Sarah E. Brown - Lead Upwards

7 PART II: GETTING STARTED: NAIL YOUR FIRST 90 DAYS CHAPTER SIX: Define Your Goals and Align with Your CEO and Board on Success YOUR FIRST 90 DAYS: ONBOARDING TO YOUR NEW ROLE AND PROVING YOUR VALUE TO THE ORGANIZATION DON'T BE SHY ABOUT MAKING AN IMPACT RIGHT AWAY GET POINTS ON THE BOARD EARLY BY FOCUSING ON ACCOMPLISHING SEVERAL LOW EFFORT, HIGH IMPACT INITIATIVES IN YOUR FIRST 90 DAYS WORK WITH YOUR CEO TO IDENTIFY SUCCESS “ARE WE SEEING THE SAME GAME?” ADVICE FROM A CEO TO STARTUP EXECUTIVES: REMEMBER THAT THE CEO ROLE IS TOUGH ONBOARDING SUCCESSFULLY AS A STARTUP LEADER REQUIRES BALANCING SHORT‐TERM WINS WITH LONG‐TERM PRIORITIES SETTING YOUR OBJECTIVES AND KEY RESULTS (OKRs) SETTING OKRs—EXAMPLE: SAMPLE MARKETING OKRs OKRs AND BONUS COMPENSATION DELIVERING YOUR FIRST QUARTERLY BUSINESS REVIEW (QBR) HERE'S A GUIDE FOR WHAT TO INCLUDE IN YOUR FIRST 90‐DAY QBR PRESENTATION NOTE CHAPTER SEVEN: Build Key Relationships: CEO, Board, Team BUILDING A RELATIONSHIP WITH YOUR CEO AND/OR CO‐FOUNDER HERE'S A SAMPLE CEO 1:1 AGENDA BUILDING TRUST WITH YOUR CEO: VALUES ALIGNMENT SET UP COMMUNICATION EXPECTATIONS WITH YOUR CEO AND LEADERSHIP TEAM GET TO KNOW YOUR CROSS‐FUNCTIONAL PARTNERS AND BUILD RAPPORT LEARN HOW YOUR KEY STAKEHOLDERS LIKE TO WORK DON'T BE AFRAID TO DISAGREE—RESPECTFULLY WHY COMPANIES BRING IN “BIG COMPANY EXECUTIVES” AND HOW TO WORK WITH THEM IF YOU'RE COMING FROM A STARTUP BACKGROUND BUILDING STRONG RELATIONSHIPS WITH YOUR BOARD MANAGING TO YOUR BOARD'S EXPECTATIONS LEARN THE INTERESTS, HOBBIES, AND FAMILY MEMBERS OF YOUR EXECUTIVE TEAM NOTE CHAPTER EIGHT: Know Thyself: Strengths, Weaknesses, and Areas to Improve YOUR RELATIONSHIP WITH YOURSELF AS A STARTUP LEADER IDENTIFYING YOUR STRENGTHS WEAKNESSES: THINGS THAT MAKE YOU FEEL IMPOSTER SYNDROME UNTIL YOU ADDRESS THEM EXPECT TO HIRE AROUND YOUR WEEKNESSES BUT SEEK TO UNDERSTAND THEM AND NOT AVOID THEM UNDERSTANDING HOW TO HANDLE WEAKNESSES MEASURING YOUR EFFECTIVENESS AS AN ENGINEERING LEADER: GET HONEST ABOUT YOUR SKILLS AS YOU TRY TO LEVEL UP BEING HONEST ABOUT OUR STORTCOMINGS: ENTREPRENEUR RAND FISHKIN'S PERSPECTIVE IDENTIFY: WHAT ARE YOU NOT STRONG AT THAT YOU'LL WANT TO IMPROVE? HIRING FOR COMPLEMENTARY SKILLS GOING DEEPER: GETTING TO KNOW OUR MOTIVATIONS FOCUSING ON ADDING VALUE, REGARDLESS OF TITLE EMBRACE IMPROV AS A WAY TO BECOME A MORE PRESENT, COLLABORATIVE LEADER GET TO KNOW YOURSELF THROUGH “PERSONAL RETROSPECTIVES” UNDERSTANDING OUR PRIVILEGE AND HOW IT IMPACTS OUR WORK EMBRACING ALL OF OURSELVES, INCLUDING OUR “SHADOW” SIDES ARE YOU