The CIO Reading List: The Hard Thing About Hard Things

The CIO Reading List: The Hard Thing About Hard Things
The CIO Reading List

“Humans, particularly those who build things, only listen to leading indicators of good things.”

–Ben Horowitz, Author, The Hard Thing About Hard Things

Most management books are about the author’s successes — great decisions, great hires and great outcomes. The Hard Thing About Hard Things, by top VC and former CEO Ben Horowitz, goes the other way.

Rather than focusing on advice for when things are going well, Horowitz focuses on those moments when leadership is hardest: when things are going horribly wrong. The book is packed full of stories from his time as CEO of Opsware (formerly Loudcloud, one of the early IaaS companies), and the tumultuous time it faced after the dot-com bust of the early 2000s.

What I really appreciate is Horowitz’ brutally honest assessment of his own decisions (both good and bad) in response to the position his company found itself in.

Aside from just being a refreshing perspective, it resonates with me as a CIO. Because, let’s face it, this job is hard. If you’re leading a digital transformation initiative, it isn’t always clear what the right answer is. And you’re going to be making all sorts of high-stakes, often irreversible decisions.

Leadership Takes Courage

Horowitz tackles a number of tricky subjects — from demoting friends to promoting people who aren’t ready to lead to the invisible forces of company politics.

But one big point that cuts across all of this is the need for courage. It sounds like an obvious quality for a leader, but too often, I think we fail to acknowledge its importance.

Strategic CIOs see the same kinds of challenges entrepreneurs face every day — and do it in a similarly uncertain landscape. If you’re not feeling a fair amount of fear and self-doubt, you’re probably doing it wrong.

Scale, Process and Culture

In among his personal anecdotes and leadership advice, Horowitz spends a lot of time advising entrepreneurs and startups on how to grow, how to get processes right, and how to ‘program’ the right culture.

You’ll recognize all of these as CIO challenges as well. As you move your company away from legacy infrastructure and processes, you’ll likely try to work more like startups do: leverage cloud, deploy next-generation analytics, and drive customer-centric strategies to increase customer engagement.

But while large enterprises may come at these issues from a different place than startups, all companies suffer with the same problems of miscommunication, misalignment, and mismanaged incentives.

So even though it’s not a book written for CIOs, it’s packed with great ideas and compelling stories that made me think differently about technology, change, and leadership.

I highly recommend this book to fellow CIOs. We’re all experiencing the hard things about hard things every day.

Do let me know what you think of the book in the comments. Or if you’re on Twitter, please tweet me @e_graeme.

For additional CIO Reading List recommendations, be sure to check out my previous post The CIO Reading List: The Undoing Project.