite. We’re told to minimize risk, communicate a clear plan, and document every step. As product managers, our most important job is to help our teams find the place of optimal discomfort—the goldilocks zone of ambiguity and uncertainty.

The same day I read Gretta Harley’s The Slow Listening Revolution, about why she still has a vinyl collection:

Why vinyl? Commitment. In this mid-second decade of the 21st century, music is being taken for granted on a collective scale. An entire generation of music listeners will never pay for music, nor do they believe that they should. The long form music medium has taken a back seat to song culture, yet the average person only listens to a song for approximately 24 seconds before deciding if it’s worth their time to continue to listen. I ponder the substantive value of something that our capitalistic, corporate-model culture places on “free.” When we can listen to a whole song, or usually only 24 seconds of a song without paying for it, do we really value the music? I wonder if we listeners are as committed to music as we were pre-internet? I really like the internet, so these words are in no way a complaint or indictment, but merely observation.

All of this—jazz, new music, old habits—came together as I picked up Dire Straits’s 1985 CD Brothers In Arms, which in some versions had this cover:

It used to be that proclaiming “A FULL DIGITAL RECORDING” was a selling point. Now, the first thing I look for when I buy an album is the phrase Mastered from the original master tapes, a sure sign of its 100% no-digital, analog-only experience.

Or, wait, maybe we’re just being anti-technology in our criticisms of digital music? There has always been a reluctance to adopt new things—a longing for the past and how things used to be. Clive Thompson gives us another example of this historical skepticism in That cursed newfangled technology, “electric lights”:

Robert Louis Stevenson penned “A Plea for Gas Lamps” in 1878, hoping to dissuade London’s authorities from installing obnoxious electric streetlamps like those in Paris. “A new sort of urban star now shines at night,” he wrote, “horrible, unearthly, obnoxious to the human eye; a lamp for a nightmare!”

So I don’t think we’ll solve this particular “which one is better” musical argument any time soon. But if history teaches us anything, it’s that it’s not a new argument, so we should just roll with it. And rock with it1.


  1. Sorry, that’s a really bad joke. I’ll see myself out. 

How to make a product roadmap in 4 days

I just published a big post on our company blog about how we came up with our priorities and roadmap for Postmark for the next few months. From the intro to How we built a product vision and roadmap:

So, armed with some whiteboard markers, a mountain of sticky notes, and one very enthusiastic team, we set off to plan out the next few months of our product. In this post I’d like to give an overview of what we did, why we did it, and how it’s going to help us (and our Postmark customers!) in the coming months.

This one took a while to write and edit, and there’s some nice illustrations as well as downloadable templates, so take a look!

Talk slides: User research challenges and solutions for the enterprise

Today I’m lucky enough to attend Industry Conf in Newcastle, and also do a talk on user research in large enterprises. Industry is a fantastic conference to speak at, and it’s run by one of the best and nicest people in our community—Gavin Elliot. I can’t say enough good things about the conference organization, the venue, and the quality & usefulness of the talks we’re exposed to here.

The slides for my talk, entitled User Research Challenges and Solutions for the Enterprise, are embedded below. For a more detailed write-up you can download a free e-book I made with the folks at UX Pin, called Practical User Research for Enterprise UX.

I want to thank Gavin for giving me the opportunity to speak at Industry this year. I had a blast!

Remote work, open offices, and focus

I recently started a new remote role as a Product Manager at Wildbit. And by “recently” I mean I’m on Day 4, so my experiences with full-time remote work is demonstrably limited. That said, there is one thing so far that I appreciate more than anything else about working in a dedicated office space in my basement: The Calm.

I say The Calm with due reverence because I don’t just mean quietness (I have music playing most of the time). I mean the relaxed ability to work focused and uninterrupted for long periods of time. The joy of this kind of work environment is hardly a new discovery, but since I’ve always worked in open offices this is a brand new and extremely joyful thing for me.

I suspect this is also the reason why everyone in our main office in Philly has their own office. It’s not that I (we) don’t like people. It’s that I get so much more done in a day while working in an environment where I’m able to shut everything else out and just work. The problems with open offices are well documented, of course. From The Economist’s Inside the box:

Open-plan offices are noisier and more interruption-prone. Too much noise causes high blood pressure, sleep problems and difficulty in concentrating. And cubicles’ flimsy walls do little to dampen sound. In studies where sound levels were raised from 39 to 51 decibels—roughly equivalent to moving from an average living room to a road with light traffic—participants were more tired and less motivated.

