Author: Andrew Savikas

Investor, advisor, writer, father. Former B2B ed-tech executive (ex O'Reilly Media, Safari). Consultant, author, speaker. Chronic reader.

On Writing Well

William Zinsser’s On Writing Well isn’t a business book per se, but reading and following his advice is one of the highest leverage things you can do for your career, especially if you are (or aspire to be) a leader. Why? Well, you won’t land big deals every day. You won’t fire people every day (I hope!). You won’t pitch investors every day. You won’t launch or kill product lines every day. And you won’t give grand speeches every day. But you will communicate in writing, every single day. All day.

And because clear and effective writing comes from clear and effective thinking, not only will you get more effective at communicating with those around you, you’ll get better at thinking. How cool is that? And as Zinsser points out, if you don’t work to improve the clarity and simplicity of your writing, there are consequences:

Managers at every level are prisoners of the notion that a simple style reflects a simple mind. Actually a simple style is the result of hard work and hard thinking; a muddled style reflects a muddled thinker or a person too arrogant, or too dumb, or too lazy to organize his thoughts. Remember that what you write is often the only chance you’ll get to present yourself to someone whose business or money or good will you need. If what you write is ornate, or pompous, or fuzzy, that’s how you’ll be perceived. The reader has no other choice.

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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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Start with Why

Great companies don’t hire skilled people and motivate them, they hire already motivated people and inspire them.

— Simon Sinek

I spent much of my career at O’Reilly Media, where, as happens at many companies, there are quarterly “all-hands” meetings. My favorite thing about those—especially early on when I was still pretty low on the proverbial totem pole—was hearing Tim O’Reilly talk about what the plans were for the months and years ahead. There aren’t many people out there who get more excited talking about the future than Tim O’Reilly, and I usually left those meetings incredibly inspired and feeling like I was part of something that really was helping to change the world.

At one of those meetings, Tim shared a story that I remembered quite vividly, so much so that I smiled when I saw it show up in Simon Sinek’s book “Start with Why”:

Consider the story of two stonemasons. You walk up to the first stonemason and ask, “Do you like your job?” He looks up at you and replies, “I’ve been building this wall for as long as I can remember. The work is monotonous. I work in the scorching hot sun all day. The stones are heavy and lifting them day after day can be backbreaking. I’m not even sure if this project will be completed in my lifetime. But it’s a job. It pays the bills.” You thank him for his time and walk on. About thirty feet away, you walk up to a second stonemason. You ask him the same question, “Do you like your job?” He looks up and replies, “I love my job. I’m building a cathedral. Sure, I’ve been working on this wall for as long as I can remember, and yes, the work is sometimes monotonous. I work in the scorching hot sun all day. The stones are heavy and lifting them day after day can be backbreaking. I’m not even sure if this project will be completed in my lifetime. But I’m building a cathedral.”

While I’m sure some of it was natural talent, Tim has become a master at showing people those cathedrals, and convincing them to bring their tools and get to work. But for the rest of us who could use some help in the Inspiration department, Sinek’s book is a must-read.

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Technological Revolutions and Financial Capital

One of the signals I use in deciding whether a book is worth reading is whether it is somehow connected to the people and organizations I already know and respect. Technological Revolutions and Financial Capital, by Carlota Perez, is one of my favorite examples.

I first heard of the book from a reference on Simon Wardley’s blog. Simon is one of my favorite writers on strategy (and he’s a blast to watch in action giving a conference talk). Then, when I looked the book up, I was pleasantly surprised to discover that it’s published by Edward Elgar Publishing, which was actually a customer of Safari, my employer at the time. And finally, when the book arrived in the mail, I was positively delighted to see that one of the testimonials on the back cover was from Bill Janeway, one of the sharpest minds around at the intersection of economics, technology, and venture capital (and also a board member at O’Reilly Media, Safari’s then-parent-company).

So it’s fair to say I started reading with high expectations — and Perez quickly exceeded them. After finishing this book, you will have a new framework through which to understand and analyze not just technology changes, but how they fit into the wider social, political, and economic landscape.

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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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Your Brain at Work

Would you have a great empire? Rule over yourself.

–Publilius Syrus

Leading a business (or even just a team) is rightly called “knowledge work” and for most people it requires far more mental effort than physical effort. But even though what we think and feel produces most of that mental effort, we rarely spend enough time thinking about how we think and feel.

For example, in the context of how our species evolved, some of our brain’s most primitive responses (i.e., the “fight or flight” response) are supposed to take over when there’s danger, the same way the nerves in our spine will pull our hand away from a hot stove before our brain even knows something is wrong. But that’s cold comfort when a confrontation with a co-worker or a critical word from a board member leaves us feeling (and behaving) like we’re literally fighting for our lives.

David Rock’s Your Brain at Work is no substitute for formal training in neuroscience, but it offers accessible and practical explanations of some of the ways that our brain’s evolutionary heritage ends up at odds with the demands of the modern workplace:

I am not a neuroscientist. I am a business consultant. I help organizations such as Accenture, EDS, Ericsson, and NASA improve their people’s performance. Over the course of a decade of this work, I’ve discovered, somewhat by accident, that teaching employees about their brains made a big difference to their performance, and often to their lives, too. When I couldn’t find a book that explained the most useful discoveries about the brain in simple language for people at work, I decided to write one.

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Thinking in Systems

The title of Donella Meadows’ masterpiece Thinking in Systems explains precisely what the book will do in 254 concise pages that are a joy to read: it will very likely—and very likely permanently—change the way you think about the world around you.

Key concepts like stocks, flows, and feedback loops are introduced using simple models and metaphors like a bathtub filling and draining, or a home’s temperature adjusted via thermostat:

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The tub can’t fill up immediately, even with the inflow faucet on full blast. A stock takes time to change, because flows take time to flow. That’s a vital point, a key to understanding why systems behave as they do. Stocks usually change slowly. They can act as delays, lags, buffers, ballast, and sources of momentum in a system. Stocks, especially large ones, respond to change, even sudden change, only by gradual filling or emptying.

(And speaking of bathtubs, if you’ve ever had to adjust the temperature in a shower with a knob unusually far away from the faucet, you’ve experienced the challenges of dealing with a delayed feedback loop.)

Quickly, yet almost imperceptibly, Meadows builds on these simple models and begins describing much more complex systems, including the kinds present all around us:

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After the first chapter introducing these core concepts, you will already start seeing them all around you, and soon find yourself thinking about the relationship between stocks and flows in your home, your work, your city, and the economy.

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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.

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