We’re all works in progress – a collage of our intentions, a Frankenstein of the things we already are and the set of things we want to be.
To that end, Working Assumptions has been a way for me to workshop long-contemplated ideas. Writing them out and collecting your feedback on them has matured my arguments. Despite the progress I’ve made, I still think that all of these ideas remain works in progress.
As a result, it’d be silly to write my posts once and leave them at that – the benefit of publishing something on my own platform is that I can revise my posts to make them better. In the words of a now canceled hip hop artist who takes up too much space in my brain, “ima fix wolves.”
This week’s 10 links are actually posts I’ve already written that you’ve helped me improve. I updated them based on discussions we’ve had, notes you’ve sent me, and thoughts you’ve sparked. Thank you for engaging, it means so much to me.
The Independent Thinker’s Guide to Product Process
My goal in publishing this post was to help guide implementers of product process do better. Bad processes are cargo-culted from other companies. Good process is actually generated as a response to the specific pain of the organization.
When I published this post, friends gave me the following feedback: “Reading this with the “young head of product” hat on, it’s hard to implement these principles. It’s because these items are often in tension, and figuring out where to sit on the spectrum of these conflicting principles (all of which individually make sense) is the hardest thing for me to do.”
Very fair feedback, and I went through each principle on my list to better flesh out the tension and make them easier to operationalize.
Ultimately, the way to navigate the tension between the conflicting principles is to think very intentionally about the nature of the business model and the nature of the team in question. Let’s say you were navigating the conflict between two of my principles: “you say that good product process is about alignment on the problem area and not nitpicking solutions, yet you also say to not shy away from being directive – what gives?!”
To navigate that tension, first think of the business model. Ivan from Notion and MLM spoke about the Stripe model of product review and how that didn’t apply at Notion, because Stripe’s product suite was more decomposable than Notion’s. Notion needed to be nitpicky and directive about the compatibility between products.
Next, think about the team. If the team is junior, if the organization is especially information siloed, or the upside in a particular opportunity is pretty minimal, you should err on the side of directiveness.
What I’ve learned in my first three years as an executive
I met with a founder who asked for advice on hiring a head of product. “So, I read your substack post on being an exec,” he said. “And at the end, you mention that you cared a lot at Stripe and found it hard to care at Watershed. How does that work? Do you know how to make yourself care? How can I tell if someone’s going to care, so that I can hire the right person?”
He’s referring to the closing part of the post, where I talk about how “being an executive is like being in an arranged marriage.” Like in an arranged marriage, an executive might commit because the partnership looks good on paper. But making the partnership successful goes beyond doing one’s duty – it requires falling in love.
I expanded on the post with my response to his question. “As an executive, you have to fall in love with at least one of two things: the why or the how. You could fall in love with the mission of the company. Or you can fall in love with the process – maybe you are a VP of Engineering who loves getting the team’s uptime to 99.999 and don’t care about the mission.
You cannot expect an exec who loves the specific team, or loves the success, to truly fall in love with the company itself. Loving the team means they’re loyal to the people over the company, and you’ll see that difference when you want them to act “ex officio.” Loving success is too mercenary, and they’ll quit at the first sniff of decline. When you’re looking for someone, look for the kernels of “why” love or “how” love. Don’t get tricked by their affinity for success or specific team members!”
Note to past self
This is my favorite post that I’ve done. I was so touched by your replies. I have made a bunch of copy edits and cleaned up some ideas.
Anxiety is the dizziness of freedom
This is my least popular post! I got so many emails and texts from friends saying they really disliked it. The gist of the feedback was that it was more of a book review instead of a real post on my thoughts regarding the choice paradox. I love getting critical feedback, and may do a new post on the “Tara-thoughts” some time. However, there was an email reply that I thought was a worthy addition to the current “book review”:
From K.:
[When I met Ted Chiang, he told me how he writes UX first. He’s a technical writer at Microsoft!] He used Anxiety is the Dizziness of Freedom as an example. He first imagines what the machine does within the sci-fi conceit. What dials does it have? Which parameters are important to be available to the user? Then he uses the realizations of this exercise to create a story around it. This makes sense given his day job. And also explains why his sci-fi is so much better than everyone else.”
It is so funny to me because it’s the exact opposite way we design software/hardware – user story first, spec second. His stories are spec first, user story second.
The downside of mental models
Mental models are a dangerous weapon.
Quoting a friend, S.:
“Some people "integrate knowledge" naturally. The labels that Farnam Street provides reminds you of things you have integrated. Others don't and the labels are just the handle of an empty suitcase (as you might remember from Creativity Inc.) People that don't integrate knowledge know they’re missing something, and then try to make it up by collecting mental models. I don't think that helps them too much.”
