Cracking a new book is a moment of suspense, of promise. Will it be worth your time? You hope so. Then there’s the possibility you might be embarking on something greater: you could be opening one of those rare and exciting books that fundamentally alters the way you look at the world, at life, at work, at your own happiness.
Here are some of the books that did that for us. Happy reading!
1. Getting Real: The Smarter, Faster, Easier Way to Build a Successful Web Application by 37signals
Nick Francis, CEO
This is my favorite book on building a software business—it very clearly formed my opinion on almost everything related to building a software company. The three chapters that informed the way things work at Help Scout:
Embrace Constraints: “Let limitations guide you to creative solutions. Constraints drive innovation and force focus. Instead of trying to remove them, use them to your advantage.”
Make Opinionated Software: “The best software has a vision. The best software takes sides. When someone uses software, they’re not just looking for features, they’re looking for an approach. They’re looking for a vision. Decide what your vision is and run with it.”
Half, Not Half-Assed: “Stick to what’s truly essential. Good ideas can be tabled. Take whatever you think your product should be and cut it in half. Pare features down until you’re left with only the most essential ones. Then do it again.”
You can get through the whole thing in 90 minutes. It’s available for free here.
2. Algorithms by Robert Sedgwick
Beenish Khan, Engineering
This was a course book in my second semester at the university. I had joined the engineering program but I wasn’t too sure what I’d be studying, and hadn’t studied computer science at any level before. This book told me what I had signed up for. It introduced me to the fundamentals: the sorting, searching, and string manipulation algorithms. I instantly fell in love with computer science. I had taken a gamble at an engineering degree, and Sedgwick’s Algorithms confirmed the gamble had paid off.
It’s still exciting to pick it up and read about the knapsack algorithm (its “problem statement” asks how best a thief can fill a knapsack with stolen items and carry maximum weight…not sure how law enforcement feels about it), the bridges of Konigsberg, the brute force, the bubble sort, the graphs—that’s really where the beauty of computer science lies for me.
3. 168 Hours: You Have More Time Than You Think by Laura Vanderkam
Mel Larsen, People Ops
At a high level, this book had me work through an exercise that made me feel confident about the direction of my career. Vanderkam recommends journaling about the times you’ve tapped into “flow.” She instructs: “Think about the times when you felt most creative and productive. Try to identify the Who, What, Where, When, Why.” As I took stock of what ended up on my list, there were two prominent themes: organizing information in ways that make data easy to understand, and helping or teaching people. It solidified that a career in operations—people operations, to be specific—was where I wanted to head.
On a more day-to-day level, this book also helps me plan out what work I want to tackle at Help Scout. A lot of people worry about how to respond when their supervisors come to them with a problem. Vanderkam challenges you instead to think about what would happen if everything went right with this thought experiment: if the CEO walked in and asked to put you on your dream project, what would you ask for? That informs my larger view of how I want to tackle a quarter: if leadership asked me, “What’s next?” I’ve already thought about that question and have a good answer.
4. Anything You Want: 40 Lessons for a New Kind of Entrepreneur by Derek Sivers
Dave Martin, Design
Anything You Want has a higher highlight-to-page ratio than any other book I own. A few particular examples that stick out to me:
“Business is not about money. It’s about making dreams come true for others, and for yourself.”
“Focus entirely on your existing customers. Just thrill them, and they’ll tell everyone.”
“When someone is doing something for money, people can sense it, like a desperate lover. It’s a turnoff.”
I’ve probably read it a dozen times. I return to it regularly. It has deeply impacted the way I think about business, and been a critical resource in helping me discover what I want from my career. Sivers has inspired me to wake up, figure out what I want from life, and then pursue it.
5. Bird by Bird: Some Instructions on Writing and Life by Anne Lamott
Emily Triplett Lentz, Marketing
Lamott’s book totally upended my process. She gives you permission to slap down an ugly draft, versus getting every sentence perfect before moving on. You can always go back to edit; just get your ideas down. I wouldn’t have finished my thesis on time without making that shift.
