How To Use A Book Club To Turn Your Startup Into A Learning Machine

For me and my co-founders, building our first tech company from the ground up has been both an exhilarating and humbling process. Coming from a corporate background, we had limited experience in scaling a business — and there was a lot of learning to do.

As the team grew, the challenges multiplied; many of us were adjusting to the shifting needs of a startup. There was an anxiety to keep pushing ahead. We were certainly not the first to encounter many of the hurdles, but when you are resource-constrained and the work piles on, how do you find the time to learn?

Sometimes you need to slow down to speed up. To grow ALICE from three of us to 30 people, and to get through the early stage hurdles, we had to find a way to prioritize learning as a team. So we started an office book club. No other tradition has had more of a positive impact on our culture, our processes and our product.

Why start a book club?

The idea to start the book club came to fruition over a year ago when we were dealing with a customer training problem. I made a suggestion to our team based on something I read in Delivering Happiness, a book by Zappos CEO Tony Hsieh detailing how he created a corporate culture with a commitment to support. That’s when one of our team members turned to me and said, almost bewildered, “How do you have time to read?”

As a leader, this raised a huge red flag. The short answer is: We don’t. In the startup world, the days are long, the tasks are endless, your ambitions are growing and there is not enough time to get dinner, let alone read a book at your leisure. I realized we had to prioritize learning as a culture, or we would never find the time — and be doomed to constantly reinvent the startup wheel.

The books did not always have the answers, but they always fostered a good conversation.

One of the things I love about startups is that in the first few years, we all share the same problems: finding investors, hiring, building MVPs, discovering customers, driving sales, etc. If you look at a company like a baby, everyone has the same growing pains at first. As we approach high school, college and full-time employment, our problems diverge, but early on we all need to learn how to walk. That’s when relying on the collective wisdom of experienced practitioners is critical.

Given that 80-90 percent of startups fail, books provide direct access to people who have done it and can help you “grow up” before you run out of funds.

That is why we made the book club a part of our monthly traditions. Here’s how you can use a book club to turn your own startup into a learning machine.

How to structure your book club

The specific format of the book club is really important. It’s easy to kill a good idea with bad execution. For us, the book club aligns directly with the challenges the company is about to face at each stage. The book we read is one step ahead of us, clearing the path for good decision making in the face of extreme uncertainty. We like to switch up the style between books focused on a given company, a prophetic leader or a particular philosophy. Some are anecdotal, while others are prescriptive.

We have gone through a few iterations of the book club, trying various cadences, ways of selecting books, approaches to running sessions, etc. We started with one session but quickly saw that learning about the book, and trying it on for size, required two different mindsets. So we created two sessions. There were many other tweaks, and will be more in the future. It comes down to doing what works for the culture. Below is the format we currently use:

Frequency: One book a month. It is important to get into the rhythm. Much like going to the gym, it’s easy to fall out of habit. A book is five to 10 hours, so it’s manageable.

Format: Paperback, audible, Kindle, whatever is easiest. Some people are fast readers, others prefer listening to the book.

Selection: The book club “brain trust” (based on  Creativity, Inc.) selects a relevant theme, the entire company makes book suggestions and everyone votes.

Participation: Reading is optional. Ultimately, not everyone can read the full book each month. We encourage reading part of the way or a summary so there is context.

Ownership: Each book has one lead who volunteers to be in charge of the group learning. If no one steps up, a member of the “brain trust” will take the lead.

Session 1 (Learn): One hour. The lead conducts a discussion of the main points. People discuss what resonated most and debate controversial ideas. The focus is on the concepts, our experiences with them and how they relate to our company.

Session 2 (Apply): One hour. The lead conducts a session where the company engages in applying the insights to our day-to-day. This can be through breakout groups, exercises or debates. Remote teams get on video calls with local teams.

Where to start

As we started to grow the company, we tried to point out the greatest challenges ahead of us each month and match a book to meet that need. This is not the only thing we do to educate. We also have guest lecturers, as well as share articles and videos — but the book club is our most comprehensive learning tool.

Here is a list of the challenges we faced as a company and how we addressed them with books. Although each title is specific to the particular challenges we faced each month, we recommend anyone of them as a great starting point for your own book club.

Book 1

How to build a great company

Good to Great

Book 2

How to direct our product

Zero to One

Book 3

How to train, sell and market


Book 4

How to encourage innovative thinking


Book 5

How to grow the customer base

Crossing the Chasm

Book 6

How to deepen user engagement


Book 7

How to create a marketing machine

Behind the Cloud

Book 8

How to manage a creative process

Creativity, Inc.

Book 9

How to empathize with hotel staff

Heads in Beds

Book 10

How to hire incredible talent

Who: The A Method for Hiring

Book 11

How to remain effective as we grow

Scaling Up

Book 12

How to focus our prioritization


How your startup can benefit

Our company and how we do business has changed quite a bit with the book club tradition. The books did not always have the answers, but they always fostered a good conversation. Sometimes we applied the things we learned directly, sometimes we adjusted to our culture and other times what we read simply reinforced what we were already doing. Each session brought the team closer and helped us understand our company better.

When we run an interview process, we rely on “role scorecards and topgrading” (Who: The A Method for Hiring). When we evaluate culture-fit during an interview, we ask if the candidate is “the right person for the bus” (Good to Great). When we strategize market penetration, we think about identifying our “early majority” (Crossing the Chasm). When we decide on the best place to focus our product, we ask if our solution “is 10x better than anything available” (Zero to One).

ALICE is three years old now, and we have a lot of learning ahead. We have made it through multiple funding rounds, grown to a staff of more than 30 and are getting ready to double our staff. If startups are like babies, we have learned to walk and talk, but there are many growth spurts ahead. It won’t be easy, but the book club will help guide us through the next milestone.

As many of today’s leaders plot their reading lists, a collection of books they have read and loved and think you ought to read, we hope we’ve inspired you to turn that list into a tradition that grows your team, your culture and your business.