Creativity Inc.’s Ed Catmull:
Imagine an old, heavy suitcase whose well-worn handles are hanging by a few threads. The handle is “Trust the Process” or “Story Is King”—a pithy statement that seems, on the face of it, to stand for so much more. The suitcase represents all that has gone into the formation of the phrase: the experience, the deep wisdom, the truths that emerge from struggle. Too often, we grab the handle and—without realizing it—walk off without the suitcase. What’s more, we don’t even think about what we’ve left behind. After all, the handle is so much easier to carry around than the suitcase.
Growth Gear
My friend works at a big, multi-national company that does “financial structure for the internet.” We’ll call it Polka Dot. This friend asked the following question about my Growth Gear post: “Makes sense. I still struggle with the question of lieutenants. When you have a CEO who has delegated a lot of power to a VP layer, how do you pick which teams are in Growth Gear? Do you leave it to the CEO? Do the VPs decide? Do lieutenants decide for themselves?”
Everything gets harder when the organization has so many layers! In Growth Gear, the idea is that most people should focus on execution over vision. You really have to let the CEO run strategy as their default responsibility. Yet, in a big multilayered company, the CEO must delegate that to others – they don’t have infinite bandwidth. The CEO can deliver constraints along with that delegation — “you should get this multi-processor payments product to $XXB volume, run it with this team size and get results by this date. Forrester should say we are a leader.” What that all hinges on, unfortunately, is the quality of the lieutenant to make “CEO-like” decisions once they receive the power. If a lieutenant can’t make good strategy choices, you’re in a pickle.
As you scale, you need to delegate more. But as you scale, you find the quality of your lieutenants goes down on average. The thing that degrades faster as you scale is not the IQ of your hires, but agency and motivation. This is the fundamental issue across every single company everywhere, and why the best executed Growth Gear companies involve obsessive, bossy CEOs who are willing to either eliminate middle management (Jensen has 70+ direct reports!) or fire really fast.
Daily practice
A wonderful comment from a friend E. that made me reflect:
“Why is it so hard to just do something just for the love of doing it vs. needing to be "good" at it? I feel like I was not always like this. Was it my SF experience? Is it my insecure overachiever peer group? Or maybe I was (and everyone is) like this all along? Even if I want to be excellent at *something* why do I need to be excellent at everything I do? I think that part of it is that —as a meta "hobby"—I enjoy learning. So if I'm not getting better, it means I'm not learning. But I'm trying to re-find the joy in doing things just because I enjoy them and not because I need to be great.”
My response: “I used to be very dedicated to music and practiced for hours every day. But after I didn’t go to conservatory for college, I completely stopped. I would feel a weird twinge when I heard music, my insecurity and the knowledge I couldn’t cut it eating at my enjoyment of music itself. I haven’t played music since. Writing is the opposite: I have become so prolific because I want to get better. These days, I think about the following question: when is the desire to be excellent holding me back from doing what I want, versus when is it driving me to do more of what I want?”
Friendship
I wrote something in my “10 ways to make my friends be friends” post that I immediately empirically tested. The experiment, ahem, showed I was wrong. My hypothesis was that you could get people closer via disclosure and confession. But in reality, too much confession too soon feels incredibly awkward! Many of you could have guessed this from first principles, but I had to learn it via reinforcement. In my experiment group of 8 loosely connected friends on a weekend away, I brought out a prepared question, “How has your view on love changed as you’ve gotten older?” at a dinner. The conversation immediately became uncomfortable. It was too much too soon.
My friend Jialu:
“I think what we are really looking for in our friends is intimacy, which I think is best formed when you spend a long, consolidated time with someone. You need to get the boilerplate catching up out of the way (how's work going?) before you can get down to the real stuff, "My wife and I are having the worst argument we've ever had and it's about sleep training our kid" or "I'm reading a book about hookup culture in American colleges and it's really got me thinking about how a lot of my behavior is related to status and insecurity."”
Universal Basic Meaning
This post was always great because it includes a photo of my grandmother on a visit to Polynesia, dancing with coconuts, wearing a sari, and standing next to a topless white woman. Unbelievable.
The prose, however, needed some edits. I started off Working Assumptions talking about complex topics (!) and inevitably missed some nuances. I went back and edited this post with many of these nuances and disclaimers. I love the concept of Universal Basic Meaning, and I think it’s made stronger by addressing things like the point that my friend S. makes here:
If you have a terrible job, you are unhappy. But I think you have a lot less time to be self-destructing which seems to be what many people end up doing. This is a very paternalistic observation that I don't want to be true but seems to be at least partially true. Nonetheless, I agree with your main observation: in many cases, it is the job that is dehumanizing, not the automation.
I rewrote this piece almost entirely, and added an unhinged science fiction story. Please take a look!
Thank you again.
I am so grateful. You have helped me mature ideas and build my toolbox. I am forever in your debt for engaging with these ideas. You’re the best.