Book Notes: The Hard Thing About Hard Things

Something new I’m doing this year is book notes. I believe writing down your thoughts helps you develop, harden, and remember them. Books take a lot of time to read, taking time to document lessons learned is worth it.

Here are the notes for The Hard Thing About Hard Things by Ben Horowitz. Definitely worth reading, especially if you are actively building a company, although I wouldn’t say it’s in the must-read category.

Below are my notes! Enjoy.

A much better idea would have been to give the problem to the people who could not only fix it, but who would also be personally excited and motivated to do so.

I think any good leader feels personally responsible for the outcome of whatever they are doing. Everything is their job, in the sense that ultimately if the project isn’t successful it is their fault.

However, I think Ben’s framing is important: it’s the leaders job to clearly describe problems—instead of hiding them—no matter how large, and get the right people aligned to the problem who are energized by big scary problems that need to be solved.

The more you communicate without BS—describing reality exactly how it is—the more people will trust what you say. There are no lines to read between. It takes time for this trust to filter its way through an organization, but it makes any other communication (which is a prime job of a leader) way easier in the future.

Former secretary of state Colin Powell says that leadership is the ability to get someone to follow you even if only out of curiosity.

Sometimes only the founder has the courage to ignore the data;

It’s nice to lean on data to make decisions. All of the great decisions in life need to be made out of an absence of data; in the absence of certainty. The safety of the modern world has made us less comfortable with taking risks and being decisive in areas of life where it is impossible to get certainty.

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.

Ben has a lot of counterintuitive thinking about executive management throughout the book. I found the thinking around executive hiring, management, etc the part of the book most worth reading.

He articulates the executive hiring, management, and firing process as incredibly messy, opaque, and constantly changing. I think this is the thing that technical founders struggle with a lot—it’s not straightforward, requires a lot of tacit knowledge that can only be acquired through experience, and requires lots of conflict-laden conversations which everyone hates.

Part of the leader’s job is the ability to step-in and cover any of the executive’s job if they leave or are fired. This helps the leader understand what’s really needed in that role at this stage of the company.

What is needed from an executive changes quickly as a company grows. It’s your job as a leader to understand what is needed right now, communicate that expectation, and then measure their performance off that revised standard. It’s up to the executive to figure out how to retool their skills to meet the new requirements; you don’t have time to help them here. If they can’t figure out the new role you need to let them go fast.

Management techniques that work with non-executives don’t work with executives. You can’t lead professional leaders in the same way. For instance, the "shit sandwich" approach feels babying to a professional when it may work well for a lead-node individual contributor. What works on a lead-node team doesn’t work when running a management team.

in my experience, look and feel are the top criteria for most executive searches.

Developing and holding to an independent standard in any of life is incredibly hard. We are deeply mimetic and avoiding pattern-matching on what the herd believes is right is one of the hardest tasks of leadership.

Consensus decisions about executives almost always sway the process away from strength and toward lack of weakness.

You want someone who is world-class at thing you are hiring them for. Make sure your organization can swallow their faults; don’t try to avoid faults—even major ones—completely.

Relatedly, the concept of "madness of crowds" is a good mental model to keep in mind.

This is why you must look beyond the black-box results and into the sausage factory to see how things get made.

Understanding how things work at the ground-level in an organization is key to improving performance. I always thought Stripe’s leadership did a great job here: jumping into engineering teams for a week to understand what the real problems were can’t be replaced by having 100 1:1s.

I describe the CEO job as knowing what to do and getting the company to do what you want.

This is what I liked most about the book—plain descriptions of commonly amorphous concepts.

as often candidates who do well in interviews turn out to be bad employees.

If someone is good at cracking an interview, it could be a signal that they aren’t good at the core work. If someone is exceptional, they aren’t going to care about interviewing well or understanding the big-company decision-making matrix around hiring: they know they are smart and want to work at a place that values the work.

This is a distinct advantage startups have. I love the interview process at one of my new favorite productivity apps:

We don’t do whiteboard interviews and you’re always allowed to google. We’ll talk about things you’ve previously worked on and do a work trial – you’ll be paid as a contractor for this.

