My five favorite books on leadership

Issue 156: The vial few reads I re-read for guidance

I did not love reading as a kid until I was incentivized Pizza Hut’s book it program. When I read, it’s usually in stacks of five, the number of books you need to complete reading to get a Personal Pan Pizza (they are so good!). This is why I’m recommending five of my favorite books on leadership. The recommendations are more about company building and business leadership than domain-specific. I won’t have books that focus on how to improve your design or engineering technical knowledge. It should be assumed if you’re in a leadership position you’re already prolific at it.

My philosophy on books before you take the recommendation:

1. Books won't make you better in practice. Do not get paralyzed by trying to improve by only reading. You gotta do the work too

2. Take what is valueable from books. You don't have to agree with every point

I present you the list in the style of Tyra Banks on America’s Top Model—in no particular order, my favorite books in leadership.

---

The Score Takes Care of Itself

American Football is unique sport. It’s one where the strategies and tactics of it looks more like war than it does other sports. Football is if World War II and Rugby had a baby. Whether people are a fan of the sport or not, they’re likely familiar with Bill Walsh (and Joe Montana), the legendary San Francisco 49ers coach. “The Score Takes Care of Itself” was published after his death and shared Walsh’s philosophy on leadership. Like the unique game of football, Walsh was more teacher than NFL head coach, which is what made him great. This book is written by the late great Bill Walsh and published after his death.

As the title of the book alludes to, Walsh’s philosophy is if you do all the small things right in execution and preparation, the score will take care of itself and you’ll win. Don’t focus on the final outcome (the score) and instead work on the behaviors and commitment to excellence that leads to those outcomes.

---

The Leadership Pipeline

My friendtor (friend + mentor) Michelle recommended this one to me many years ago. I read it when I first started managing direct reports, again when I I began managed managers, and again when I moved to managing directors. The reality is most people don’t have a good benchmark of what good looks like when becoming managers. It’s not because of them, but they don’t have good examples of success around them. We're often punching way below our belt. “The Leadership Pipeline” gives a great overview of the different levels of management and how they're organized across companies.

If you've ever wondered what your manager does (or supposed to do), this book provides a wonderful baseline for reference. This book is great for new managers and seasoned leaders.

---

What Got You Here Won’t Get You There

Marshall Goldsmith is a renowned executive coach and leadership thinker. As you move through the leadership pipeline, there are core expectations and skills needed in order to advance, and not everyone necessarily advances. I enjoyed this read and really helped me a lot on the EQ aspects of the job, such as the importance of feedback, behavioral change, paying it forward, and other key aspects to be a high-impact leader.

---

High Output Management

This classic by Andy Grove is probably on everyone's list. Though the output is different from the time Grove wrote the book, many aspects of it reman relevant today, such as the emphasis on clear communication, setting objectives, and providing feedback to enhance performance. The idea of leveraging one’s time and resources efficiently is also still applicable. However, in the context of modern supply chain-focused management, some aspects may be less relevant, as today’s management strategies have evolved to include complex global supply chains, technology integration, and data-driven decision-making. Management is less like a supply chain and more about experiences and outcomes that lead to value.

---

Making the Manager of a Manager: What to Do When Everyone Looks to you

This book is the Batman: Year One for managers. It’s especially a great read for people starting their management journey. Julie Zhuo, former VP of Design at Facebook, shares personal stories and important advice for new managers. I wish I had this book when I first became a manager. Zhuo’s book emphasizes the mindset shift of going from individual contributor and people manager; a transition people struggle with. She provides clear foundations, such as prioritization, coaching and development, delegation, conflict resolution, and much more.

Don’t let the title fool you. This is also a great read for experienced managers as a refresher. I’ve been reading Zhuo's writing since her Medium blog days of The Year of the Looking Glass, and look forward to everything she writes.

---

Bonus recommendations

Now that you’ve earned your Personal Pan Pizza from reading these five books, I want to share bonus recommendations.

• Accelerate → Don’t let a DevOps book fool you. This is a great read on scaling high performing technology organizations for anybody

• Build → Tony Fadell’s book is filled with personal stories paired with practical advice

• Org Design for Design Orgs → One of the great reads on how to build and manager in-house design teams

• Scaling People

  ¹
  → I just started reading this, but this one seems to be a classic. It’s written like it’s personal career advice for me as someone who really cares about early stage company building

---

I hope sharing these either gives you new interesting books to read or re-visiting some classics. Some day I’d like to clean up my notes and share it in a GitHub repository for people. Do you have any leadership books you recommend or have been inspired by? I’d love to add to my list.

Weekly recap

We spent the last week in the big island of Hawaii. Though we were safe from the wildfires in Maui, it’s devastating to see what happened. If you want to donate to those affected by the wildfires in Maui, here’s a link Ben Blumenrose posted.

When I left Webflow in April, my plan was to take a few months off and have myself a sabbatical. Instead, I jumped right into Replit—classic. It’s been a wild ride so far (in the best way possible) and felt my mind and body needing rest. After a week of swimming in the ocean, spending time with loved ones, no video calls, no computer screens, and no sitting hunched over at a desk for hours, I feel great; looking forward to seeing my coworkers and getting back at it.

---

Hype links

A collection of links I read through RSS feeds and read later with Omnivore.app.

• Could Apple Really Buy Disney?

• Authentically Human

• Announcing Callsheet → Congrats Casey Liss on launching a cool app that could be an alternative for IMDB

• 15 Years Ago, Apple’s App Store Changed Everything. Now It Needs a Reboot → It feels like yesterday the App Store launched. A wonderful read by the great Christina Warren

• Newcomer: Scaling People (with Claire Hughes Johnson) → Great podcast with the former Stripe leader; I just bought the bookit

• Bricolage Grotesque → An incredibly designed font and open sourced

---

Job opportunities

A list of personal recruiting and roles I found (not sponsored)

• We're hiring at Replit

  • Lead Brand Designer

  • AI Engineer

  • Product Engineer

• Braze is hiring a Director, Product Design

• StitchFix is hiring a VP of Product and Design

• Atlassian is hiring a Head of Design, Growth (Expansion)

• Docusign is hiring a Lead Product Designer - AI

1. I began reading this last. Based on how it’s trending, I would put it in the top books on this list but want to hold off since I haven’t finished it