I've said it before -- I think that almost everything you need to know can be learned through books. Learning is the only shortcut I've learned in my career -- and books are by far the cheapest and fastest way to level up and become a learning machine. 

So, as we look to 2020, here are five books that have made an impact on me and that I'm recommending to my team this year. 

1. What You Do is Who You Are: How to Create Your Business Culture by Ben Horowitz 

As my company has continued to grow, I've had to think a lot about our culture and what we stand for. I really subscribe to Horowitz's idea that "your culture is how your company makes decisions when you're not there" -- and also that culture is not a one-size-fits-all concept. What works for one company won't necessarily work for another, but it can be interesting and eye-opening to examine different techniques that companies use and think about how I could replicate it at Drift.

The best part of What You Do Is Who You Are is that Horowitz doesn't just focus on modern examples. He brings in examples from history, like how Genghis Khan built the world's biggest empire -- and reflects on what history can tell us about people and culture. 

2. The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky

One of the most important things you can do as an entrepreneur is to learn from other people who have experienced the same things you have -- or might currently -- be experiencing. Scott Belsky is the Chief Product Officer at Adobe and has been an advisor for companies like Pinterest, sweetgreen and Periscope -- so he's seen it all. 

The Messy Middle shares over 100 lessons and focuses not on the beginning or end of a venture, but on the part that is really the most important: the middle. This is currently where my company is and I believe that this is when the real work starts and where the real results come in. 

3. Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts by Annie Duke

One thing I've tried to do at my company is to empower others to make decisions. But I recognize that making decisions can be really hard -- and you need to be OK knowing that you might not make the right decision the first time. But if you learn from that, it can make all the difference. 

I loved Thinking in Bets because in it, Annie Duke, a former professional poker player, talks about how you can embrace the uncertainty that comes with making a decision -- and how to analyze what could happen. 

4. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott

I believe Radical Candor can change your life as a manager. The author, Kim Scott, worked for Sheryl Sandberg at Google and then went to Apple, and so this book is full of lessons she learned from those companies and others. 

This book teaches you how to focus on radical candor when giving feedback, because too often managers (not matter how junior or senior they are) want to be liked, and so they don't give feedback that is critical, or needs to be given. Instead, managers will often just give out "atta' boys" or "good jobs" in order to make their reports feel good.

But by doing that, they're undermining their direct reports -- and setting them up to fail because no one is growing. I believe that if you really care about someone, you're going to give them the feedback they need -- not just what they want to hear. 

5. Atomic Habits by James Clear 

I fall into the trap of wanting to "wait for perfect" all the time. 

But perfect is the enemy of good. One thing Atomic Habits taught me that has stuck with me is that you should aim to get just one percent better every day. Clear explains that while improving one percent might not even be noticeable, it adds up and if you do that every day for a year, you'll be 37 percent better. Conversely, if you get one percent worse every day for a year, you'll end up back down at zero. 

This always reminds me that when you want to do something, just get started -- and  improve one percent each day. 

If you are interested in bettering yourself -- as an individual contributor or as a manager -- I highly recommend that you make 2020 the year of reading. Reread books that you've read before, or ask for suggestions from others. You never know what you'll uncover. 

Published on: Dec 17, 2019
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