When friction in software is not a bad thing

Clive Thompson digs into software that aims to add friction to our lives in his Wired essay We Need Software to Help Us Slow Down, Not Speed Up:

It’s certainly possible to slow our software, and thereby ourselves. But it’ll happen only when we become too unsettled by the speed of our journey.

His post reminds me of some other ideas I’ve read about this in the past. Chris Palmieri in A Practice of Ethics:

But some friction is borne of respect, when we present information about the choices available to users and help them make better decisions. An emailed invoice could remind a customer they were paying for a service they no longer use. A checkbox could assure a user of their current content privacy settings before posting a sensitive photo. Recognition of a past purchase can save a customer the hassle of having to return a book they already have, or confirm that they are re-buying exactly the same shampoo.

And here is Andrew Grimes in Meta-Moments: Thoughtfulness by Design:

Meta-moments can provide us with space to interpret, understand, and add meaning to our experiences. A little friction in our flow is all we need. A roadblock must be overcome. A speed bump must be negotiated. A diversion must be navigated. Each of these cases involves our attention in a thoughtful way. Our level of engagement deepens. We have an experience we can remember.

Not all friction is bad…

Vinyl Me, Please and the power of product thinking

I’ve been a Vinyl, Me Please customer since January 2015. Back then things were pretty basic. For roughly $25/month they would send you a “Record of the Month”, along with a custom art print and cocktail recipe. It was cool, and helped to expand my musical palate quite a bit.

But sometime over the over the past year or so they kicked things into high gear. VMP now offers a “Classics” track (my favorite!) and a “Hip Hop” track in addition to their “Essentials” track (the original “Record of the Month”). But what’s even more apparent now is how Vinyl Me, Please has grown into a role model of how to provide value to music lovers in the digital era. The thought and care that went into this month’s “Essentials” release proves it once again.

I noticed yet another example yesterday. The Vinyl Me, Please store now shows the “nutrition content” of each record they sell:

Vinyl nutritionn facts

Ask any vinyl collector and they will tell you how much this small detail improves the shopping experience. This is all the information we usually have to hunt for on product pages and do multiple Google searches about — but presented in a consistent, easy-to-read format. It’s such a relief and a breath of fresh air.

I’ve seen quite a few attempts to define “product thinking” lately. This example, to me, sums it up perfectly. “Product thinking” means gaining a deep understanding of what users need and what kind of friction they experience, and then providing a product solution that makes that friction go away in a delightful way.

Teens, cheap Instagram marketing, and our weird future

I continue to be fascinated by Instagram’s cultural and economic impact. Taylor Lorenz writes in Posting Instagram Sponsored Content Is the New Summer Job:

Helen Boogzel, CEO of Boogzel Apparel, said her company receives a steady stream of messages from young people — almost universally girls — looking to make extra money, and that teen marketing has been critical to the young company’s growth. “Some companies buy positive reviews or try to get into fashion magazines,” she said. “That’s fake and it kills your brand. It’s better to work with teenagers directly and know their honest opinion about your brand. Our clothes are inspired by culture and the internet. Young people create this culture.”

They also, crucially, don’t charge much: Depending on the teen’s audience and experience, most shops typically pay $5 to $20 for a post.

“Teenagers are more affordable to work with because of their follower count and age,” said Christy Oh, an 18-year-old who handles marketing for DouxLashes, which sells fake eyelashes. “They’re not doing insta as a full time thing, they’re just trying to make extra money, so it’s not super expensive to partner with them.”

Here are a few other interesting articles about Instagram’s impact and… bizarreness:

How not to run a remote team

In their article 5 Best Practices for Running a Successful Remote Team, “Sparky” writes:

All team members should have their working hours posted publicly, so colleagues know when they’re “on the clock,” so to speak. If you have a hybrid environment where some people are remote and others aren’t, this will help alleviate pressure on the remote employees to feel like they always have to be available. […]

It’s also a good idea to schedule daily syncs with remote people, as well as weekly feedback sessions where you can dive deeper into anything that needs a course correction.

I’m excited about this awful advice because I get to tell you one of my favorite Wildbit stories.

I joined Wildbit a week before our yearly in-person retreat. It was a little daunting but really exciting to meet everyone I would be working with mostly remotely. Anyway, one of our team sessions was a discussion about the tools we use, and specifically Slack. Up to that point we had this unwritten convention where everyone would say “Hi!” and “Bye!” in the #general room when they come and go. Remote workers went a bit further with messages like “Stepping away to make coffee!” During our discussion it became clear that no one — no one — liked this. It caused noise, didn’t add any value, and just felt like a chore.

