A strategy should hurt. / Leadership is disappointing people at a rate they can absorb.
First, let my biases be explicit: while I didn’t work closely with Claire during my time at Stripe I certainly enjoyed my time in her orbit. My working understanding of her was largely in concordance of her presentation in the introduction: extraordinarily competent, with an ability to context switch from granular to big-picture, deeply empathetic, entertaining and charming. She was a great executive, and I was saddened to see her step back from her role as COO.
That being said: who is this book for? Hughes Johnson attempts to give a very explicit answer early on, joking that “yes, you should do weekly chats with your direct reports, but if you need to know that then this is not the book for you”. And yet, this book is presented as a very practical guide:
There’s a Pablo Picasso quote we like to repeat at Stripe: “When art critics get together, they talk about Form and Structure and Meaning. When painters get together, they talk about where you can buy cheap turpentine.” Sometimes you want to read a book about Picasso’s life, and sometimes you just want to know where to buy the cheapest turpentine. Consider this the latter: an insider’s guide to management turpentine.
If I were to be slightly catty, I would say this is less of an insider’s guide to turpentine and more an explanation on: here is why turpentine is important, here are some ways other artists have used turpentine, here are some challenges that other people have faced when dealing with a lot of turpentine. The entire book feels cursory, and I use that word deliberately: Hughes Johnson never knows quite what level of specificity she wants to dwell, and instead flits around from topic to topic — nothing she says is wrong or even, I think, controversial, but each of the major points (goals/planning, team structure, hiring, and perf) are neither thorough enough to be a primer nor idiosyncratic enough to be novel.
The book is buttressed by a series of sidebars that are largely “here’s how it worked at Stripe.” A lot of these were fun trips down memory lane; some of them were, to a person who lived through them [1], slightly undermining Claire’s theses:
- She cites Stripe Home as an example of Stripe’s outsized investment in internal tooling, even though Home was a hackathon project and its running joke during my tenrue was that its staffing was HDD — hackathon-driven development, because Stripe could never actually devote resources to it;
- She cites Stripe’s (now-deprecated, I assume) “TPP” as a way of rolling up many disparate and discrete goals into a legible shortlist of 3—5 true priorities for an organization; when I left Stripe, TPP had ballooned to twenty, and a long-standing joke was whether or not those twenty priorities were stack-ranked or not.
I bring up these nits self-servingly, to a certain extent. My already-foggy memory of my time at Stripe was that its late-period success was less about the systems and processes it developed and more about the fact that its culture and talent base was so overwhelmingly strong (in terms of empathy, in terms of agency, in terms of ability) that folks overcame the myriad systems and processes. [2] I don't think Stripe's perf or resource planning is that much different than, say, Amazon's — and even if I don't like Amazon's system, Working Backwards is a much better and specific resource for implementing that kind of thing, and I didn't like that book either.
Maybe this kind of book is simply Not For Me. I think organizational design and growth is a really tricky, really nebulous subject that resists easy text (High Output Management being a singular exception, and of course cited heavily in Scaling People.) Many things are either so obvious that if you need a book to tell you how to do them you're probably not in the right role or so nuanced and specific that any broader discussion is worthlessly anodyne.
All of this to say: skip this book, perhaps skip all of these books and listen to some of her interviews instead. They’ll be more informative, and more real.
★★