They can focus on the work and ignore the mess of other signals that are only important when you need to ensure quality at scale.

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.

Simple and true description of what makes a company great, and conversely what makes bureaucratic organizations painful to operate in.

Companies execute well when everybody is on the same page and everybody is constantly improving.

Constant improvement compounds over time.

What do I mean by politics? I mean people advancing their careers or agendas by means other than merit and contribution.

Good definition of politics.

I’d love to understand what companies have designed a performance process for higher management tiers that isn’t political. At larger companies, getting promoted to higher levels becomes more political almost by definition: it’s harder to describe your impact quantitatively because your work is more people-oriented and dependent on your leadership ability.

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

I’d love to hear more stories about well-designed communication systems in companies.

Perhaps most important, after you and your people go through the inhuman amount of work that it will take to build a successful company, it will be an epic tragedy if your company culture is such that even you don’t want to work there.

Reminds me of the parenting idea "don’t raise kids that you don’t want to hang out with."

the challenge is to grow but degrade as slowly as possible.

Ben makes the assumption that all companies degrade over time. Things that were easy become difficult when you add more people: mostly because of the communication overhead/coordinate and knowledge gaps across the organization.

I want to learn more about what organizations fought against this and when they felt there was an inflection point of degradation. How big can you grow before things degrade quickly?

big company executives tend to be interrupt-driven.

They wait for problems to come to them, and they don’t execute work individually. Be aware of when you’ve reached this stage and then hire for these people. Hiring this type of person too early will most likely fail—if you are used to working in this style, it’s hard to change.

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.

Resonates with my experience. It’s amazing how one or two B players can destroy the ability to get anything significant done. The Elon Musk biography talks about how Elon’s employees were terrified about being "the blocker" and would do anything they needed to in order to avoid being that person. He would ask for status update multiple times a day and force you to do whatever needed to be done to eliminate yourself as the primary blocker.

However, if I’d learned anything it was that conventional wisdom had nothing to do with the truth and the efficient market hypothesis was deceptive. How else could one explain Opsware trading at half of the cash we had in the bank when we had a $20 million a year contract and fifty of the smartest engineers in the world? No, markets weren’t “efficient” at finding the truth; they were just very efficient at converging on a conclusion—often the wrong conclusion.

[managing by the numbers] penalizes managers who sacrifice the future for the short term and rewards those who invest in the future even if that investment cannot be easily measured.

Not everything can be measured. You need to have qualitative and quantitative metrics, and you can’t rely too strongly on quantitative metrics. Building anything great requires great conviction in the absence of evidence supporting the outcome you believe is inevitable.

As Andy Grove points out in his management classic High Output Management, the Peter Principle is unavoidable, because there is no way to know a priori at what level in the hierarchy a manager will be incompetent.

This is the sort of thing that makes management so incredibly hard.

If you become a prosecuting attorney and hold her to the letter of the law on her commitment [to fix a problem that she discovered], you will almost certainly discourage her and everybody else from taking important risks in the future.

No easy answer to this question. You have to hold people accountable but understand the situation enough not to disincentivize critical behavior which improves the company. If you don’t do this right, people notice and will manage their work towards what is indirectly rewarded.

the best ideas, the biggest problems, and the most intense employee life issues make their way to the people who can deal with them. One-on-ones are a time-tested way to do that,

This rings true to me. Although, I think it’s critical to get as much state out of meetings into central systems as possible so 1:1s can mostly focused on the small batch of critically important stuff that cannot be handled async.

There’s an interesting thread in the story of OpsWare that could yield the lesson "Don’t rely too much on whales". I don’t think anyone would disagree with this advice in the abstract, but I think practically it’s hard to build a big business without whales. I think you want to avoid being too reliant on whales, but I believe you also need to be ok pandering to your largest customers in B2B SaaS and doing what needs to happen to keep them thrilled with you.

There was a really helpful appendix with some great questions and guides to hiring a sales leader. I think these people-oriented jobs can sometimes seem as a black art to the hyper-logical work that technical founders start out doing.