Table of Contents

The Breaking Point covers a wide variety of topics about leadership, decision making and technology. They are all organized here by topic to make it easy to find what you’re looking for quickly and easily!

Analytics & Data

• Success & Velocity

• Second Order Metrics

• You Have Too Many Metrics

• The Meaning of Metrics

• The Limits of Data

• Data is a People Problem

• Can a Customer Be a Number?

• Your Data is Lying to You

Business Planning

• Annual Planning The Actually Works

• The Plateau of Death

• Making Big Bets

• How is Your Business Doing?

• Do You Need to Win Today, or Tomorrow?

Career Planning

• Opening and Closing Doors

Company Culture

• Corporate Ethics

• Company Culture

• The Downside of Optimism

• Where do Corporate Politics Come From?

• Transparency is Hard to Do Well

• When Perceptions Become Reality

Competition

• When Competition Matters

• Everyone has a Weakness

• Your Competitive Landscape is a Junkyard

• How To Beat Larger Competitors

• Your Competitors Are Lying About You

Decision Making

• Planning for a Crisis

• Beware One-Way Doors

• Types of Risk

• The Root Cause of Mediocre Decisions

• In Pursuit of the Perfect Decision

• So, You Made a Mistake

• Stop Arguing, Start Debating

• Are You Right on Purpose?

• Getting Ahead of Negotiations

Investors, Board Relations & Fundraising

• Investors Buy Tomorrow, Not Today

• Great, Good, Bay & Ugly

• Board Meetings are not Status Meetings

• Investor Relations Should Not Be Scary

Leadership

• Communicating Change

• Don’t Confuse Motion with Progress

• The Art of Being Unreasonable

• Leading By Example Doesn’t Scale

• The Well of Good Will

• The Three Levels of Leadership

• Executive Coaching Can Be Your Secret Weapon

• Confidence vs Arrogance

• Why It Is Good To Be Bad At Estimation

• Managing Up and Managing Down

• How to Avoid Doing Fraud

• Urgency

Mental Health

• Coaches vs Cheerleaders

• Give Yourself a Break

• The Confidence Game

• Why Being a Leader is Lonely

People

• Layoffs are Horrible

• What Does Your Company Remember?

• Personal Growth

• Scaling Fault Lines

• The Ties That Bind Us

• Mis-hires

• A Grand, Unified Theory of Team Conflict

• The Secret to Effective Employee Onboarding

• Incentives Rule the World

• Are Bigger Teams Better?

• Managing Up and Managing Down

• Hire Before It’s Too Late

• You Cannot Be Afraid of Your Team

• 1:1s

• How Many Chances Are Enough?

Productivity

• You Don’t Work For Your Calendar

• Unlocking Your Peak Performance

• The Other Bucket

• Say/Do Ratio

• Switching Costs

• Efficiency Isn’t Always Good

Recruiting

• Two Types of Team Building: Up and Down

• A Better Hiring Process

Product

• The Three Product Roadmaps

• Your Three Kinds of Customers

• The Energy of Innovation

• The Day Zero Problem

• Your Product is Boring

Sales and Customer Success

• When Customers Attack

• Going Up-Market Will Not Solve Your Problems

• How To Make Happy Customers

• Customers Don’t Know What They Want

• The Missing Customer Criteria

Strategy

• Do you have Product/Market Fit?

• You Are Not a Business, Yet

• Never Lose Your Focus

• What’s the Worst That Can Happen?

• Problem/Market Fit

• You Need A Strategy

• Do The Hard Parts First

• Avoiding Imaginary Constraints

• Managing Distractions

• Surviving a Slowdown

• Your Strategy is Happening To You

• When You Lose Product/Market Fit

• Don’t Confuse Strategy and Tactics