defi-naly

hard-thing-about-hard-things

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# Description

Ben Horowitz's battle-tested advice for leading through crises, making hard decisions, and building companies.

# SKILL.md


name: hard-thing-about-hard-things
description: "Ben Horowitz's battle-tested advice for leading through crises, making hard decisions, and building companies."

dimensions:
domain: [leadership, management, entrepreneurship, crisis-management]
phase: [crisis, scaling, layoffs, executive-hiring, culture-building]
problem_type: [hard-decisions, wartime-leadership, firing, organizational-challenges]

contexts:
- situation: "company in crisis"
use_when: "need wartime CEO mindset and tactics"
- situation: "need to do layoffs"
use_when: "how to execute layoffs with dignity and speed"
- situation: "executive isn't working out"
use_when: "deciding whether and how to fire an executive"
- situation: "no good options"
use_when: "framework for choosing between bad and worse"
- situation: "building company culture"
use_when: "defining culture through actions, not words"

combines_with:
- founders-at-work # early stage patterns before scaling challenges
- how-to-win-friends # softer influence techniques to balance
- thinking-fast-and-slow # decision-making under pressure
- playing-to-win # strategy when not in crisis mode

contrast_with:
- skill: how-to-win-friends
distinction: "Hard Thing is direct/wartime leadership; Carnegie is relationship-first influence"
- skill: founders-at-work
distinction: "Hard Thing is SCALING and crisis; Founders at Work is FOUNDING and early stage"


The Hard Thing About Hard Things

Core Philosophy

There's no recipe for building a company. The hard things are hard because there are no good answers—only hard choices between bad options.

The Struggle is where greatness comes from. Every great entrepreneur has gone through the Struggle and come out the other side.

The Struggle

The Struggle is when you wonder why you started the company in the first place. When people ask you why you don't quit, and you don't know the answer. When your employees think you're lying and you think they might be right.

What it feels like:
- Self-doubt becomes constant
- Sleep becomes impossible
- Motivation disappears
- Every decision feels wrong
- Isolation despite being surrounded by people

What helps:
- Don't put it all on your shoulders
- This is not checkers; this is chess (there's always a move)
- Play long enough and you might get lucky
- Don't take it personally
- Remember: most great founders faced worse

Peacetime vs Wartime CEO

The same person must be two completely different leaders depending on context.

Peacetime CEO Wartime CEO
Expand market Survive
Build culture Win at any cost
Encourage creativity Enforce discipline
Delegate broadly Make decisions fast
Hire for growth Cut ruthlessly
Long-term focus Immediate survival
"Let's explore options" "Follow me, now"

Peacetime: Company has clear advantage, expanding market, growth mode.
Wartime: Company survival threatened, existential competition, crisis mode.

The trap: Peacetime CEOs fail in wartime. They're too nice, too slow, too consensus-driven. The company dies while they're still processing.

Know which mode you're in. Act accordingly.

Making Decisions Without Good Options

Most CEO decisions are between bad and worse. There's no good choice—only the best of terrible options.

Framework

  1. Don't delay. Bad news doesn't age well. Delaying makes everything worse.

  2. Get the information. But recognize you'll never have complete information.

  3. Decide. A mediocre decision now beats a perfect decision too late.

  4. Commit fully. Once decided, act as if it's the right choice. Ambivalence destroys execution.

  5. Accept consequences. You'll be wrong sometimes. Accept it and move on.

The "What Would You Do" Test

When facing a hard decision, ask: "What would I recommend if I were an advisor to this company, not the CEO?"

This removes emotional attachment and ego from the decision.

Layoffs

Firing people is the hardest thing. There's no way to make it not painful. But there are ways to make it worse.

How to Do It Right

1. Get your head right first.
You're not the victim here. The people losing jobs are. Stop feeling sorry for yourself.

2. Don't delay.
The moment you know layoffs are coming, act fast. Delaying leaks, rumors spread, trust evaporates.

3. Be clear about why.
"Company performance" not "your performance." Own the failure as leadership.

4. Train your managers.
Managers should deliver the news face-to-face, not you, not HR, not email. But train them first.

5. Be generous.
Severance, references, job search help. Go beyond what's required.

6. Be present.
Walk the floor. Be available. Don't hide.

7. Don't forget the survivors.
They're traumatized too. Address their fears directly.

What to Say

"We [leadership] failed. We didn't hit our targets. As a result, we have to reduce the size of the company. This has nothing to do with your performance. I'm sorry."

What NOT to Say

  • "This is actually an opportunity..."
  • "We're rightsizing..."
  • "This will make us stronger..."
  • Anything that minimizes the impact

Firing Executives

Different from layoffs. This is about performance or fit failure.

Common Reasons

  1. Hired wrong. Wrong skills, wrong style, wrong level.
  2. Company evolved. Role outgrew the person.
  3. Performance issues. Not delivering results.
  4. Cultural mismatch. Right skills, wrong values.

