The Hard Thing About Hard Things

business
management
leadership
entrepreneurship
There’s no formula for the hard things in business. This Learnerd summary of Ben Horowitz’s “The Hard Thing About Hard Things” provides battle-tested wisdom on managing your own psychology, firing friends, minimising politics, and leading when there are no good options. Learn the difference between a Peacetime and Wartime CEO and how to embrace the Struggle.

1 Listen to The Hard Thing About Hard Things Summary

2 Book Summary: The Hard Thing About Hard Things by Ben Horowitz

Ben Horowitz shares unflinching, battle-tested advice from his own experience as an entrepreneur and CEO. Unlike management books that present clean formulas for success, this book focuses on the messy, painful, and complex challenges that every leader faces when things go wrong. It’s a guide to navigating the “hard things” for which there are no easy answers.

2.1 The Struggle

The Struggle is the inevitable period of intense pain, doubt, and pressure when a CEO’s dreams turn into nightmares. It’s not failure itself, but it causes failure if you are weak.

  1. What is it? The Struggle is when you question why you started the company, when food loses its taste, and when self-doubt turns into self-hatred. It’s when you know you are in over your head, but you cannot be replaced.
  2. Greatness Comes From The Struggle: Every great entrepreneur, from Steve Jobs to Mark Zuckerberg, has gone through it. The Struggle is where character is forged and greatness is born.
  3. How to Survive: There are no easy answers, but Horowitz offers some advice:
    • Share the burden: Don’t carry it all yourself. Get the maximum number of brains working on the existential threats.
    • There is always a move: In the complex, three-dimensional chess game of a technology business, there is always a strategic option, no matter how bleak things seem.
    • Don’t take it personally: The predicament is probably your fault, but evaluating yourself and giving yourself an F doesn’t help. Everybody makes mistakes.
    • Remember this is what separates the great from the good: If you want to be great, this is the challenge you must face.

2.2 Peacetime CEO / Wartime CEO

Horowitz argues that leadership requires radically different styles depending on the company’s situation. Most management books are written about peacetime.

  • Peacetime CEO: Leads when the company has a significant advantage and can focus on expanding the market and fostering creativity. They build scalable systems and focus on the big picture. They work to minimise conflict and seek broad buy-in.
  • Wartime CEO: Leads when the company is fighting for survival against an existential threat (competition, market shifts, etc.). They are completely intolerant of deviation from the mission. They care about every detail, heighten contradictions to force clarity, and violate protocol to win. They know that sometimes you just have to roll a hard six.
  • Peacetime CEO spends time defining the culture. Wartime CEO lets the war define the culture.
  • Peacetime CEO focuses on the big picture and empowers her people to make detailed decisions. Wartime CEO cares about a speck of dust on a gnat’s ass if it interferes with the prime directive.
  • Peacetime CEO strives to tolerate deviations from the plan. Wartime CEO is completely intolerant.
  • Peacetime CEO works to minimise conflict. Wartime CEO heightens the contradictions to force clarity.

2.3 Telling It Like It Is

One of the biggest mistakes a CEO can make is being overly positive and hiding bad news from the team. Brutal honesty is essential for three reasons:

  1. Trust: Communication is inversely proportional to trust. When you tell the truth, you build trust, which makes all communication more efficient.
  2. More Brains: The more people who understand the real problems, the more brains you have working to solve them. As the open-source saying goes, “Given enough eyeballs, all bugs are shallow.”
  3. Culture: A healthy culture is one where bad news travels fast. If you hide problems, you create an environment where nobody speaks up until it’s too late.

These are some of the hardest things a CEO must do. Doing them correctly is crucial for the trust of the employees who remain.

The Right Way to Lay People Off:

  1. Get Your Head Right: Focus on the future, not the past failure that led to this.
  2. Don’t Delay: Execute quickly once the decision is made to prevent rumours and anxiety.
  3. Be Clear: The message is that the company failed, not the individuals. Admitting failure is key to rebuilding trust.
  4. Train Your Managers: Managers must lay off their own people. Give them a script and prepare them for the conversation.
  5. Address the Company: The CEO must deliver the news to everyone, setting the context for the managers. The message is for the people who are staying.
  6. Be Visible: Don’t hide. Talk to people, show you care, and help them through the process.

Firing an Executive: This is an interview/integration process failure, not just an executive failure.

  1. Root Cause Analysis: Why did you hire the wrong person? Did you hire for lack of weakness instead of strength? Did you hire for scale too early?
  2. Inform the Board: Get their support, get approval for the separation package, and preserve the departing executive’s reputation.
  3. Prepare the Conversation: Be decisive, clear on the reasons, and ready with the severance package. Let them keep their respect.

2.4 Other key ideas

  1. Hire for Strength, Not Lack of Weakness: You need world-class strengths where it counts. A candidate with no sharp weaknesses is often mediocre where you need them to be great.
  2. Hire for the Next 18 Months: Avoid the “scale anticipation fallacy.” Hiring an executive who will be great in 5 years but is wrong for today’s challenges is a common and fatal error. The job changes as the company grows.
  3. Look for the Right Ambition: The best executives have ambition for the company’s success, with their own success coming as a by-product. Beware those who prioritise their personal career path over the company’s victory.
  4. Ones vs. Twos: “Ones” are strategic leaders who are comfortable setting direction with incomplete information. “Twos” are operational leaders who excel at making the company run efficiently. A great CEO must be competent at both. This distinction is critical when thinking about CEO succession.

Horowitz argues this is the most difficult CEO skill. The pressure is immense, everything is your fault, and it’s a lonely job.

  1. Don’t Take It Too Personally: You must be urgent without being insane. Separate the importance of the issues from how you feel about them.
  2. It’s a Lonely Job: The knowledge gap between you and your board/employees is vast. You are often alone in the final decision. This is normal.
  3. Techniques to Stay Sane:
    • Make friends with other CEOs who have been through it.
    • Get thoughts out of your head and onto paper to achieve clarity.
    • Focus on the road (where you’re going), not the wall (what you’re trying to avoid).
    • Don’t punk out and don’t quit. Great CEOs face the pain.

Politics almost always starts with the CEO, often unintentionally. The key to minimising it is to build strict, transparent, and fair processes for politically charged activities.

  1. Performance & Compensation: Have a formal, airtight process. Don’t grant raises on a first-come, first-served or squeaky-wheel basis.
  2. Organisational Design & Promotions: Evaluate these on a regular schedule, not in response to lobbying. Make promotion criteria objective and decisions defensible.
  3. Handling “He Said, She Said”: For behavioural complaints, get both parties in a room together. For competency complaints, immediately stop the conversation to avoid crippling the accused executive, then investigate the facts yourself.

2.5 Key Phrases to use

  • Take care of the people, the products, and the profits—in that order.
  • What are we not doing?
  • There are no silver bullets, only lead bullets.
  • Focus on the road, not the wall.
  • If you are going to eat shit, don’t nibble.
  • The Struggle is where greatness comes from.
  • Nobody cares, just run your company.

3 Summary Video

4 Practise

Reflect on a “Wartime” situation in your own career or organisation—a moment of existential crisis.

  1. What was “The Struggle” like for you personally?
  2. What was the single hardest decision you had to make?
  3. Did it test your courage more than your intelligence? How?
  4. Looking back, would you have benefited from a more “Wartime CEO” approach?

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