At that point I spoke up and mentioned that I think the reason why remote folks tend to tell everyone when we’re getting coffee or lunch is that we don’t want it to look like we’re slacking off. I said something to the effect of, “I don’t want everyone to think I went to a movie in the middle of the day, or something!” The answer I got to that statement was not what I expected. Someone said, “Well, what’s wrong with that? Maybe you needed to go to a movie to clear your head so you can come back later, refreshed and ready to go!”. If I recall correctly, my response to this was, “Uh, this thing where you guys all trust each other? It’s really weird…”

We all had a good laugh together, but I learned pretty quickly that this is just how the company works. The two things that make Wildbit’s remote culture different are:

  1. We all implicitly trust each other.
  2. We optimize for asynchronous communication.

We do this because we learned something that should be painfully obvious. When people have the freedom to work when they are feeling their best, they do their best work, and they enjoy the work more.

So anyway, back to “Sparky”. I don’t want to tell people how to live their lives, but that advice really is terrible. It’s the type of advice you give when you believe the purpose of remote work is to replicate an office. Once you realize that the purpose of remote work is to enable everyone to do their best work, everything changes.

I guess my one piece of advice for remote cultures is this: try trusting each other first. Imagine what your work environment would look like if every employee is trustworthy. And if that’s too difficult to imagine, maybe ask why you’re not able to trust your employees.

Products as functions

I’ve been really intrigued by Ryan Singer’s thinking around Products as Functions:

Products are easier to reason about when you think of them as functions. They transform an input situation into an output situation.

This lets you describe what the product does as a transformation of the user’s circumstance instead of a bundle of features.

I’ve been using this thinking on a new project we’re working on at Postmark. I like this approach because it gives us a framework to communicate why something is a good idea to work on, and it focuses on the benefit for customers. If our answer to the question “How much better is this new outcome?” is “Not better enough”, then we need to define a better Output situation, which would lead to a better Process.

Is it a bug or a feature?

Nicholas Carr chases down the origin of the phrase ”It’s Not a Bug, It’s a Feature.” This bit stuck with me:

INABIAF—the initialism has earned a place in the venerable Acronym Finder—is for programmers as much a cri de coeur 1 as an excuse. For the rest of us, the saying has taken on a sinister tone. It wasn’t long ago that we found software ­dazzling, all magic and light. But our perception of the programmer’s art has darkened. The friendly-seeming apps and chatbots on our phones can, we’ve learned, harbor ill intentions. They can manipulate us or violate our trust or make us act like jerks. It’s the features now that turn out to be bugs.

It seems that more and more, we simply don’t trust our software any more. And I don’t think that’s a bad thing.

  1. I googled this so you don’t have to. It means “passionate appeal, complaint, or protest.” 

The Instagram Generation

The truth, then, is this: our generation was raised with an understanding that the image we portrayed mattered more than who we actually were. We believed this not out of some malevolent, externally imposed agenda, but because it was actually true. The result was that nothing we ever did felt organic; instead, everything felt like a checked box. You played sports to prove you were competitive. You took classes to get grades, those wonderful letters that separated friends and induced panic attacks and never really went away and felt like the world for as long as I can remember. You took AP classes because they were decidedly not interesting; they were just faster, and for that reason, better signals of competence. You participated in extracurriculars because if you didn’t, there would be more empty boxes on your applications than there would be on those of your competition

— Zander Nethercutt, The Instagram Generation.

The uncertainty of friendship

The most fatal disease of friendship is gradual decay, or dislike hourly increased by causes too slender for complaint, and too numerous for removal. Those who are angry may be reconciled; those who have been injured may receive a recompense: but when the desire of pleasing and willingness to be pleased is silently diminished, the renovation of friendship is hopeless; as, when the vital powers sink into languor, there is no longer any use of the physician.

— Samuel Johnson, No. 23. Uncertainty of friendship.

Remote product management: challenges and opportunities

Even though more and more companies are getting comfortable with remote work, the field of product management still seems to push back against this trend quite forcefully. There is a general sense that product managers can’t do the things they need to do unless they are physically located with their teams. This has some ironic consequences, such as that Slack — a company that builds a tool “where work happens” — doesn’t hire remote employees.

I confess that at first I was skeptical as well. But as we started to work together and make progress at Postmark, my skepticism fell away. I do believe it’s harder to make the product management role work remotely than some other roles like customer success or development. But it is possible, and I believe that companies need to start being more open to hiring remote product managers.

We often hear about the drawbacks of remote work, but it’s important to remember that there are certain things that remote work is naturally better suited for than on-premise work. Most importantly, remote work makes it much easier to develop and instill a rhythm of collaboration and focused time for a team. This rhythm will be different for every team, but I like to think of it as a wave. Here’s one example of what a cycle of private and public work could look like in a team:


Because it’s easier to shut down distractions as a remote worker, the deep work part of that cycle can be immensely efficient and dramatically increase both the speed and quality of work that gets done.

But of course, we can’t ignore the parts of remote work that are challenging and need to be figured out. So in this post I want to share a few lessons I’ve learned over the past 2 years that have helped me to overcome some of the more severe challenges to being an effective remote product manager.