How to Handle It

Don't drag it out. Once you know, act within days.

Be direct. "This isn't working. Today is your last day."

Be generous. Good severance, help with job search, positive reference where honest.

Control the narrative. Announce it quickly, explain briefly, move on.

The cover story: Find a dignified exit narrative that's technically true. "Pursuing other opportunities" is fine.

The "Do You Have What It Takes" Audit

When questioning an exec, ask:
1. Does the person know what to do?
2. Can the person do it?
3. Is the person capable of growing into the role?

If no to any, move quickly.

Hiring

Hire for Strength, Not Lack of Weakness

Don't hire safe candidates who lack obvious flaws. Hire people with spiky strengths, even if they have weaknesses.

Mediocrity: Someone with no major weaknesses but no major strengths.

Excellence: Someone exceptional at what matters, even if imperfect elsewhere.

Hiring Executives

The key question isn't "Is this person smart?" but "Do they know how to do the specific thing I need?"

Functional knowledge: Do they actually know how to run this function?
World-class strength: Where are they clearly excellent?
Trajectory: Are they improving or coasting?
Cultural fit: Will they thrive in our specific culture?

Reference Checks

Back-channel references matter more than provided references.

Ask:
- "Would you hire this person again? For what role?"
- "What would I need to know to manage them well?"
- "Where did they struggle?"

Building Culture

Culture is not free food or ping pong tables. Culture is what people do when you're not there.

How Culture Actually Forms

  • Who you hire (and fire) first
  • What behaviors you tolerate
  • What gets rewarded and promoted
  • How decisions get made
  • What you say no to

Design Virtues, Not Values

Values are too abstract. Design specific virtues—concrete behaviors you want.

Example: Instead of "We value honesty," try "Bad news travels fast" or "Disagree, then commit."

Culture Debt

Just like technical debt, you accrue culture debt by tolerating behavior that violates your standards. It compounds.

Fix violations immediately. One exception becomes the new rule.

Management Concepts

The Most Important Management Skill

Giving feedback. Everything else follows from your ability to tell people directly what's working and what isn't.

Framework: "The feedback sandwich is a lie."
- Be direct
- Be specific
- Be timely
- Don't soften so much the message is lost

One-on-Ones

The most important meeting you have. It's their meeting, not yours.

Structure:
1. What's on your mind? (They set agenda)
2. What's the biggest impediment to your work?
3. What feedback do you have for me?

Frequency: Weekly for direct reports. Never skip.

Managing Brilliant Jerks

Exceptional performers who are toxic to culture present a false dilemma.

The truth: Tolerating jerks tells everyone that performance matters more than values. Culture erodes. Good people leave.

The answer: Coach clearly, set deadlines, then fire if no change. No one is irreplaceable.

Psychological Challenges

CEO Psychology

The loneliness problem: You can't tell employees the company might fail. You can't show weakness. But you need to process.

Solutions:
- CEO coach or therapist
- Other CEOs in same situation
- Board member you trust completely
- Spouse/partner who can handle it

The "Lead Bullet" Trap

When things are going wrong, you'll look for a silver bullet—the one thing that will save everything. A new VP. A big partnership. A pivot.

The truth: There's no silver bullet. Only lead bullets—doing the hard work across every area.

Ask: "If I'm honest, what are all the things we need to fix?" Then fix them all.

Embrace the Suck

Some situations are just terrible. There's no reframe that makes them good. Layoffs suck. Missing numbers sucks. Losing key people sucks.

Don't pretend otherwise. Acknowledge reality, then deal with it.

Decision-Making Rules

When to Stay vs. Go

Stay if:
- You still believe in the mission
- There's a viable path forward
- You're uniquely able to execute it

Go if:
- You've lost belief
- The situation is truly hopeless
- Someone else would do it better

Speed of Decisions

In a startup, speed matters more than perfection.

10% better decision with 50% more time = bad trade

Make the best decision you can with available information. Move on. Correct course as needed.

First Principles Thinking

Don't ask "What would other companies do?"
Ask "What would the ideal company do in this exact situation?"

Then figure out how to close the gap.

Horowitz's Laws

  1. All good companies are different; all bad companies are the same. (Uniqueness comes from doing something hard.)

  2. The only thing that prepares you to run a company is running a company.

  3. If you're going to eat shit, don't nibble. (When facing hard things, do it fast and completely.)

  4. Take care of the people, the products, and the profits—in that order.

  5. In business, there's no magic move. Just lead bullets.

Crisis Checklist

When facing company crisis:

  • [ ] Don't panic (at least not publicly)
  • [ ] Assess situation honestly—how bad is it really?
  • [ ] Identify the one or two things that matter most right now
  • [ ] Communicate clearly to team (what you know, what you don't, what you're doing)
  • [ ] Make decisions fast, even with incomplete information
  • [ ] Accept you'll make mistakes—correct them quickly
  • [ ] Take care of yourself enough to function
  • [ ] Remember: every great company faced moments like this

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