The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
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the CEO job as knowing what to do and getting the company to do what you want. Designing a proper company culture will help you get your company to do what you want in certain important areas for a very long time.
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the black art of scaling a human organization.
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When an organization grows in size, things that were previously easy become difficult.
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when you are small become big challenges as you grow:   Communication   Common knowledge   Decision making
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the challenge is to grow but degrade as slowly as possible.
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when adding people into the company feels like more work than the work that you can offload to the new employees,
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The first scale technique to implement is specialization. In startups, everybody starts out as a jack-of-all-trades.
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As the company grows, it becomes increasingly difficult to add new engineers, because the learning curve starts to get super-steep. Getting a new engineer up to speed starts to become more difficult than doing the work yourself. At this point, you need to specialize.
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organizational design and process.
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at some point the monolithic design of one huge organization runs out of gas and you will need to split things into smaller subgroups.
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Do client engineering and server engineering have their own groups or do you organize by use cases and include all technical components?
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If you want people to communicate, the best way to accomplish that is to make them report to the same manager.
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The organizational design is also the architecture for how the company communicates with the outside world.
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1. Figure out what needs to be communicated.
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2. Figure out what needs to be decided.
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3. Prioritize the most important communication and decision paths.
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4. Decide who’s going to run each group.
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optimize the organization for the people—for the people doing the work—not for the managers.
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5. Identify the paths that you did not optimize.
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6. Build a plan for mitigating the issues identified in step five.
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The purpose of process is communication. If there are five people in your company, you don’t need process,
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you can maintain high-quality transactions with no bureaucratic overhead.
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A process is a formal, well-structured communication vehicle.
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When communication in an organization spans across organizational boundaries, processes will help ensure that the communication happens and that it happens with quality.
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it’s much easier to add new people to old processes than new processes to old people.
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Formalize what you are doing to make it easy to onboard new people.
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The process of scaling a company is not unlike the process of scaling a product.
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Managing at scale is a learned skill rather than a natural ability. Nobody comes out of the womb knowing how to manage a thousand people. Everybody learns at some point.
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The act of judging people in advance will retard their development.
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Hiring scalable execs too early is a bad mistake.
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Don’t separate scale from the rest of the evaluation. The relevant question isn’t whether an executive can scale; it’s whether the executive can do the job at the current scale.
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Make the judgment on a relative rather than an absolute scale.
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Predicting whether an executive can scale corrupts your ability to manage, is unfair, and doesn’t work.
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Investing in courage and determination was an easy decision for me.”
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focus on what I needed to get right and stop worrying about all the things that I did wrong or might do wrong.
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the most difficult skill I learned as CEO was the ability to manage my own psychology.
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The first rule of the CEO psychological meltdown is don’t talk about the psychological meltdown.
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someone doesn’t become a CEO unless she has a high sense of purpose and cares deeply about the work she does.
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a CEO must be accomplished enough or smart enough that people will want to work for her.
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No training as a manager, general manager, or in any other job actually prepares you to run a company. The only thing that prepares you to run a company is running a company.
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Even if you know what you are doing, things go wrong.
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Seeing people fritter away money, waste each other’s time, and do sloppy work can make you feel bad. If you are the CEO, it may well make you sick.
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If the CEO is outwardly focused, she ends up terrorizing the team to the point where nobody wants to work at the company anymore. If the CEO is inwardly focused, she ends up feeling so sick from all the problems that she can barely make it to work in the morning.
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Tip to aspiring entrepreneurs: If you don’t like choosing between horrible and cataclysmic, don’t become CEO.
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it’s important to understand that nearly every company goes through life-threatening moments.
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The problem with psychology is that everybody’s is different.
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Make some friends. Although it’s nearly impossible to get high-quality advice on the tough decisions that you make, it is extremely useful from a psychological perspective to talk to people who have been through similarly challenging decisions.
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Get it out of your head and onto paper.
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Focus on the road, not the wall.
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Focus on where you are going rather than on what you hope to avoid.