Welcome to The Overlap, a biweekly newsletter somewhere between product and org design.
This one’s on why you should really get feedback on that doc (and how it helps your company).
Learning in public is having a moment
I’m excited by the learn in public movement on Twitter. Folks have different names for the same idea: Shawn Wang talks about learning in public, Maggie Appleton talks about digital gardens, Andy Matuschak talks about working with the garage door up.
The core idea is to shift your default from sharing finished work to sharing unfinished work, back-of-the-napkin ideas, and lessons you learn on the way. Here’s Andy:
One of my favorite ways that creative people communicate is by “working with their garage door up,” to riff on a passage from Robin Sloan (below). This is the opposite of the Twitter account which mostly posts announcements of finished work: it’s Screenshot Saturday; it’s giving a lecture about the problems you’re pondering in the shower; it’s thinking out loud about the ways in which your project doesn’t work at all. It’s so much of Twitch. I want to see the process. I want to see you trim the artichoke. I want to see you choose the color palette. Anti-marketing.
By defaulting to sharing your work in progress, you’re:
inviting others to give feedback,
benefiting others who are working on a similar thing, and
creating serendipitous connections.
More from Andy:
I suspect [working with the garage door up] also creates more invested, interesting followings over the long term. That effect’s probably related to Working on niche, personally-meaningful projects brings weirder, more serendipitous inbounds.
As a writer, I couldn’t agree more. The Overlap helped me draw connections between weird ideas, like death, self-governance, and the Hamilton musical. And I’m fortunate to hear from readers. I’ve met interesting people who have been thinking about similar things, just from sending this newsletter every other week.
The downside to building in public? Everyone is doing it. Our Twitter feeds are filled with Notion Docs, Substacks (👋🏽 ), and “meh” tweetstorms. Also, remember Medium? Ah, Medium.
Will this snowball of unfinished work lead to less remarkable work in the long-term?
And, we’ll see even weirder work. Which is good for the internet, in my opinion. Ben Thompson says that the internet enables never-ending niches:
What is important to note, though, is that while quality is relatively binary, the number of ways to be focused — that is, the number of niches in the world — are effectively infinite; success, in other words, is about delivering superior quality in your niche — the former is defined by the latter.
Maybe I’m overly optimistic. But I’ve learned that you can’t write well until you’ve written blog posts that make your future self cringe. I think the same applies to learning in public: remarkable work comes from doing a lot of less remarkable work.
Let’s tolerate the half-baked Notion doc. It might just evolve into the best essay you’ll ever read.
Organizations as works in progress
I’m starting to go back to a frame that I learned during my time at The Ready: progress over perfection. Instead of focusing on the perfect hire, the perfect design, the perfect OKR, or the perfect decision, focus on making progress towards your desired outcome.
Progress over perfection creates that dread in your stomach at 4:30pm when you planned to workout at 5pm. You’re tired AF. You don’t want to do it. But you do it anyway.
From this beautiful essay on how organizations should be like octopuses:
Adaptability and fluidity are superpowers of the octopus. Octopuses are well known for their impressive survival skills—from their ability to fit into impossibly small spaces and regrow lost limbs, to their quick camouflage capabilities and ink that clouds predators’ senses of sight and smell. Companies are fundamentally built for rigidity. Regardless of organizational model, companies tend to be extremely fixed and built for stability. But those structures are often in stark contrast to the pace of change most companies must endure today.
The key shifts for business
Optimize against progress, not efficiency
Align incentives, measurement, and operations around tangible output and progress rather than efficiency.
Progress over perfection is easier said than done. Chances are, your org is optimized for predictability, not adaptivity. You wonder why leadership touts Harvard Business School buzzwords like “adaptivity” and “experimental mindset” when you know you work at a feature factory, waiting for the next feature you need to crank and send down the assembly line. You know your org’s way of working needs to change.
From Martin Fowler’s seminal essay, The New Methodology:
So if you are in a situation that isn't predictable you can't use a predictive methodology. That's a hard blow. It means that many of the models for controlling projects, many of the models for the whole customer relationship, just aren't true any more. The benefits of predictability are so great, it's difficult to let them go. Like so many problems the hardest part is simply realizing that the problem exists.
However letting go of predictability doesn't mean you have to revert to uncontrollable chaos. Instead you need a process that can give you control over an unpredictability. That's what adaptivity is all about.
Adaptivity doesn’t have to feel chaotic. And you, dedicated reader, know how to help your company adapt: get clear on what your org needs to say no to, iterate your process as if it’s a product, and never skip retrospectives.
I think learning in public shows us another way to build adaptivity in our organizations. That way is to default to sharing unfinished work.
Default to sharing unfinished work
To nudge your organization towards adaptivity, share unfinished work with your colleagues early and often. And yes, share it with your manager.
You’ll end up solving the right problem. You don’t want to waste time solving the wrong problem. If you get feedback from the right people earlier in your creative process, you’ll end up solving the right problem.
You’ll prevent misalignment. Or more positively put: you’ll be an alignment catalyst. If a PM asks you to mock up wireframes of the spec they put together, chances are, no one knows you’re doing this work except your PM. What if another designer ends up doing the same thing?
Your work will end up being used! Nothing is more fulfilling than your hard work being used.
Three common responses I hear:
“I have high standards for my work.”
