People Ops: Lessons in Culture and Leadership From Building Startups (real.pdf)

Learn how to deal with difficult employee demands, what candidates actually think about recruitment processes, how to navigate layoffs, address the gender pay gap, and protect your time and wellbeing. People Ops is a collection of candid lessons, stories, and principles in leadership, people, and culture from startup environments. It reveals the hard truths and sometimes uncomfortable realities that we all know exist but struggle to articulate. For decades, business and HR leaders have struggled to navigate the complexities of managing people and teams within startups and scaling companies, instead relying on the broad rhetoric of management theory to tackle these challenges or leaning on their networks of leaders who have encountered these challenges before. In parallel, the HR industry has been undergoing a transformation with the growth of People Operations. It’s a distinct field in HR that relentlessly focuses on engagement, culture, automation and putting people at the heart of all business operations. At the intersection of startups and people operations is an increasingly ambiguous business challenge for how startups can apply leading people practices to drive their growth, rather than in spite of their growth. People Ops is a tactical companion for business and People Operations leaders designed to support them in their roles, spark inspiration and challenge conventional thinking. It supplements author Patrick Caldwell's own experience across multiple startups with stories and examples from his network of investors, CEOs, Founders and C-Level HR executives. What You'll Learn Lessons from a path walked building People Operations in a startup environment Uncomfortable truths around the complexities of managing people The key components of a People Operations strategy within a small business Who This Book is For Those in small-mediumsized businesses, especially startups, where the reader is in a position of responsibility for people and culture. They’ll likely hold business leadership positions such as Founder, CEO, COO, VP and Director, or they’ll be directly within the HR and People Operations space with titles such as CHRO/CPO, Head, Director, Business Partner or Advisor Table of Contents About the Author Preface Chapter 1: Building from Scratch Ground Your Decision-Making Simple Is Sexy Done > Perfect Self-Service FTW Decision by Committee Sucks Beware the Magpies Your People Strategy Is Your Business Strategy Summary Chapter 2: Leadership Red Flag 1: Lack of Leadership Red Flag 2: The Wrong Leaders Red Flag 3: Accidental Leaders Not Everyone Wants to, or Should, Be a Leader The Psychological Safety of Leaders If Difficult Conversations Don’t Affect You, You Shouldn’t Be Having Them Sometimes to Show You Care, You Need to Show Your Teeth Summary Chapter 3: Culture Culture Is Not Free Beer, Fruit, and a PlayStation Culture Contribution or Culture Fit What Does Autonomy Look Like for You? Process: The Enemy or the Hero? Cut Only When Is Absolutely Necessary to Survive Exhaust Every Other Option First to Bring Spend Down Explore Staff Cost Reductions That Don’t Eliminate Jobs Do It Right and Look After Your People Communication Severance Benefits Diversity Redeployment Find a Common Language Values Ambitions and Goals Work Styles Getting Past the Values Fluff Summary Chapter 4: Inclusion Inclusion > Diversity Leadership Backyard Pitch at 80% Be Judged by Your Actions, Not Your Intentions Get Under the Skin of Your Gender Pay Gap Area 1: Recruitment Area 2: Progression Area 3: Compensation Framework The Myth of Removing Bias Summary Chapter 5: Recruitment Respond to Every Single Job Applicant As Though Your Brand Depends on It Start with Your Best Offer and Don’t Budge Your Candidate Experience Is As Important As Your Customer Experience Turn the Tables Don’t Join This Company If... The Candidate Was Great! I’d Like to Meet a Few More Though Summary Chapter 6: Reward Design for the 99% Learning Budgets Parental Leave Pay Transparency The “Pay Me More or I’ll Leave” Ultimatum Mitigate the Likelihood of Ultimatums When We Get Pay Wrong When We Don’t Get Pay Wrong The Law Is the Floor All Benefits Are for Day 1 You Probably Won’t Retire Early Because of Equity Equity Requires a Framework More Sophisticated Than What We Use for Salaries Understand the