In-person time is still important (but maybe not for the reason we think)

I joined Wildbit at the right time: one week before our yearly in-person company retreat. That gave me an opportunity to meet everyone in person, work together, and most importantly, have meals together. Once you’ve eaten a meal with someone, they’re not an anonymous “colleague” any more. Which means that when conflict arises (and of course it will), you’re way more likely to work through it kindly and respectfully. It’s very difficult to be mad at someone you’ve broken bread with.

The point is that in-person time is extremely important for remote teams. But you don’t need it every day, and the reason you need it is not to get more work done. The reason you need it is to sustain the human relationships that will enable you to get more work done.

When I spend time with our team in person, yes we spend quite a bit of time working together in meetings. But the biggest value for me is the lunches, the coffee chats, and the after-work catch-ups. That’s where we begin to see each other as whole people, and it’s at the core of our ability to work together and grow together.

This is certainly true for the whole team, but it’s especially true as a product manager, where your ability to do your job lives and dies with your ability to have good relationships with the team.

Love your tools (and be prepared to do a bit more of the heavy lifting)

One of our principles at Wildbit is that we optimize for asynchronous communication. We don’t hate meetings. We just value focused work extremely highly, so whenever we can we try to protect that work by giving each person the opportunity to work on something when it’s best for their schedule.

To make this work, you need tools. And those tools have to be light-weight and not a pain to use. Sure, we use Slack (although we’re trying to wean ourselves off it), but most of our collaboration work happens in Dropbox Paper and Basecamp. Those tools are designed for the type of collaboration and asynchronous communication that feels good. It can’t be overstated how important it is for remote teams to love their collaboration tools. If everyone hates the tools, the work will find a way to not get done. You’ll end up blaming “remote culture” and hire an onsite product manager, when the problem lies with crappy tools instead.

The catch is that these tools are just like comments on the internet: if you want them to be useful, you need to be prepared to spend quite a bit of time managing the process and the flow of information. As product manager a big part of my role has become making sure the right people know about things, and the wrong people don’t get distracted by things they don’t need to be involved in. This needs time and care, and doesn’t just happen automatically. The good news is this will still take way less time than “back-to-back meetings” every day…

Make prioritization and planning a team effort (and embrace the benefits of that)

Prioritization and planning of work is difficult under the most ideal circumstances. When you’re working on a remote team, the challenges are even bigger. This is where a combination of the right tools and some deliberate time management can make all the difference. The thing is, we know we do better work when all of our team’s perspectives are taken into consideration — not just in terms of the details of a project, but also what we should work on.

As product manager my role in the prioritization and project planning process is way more traffic controller than it is decider. We use our asynchronous tools to discuss ideas, post and gather feedback on initial drafts of plans, and occasionally even make radical changes to a plan as we learn more from customers and everyone on the team. My one goal is to keep the conversation going. It can be a little chaotic at the start, but I always feel like we end up in a better place than if we used a more traditional prioritization process.

Being a remote product manager is not without its challenges. It can be difficult to get the whole team aligned around a common vision, and you’re not always going to be able to get your questions answered right at the moment you want it. But if you can find a way to focus on and nurture the benefits that are unique to remote work, the challenges tend do get pushed to the background.

To put it another way, I understand why people think that product management isn’t a role that can be done remotely. There’s a lot of team communication involved, and of course that can be challenging over electronic channels. But with a slight shift in the lens you view product management through, those challenges fade away as the benefits of deliberate focused work and carefully considered collaboration come to fruition. I’ll say this: it’s totally worth it.

A pragmatic approach to digital ethics

Cal Newport has some thoughts on the “digital ethics” movement. In his post Beyond Digital Ethics he argues that large companies will never turn their backs on revenue just because it’s “the right thing to do”:

Instead of quixotically convincing some of the most valuable business enterprises in the history of the world to behave against their interests, we should convince individuals to adopt a much more skeptical and minimalist approach to the digital junk these companies peddle.

We don’t need to convince YouTube to artificially constrain the effectiveness of its AutoPlay algorithm, we should instead convince users of the life-draining inanity of idly browsing YouTube.

This approach will be challenging too, because we are up against some really strong brain psychology. As Don Norman notes in Why bad technology dominates our lives:

Curiosity is, on the whole, a virtue. We have evolved to be curious. Our nervous system is especially sensitive to change, and changes in the environment attract attention. But the technology-centered view labels this natural, creative trait as a liability: Curiosity is renamed as distraction. A human virtue is now turned into a liability.

Worse, many businesses have learned to exploit our curiosity. The continual bombardment of tantalizing tidbits of information deliberately designed to grab our attention away from other, potentially more valuable activities are distractions that can lead to accidents, injury, and interpersonal problems.

We are in uncharted territory and there are no easy solutions.


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