“It’ll reflect poorly on my performance.”
“My team expects nothing but quality.”
Sharing unfinished work is counterintuitive. I know. I used to think these things. I still do. But here’s what helps me.
Don’t prove value. Create it.
Several times, I’d work four to sixteen hours on an essay, presentation, or diagram. I’d rarely ask for feedback early on. I’d ask for feedback only when I thought my work was 95% done. Almost every time I do this, I learned that I was working on the wrong problem. If I worked towards a different direction, my deliverable would be 1000% more valuable.
Here’s what I learned: When I do this, I want the deliverable to reflect how impressive I am. How you should see me as valuable. How you should take me seriously. As a result, the deliverable isn’t valuable to my client, team, or organization.
My longing to be seen as valuable makes my work less valuable. Therapy-level stuff, I know.
So, I remind myself to share unfinished work.
In 2019, I wrote:
Before diving into any project or piece of work, ask yourself two questions:
“What’s the impact I want to make?”
“Will I reach the impact I want to make by doing this thing?
If your answer to 2 is a yes, do that thing.
If your answer to 2 is a no, don’t do that thing. Figure out what you need to do instead to reach that impact.
If your answer to 2 is “I’m not sure,” you probably need more information. Ask for advice from a trusted friend or colleague. Do a small portion of the work you’re trying to complete, look at the data, and evaluate whether it’s on its way towards making that impact or not.
Turns out I was writing to my future self.
As Tom Critchlow points out in The Consultant Out of Time:
The key here is delivering unfinished work. Delivering a WIP solution allows you to iteratively uncover the clients’ reaction, and find out what they’re going to do with it.
You might just change your company
My colleagues and I share unfinished work with each other all the time. We share Figma links of unfinished designs, client presentations we’re noodling on, Roam links to our notes. We work on design problems with our clients. And we joke that everyone on this team is a “process head” because everyone loves improving our process.
Here’s what I’m proud of: an improvement in our own process led to an improvement in our broader organization’s process. Knock on effects!
We’re currently working on a content architecture project. This project is complex. It serves different kinds of content. It shares content through different mediums (text, video, audio). And it’s meant to meet the needs of several types of users.
We needed help from a technical lead: a developer who can help us nail the content and data model so that we don’t waste a ton of time during development. But as a client services studio, we’ve always scoped design and development as separate engagements, both scoped and billed separately. Meaning designers and developers usually work on different projects.
We realized that design and development as separate workstreams works for predictable projects. This content architecture project was less predictable. As Martin Fowler mentioned, “If you are in a situation that isn't predictable you can't use a predictive methodology.”
So we adapted our approach for this project to include developers in our design process. It sounds simple, but it’s been a gamechanger.
Here’s the rad part: Our change to including developers in our design process produced a knock-on effect: including designers and developers in our discovery process. Our studio gets tons of interesting, yet challenging work, so there’s a lot of uncertainty to reduce. So, we’re now teaming dynamically: where strategists, designers, and developers start product discovery together.
Since then, we’ve signed two engagements in this dynamic teaming model! And our clients have responded well to it. One client shared, “We’re glad to work with a studio that works the way we prefer to.” Baller.
Of course, it’s a work-in-progress. We’ll continue to learn and adapt. We intend to write more about this on Sanctuary’s substack, which you can subscribe to here. (Spoiler, we have a post coming out tomorrow about our journey of becoming a decentralized organization.)
Your challenge: Share WIP this week!
Sharing unfinished work helps you provide the most value possible. It increases the quality of your work because you get the right feedback at the right time. And it nudges your organization to adapt.
If you need even more motivation, check out Matt Lemay’s One Page / One Hour. The gist: spend no more than one page and one hour working on any deliverable before sharing it with your colleagues:
If we want to spend less time working individually on decks and deliverables, we need to spend less time working individually on decks and deliverables.
One Page / One Hour is a small promise that makes a big difference—a promise to spend no more than one page and one hour working on any deliverable before sharing it with your colleagues.
Your challenge: do it within the next two weeks! And if you do it, write a comment here to let us know how it goes.
🚀 My team just launched our site
Manhattan Hydraulics is a down-to-earth studio that designs and ships remarkable products.
In October 2019, we started as Sanctuary Computer’s UX design arm. Since then, we've been working on challenging product work and shaping our own way of working. Today, we shared our identity with the world!
Our studio is popping off with work right now, but we love a good chat with a smart, kind human.
Reach out to us at email@example.com.
What I’m reading
Compassionate action over empathy - Tatiana Mac
How good product strategy makes decisions easier - Adam Thomas
Brand Designer at Murmur. Murmur aspires to be the Github for working agreements. The idea is that any team can remix other company’s parental leave policy, OKR structure, or performance review framework. Full transparency: I am a shareholder at The Ready (as a former employee), the company that incubated Murmur. If you know a rad brand designer who wants to help teams work better together, send ‘em to this link.
Product Manager at Bella. Bella is a financial services company that offers a fun, compassionate, and user-friendly banking experience. I think what’s most cool about Bella is their Karma account: a stranger can securely spot your coffee or meal purchase, and you can do the same for others. If you’re a product head interested in financial services, consider applying!
See you in two weeks,
Thank you Simone Robert for feedback on an unfinished draft of this essay!