A lot of writing is fretting about writing—we allow ourselves to be daunted by what seem like insurmountable tasks. I stopped including big, scary to-dos like “write Chapter 4” on my list. Smaller tasks like “create an outline” or “draft the conclusion,” however, get checked off and drive actual progress. I probably owe that to Lamott:
“Thirty years ago my older brother, who was ten years old at the time, was trying to get a report written on birds that he’d had three months to write, which was due the next day. We were out at our family cabin in Bolinas, and he was at the kitchen table close to tears, surrounded by binder paper and pencils and unopened books about birds, immobilized by the hugeness of the task ahead. Then my father sat down beside him, put his arm around my brother's shoulder, and said, ‘Bird by bird, buddy. Just take it bird by bird.’”
6. Delivering Happiness: A Path to Profits, Passion, and Purpose by Tony Hsieh
Kelly Herring, Customer Support
This book was a game-changer for me. It was fascinating to read about Hsieh’s journey from childhood to co-founding and building Zappos, and all of his views on customer support, building a company culture, and “WOW”-ing customers.
The quote that stuck with me is, “Remember that at the end of the day, it’s not what you say or what you do, but how you make people feel that matters the most.” It’s a great reminder as I interact with our customers every day.
7. The Score Takes Care of Itself by Bill Walsh
Gregory Ciotti, Marketing
This book left a lasting impression on me. In it, Bill Walsh—one of the NFL’s most successful coaches—details his internal struggle with a practice called Standards of Performance, his written guidelines for excellence in every area imaginable of running a professional football organization.
Walsh attributes his Standards of Performance as a key part of turning around a then rock-bottom 49ers team. At the same time, one of Walsh’s biggest regrets is not letting the excellent people he hired fully own their roles—he, like many leaders, struggled to trust and let go.
Whether you’re a manager or not, nearly everyone has their “baby,” the thing for which they feel personally responsible. It’s natural to feel this way. But you can’t be so arrogant as to think you are the best person for every job at every moment. To hear someone like Walsh call it arrogance was my biggest sticking point. Passion for whatever it is you oversee has turned into arrogance if you truly believe you are always the best person for the job. If that’s the case, you’ve hired poorly. Where the individual peaks, the team should transcend.
8. The Year Without Pants: WordPress.com and the Future of Work by Scott Berkun
Chris Brookins, Engineering
This book changed my view about how rewarding and productive remote work could be. It helped me understand the value of truly asynchronous communications and how that’s not isolated to long periods of coding, but could extend to all types of work, even onboarding.
9. Quiet by Susan Cain
Becca Van Nederynen, People Ops
Remote teams tend to include a lot of folks on the introvert side of of the spectrum. As an extrovert, I tend to try to “bring people out of their shell” but this book taught me that I’d been going about that in a very extroverted way. For example, I err on the side of inclusivity and invite everyone to the party versus a thoughtful one-on-one with someone.
Related to work, this book helped in a couple ways:
Hiring: Cain wrote, “There’s zero correlation between being the best talker and having the best ideas.” That stuck with me because I tend to be “wowed” by charismatic candidates who say the right things. Since reading her book, I’m on “high alert” for people who seem to be telling me what I want to hear, and I challenge them to give me specific examples and look for thoughtfulness—not just getting the right answer and being charming to boot.
New policies: I’m more mindful of creating programs, planning retreats, and making policies. Typical things like employee-of-the-month awards are not as comfortable for introverts, but that doesn’t mean they don’t want to be recognized—we just do it in a less attention-seeking way now with spot bonuses that are given privately. We’ve also made sure that our team retreats give people the option to re-charge—not just non-stop people time for four days.
I also started sending questions ahead of time before I have a scheduled chat with someone so I’m not making them anxious and they have time to prepare. Quiet made me more aware of how introverts like to communicate, so I’ve tried to be mindful of that!