From Maria Konnikova’s The Open-Office Trap:

In 2011, the organizational psychologist Matthew Davis reviewed more than a hundred studies about office environments. He found that, though open offices often fostered a symbolic sense of organizational mission, making employees feel like part of a more laid-back, innovative enterprise, they were damaging to the workers’ attention spans, productivity, creative thinking, and satisfaction. Compared with standard offices, employees experienced more uncontrolled interactions, higher levels of stress, and lower levels of concentration and motivation. When David Craig surveyed some thirty-eight thousand workers, he found that interruptions by colleagues were detrimental to productivity, and that the more senior the employee, the worse she fared.

And yet, despite all the evidence against it, open office plans persist in most companies, and will for a long time to come.

But yeah, it’s Day 4. Let’s see if I go crazy after a couple of weeks…

Boxes and arrows: more powerful than we think

Alex Maughan voices some things I’ve been thinking about as well in a great post on user journey mapping. After one particular project he observed this:

This user flow may seem an obvious solution, but it wasn’t obvious to the company hired to design the app before I got involved, which had up to that point resulted in some very limiting and confusing design flows. I don’t say this to blow my own horn. The point I’m making is had they explored the designs with some rough, high-level journey sketching upfront, they probably would have realised this themselves.

I’ve become increasingly convinced that there is no complicated design problem that can’t be solved with a few hours of collective thinking and some boxes and arrows. Yeah, I get some eye-rolls for my boxes-and-arrows reliance sometimes—especially because the outcome sometimes feels just too simple. But I’m with Alex on this one—these things are only simple in retrospect.

I recently worked on a project where we had to figure out the migration paths of 6 different products, and how they will all work together. We were talking for a long time, but we didn’t really get anywhere until I started drawing it out on the whiteboard. The end result was deceptively simple (some parts blurred out because it’s roadmap stuff):

“That’s it?” we all said of what came to be known as the Tron diagram. Yep, we realized together: that’s it. But it took a few hours of discussion and drawing to get us to the “that’s it” state. So this is me adding my voice to Alex’s in saying: never underestimate the power of sketching flows and user journeys to help us solve difficult problems.

Online experiences begin and end offline

A few years ago I almost went insane with commute-madness (which I’m reasonably sure is a thing). We lived in Bloubergstrand in South Africa, and I worked in the city of Cape Town. This meant that I had to be out of the house and on the road before 6am every morning (and leave work before 4pm), otherwise I would spend upwards of 90 minutes in traffic, as opposed to the more manageable (or so I thought…) 50-60 minutes.

It’s a little too soon for me to talk about the effect that commute had on my mental health, so I’ll just say this: I didn’t handle it well.

So I, along with thousands of my fellow commuters, rejoiced when the city of Cape Town extended the popular MyCiTi bus service out to where I lived. My joy was short-lived though. It turned out that even though they extended the bus line, the City decided not to provide parking nearby. So unless you lived within walking distance of the bus stop (which I didn’t) you were out of luck.

This seemed really silly to me, so I asked about it, and found out that the City didn’t want to provide parking until they could prove that the bus line was successful. It doesn’t take much to see the gigantic failure in logic here. The City didn’t want to provide parking until they could see that enough people used the buses, but not enough people can use the buses if there isn’t parking.

We ended up moving back to the city.

I tell this story because I recently got into a discussion with Vincent Hofmann, based on this tweet of his:

I brought up the MyCiTi thing, and then mentioned how different the experience is here in Portland, where I live now. I bike to work every day, and the only reason I can do that is that the end-to-end experience is designed well. It’s not just about the city installing bike lanes. Neighborhoods have to agree to stricter traffic rules. Companies need to provide facilities for safe bike parking and showers. It’s a collaboration between public and private sectors across the city. If anyone doesn’t pull their weight, the whole thing falls apart.

Luckily, in Portland, it all hangs together really well. Here are some photos of my end-to-end biking experience in Portland:

There is, of course, a big product management lesson here. We often spend so much time trying to perfect the experience people have with our products online, and we forget about what happens before and after they get there. And that’s often where the experience breaks down and we lose customers. As an example, I mentioned in my newsletter over the weekend how frustrating it can be if you can’t contact a company after making a purchase:

It sounds obvious, but it is still amazing to me how many companies see support as a liability. Any opportunity to interact with customers is a good thing. Yes, it’s expensive, and “case deflection” is a very effective way for companies to cut costs, but at what cost? A case deflected—either through finding the answer on a forum, or a customer simply giving up when they can’t figure out how to contact the company—is a missed opportunity to build loyalty and get input on your products.

