Hard Thing about Hard Things

I ordered this book on a whim, I stayed because it gave me a front-row seat into the life of a Tech CEO. This book sobered me up to the realities of what a CEO actually does and boy is it a complex bunch of things. I’d heard about tech CEOs having coaches and it now made sense why.

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.

Sadly, there is no secret, but 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.

Nobody takes the losses harder than the person most responsible.

Technology business tend to be extremely complex. The underlying technology moves, the competition moves, the market moves, the people move. As a result, like playing three-dimensional chess on Star Trek, there is always a move.

It’s a total waste to have lots of big brains but not let them work on your biggest problems.

The most important thing to decide is that you really want to do this. If you walk into a demotion discussion with an open decision, you will walk out with a mess.

If you are a founder-CEO like I was, 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. In fact, admit that if you were a more experienced CEO, you might be able to develop him into the role, but two people who don’t know what they are doing is a recipe for failure.

There’s no silver bullet that’s going to fix that. No, we are going to have to use a lot of lead bullets.

Spend zero time on what you could have done, and devote all of your time on what you might do. Because in the end, nobody cares; just run your company.

Hire for strength rather than lack of weakness.

If he didn’t have the things wrong with him that you enumerated, he wouldn’t be willing to join a company that just traded at thirty-five cents per share.

As organizations grow large, important work can go unnoticed, the hardest workers can get passed over by the best politicians, and bureaucratic processes can choke out the creativity and remove all the joy.

The more I thought about it, the more I realized that while I had told the team “what” to do, I had not been clear about “why” I wanted them to do it. Clearly, my authority alone was not enough to get them to do what I wanted. Given the large number of things that we were trying to accomplish, managers couldn’t get to everything and came up with their own priorities. Apparently, this manager didn’t think that meeting with his people was all that important and I hadn’t explained to him why it was so important.


Do you know the difference between a good place to work and a bad place to work?

Let me break it down for you. In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally. It is a true pleasure to work in an organization such as this. Every person can wake up knowing that the work they do will be efficient, effective, and make a difference for the organization and themselves. These things make their jobs both motivating and fulfilling.

In a poor organization, on the other hand, people spend much of their time fighting organizational boundaries, infighting, and broken processes. They are not even clear on what their jobs are, so there is no way to know if they are getting the job done or not. In the miracle case that they work ridiculous hours and get the job done, they have no idea what it means for the company or their careers. To make it all much worse and rub salt in the wound, when they finally work up the courage to tell management how fucked-up their situation is, management denies there is a problem, then defends the status quo, then ignores the problem.

Are you aware that your manager Tim has not met with any of his employees in the past six months?

Now that you are aware, do you realize that there is no possible way for him to even be informed as to whether or not his organization is good or bad?


In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally.

Most managers feel that training employees is a job that should be left to others. I, on the other hand, strongly believe that the manager should do it himself.

Be careful with “he said, she said”: Once your organization grows to a significant size, members of your team will from time to time complain about each other. Sometimes this criticism will be extremely aggressive. Be careful about how you listen and the message that it sends. Simply by hearing them out without defending the employee in question, you will send the message that you agree. If people in the company think that you agree that one of your executives is less than stellar, that information will spread quickly and without qualification. As a result, people will stop listening to the executive in question and the executive will soon become ineffective.

Being effective in a company also means working hard, being reliable, and being an excellent member of the team.

If people trust you, they will listen to your vision even if it is less articulate. If you are super-competent, they will trust you and listen to you. If you can paint a brilliant vision, people will be patient with you as you learn the CEO skills and give you more leeway with respect to their interests.

As a CEO you should have an opinion on absolutely everything. You should have an opinion on every forecast, every product plan, every presentation, and even every comment.

Jan 2021. Built with Tailwind and Jekyll.