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.

Leadership

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.

Company building

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?

Management

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.

Sales

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.

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Book Notes: Successful Fathers

An older book (no kindle version!), Successful Fathers, was recommended to me by a father I really respect. Here are my book notes for it.

Fathers and mothers today, isolated as they are from their own parents and extended family, need as much experienced advice as they can get. In our own era, they need to work harder to get it.

Rings very true. Most parents, who aren’t under some other massive life stress (finances, health, etc) are very concerned about raising their kids the "right way". I am too.

However, parenting advice is an industry. It’s a business. There’s lots of advice in books, videos, courses, etc and much of it is conflicting. We aren’t missing advice, we are missing advice we can trust.

What he identifies here is this didn’t use to be a problem. Your parents, cousins, tight-night community passed down what they learned and that was it. You trusted them because you saw the outcome and didn’t try to look anywhere else. It’s definitely more complicated now.

Love is the capacity and willingness to embrace hardship for the sake of someone’s welfare

Beautiful definition.

From the earliest infancy, we acquire [values] by imitating people whose character we admire, principally from our parents.

I really enjoyed Wanting which explores the idea of mimetic desire. This is another example of how we are deeply mimetic. It’s not something that’s good or bad, it just is, and it’s important to take into account when thinking about human nature.

If my kids copy who they admire, it’s important that I become someone they can admire. This may sound obvious, but it results in interesting tradeoffs: should I spend time with my kids, or time doing something that powers the rest of my life?

I think the answer is complicated. Modern parenting advice and the current cultural norms—at least in how I perceive them—seem to push for spending more time with your kids, always. You aren’t a good dad unless you are at the soccer game, dance practice, reading to your kids, etc. Those are all good things, but the equation is more complex when thinking about how to spend your time when you have kids: making sure you are living life to the fullest is a critically important thing and can’t be sacrificed on the altar of maximizing time with your kids.

A husband’s neglect for his wife, a failure to support her authority, leads eventually toward the children’s saas and disobedience at home.

Parents need to be fully aligned in how they are raising kids—standard of behavior, discipline, etc. If dad isn’t fully behind mom, and vise-vera, kids will naturally use this against their parents to get what they want.

It’s up to parents to ensure kids don’t get what they want, but get what they need.

Psychologists have noted that much of the posturing and verbal defiance of adolescents is really testing and questioning of their father’s standards.

This aligns closely with the "high standard, high connection" parenting approach that most of the "emotion coaching"-type parenting books espouse.

The idea is that kids really want boundaries and rules and bad behavior—when they are young, or older—is their way of testing where the boundaries really are. This has felt very true in my experience.

Middle-class children today almost never see their father work

I think this is changing with remote work, but in a sense, it’s hard to ‘see’ the work that dad (or mom!) might be doing on a call or on the computer.

The idea still holds that kids rarely see dads working in an area where they excel. This decreases the respect for their parents and naturally encourages them to look elsewhere for a mimetic model for their life.

Bringing kids into your work in creative and sometimes strange ways feels key to giving them a greater understanding of what you do and why they should respect you for it.

Television and other entertainment have become the principal means by which children concepts of adult life

The core of this statement is true: rather than kids learning about adult life through a group of adults, kids do infer what ‘real life’ is like through screens. Videos, social media, news, articles, etc have an outsized influence on how kids decide how the real work operates.

The book makes the argument that this influence has grown over time because of the decreased interaction with other adults. I think this is more true than ever before—we don’t interact with nearly as many people as we used to, because we don’t have to. Mostly everything you need can be ordered quickly on a phone, work can be done remotely, neighborhoods are more isolated, etc. The lack of adult interaction changes how kids build a model of how adult life really is.

Material riches crowd out the central realities of life

The more wealth we have, the more we are comfortable and forget the suffering of others. It’s easier to empathize with others’ suffering when you are experiencing it yourself.

children come to know their father’s mind inside and out

Letting kids into your inner life—what you are experiencing, what you are feeling, how you are thinking about a problem, how you are approaching a situation is key to giving them an understanding of who you are. If they don’t know who you are, they can’t decide if they should model their life after you.

I’ve always loved families that have intense discussions. Vigorous debate and explaining how you are thinking are key to a child’s formation.

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Book Notes: Making it All Work

Something new I’m going to try doing this year is book notes. I’m continually more bought into the idea that writing down your thoughts helps you harden and remember them. Books take a lot of time to read: if I’m going to invest the time in a book, I should be ok investing another ~hour in calcifying the lessons I learned—so that’s what I’m going to try to do. This should help me better filter what books to read: if it’s not worth spending the time to write the notes, I probably shouldn’t read the book (obviously excluding entertainment-only reading).

Here are the notes for Making it All Work. The book wasn’t great, I wouldn’t read it unless you haven’t read Getting Things Done and are new to personal productivity. Here are the notes! Enjoy.

Improving your productivity system David Allen has a zen feel to how he describes things. Meditation, and the idea of generally being self-aware about what you are thinking, feeling, experiencing, etc is a very useful tool. When I sat back and thought about how I ‘felt’ when trying to work on something, I was able to identify various little blockers and better determine what the best thing to do at the moment is. In other words, being aware of where you aren’t performing well is key to improving. This takes time & effort. For instance, there were times I just felt distracted and I didn’t have any state of a specific project ‘loaded up’ in my mind. When I already have ideas around a project, email, etc ‘loaded’ into my mind I can work much more quickly on executing. Doing something physical—kettlebell swings, going for a run, pull-ups, etc—can shift me out of a distracted mode and convince my mind to focus its attention on the next project. I find that this sort of ‘focus shift’ using something physical can help when I’m switching between projects. I find this is true with parenting too. If your kid is in a bad mood / having a meltdown, shifting the physical environment can solve the problem. When my toddler is having a meltdown I suggest we go on a "barefoot walk" around the neighborhood (I’m weird and like walking without shoes on) and she immediately stops crying is ready to go.

