Good Reads: The Hard Thing about the Hard Things

Katy Montgomery

Katy currently serves as the Global Director of the Career Development Centre at INSEAD where she manages career services professionals across three campuses: Abu Dhabi, Fontainebleau, and Singapore. Katy previously served as the Associate Dean for Student Development at the Johns Hopkins Carey Business School.

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I just finished the best business book I have ever read: The Hard Thing About the Hard Things by Ben Horowitz. Horowitz knows business. He is co-founder of one of the most respected venture capital firms worth $4 billion, Andreessen Horowitz, and co-founder of start-up Loudcloud, which became Opsware and was eventually sold to HP for $1.6 billion in cash.

Why is this book so good? It is authentic, passionate, and quotes rap lyrics to bring a point home. But, what really resonates with me is that Horowitz talks about what you should do when the going gets tough; when there are no easy answers. He addresses lead bullets (not silver bullets), the law of crappy people (“For any title level in a large organization, the talent on that level will eventually converge to the crappiest person with that title.”), and the struggle (when your dreams turn into nightmares).

While reading this book I was constantly thinking about good vs. bad management, the right kind of ambition, and being a courageous and not a cowardly leader.

I’d hate to enumerate the takeaways from this book because I don’t want to provide anyone a possible excuse not to read it. Instead, here are some of my favorite lessons:

Good Product Manager vs. Bad Product Manager: Having a difficult time articulating to your team what makes a good vs. bad employee or what your actual expectations are for the job? Or maybe everyone comes to the job with a different set of experiences or interpretation about their duties? Draft two job descriptions: one describing a bad employee and the other highlighting what a good employee does.

One-on-Ones: Whether or not you agree that one-on-one meetings are important—and I believe they are as does Horowitz—we can all agree that they should be done well and effectively. Horowitz provides sample questions to ask an employee in a 1:1 meeting that get the employee talking, thinking strategically about issues, and brainstorming.

What are we not doing? Meeting agendas often include addressing immediate problems or initiatives, often leading organizations to ignore what they should be focusing on or issues to be anticipated. This question is also great for managers—just replace “we” with an “I”.

Embrace your weirdness, your background, your instinct:” On the last page of the book Horowtiz provides this mantra as a piece of advice he shares with all entrepreneurs. I loved the wording and believe this mantra applies to everyone. When the going gets tough, you have to trust yourself and what feels most comfortable. The answers to leading when leading is tough and handling the stickiest of problems is not in a book.

It is in you.

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