OUTSOURCING A PART OF YOURSELF TO YOUR TEAM? CREATING HEALTHY BOUNDARIES NOTES CHAPTER NINE: Learn the Company Culture and Define It with Your Team UNDERSTANDING STARTUP VALUES COMPANY VALUES DRIVE BEHAVIOR OTHER WAYS CULTURE IS IMPACTED BY VALUES BUILDING TRUST AMONG YOUR TEAM AS A STARTUP LEADER CREATING A CULTURE THAT ISN'T “ALWAYS‐ON” CREATING INCLUSIVE TEAMS WHERE INDIVIDUALS FROM DIVERSE BACKGROUNDS CAN EXCEL TOGETHER CREATING “BALANCE” ON TEAMS CREATING HEALTHY WORK EXPECTATIONS THAT SUPPORT INCLUSIVITY AMONG YOUR TEAM CULTIVATE PSYCHOLOGICAL SAFETY ON YOUR TEAMS COMPASSIONATE BOSSES MAKE PEOPLE'S LIVES BETTER, SO ASPIRE TO BE ONE OF THEM GET TO KNOW YOUR TEAM AS INDIVIDUALS NOTES

8 PART III: BUILDING AND MANAGING YOUR TEAM AND DEPARTMENT CHAPTER TEN: Recruit Smart and Build Belonging RECRUITING NEW TEAM MEMBERS WHAT TO DO IF YOU'VE INHERITED A TEAM HIRING YOUR TEAM DESIGNING YOUR ORGANIZATION CHART HIRING TIP: CREATE A SCORECARD REDUCING BIAS IN THE HIRING PROCESS CULTIVATING EQUITABLE, DIVERSE, AND INCLUSIVE TEAMS HIRING PEOPLE: HOW TO RETAIN TALENT ON YOUR TEAM IN TODAY'S COMPETITIVE LABOR MARKET NOTES CHAPTER ELEVEN: Alignment: Set the Strategy to Get Your Team Working Toward the Same Vision and Goals HELP YOUR TEAM TO UNDERSTAND THE MISSION AND THE “WHY” BEHIND THE STRATEGY SETTING OKRS WITH YOUR TEAM BONUSES TIED TO OKRS UNDERPERFORMING TEAM MEMBERS GET IN THE WEEDS IN ORDER TO UNDERSTAND THE NATURE OF PROBLEMS LEAD WITH THE BEHAVIOR YOU WANT TO SEE CONFLICTS ON YOUR TEAM: HOW TO IDENTIFY AND WORK THROUGH THEM PAY ATTENTION TO THE DETAILS LONGER THAN FEELS NECESSARY NOTES CHAPTER TWELVE: Attunement: Creating a Culture Where People Contribute Their Best Work BEGIN WITH THE GOAL IN MIND: EMPLOYEE EMPOWERMENT MAKE BUILDING A HEALTHY CULTURE A TEAM PRIORITY TEAM EMPOWERMENT STARTS WITH BUILDING TRUST GET SUPPORT ALONG YOUR JOURNEY THROUGH A SUPPORT CIRCLE ENSURE YOUR TEAM HAS ENOUGH RESOURCES TO BE SUCCESSFUL LET YOUR TEAM KNOW YOU, TO THE DEGREE YOU FEEL COMFORTABLE WITH EMPOWERING YOUR TEAM TO DELIVER AND LET GO OF TASKS IN YOUR “ZONE OF EXCELLENCE” BUILD PSYCHOLOGICAL SAFETY BY CREATING AN ENVIRONMENT WHERE MISTAKES ARE HANDLED WITH CARE, NOT BLAME CONSIDER INSTITUTING A “NO MEETING” DAY A WORD ON BEING A MEMBER OF AN UNDER‐REPRESENTED GROUP AND NAVIGATING MAKING MISTAKES CREATE A ROADMAP WITH INDIVIDUAL PREFERENCES AND AGREEMENTS FOR WORKING TOGETHER AS A TEAM NOTE CHAPTER THIRTEEN: Building a High‐performance Team Culture STEPS TO BUILDING A CULTURE OF SUCCESS CREATING A PERFORMANCE CADENCE WITH YOUR TEAM THE 1:1S WITH YOUR DIRECT REPORTS