And this, ultimately, is why customer journey mapping is such an essential activity for any product. It forces us to think about designing the end-to-end experience, from long before people get to our site, until long after.

Evidence of the danger of only focusing on the product experience itself is all around us—just look at the way our cities design public transport and bike commutes. Notice the differences between the two examples I shared above—one set up for failure, the other for success. And let that be a challenge to all of us to think about how people experience our products even when they’re not using our products.

Expanding the role of wireframes

I’ve done a fair bit of hand-wringing about wireframes myself (see here and here), so I read Travis LaFleur’s Toward a More Expansive View of Wireframes with great interest. I really like Travis’s approach of expanding wireframes beyond their traditional use:

Rather than thinking of the wireframe as a low-fidelity, grayscale snapshot of what a page will eventually look like, coming further and further into focus as the design is refined, we can embrace a broader view of the wireframe as a thematically rich conceptual model — one that is now depicting page-level details, reinforcing previous models of the system as a whole.

Click through to his post for some examples.

The core elements of healthy, productive teams

Charles Duhigg has a long feature in the New York Times called What Google Learned From Its Quest to Build the Perfect Team. It includes a summary of really fascinating research on the core elements of a healthy, productive team:

As the researchers studied the groups, however, they noticed two behaviors that all the good teams generally shared. First, on the good teams, members spoke in roughly the same proportion, a phenomenon the researchers referred to as “equality in distribution of conversational turn-taking.” On some teams, everyone spoke during each task; on others, leadership shifted among teammates from assignment to assignment. But in each case, by the end of the day, everyone had spoken roughly the same amount. “As long as everyone got a chance to talk, the team did well,” Woolley said. “But if only one person or a small group spoke all the time, the collective intelligence declined.”

Second, the good teams all had high “average social sensitivity”—a fancy way of saying they were skilled at intuiting how others felt based on their tone of voice, their expressions and other nonverbal cues. One of the easiest ways to gauge social sensitivity is to show someone photos of people’s eyes and ask him or her to describe what the people are thinking or feeling—an exam known as the Reading the Mind in the Eyes test. People on the more successful teams in Woolley’s experiment scored above average on the Reading the Mind in the Eyes test. They seemed to know when someone was feeling upset or left out. People on the ineffective teams, in contrast, scored below average. They seemed, as a group, to have less sensitivity toward their colleagues.

So, effective teams are built on equality and empathy. Seems terribly obvious, of course, but I feel like very few teams actually live these values. We can do better.

Build software to feed the world, not eat it

Kevin Slavin’s Design as Participation is one of those articles that stays with you for days. There are multiple ways to read it, but I view it as a thoughtful critique of my primary field of focus: user-centered design (UCD). There have been other discussions on this topic, most notably Cennydd Bowles’s excellent Looking Beyond User-Centered Design, and Mike Long’s Stop Designing for Users. Kevin’s is a worthy addition to the debate.

Kevin’s main thesis is that UCD is selfish (since it puts a user at the center of everything), and we should instead see users as active participants in a design:

Broadly, UCD optimizes around engagement with the needs, desires and shortcomings of the user and explores design from the analysis and insight into what the User might need or want to do. Simply, it moves the center from the designer’s imagination of the system to the designer’s imagination of the user of the system.

But we are no longer just using computers. We are using computers to use the world. The obscured and complex code and engineering now engages with people, resources, civics, communities and ecosystems. Should designers continue to privilege users above all others in the system? What would it mean to design for participants instead? For all the participants?

Also:

Some contemporary work suggests that we are not only designing for participation, but that design is a fundamentally participatory act, engaging systems that extend further than the constraints of individual (or even human) activity and imagination. This is design as an activity that doesn’t place the designer or the user in the center.

If this all seems overly academic, fear not, practitioners! Kevin shows several examples of “Design as Participation” in his essay, and also ends with this call to action:

A new generation of designers has emerged, concerned with designing strategies to subvert this “natural default-setting” in which each person understands themselves at the center of the world.

These designers do this by engaging with the complex adaptive systems that surround us, by revealing instead of obscuring, by building friction instead of hiding it, and by making clear that every one of us (designers included) are nothing more than participants in systems that have no center to begin with. These are designers of systems that participate – with us and with one another – systems that invite participation instead of demanding interaction.