And frankly, if you have any thought more than once, in the same way about the same subject, you’re probably involved in unnecessary work and exhausting your creative energy.

Thinking about the same thing over and over is a ‘process smell’: you aren’t clear on what you need to do next and don’t trust your system.

Paying attention to what has your attention

Good catchphrase from the book that encompasses this.

GTD is fundamentally much more about mind management than about time management

Time management tools have never worked well for me, but GTD has.

Given the vast changes in speed, volume, and ambiguity of what grabs our attention these days, we face an increasing need to have an “extended mind” that can truly relieve the pressure from our psyche and free it up for more valuable work.

I have felt the increase in information throughput in my life and have spent a lot of time intentionally decreasing it. The other half of the equation is developing processes and systems to help manage the information you do ne ed to care about. Todoist and Obsidian have been helpful here, but I need to continue to improve my processes.

Create clarity about your work He talks a lot about ‘task dumping’: getting everything you are thinking about dumped somewhere where you know you are going to look at it again. I’ve made this an obsessive habit over the last decade, but reflecting on it I need to do better at this in the mornings. I pray & read every morning, and tasks / projects can distract me during this time. Having a pad of paper (explicitly not using your phone, since it can be distracting just to have it around) to jot down thoughts to ‘clear’ them from your mind is an effective practice for me that I need to get better at. He defines this as "accepting, clarifying, sorting, reflecting, and engaging". I think this is a good articulation of the process we need to go through before intentionally working on the right thing. Chunking down loosely defined tasks (I use todoist) is something I don’t spend time on right now. Without a clearly defined next action, it’s hard to complete the task, and it takes extra cognitive overhead to start working on the task (because it has multiple components). An easy improvement here for me is task splitting. If there’s a large task, even if it’s well defined, I can punt the ‘large’ task to be due in the future, and add a simple next action to my near-term todo list. This applies to parenting too. A task can seem complex and overwhelming to kids, even if they have done it before and seems obvious to you. "Unload the dishwasher" is more ambiguous than "put the forks and spoons away that are in the bottom of the dishwasher". I’ve seen breaking down the task for my kids be an important way of getting them engaged with a project more. In my todo list, there are a bunch of investigative tasks. Writing or researching something I’m interested in. This could be anything from thinking about a parenting problem with my wife, investigating a new productivity tool like Raycast, implementing a new health habit, etc. These are rarely ever things I’m going to be able to complete in one sitting, and I’m rarely able to do more than one per day. However, they clutter up my todo list and weigh down on my psyche (i.e. if I see a ton of tasks due in one day, I get overwhelmed, even if I know they don’t need to be completed right now). I need to think through this and determine how to automatically limit these types of tasks each day.

Ambiguity is a monster that can still take up residence and lurk in the sharpest, most productive places and among the most sophisticated people.

Unlocking the creative process Whenever I’m hugely productive I feel this: "Loss of control and perspective is the natural price you will pay for being creative and productive. The trick is not how to prevent this from happening, but how to shorten the time you stay in an unsettled state. " Spending time organizing yourself is an important function: "Much of the energy in propelling a rocket is spent in course correction—it is, in a way, always veering out of control and off-target." Patrick Lencioni’s work is aligned with the idea that the unsaid human issues in the room (whether at work or home) affect your ability to be creative and solve problems together: "Perhaps we all are more attuned to one another than we realize, and if someone is disconnected from the mutual intention of the occasion because of unacknowledged issues, they just won’t participate fully in the game, which will mitigate the group’s cohesion and positive energy." Separating creativity from analysis or rigor is important. I’ve found you can spark creative thoughts by intentionally including bad, wild, or dumb ideas in a list. It makes it feel easier—even if it’s an exercise you are doing with yourself—to express more creative ideas. "Good brainstorming is stifled by any attempt to analyze and evaluate the meaning and merit of those ideas too soon." Levels of perspective

I’ve always felt it’s hard to calculate the next best thing to do. There are too many options, there is too much to do. In the book, it’s articulated that the reason this is hard is that there are too many inputs and it’s impossible to determine the next best thing. By organizing your tasks and thoughts well, you can make a better intuitive judgment aided by your best-effort prioritization and your psyche will slowly trust your judgment. For me, I often feel mental friction when I’m not certain about what to do next and I think this idea will help me here.

He makes the argument that it’s critical to think in terms of "level of perspective" or "horizons of focus":

Purpose/Principles Vision Goals Areas of Focus Projects Tasks

I think this is a good model, even if the exact wording of these categories might change depending on how you think about the world. I need to refine some of my thinking on the higher-level areas of focus; reflecting on this during reading the book made me realize how much I’m missing at the "top".

The true power in a long-range vision is the acceptance that holding that picture inside your consciousness permits you to imagine yourself doing something much grander than you would normally allow yourself.

Big thinking is a skill. Some people don’t have it naturally (like myself). Clarity around a long-range vision does seem to enable your mind to think bigger.

No effective framework will ever get any simpler than the continuum of purposes/principles, vision, goals, areas of focus, projects, and next actions.

This was a helpful structure for me. I was missing the higher-level categories and need to work on defining them and putting them in a place where I can be reminded and structure the lower levels around them.

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