Book Review: Scaling People

25 January 2026

So, I'm about to finish stripe book #12 (The Dream Machine), but this book was actually book #11. I'm trying to write this review while the content is still fresh, and frankly because I want to get this review out of the way.

This is the second book I've read in the "How to run an organization" category, and gosh I hated it. All of the wonder about lack of bureaucracy, risk taking, and flat organizations from previous books was gone. The tone was also that of a lecturing HR rep rather than a inquisitive elder. In other books, notably Pieces of the Action and Learning to Learn, the author tends to talk more about their mistakes, and attributes their successes to luck (in a word, humility). I noticed early on that all of Claire's personal anecdotes were always others' mistakes, and she didn't point to a failing of hers until over halfway through the book.

Another parallel thing that was very annoying was how many Stripe Press books were about taking risks, taking chances on oddballs, leaping into the unknown without a plan. This book seems to be about how to scientifically eliminate risk. For example, in the hiring process, she recommends having the candidate jump through 6+ interviews, resumes screens, references, the works, and the company is looking for a reason to say no rather than take a risk and say yes. Did your former eastern-european manager classify you in the top 25% of former employees he's worked with instead of the top 10%? Tough luck kid, look for a job elsewhere. Supposedly this is because false positives cost more than false negatives, despite the future tens of pages about how to get rid of underperformers quickly and smoothly.

Nonetheless, the book seems very useful. Not everyone can be aspiring members of the Planck Club, or get accepted into Xerox PARC, or whatever exceptional research program you have in mind. What about running *real* companies? That's what this book is about. If you're a member of corporate america, much of it will be very familiar: meetings, interviews, offsites, performance reviews, personality types, "Working with me" docs, managing styles, the works. It's very useful as a baseline of how to do X or Y process, for a startup that is transforming into a unicorn (or for an established company that never caught the memo). I get the vibe that future Stripe Press books I haven't touched yet (High Growth Handbook and An Elegant Puzzle) also target this group. The precise target, though, is a manager of individual contributers at a relatively big Co.

Here's the summary. This summary is easier to write, since the book is very organized and signposted. It also makes it easier to jump around the book and use it as a reference (indeed each chapter ends with some sample material meant to be templates for various processes).

Summary

• Introduction: 4 core frameworks, who this book is for.
• Chapter 1, Essential Operating Principles: be self-aware, be honest, distinguish between management and leadership (think high-level ICs), come back to your personal "operating system".
• Chapter 2 (CF1) resource and goal planning: founding documents, company operating system (3 horizons, financial planning, etc), operating cadence (goals and metrics). Theres a useful house analogy at the start of foundation/frame/pipes for the three concepts.
• Chapter 3 (CF2), hiring: recruiting (events, referrals, screening, scaling the process), hiring (initial interviews, the onsite, candidate review (hiring panel), references, job leveling, offers), onboarding (initial bootcamp, initial 1:1 meetings and todo list, hiring leaders special considerations), "hiring mistakes" (quick fires for obvious reasons).
• Chapter 4 (CF3), teams: team structures (permanent teams vs temporary task forces, directly responsible individuals), diagnosing team state (forming/storming/norming), re-orgs, teambuilding (offsites), team rituals, DEI, manager communication.
• Chapter 5 (CF4), performance reviews: hypothesis-based coaching, giving hard feedback, creating a culture of informal feedback, formal performance reviews, compensation, managing high performers (pushers and pullers), managing low performers (form hypothesis on why the low performance, skill/will matrix from the teams chapter, switch teams or start PIP), managing managers, PIPing/firing/layoffs.
• Conclusion, your career: managing your time and energy, networking/relationships, taking the long view (18month/5year/10year retros).

And the takeaways.

• Like a lot of Stripe Press books, I spent a lot of time imagining the author's inner world and experiences that led them to write what they did, the metastory. It's clear this type of corporate work comes naturally to Claire and she loves it, so much so that I don't think she can really put herself into the shoes of low or high performers for whom this work is either a Kafka-esqe hell or an elaborate way to waste their time, respectively (it also means she probably doesn't even notice she writes in that HR-voice style). But I thought to myself: these companies matter, they do important things, it matters that they are run well. And I'm going to be in large corporations for probably the rest of my life. So it it worth the effort to perform the role of employee well; and to understand the beast to make a true impact.
• It's insane how many different forces are fighting for managers and higher-ups time. Planning, 1:1s, commenting on proposals, hiring. As an IC, it's somewhat easier to disappear, but if you are higher up, your time is easily eaten. I need to make to not disappear, to think of my time as valuable and do valuable things with it. As for managers, good luck to them, hah.

Overall, I do not regret reading Scaling People. It was worthwhile. Throughout this project to read all the Stripe Press books, I have intentionally limited myself to reading one book at a time so that I don't avoid books like these, which are probably especially valuable to me because I am avoiding them (train your weaknesses!). But it just didn't have that special shine, that belief in the mission of "Ideas for Progress" that most other Stripe Press books have.

I'm about to finish The Dream Machine. After that is the efficiency book, then I don't know what. I also don't know what I will review next, probably an older book. I'm behind on reviews, so I really need to start cranking them out.