We can build software to eat the world, or software to feed it. And if we are going to feed it, it will require a different approach to design, one which optimizes for a different type of growth, and one that draws upon – and rewards – the humility of the designers who participate within it.

It’s always hard to see one’s views challenged, but Kevin does it in the best possible way here. He understands UCD and why it came about, he presents a compelling argument about its issues, and then he shows us how we can do better.

I don’t think this means the end of UCD (or even that we should stop using its basic methods like personas and usability testing). But I do agree that we need to shift our thinking so that we’re less concerned about the success of an individual user (or groups of users), and more concerned about how different systems interact with each other. Alan Cooper touches on this topic in his wonderful essay The Edges:

What each organization has to do today is to regard the edges of its products with as much diligence and attention as they give the center. The quality of both their outside system connections (known as application program interfaces, or APIs) and their user interfaces demand levels of expertise and investment that have historically fallen short.

As nebulous as Kevin’s idea of “building software to feed the world” sounds, I like the sound of it. I like the hope and the desire to do good in the world that it communicates. We need to make that idea concrete in our daily design worlds, and I don’t think we quite know how to do that yet. But every practical mission starts with a grand vision, and I quite like this one.

Meetings and email: maybe they’re not so terrible after all

There are two things everybody in business (say they) hate: meetings and email. So the past few years have seen a great many startups that try to re-invent, revolutionize, and strategerize the crap out of meetings and email. However, recently we seem to have come to a disappointing realization: meetings and email are the worst ways to get things done, except for all the other ways.

In Meet Is Murder Virginia Heffernan goes deep on the topic of meetings: why we hate them, what people have tried differently, and how we just can’t seem to quit them. Her resigned conclusion hints at what really might be the source of our meeting hatred:

What’s so bad about meetings, after all? At bottom, they are nothing but time with your fellows. Which suggests that hating meetings might be akin to hating traffic, families or parties—just another way to express our deep ambivalence about that hard fact of existence: other people.

Meanwhile, in Slack, I’m Breaking Up with You Samuel Hulick shares his dismay with Silicon Valley’s latest darling company. These kinds of articles are inevitable at this point—we’re almost certainly approaching 6 PM SVT (Silicon Valley Time) for Slack. Anyway, Samuel wrote a break-up letter to Slack, but at times it reads more like a subtle “Please come back!” letter to email. For example:

While it’s true that email was (and, despite your valiant efforts, still very much is) a barely-manageable firehose of to-do list items controlled by strangers, one of the few things that it did have going for it was that at least everything was in one place.

And this:

When work gets done over email, there’s a general expectation of a response buffer of at least an hour or two. In you, though, people can convene and decide on anything at any time.

Also this:

When I started feeling like our relationship was getting to be just a little too much, I decided to take a few days off. That was never a problem when I was with email—I’d just fire up a vacation autoresponder and be on my merry way.

I’ve always liked email (which, sorry, I know, is like a Portlander saying “Oh you just found out about Kale? I’ve been eating Kale all my life!”), and felt that the bigger problem is not the system but the way we deal with it. I tried Google Inbox and that Mailbox thing that Dropbox bought and shut down, but I could just never get into a groove with a system that tries to sort my email for me. Instead I just do something that works really well for me: I read every email, and file each message in the appropriate place when I’m done dealing with it. That’s it.

I’m also not as against meetings as I used to be. My rules there are equally simple: always walk out of a meeting with an artifact. This could be a whiteboard sketch or a note about a thing you need to go research—it doesn’t really matter. Just walk out of there with something. Meetings should focus on facilitating the things that meetings are good at: collective thinking. Meetings that energize me are the ones where most people are standing, working together on a common goal. From customer journey workshops to design studio sessions to analyzing usability testing results, there are plenty of useful ways to spend our times in meetings. That’s my only criterium for a good meeting: make progress.

These guidelines are probably way too simple for the majority of businesses and people. But I do think that when we try to “reinvent” meetings and email we’re trying to solve a people problem with technology, and that’s just never going to work. Technology can help, for sure, but at its core we need to figure out why we hate email and meetings, and then fix that first. And I think the main problem with meetings and email is that we don’t spend enough time taking personal responsibility to make them more effective. Until we stop trying to offload our personal responsibility on the shoulders of technology, nothing will change.

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