The Hard Thing about Hard Things

There’s a lot of books written by CEOs that are filled with advice about what to do, but not many talk about what it’s really like mentally and emotionally to be a CEO, especially the profound sense of loneliness that comes with the job. Ben Horowitz’s The Hard Thing About Hard Things was the first business book I read after becoming a CEO that realistically described what it’s like (especially for someone doing it for the first time):

This means that you will face a broad set of things that you don’t know how to do that require skills you don’t have. Nevertheless, everybody will expect you to know how to do them, because, well, you are the CEO.

Much of the book is an extended pep talk for founder CEOs struggling with the demands of a high-growth startup environment, where each day can bring a new existential threat to a still-fragile firm:

If there is one skill that stands out, it’s the ability to focus and make the best move when there are no good moves. It’s the moments where you feel most like hiding or dying that you can make the biggest difference as a CEO. In the rest of this chapter, I offer some lessons on how to make it through the struggle without quitting or throwing up too much.

And having weathered quite a few such existential crises as a CEO himself, Horowitz’s pep talks rise above just rah-rah motivation and read more like a cold splash of water on the face:

There are always a thousand things that can go wrong and sink the ship. If you focus too much on them, you will drive yourself nuts and likely crash your company. Focus on where you are going rather than on what you hope to avoid.

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How Will You Measure Your Life?

If you’re tired of hearing the phrase “disruptive innovation” you can blame Clay Christensen. And while his book that popularized the term (The Innovators Dilemma ) is outstanding, there’s actually another one of his that I like even better. In How Will You Measure Your Life? Christensen (with co-authors James Allworth and Karen Dillon) expands on a lecture he gave on happiness and career satisfaction, prompted in part by several serious health scares.

Some of what the book offers at first feels like vanilla career and life advice:

In order to really find happiness, you need to continue looking for opportunities that you believe are meaningful, in which you will be able to learn new things, to succeed, and be given more and more responsibility to shoulder.

But what comes through as you get further along is wisdom forged in part from having witnessed many ostensibly “successful” people end up deeply unhappy following years in an unfulfilling career, along with the sense of urgency that comes from facing down your own mortality:

If the decisions you make about where you invest your blood, sweat, and tears are not consistent with the person you aspire to be, you’ll never become that person.

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Good Strategy, Bad Strategy

The word “strategy” could use a strategy.

It’s used too broadly, rarely meaning the same thing for two people. It’s frequently stretched and contorted to incorporate myriad plans, priorities, and processes. And even when a CEO really does have a strategy, too often the people charged with carrying it out don’t actually know how to translate it into their day-to-day decisions.

Robert A. Heinlen wrote, “Man is not a rational animal; he is a rationalizing animal,” and that’s what’s seen in much of what passes for “strategy” in many companies: a collection of loosely related projects and initiatives that are already underway (or which executives desperately want to be underway) and which are assembled into a list upon which an amorphous “strategy” title is conferred.

In full disclosure, it took me years to really understand what strategy was, much less how to design one. The one book I wish I’d read much earlier in that journey is Good Strategy, Bad Strategy by Richard Rumelt.

If you’re like me, when reading it you’ll find yourself humbly nodding in guilty recognition of past sins as you read Rumelt’s descriptions of bad strategy:

A long list of “things to do,” often mislabeled as “strategies” or “objectives,” is not a strategy. It is just a list of things to do. Such lists usually grow out of planning meetings in which a wide variety of stakeholders make suggestions as to things they would like to see done.

Rather than focus on a few important items, the group sweeps the whole day’s collection into the “strategic plan.” Then, in recognition that it is a dog’s dinner, the label “long-term” is added so that none of them need be done today.

While it’s easy for most people to start coming with up with ideas about what to do (which is often what people end up calling their strategy), Rumelt succinctly articulates a picture of strategy that includes what too often is missing, which is first and foremost a thorough understanding of the situation, followed by a set of guidelines that are as much (or more) about determining what not to do as they are in determining what to do next:

A good strategy has an essential logical structure that I call the kernel. The kernel of a strategy contains three elements: a diagnosis, a guiding policy, and coherent action.

Learning about how to develop what Rumelt calls the diagnosis was the most fun part of the book for me, and he gives plenty of examples along the way. He also gently scolds the common pattern of labeling the problem as “underperformance”, which leaves an organization without a useful narrative besides “do better”:

When a leader characterizes the challenge as underperformance, it sets the stage for bad strategy. Underperformance is a result. The true challenges are the reasons for the underperformance. Unless leadership offers a theory of why things haven’t worked in the past, or why the challenge is difficult, it is hard to generate good strategy.