Risk and Likelihood of Dilution Liquidation Preference Equity Is Worth Nothing, Until It’s Worth Something Minimum Leave, Not Unlimited Leave Summary Chapter 7: Learning Water Your Plants Growth Culture Great Managers Onboarding Learning Is About Experiences, Not Just Knowledge The “Best” Career Advice I Ever Received Do I Even Want to Progress? Underperformers Are Rarely Promoted What Prompts a Manager to Say “You’re Ready for a Promotion”? Approach with Planning: Peer Feedback Giving Feedback Is a Skill Anonymous or Identifiable The Filter of Perception The Perfect Resignation: When the Time Is Simply Right Summary Chapter 8: Performance The Trinity: What, How, Where? I Messed Up OKRs, Twice! People Outgrow Startups; Startups Outgrow People If I Hear “Hire Slow, Fire Fast” One More Time... The Death of Performance Reviews? Forced Distribution Review Bias Deferred Feedback Rating Emphasis Summary Chapter 9: Remote Working The Covid-19 Acceleration Remote Work Is Uncovering Our Dirty Laundry Performance Trust Culture Know the Difference Between Flexible and Remote Work Remote Hybrid Flexible The Remote Manager Synchronous and Asynchronous Communication Onboarding In Tune with Work and Well-being Burnout Is Our New Thanos Summary Chapter 10: Your Career Know the Difference Between Who You Are and What You Do Be Clear on What Your Role Is and What It Isn’t “I Don’t Know” Find Your Outlet Be Ruthless with Your Time Reduce Default Meetings to 20 and 45 Minutes Set Meeting-Free Blocks Confirm the Purpose of Attendance Define the Outcome of the Meeting If You Do Nothing Else, Do These Three Things Everyone Is a People Expert It’s Great to Experience a Truly Shit Company at Least Once Scaling Part 1: Keep Your Team As Small As Possible Work Is Thoughtfully Managed, Not Just Executed Work Is Ruthlessly Prioritized Scaling Part 2: Make Yourself Redundant Summary Chapter 11: TL;DR Too Long; Didn’t Read: A Summary of Text That Was Too Lengthy Chapter 1: Building from Scratch Chapter 2: Leadership Chapter 3: Culture Chapter 4: Inclusion Chapter 5: Recruitment Chapter 6: Reward Chapter 7: Learning Chapter 8: Performance Chapter 9: Remote Working Chapter 10: Your Career Index Learn how to deal with difficult employee demands, what candidates actually think about recruitment processes, how to navigate layoffs, address the gender pay gap, and protect your time and wellbeing. People Ops is a collection of candid lessons, stories, and principles in leadership, people, and culture from startup environments. It reveals the hard truths and sometimes uncomfortable realities that we all know exist but struggle to articulate. For decades, business and HR leaders have struggled to navigate the complexities of managing people and teams within startups and scaling companies, instead relying on the broad rhetoric of management theory to tackle these challenges or leaning on their networks of leaders who have encountered these challenges before. In parallel, the HR industry has been undergoing a transformation with the growth of People Operations. It’s a distinct field in HR that relentlessly focuses on engagement, culture, automation and putting people at the heart of all business operations. At the intersection of startups and people operations is an increasingly ambiguous business challenge for how startups can apply leading people practices to drive their growth, rather than in spite of their growth. People Ops is a tactical companion for business and People Operations leaders designed to support them in their roles, spark inspiration and challenge conventional thinking. It supplements author Patrick Caldwell's own experience across multiple startups with stories and examples from his network of investors, CEOs, Founders and C-Level HR executives. What You'll Learn Lessons from a path walked building People Operations in a startup environment Uncomfortable truths around the complexities of managing people The key components of a People Operations strategy within a small business Who This Book is For Those in small-medium sized businesses, especially startups, where the reader is in a position of responsibility for people and culture. They’ll likely hold business leadership positions such as Founder, CEO, COO, VP and Director, or they’ll be directly within the HR and People Operations space with titles such as CHRO/CPO, Head, Director, Business Partner or Advisor