The Hard Things About Hard Things

Building a business when there are no easy answers


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One of the points early in the book that Ben said his father taught him is something challenging for many people who are passionate about their work, that is, remembering to take time and focus on loved ones and friends.

Flowers are really cheap. But do you know what is expensive? Divorce.

I don’t think that his father was exclusively talking about “cheap” from a financial perspective. And really I think the point can be boiled down to doing seemingly simple, yet impactful things for friends and loved ones can mean a lot because when you don’t do anything and don’t give any attention to these relationships, they fall apart. Ben talks about how after this conversation, he had to consider priorities that weren’t purely his own.

By doing everything, I would fail at the most important thing.

Early in Ben’s career, he landed a dream job at a company run by a young Marc Andreessen. This relationship evolved into what is now one of the most well-recognized technology-focused venture capital firm, Adreessen Horowitz (known as “a16z”). Their portfolio consists of companies like airbnb, Digital Ocean, Facebook, GitHub and many, many more well-known companies. Ben describes why his relationship with Marc has been so successful and why it is important for everyone to find someone who you can challenge and that can challenge you and your ideas. But that there has to be a balance between complacency and intensity, too much of either is not productive.

Communication and Feedback

Another point that Ben makes in regards to relationships, but more specifically in communication is the importance of honesty and being able to deliver difficult messages, clearly. If instead of doing the hard thing — delivering the message in a straightforward way — you give someone a “shit sandwich” (a compliment, followed by the difficult thing that you really wanted to say, followed by another compliment), you will confuse whoever you are talking to and won’t actually get the point that you wanted to make across. Ben also mentions the importance of clarity, even when you don’t have a solution to a particular problem.

While on the topic of giving feedback, in chapter 7, there is a section titled “Feedback is a dialog, not a monologue”. In this section, Ben explains that “…your goal should be for your feedback to open up rather than close down discussion.” In code reviews, I’ve told my team that when someone gives feedback, that doesn’t necessarily mean to do exactly what the person is proposing or that the person is correct, but that it is a data point to consider and possibly discuss further if you don’t understand, or disagree. Personally, I have been trying to give feedback that is both actionable and data-backed. When I do give opinionated feedback, I make it clear that it is an opinion. On a similar note, work that you have done can and should be iterated upon; it should not be “dead”. You shouldn’t be deterred from working on something because you aren’t sure if you have the best solution. Treat it like an experiment. You probably have a reason for thinking that what you are working on could improve something — whether it be a process, safety, etc. — and if it doesn’t, or if it makes it worse, “undo” it. Your work should start a conversation that needs to be had and can be iterated upon.

…your goal should be for your feedback to open up rather than close down discussion.

Hiring and Culture

Ben, throughout the book, makes many great points on the topic of hiring and culture. One of the points that stands out most and if I had to pick just one point from this book, it would be that there is no such thing as the perfect person for the position. Or, the perfect person for the position in 18 months. But rather, that there is only the perfect person for the position at your company, right now. If you hire the person who would be perfect in 18 months, that individuals probably isn’t meeting many peoples’ expectation for the challenges that you are facing right now. In 18 months, or even 6 months, you could be a very different company and the position could have very different responsibilities. If that person is great for what your company needs in 18 months from now and you got them right now, first, they may not be as flexible as you need them to be or second, they could hate the chaos that you are currently facing and end up leaving before they even experience the company 18 months from now. Conversely, someone who is great for the position right now may not be great for the position in 18 months. “…everybody needs to requalify for the new job, because the new job and the old job are not the same.”

Hiring is risky and very difficult. Finding the right person often requires you to analyze both strengths and weaknesses, but often, we either hire or don’t hire someone because of their weaknesses. Instead, Ben suggests that we focus on someone’s strengths and what they can bring to the company.

Ben describes culture as “designing a way of working”. At Amazon, desks being made out of doors instilled frugality into its employees. While at a16z, respecting everyone’s time was something that they wanted to be part of the culture, so for every minute late you are to a meeting with an entrepreneur, you pay a $10 fine. If you were on a very important call and had to be 10 minutes late for the meeting, fine, but be prepared to pay the $100 fine. Ben ends this chapter describing what is not culture, but rather (arguably) perks (e.g., yoga classes, bringing your dog to work, etc.).

Investing in and Managing Employees

After hiring comes investing in and managing employees as to maximize potential. What you will find is that after the on-boarding of new employees, they are “let free” and the training stops there. Ben argues that training is one of the most important jobs that the CEO of a company can and should do. If the CEO spends 12 hours with 10 employees and each of those employees, who will cumulatively work for 20,000 hours in the next year, improves by just 1%, that is 200 additional hours of work gained for 12 hours spent.

Investing in employees should also be done by the managers by having frequent one-on-ones with employees where performance is evaluated and feedback is given and received, frequently. Performance should not exclusively be evaluated quantitatively or qualitative goals are guaranteed to never be met. Evaluating exclusively qualitatively is “like painting by the numbers — it’s strictly for amateurs.”

Mangement purely by the numbers is sort of like painting by the numbers — it’s strictly for amateurs.

Ben also mentions the notion of “management debt” which, similar to technical debt, is “incurred when you make an expedient, short-term management decision with an expensive long-term consequence”. There are three popular types of management debt.

  1. Putting two in the box: When it isn’t clear to employees who should make the final decision, so each decision involves twice the cost.

  2. Overcompensating a key employee, because [they get] another job offer.

  3. No performance management or employee feedback process.

As a manager, you will also have to deal with the “Accountability versus Creativity Paradox”. Do you punish an employee for working on something creative that could help the company in the future, but that lead to a missed deadline? Ben’s answer was basically, that it depends on the seniority of the individual. If the person has more experience, then yes, the individual should be held accountable for not understanding the deadlines and communicating the work or potential deadline shift properly.

My philosophy on this currently has leaned toward doing the thing that I know adds value now and will especially add value in the future, but to be consciously aware of scope creep. You need to know when to stop and when the returns of what you are working is diminishing. In certain cases, it would be acceptable to “open a ticket and put it in the backlog”, but in others, when I have a clear vision and solution for a major problem that has a significant impact on the work we are working on, that is when I suggest doing the work and asking for forgiveness later.

The Vision

Time and time again, from conversations with people and reading books, I constantly hear and see the point of market fit and the vision.

Focus on the road, not the wall

If you focus on what could go wrong, you will drive yourself crazy. “Focus on where you are going rather than on what you hope to avoid.”