Review: The Hard Thing about Hard Things

I was all prepared to find The Hard Thing About Hard Things disappointing. CEO books are frequently about self-aggrandizement (e.g., Richard Branson's memoir) and rarely give you advice you can use. Horowitz's book, however, turned out to be a rare breath of fresh air.

Sure, there's a certain amount of bragging in the book (taking a company to $1.6B is no mean feat, and Horowitz isn't ashamed to take credit for it), but that's not why you should read books anyway. You read books for practical tips that will let you avoid making mistakes when hiring, firing, or screwing up. One avoided bad hire at the executive will more than pay for the time you spend reading this book, so in that respect the book's more than well worth your time.

The book's intended audience is the CEO of a technology company. It doesn't really

Here are a few insights from my reading of the book:

• When hiring an executive, focus on whether his strengths fits your needs, rather than avoiding weaknesses. For that to work, you have to have a strong idea of what you need in that executive. Unfortunately, there's no easy way to get that insight, other than by running the organization that you need him to run for a while --- but that's OK. Better to get it the hard way than by randomly hiring people! (Note that there's a lack of emphasis on avoiding people with no integrity --- Horowitz assumes you know that and doesn't spend any time on it)
• When hiring anyone (executive or not), don't ask questions like: "He's great for the job right now, but will he scale as the company scale?" Those questions lead you to make prejudicial judgements about your executive. There's no way to know whether anyone can "scale" in a particular way, so the best thing to do is to be honest and say, "I'm looking for the best fit for the  current job. Next year, if the company changes, we'll still be looking for the best fit for that job. This applies to everyone in the company, even me!"

Deciding (with woefully incomplete data) that someone who works their butt off, does a terrific job, and loyally contributes to your mission won’t be with you three years from now takes you to a dark place. It’s a place of information hiding, dishonesty, and stilted communication. It’s a place where prejudice substitutes for judgment. It’s a place where judgment replaces teaching. It’s a place where teamwork becomes internal warfare. Don’t go there. (Kindle Loc. 2887)

• Training is a competitive advantage for startups. Don't outsource your training. In particular, you need to get your best people involved in training new people. In order to do that, however, you have to make training seem valued. The best way to do so is for the CEO to spend time training others, to lead by example. Training is also where you set expectations for your team. In particular, Horowitz include a training document he wrote for Opsware called "Good Product Manager/Bad Product Manager". In it, he defines what a product manager does, what best practices are, and how product managers will be evaluated. It's a great document that defines what a product manager does.
• Managing politics is counter-intuitive for the CEO. You have to actively manage it by setting up processes, whether it's for performance evaluation, pay raises, or promotion opportunities. If you do not do so, expect everyone on the executive team to become a squeaky wheel and playing politics. That means that the more actively non political you try to be by avoiding the usual big company BS, the more you encourage politics as people try to achieve the same goals out of band.
• Similarly, the CEO has to actively give feedback all the time. Again, this is counter-intuitive, since typically people managers are generally told to provide feedback in a "shit-sandwich" fashion --- sandwich the negative feedback between the positive feedback. The problem with the latter approach is that experienced executives see through this right away, so the only way to be consistent is to provide both positive and negative feedback as soon as you see work that deserves it.
• Organizations and Processes should be designed for the sake of the employee at the leaf node level, not for the sake of the managers. In other words, when designing or reorganizing a company, you should consider what it's like being a customer support rep or an engineer, rather than what it's like being one of the managers having to work in the environment. This may seem obvious, but keep in mind that most CEOs hang out mostly with executives and rarely reach down to the leaf nodes where people actually do the work, so it makes sense for Horowitz to emphasize this point. Furthermore, Horowitz makes the great point that organization designs all suck --- you're basically optimizing certain paths of communications between organizations while making certain other communication paths harder or even not happen at all. What this means is that along with the organization design you'll have to put into effect a plan to monitor the issues arising from the consciously designed sub-optimal paths so that if things get too bad you can redesign or hack around it.

There are other things that Horowitz say that I felt aren't necessary expressed well or are too general to be practical:

• He makes the distinction between a wartime CEO and a peacetime CEO. While that distinction has some merit, I'm not sure it makes a ton of sense. For instance, Steve Jobs was an effective asshole (and effectively an asshole) even when Apple was no longer fighting for survival. I wonder how many CEOs are going to use this chapter as a justification for being a jerk to everyone around them.
• There's an assumption that the CEO is technical, so the book doesn't discuss engineering management or the challenges peculiar to engineering management. I'm OK with that, since I did actually write a book about engineering management.
• The book actively encourages the kind of non-poaching agreement that Apple/Google/Intuit/Intel were involved in that's illegal, though of course, none of the companies involved were ever punished in any significant fashion. But you'll love Horowitz's excuse for encouraging this kind of illegal behavior: CEOs are already very lonely people and can only commiserate with fellow CEOs, so pissing off other CEOs is a bad idea since you need all the friends you can get when you're a CEO. I have no idea if Horowitz is as actively un-self-aware in real life as he seems to be when he wrote this section of the book, but there you go. Apparently, having been a successful CEO is a license to encourage others to do illegal stuff.

Finally, at the end of the book Horowitz reveals that the entire book was a marketing brochure for his VC firm, Andressen Horowitz. That's probably OK --- you didn't expect anything else, did you?

Regardless, the book's well worth a read. Like I mentioned, if it helps you avoid one of the errors I noted above, it's worth the time. Recommended.