The Hard Thing About Hard Things — Book Notes

Jorge Tovar
5 min readJan 24, 2022

The Hard Thing About Hard Things is an excellent book full of lessons from an experienced entrepreneur.

Every business book focuses on how to do things perfectly and doesn’t screw them up, but what do you do when you have already had problems?

Focus

Sometimes the things that you are not doing are the things you should be focused on.

Sometimes as engineers we overemphasize improving things instead of thinking out of the box and looking for the things that we are missing.

Struggle

Some stuff may or may not help:

  • Don’t put it all on your shoulders
  • Technology is extremely complex is like chess (There is always a move)
  • Play long enough and you might get lucky (Compound effect)
  • Don’t take it personally (Be too hard with you wouldn't help)

As a CEO you should be Transparent

Sometimes good news travels very fast and bad news too slowly, making it almost impossible to resolve things

  1. Trust: Telling things as they are is a critical part of building this
  2. The more brains working on the hard problems, the better. In order to create a great company you need to hire good people (Get things done, smart, good communication skills) and let them work on your biggest problem
  3. A good culture needs that bad news travels fast: build a culture that rewards people for getting problems to the table where they can be solved

Layoffs

Inevitable breaks the company culture

Firing an executive

  1. Probably your job definition is poor
  2. You hired for lack of weakness rather than for strengths
  3. You failed to integrate the executive (Onboarding process)

Nobody cares

Spend zero time on what you could have done, and devote all your time to what you might do.

Company

Strive for a good place to work

Why you should train your people

In a technology company, people are the most important asset. In any startup, the recruiting and interview process is one of the most important things that need to be executed properly.

  1. Productivity: Training is one of the highest leverage activities a manager can perform
  2. Performance management: set expectations
  3. Product quality: good design, easy to adapt to customer needs
  4. Employee retention: usually people left their jobs because they hate their managers or they weren't learning anything

What you should do first:

  • The most relevant topics (knowledge and skills required to do their job)
  • Document architecture nuances maybe using Architecture Decisions Records (ADRs)
  • Hold regular one on one meetings
  • Train the managers: management state of the art in technology companies is extremely poor
  • Enforce Functional and Technical training
  • As a CEO you should teach the course on management expectations

Product managers

  • Good product managers take full responsibility and measure themselves in terms of the success of the product
  • Bad product managers have a lot of excuses (engineers, design, money)
  • Good product managers are responsible for the right time and the right product
  • Good product managers define the What, CEO defines the WHY
  • Good product managers focus on revenue and customers
  • Good product managers are good communicators, take written positions on important issues

Little companies execution

In a startup as an executive, nothing happens until you make it happen

  • What will you do in your first month on the job?
  • How will your new job differ from your current job?
  • Why do you want to join a small company?

Aggressively integrate the candidate once onboard

  • Force them to create
  • Make sure they get it: bring comprehensive questions about everything
  • Put them in the mix: require a report from them on what they learned from each person

Management debt

Make people accountable (schedule, design) who?

Management quality assurance

Recruiting and Hiring

  • Sharply understand the skills and talents required to succeed in every position?
  • Interviewers are well prepared?

Compensation

  • Make sense for your company demographics?
  • Performance vs compensation

Training and integration

  • How long does it take to become productive
  • Expectations are clear

Performance management

  • Do your managers give consistent, clear feedback to their employees?
  • Quality of the written performance reviews?

Motivation

  • Are your employees excited to come to work?
  • Do your employees believe in your mission?
  • Why do employees quit?

Minimize company politics

Politics: Advancing their careers by means other than merit and contribution

Avoid rewarding behavior that has nothing to do with advancing your business!

Hire people with:

  • The right kind of ambition: view the world through the team prism
  • Process: Performance evaluation, organizational design, promotions

Titles and promotions

  • Employees want them
  • Eventually, people need to know who is who

Be aware of the Peter principle (Be promoted to a position in which they are no longer competent)

At the end titles cost nothing. :)

When smart people are bad employees

“If you hold the bus for everyone on the team, then you will be so late you will miss the game, so you can’t do that”

Old people

Hire old people to acquire knowledge and experience in a specific area

For executives is also important to measure performance:

  • Results against objectives
  • Management:
  • Innovation: Long term vision
  • Working with peers

One-on-One

Perhaps the CEO most important operational responsibility is designing and implementing the communication architecture for the company

  • If we could improve in any way, how could we do it?
  • What’s the number one problem with our organization? Why?
  • What’s not fun about working here?
  • Whom do you admire?
  • If you were me, what changes would you make?
  • What don’t you like about the product?
  • What’s the biggest opportunity we’re missing out on?
  • What are we not doing that we should be doing?
  • Are you happy working here?

Programming your culture

Embrace and rewards some shared values and behaviors

Scaling your company

Problems:

  • Communication
  • Common knowledge
  • Decision making

How to do it:

Specialization

Organizational design:

  • What needs to be communicated
  • What needs to be decided
  • Prioritize the most important communication and decisions paths
  • Decide who’s going to run each group
  • Identify the paths that did not optimize
  • Build a plan for mitigating issues

Process: the purpose of the process is communication

  • Focus on the output first: What should the process produce?
  • Figure out how you will know if you are getting what you want at each step: measures
  • Engineer accountability into the system

Most difficult CEO skill

Focus on the road, not the wall

Great leaders

  • Articulate the vision: storytellers
  • Alignment of interest
  • Ability to achieve the vision

Wartime CEO “All I have in this world is time, and you are wasting my time”

CEO

Does the CEO know what to do?

  • Strategy: Story, Why?
  • Decision making: Speed and quality of the CEOs decisions

Is easy for employees to contribute to the mission?

Closing thoughts

  • We need to be better but we also need to be different
  • The only way to learn how to be a CEO is to be a CEO
  • In the absence of hands-on experience, you’d get killed at the moment you took the field
  • Embrace your weirdness, your background, your instinct

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Jorge Tovar

System Engineer who loves coding and minimalism @jorgetovar621 in Twitter