The Hard Thing about Hard Things

There aren’t that many good articles on management in a technology company, and even less good books that go into much detail1. Square’s leadership courses reference High Output Management, written by the president of Intel in the 70s, as the classic book on management but also only one of a handful that applies to the discipline. I’m not sure The Hard Thing about Hard Things makes the list.

Ben Horowitz wrote “The Hard Things” as a superset of his excellent blog posts, both of which draw their material from Ben’s stint as CEO at his startups. For the 99.9% of people who will not hold company executive positions in their lifetimes, Ben’s stories provide a glimpse into the decisions and stress that comes from running a startup, everything from making the right hires to making rounds of hard layoffs to managing the finances and connections of a company in decline. It gives me an appreciation for what it takes to excel, at the top of the hierarchy, at successful2 startups.

But like most other management material, the advice given trends anecdotal; the stories are fun to read, but any education they impart are catered to that specific situation, and it’s tough to form more general frameworks around what makes for good management when the actions taken and the meanings behind those actions are subtle, murky, or even just contradictory. Much of the wisdom could only be applied if you happen to be in a very similar situation with similar people – which includes the person trying to apply said lesson being similar to the author.

Which gets to why management books are so hard to come by: there may be applicable high-level ideals and philosophies, but on a tactical level, what makes for good management is mostly improvisational and highly tailored to the individuals involved.

  1. Online resources I’ve found to be fruitful include Yishan Wong’s articles on engineering management, and scattered blog posts from First Round Capital.

  2. Though it’s unclear whether modern success can be equivocated to building a sustainable public business, or whether it’s attracting enough talent to make its people worth buying.

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