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There are no shortcuts to knowledge, especially knowledge gained from personal experience. Following conventional wisdom and relying on shortcuts can be worse than knowing nothing at all.

No matter who you are, you need two kinds of friends in your life. The first kind is one you can call when something good happens, and you need someone who will be excited for you. Not a fake excitement veiling envy, but a real excitement. You need someone who will actually be more excited for you than he would be if it had happened to him. The second kind of friend is somebody you can call when things go horribly wrong— when your life is on the line

An early lesson I learned in my career was that whenever a large organization attempts to do anything, it always comes down to a single person who can delay the entire project.

Figuring out the right product is the innovator’s job, not the customer’s job. The customer only knows what she thinks she wants based on her experience with the current product. The innovator can take into account everything that’s possible, but often must go against what she knows to be true.

No, markets weren’t "efficient" at finding the truth; they were just very efficient at converging on a conclusion— often the wrong conclusion.

Note to self: It’s a good idea to ask, "What am I not doing?"

Startup CEOs should not play the odds. When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same.

You won’t be able to share every burden, but share every burden that you can.

As a result, like playing three-dimensional chess on Star Trek, there is always a move.

My single biggest personal improvement as CEO occurred on the day when I stopped being too positive.

In my mind, I was keeping everyone in high spirits by accentuating the positive and ignoring the negative. But my team knew that reality was more nuanced than I was describing it. And not only did they see for themselves the world wasn’t as rosy as I was describing it; they still had to listen to me blowing sunshine up their butts at every company meeting.

Three key reasons why being transparent about your company’s problems makes sense:

  • Trust
  • The more brains working on the hard problems the better
  • A good culture is like the old RIP routing protocol: Bad news travels fast; good news travels slow.

In any human interaction, the required amount of communication is inversely proportional to the level of trust.

As a corollary, beware of management maxims that stop information from flowing freely in your company. For example, consider the old management standard: "Don’t bring me a problem without bringing me a solution." What if the employee cannot solve an important problem? For example, what if an engineer identifies a serious flaw in the way the product is being marketed? Do you really want him to bury that information?

If you run a company, you will experience overwhelming psychological pressure to be overly positive. Stand up to the pressure, face your fear, and tell it like it is.

I asked him why all the other startups failed. He replied that the layoffs inevitably broke the company’s culture. After seeing their friends laid off, employees were no longer willing to make the requisite sacrifices needed to build a company.

In other words, the wrong way to view an executive firing is as an executive failure; the correct way to view an executive firing is as an interview/integration process system failure.

There is no such thing as a great CEO, a great head of marketing, or a great head of sales. There is only a great head of sales for your company for the next twelve to twenty-four months.

The good of the individual must be sacrificed for the good of the whole.

Use appropriate language. Make clear with your language that you’ve decided. As previously discussed, use phrases like "I have decided"

It probably won’t be lost on the employee that you are just as underskilled for your job as he is for his. Don’t dodge this fact.

But despite perhaps the most massive and public early warning system ever, each CEO reiterated strong guidance right up to the point where they dramatically whiffed their quarters. He said they were not lying to investors, but rather, they were lying to themselves. Andy explained that humans, particularly those who build things, only listen to leading indicators of good news.

"Ben, those silver bullets that you and Mike are looking for are fine and good, but our Web server is five times slower. There is no silver bullet that’s going to fix that. No, we are going to have to use a lot of lead bullets."

There comes a time in every company’s life where it must fight for its life. If you find yourself running when you should be fighting, you need to ask yourself, "If our company isn’t good enough to win, then do we need to exist at all?"

I learned about why startups should train their people when I worked at Netscape. People at McDonald’s get trained for their positions, but people with far more complicated jobs don’t. It makes no sense.

If you don’t train your people, you establish no basis for performance management. As a result, performance management in your company will be sloppy and inconsistent.

I found that there were two primary reasons why people quit: They hated their manager; generally the employees were appalled by the lack of guidance, career development, and feedback they were receiving. They weren’t learning anything: The company wasn’t investing resources in helping employees develop new skills.

