How to Lead

I wanted to share my approach to leadership that I’ve refined over the past few years, especially in the last six months since I joined MeUndies. It incorporates a lot of best practices shared by leaders I’m inspired by: Brian Chesky, Tristan Walker, Keith Rabois, Ben Horowitz, among others.

Triaging: Survey the Scene, Prioritize, and Take Action

  1. At first, everything is going to feel like a mess. Too much process and predictability = not innovating/creating fast enough.
  2. New problems every day that require triaging to survey the scene, prioritize, and take action.
  3. Some things will look serious, but they are actually colds.
  4. Don’t allocate time and resources toward solving this because it’s just going to go away.
  5. Other things are going to present themselves as colds, but if not diagnosed properly, they can actually become fatal.
  6. Prioritize and allocate time and resources toward solving this.

The concept of editing is the best metaphor for leading a company:

Simplify and Focus

  1. Use red ink to simplify. The more you simplify, the better people will perform.
  2. Distill to 1-3 top goals for the company, department, and employee. Only focus on these things.
  3. Focus allows you to solve A+ problems instead of B+ problems. Need to solve A+ problems to become great.
  4. To achieve greatness, you must say NO to 99% of things.

Ask Clarifying Questions

  1. First Principles Thinking: Rather than reasoning by analogy or prior experience, break problem down to most fundamental truths to reexamine whether a better solution might be possible.
  2. Fight as if you’re right. Listen as if you’re wrong.
  3. Probe, play devil’s advocate, and uncover your team’s thought process and action steps taken.
  4. Clarity allows the team to act with conviction.
  5. “If you’re wrong, you will die. But most companies don’t die because they are wrong; most die because they don’t commit themselves…The greatest danger is in standing still.”

Allocate Resources

  1. Allocate resources from areas of lower productivity/output to areas of higher productivity/output.
  2. Top-down approach: Issue mandate from management on down. Stymies innovation and negatively impacts employee morale.
  3. Bottom-up approach: Team comes up with their own initiatives. Lacks focus and negatively impacts company.
  4. Let chaos reign, reign chaos in approach (best approach): Let chaos reign (bottom-up actions will drive toward chaos by experimenting and test different strategies) and then reign chaos in (after identifying the right path, articulate clear direction and act with conviction). Debate is encouraged (chaos reigns) and then clear decisions are made and accepted (chaos reigned in).
  5. How much red ink am I using: Measure how well I’m communicating to the team about what’s important and what’s not, about why some things are important and why some things are not. Goal over time is to use less red ink every day.

Ensure Consistency

  1. Ensure consistency across all functions: brand, priorities, responsibilities, compensation.
  2. Consistency breeds transparency. Transparency builds trust.
  3. Focus on small bites to “eat the elephant.“
  4. Consistency of effort to focus on small wins (small bites) every day to achieve the Big Hairy Audacious Goal (eat the elephant).


  1. Task Relevant Maturity: Has this person ever done this before?
  2. Conviction and Impact 2x2 Grid: Low Conviction, Low Impact: Let employee go for it and learn from their mistake. High Conviction, High Impact: Explain reasoning and take action.
  3. Keep track of social capital with each employee.
  4. Hand the pen back: When people are struggling, help, but remember to hand the pen back. The pen is responsibility, control, accountability.

Edit the Team

  1. Build a world class team (talent and cultural fit)
  2. Hire for strengths instead of lack of weakness.
  3. Hire barrels instead of ammunition.
  4. Hire thoughtfully, fire purposefully.
  5. Hiring barometer: Hire the person in X who makes you feel insecure about what you thought you knew about X.
  6. Missionaries over Mercenaries (Calling vs. Job): Hire those who will champion the mission.
  7. Expand each person’s scope of responsibility until it breaks. Keep testing and pushing the envelope (60/40 rule - 60% mastery and 40% stretch).

Cultivate a Winning Culture

  1. Focus on a core mission (a North Star) that is compelling and unique.
  2. Align each team member to play a defined, irreplaceable role in fulfilling that core mission.
  3. Uphold our culture/core values in everything we do.
  4. When the culture is strong, you can trust everyone to do the right thing.
  5. The stronger the culture, the less rules/processes a company needs.
  6. Why it’s important: First principles: Endures in the face of everyday decision making. Alignment: Aligns employees to values that matter most. Stability: Provides stability to fall back on. Trust: Provides a level of trust. Exclusion: Distinguishes you from every other company/competitor. It provides a list of what to do and what not to do. Retention: Serves as a guide to identify, hire, measure, and retain employees who fit with your mission.

Drive Performance

  1. Hear the unheard, demonstrate empathy, fulfill the team’s needs, and build trust to optimize performance.
  2. Meet people where they are and lead them where we want to go.
  3. Management style dictated by the employee (no single, defined management style).
  4. Measure output, not input. Measure progress, not motion.
  5. Pairing indicators: If you measure one thing, you optimize for that at the expense of something else that is important.

Maintain Attention to Detail

  1. "Success is a byproduct of what you do every day to get the details excellent.”
  2. Getting the details right ensures the organization is in lockstep and performs at its best.
  3. Steve Jobs was obsessed with getting the details right, even in Apple’s circuit boards that would never be seen by the customer.

Lead by Example

  1. Out-hustle everyone.
  2. 10,000 Hour Rule: To master your craft, you must achieve 10,000 hours (50 hours per week / 2500 hours per year / 4 years).
  3. To achieve greatness, you must sacrifice, work incredibly hard, and persevere through adversity.
  4. Learn from the best to become the best.

High-Level Strategy:

  1. Manage the day-to-day of the company to sharpen focus, remove road blockers, empower each person, and drive results.
  2. Maintain a pulse on the team to identify needs and effectively grow and scale.
  3. Hire and develop the best talent - both ability AND fit - to build a world class team.

How I Measure Myself:

  1. Quantitative: Senior management is measured by company performance - plain and simple.
  2. Qualitative: Am I the go-to person for problem solving when team members need to solve problems of all types?

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