The most important thing to understand is that the job of a big company executive is very different from the job of a small company executive.

In the second example, I managed the team to a set of numbers that did not fully capture what I wanted. I wanted a great product that customers would love with high quality and on time— in that order.

It’s important to supplement a great product vision with a strong discipline around the metrics, but if you substitute metrics for product vision, you will not get what you want.

MANAGING STRICTLY BY NUMBERS IS LIKE PAINTING BY NUMBERS

At HP, the company wanted high earnings now and in the future. By focusing entirely on the numbers, HP got them now by sacrificing the future.

Like technical debt, management debt is incurred when you make an expedient, short-term management decision with an expensive, long-term consequence.

"That is not the priority" is radically weaker than "That is not the fucking priority." When the CEO drops the F-bomb, it gets repeated.

Sometimes an organization doesn’t need a solution; it just needs clarity.

What do I mean by politics? I mean people advancing their careers or agendas by means other than merit and contribution. There may be other types of politics, but politics of this form seem to be the ones that really bother people.

Build strict processes for potentially political issues and do not deviate.

For a complete explanation of the dangers of managers with the wrong kind of ambition, I strongly recommend Dr. Seuss’s management masterpiece Yertle the Turtle.

While it may work to have individual employees who optimize for their own careers, counting on senior managers to do all the right things for all the wrong reasons is a dangerous idea.

For any title level in a large organization, the talent on that level will eventually converge to the crappiest person with the title.

If it makes people feel better, let them feel better. Titles cost nothing.

The proper reason to hire a senior person is to acquire knowledge and experience in a specific area.

Perhaps the CEO’s most important operational responsibility is designing and implementing the communication architecture for her company.

The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting.

Some questions that I’ve found to be very effective in one-on-ones: If we could improve in any way, how would we do it? What’s the number-one problem with our organization? Why? What’s not fun about working here?

Who is really kicking ass in the company? Whom do you admire? If you were me, what changes would you make? What don’t you like about the product? What’s the biggest opportunity that we’re missing out on? What are we not doing that we should be doing? Are you happy working here?

The primary thing that any technology startup must do is build a product that’s at least ten times better at doing something than the current prevailing way of doing that thing.

the following things that cause no trouble when you are small become big challenges as you grow: Communication, Common knowledge, Decision making

Think of the organizational design as the communications architecture for your company.

The process of scaling a company is not unlike the process of scaling a product. Different sizes of company impose different requirements on the company’s architecture. If you address those requirements too early, your company will seem heavy and sluggish. If you address those requirements too late, your company may melt down under the pressure.

If CEOs were graded on a curve, the mean on the test would be 22 out of 100.

When people in my company would complain about one thing or another being broken, such as the expense reporting process, I would joke that it was all my fault. The joke was funny, because it wasn’t really a joke.

On the other hand, talking to your board and outside advisers can be fruitless. The knowledge gap between you and them is so vast that you cannot actually bring them fully up to speed in a manner that’s useful in making the decision. You are all alone.

People who watch you judge you on what you do, not how you feel."

Social credit matrix p211

Over the past ten years, technological advances have dramatically lowered the financial bar for starting a new company, but the courage bar for building a great company remains as high as it has ever been.

When it comes to CEO succession, internal candidates dramatically outperform external candidates. The core reason is knowledge.

The very next day I informed the head of Sales Engineering and the head of Customer Support that they would be switching jobs.

Technical founders are the best people to run technology companies. All of the long-lasting technology companies that we admired— Hewlett-Packard, Intel, Amazon, Apple, Google, Facebook— had been run by their founders.

It was incredibly difficult for technical founders to learn to become CEOs while building their companies. I was a testament to that. But, most venture capital firms were better designed to replace the founder than to help the founder grow and succeed.

As a CEO, there is no such luxury. As CEO, I had to worry about what everybody else thought. In particular, I could not show weakness in public.