CREATE BETTER 1:1S BY ASKING BETTER QUESTIONS GOAL SETTING AND OKRs CARVE OUT TIME TO TALK CAREERS AND GIVE FEEDBACK SMALL GESTURES ADD UP TO A CARING MANAGEMENT STYLE MEETINGS: HOW MANY DO YOU REALLY NEED TO BE IN? IS THIS MEETING SET UP TO FAIL? HERE ARE WARNING SIGNS THIS WON'T BE A PRODUCTIVE MEETING MANAGEMENT TIP: DON'T SEND “CAN WE TALK” MESSAGES TO YOUR TEAM BE EMPATHETIC TO WHAT PEOPLE ARE GOING THROUGH WHILE SETTING HEALTHY BOUNDARIES BUILD FEEDBACK INTO YOUR REGULAR COMMUNICATION AND PROCESSES BEWARE THE PITFALLS OF “SKIP LEVELS” SOLVING CONFLICTS ON YOUR TEAM ENSURING YOUR TEAM (INCLUDING YOU) TAKES ADEQUATE TIME OFF TAKE TIME TO REALLY UNPLUG YOURSELF TO SHOW YOUR TEAM THAT'S THE CULTURE CULTIVATE AS FLEXIBLE A WORK ENVIRONMENT AS POSSIBLE EMBRACE FEELINGS WHILE ESTABLISHING HEALTHY BOUNDARIES AROUND HOW YOU DEAL WITH THEM DEFINING SUCCESS AND TRUE OWNERSHIP GET YOUR REPORTS TO THINK LIKE OWNERS A NAVY VETERAN SHARES THE CASE AGAINST COMMAND AND CONTROL LEADERSHIP HAVE YOUR TEAM'S BACK LET YOUR TEAM KNOW IT'S SAFE TO MAKE MISTAKES, AS LONG AS THEY LEARN FROM THEM TEACH YOUR TEAM TO PROBLEM‐SOLVE AND LET THEM DO THINGS IN DIFFERENT WAYS THAN YOU WOULD IF YOU'RE GOING TO BE A MANAGER, DECIDE TO CARE ABOUT PEOPLE PROBLEMS INVEST IN LEARNING HOW TO BECOME A MORE INCLUSIVE LEADER HAVE FUN AS A TEAM! PRACTICE REPAIR AND BUILD IT INTO YOUR TEAM RHYTHM DO RETROSPECTIVES TO ENSURE THE TEAM SHARES THEIR VOICES AND GROWS WISER RETROSPECTIVE PROCESS (START–STOP–CONTINUE) NOTES

9 PART IV: MANAGING YOURSELF AND YOUR EXECUTIVE COMMUNICATION CHAPTER FOURTEEN: Level Up to Scale with Your Startup MAKE AN INVENTORY OF THE THINGS YOU'D LIKE TO WORK ON HOW TO GET THE MOST OUT OF WORKING WITH AN EXECUTIVE COACH BEYOND COACHING: THERAPY IS A GREAT OPTION YOUR GROWTH IS UP TO YOU CHAPTER FIFTEEN: Leading in a Post‐covid World AS THE WORLD HAS CHANGED, PRIORITIES HAVE SHIFTED FOR MANY OF US SINCE REMOTE WORK IS HERE TO STAY, HERE'S HOW TO DO IT: IDENTIFY AND SOCIALIZE THE SYSTEMS YOU'LL USE FOR COMMUNICATION AND TRACKING WORK PLAN TO WORK AROUND TEAMS' SCHEDULES AND TIME ZONES CREATE PREDICTABILITY IN YOUR OPERATING CADENCE LEVERAGE OKRs TO KEEP EVERYONE ALIGNED TAKE EXTRA TIME TO CHECK IN ON HOW PEOPLE ARE DOING SET SAFETY PROTOCOLS AND CONSIDER HIRING A COVID SAFETY OFFICER TO GATHER IN PERSON JOSH ASHTON'S STORY: LEADING HIS TEAM AS CHIEF PEOPLE OFFICER AT TRINEO DURING THE PANDEMIC REMEMBER THAT EVERYONE IS STRUGGLING WITH SOMETHING DIFFERENT NOTES CHAPTER SIXTEEN: Managing Up: How to Work with Your CEO and Board WORK WELL WITH YOUR CEO BY UNDERSTANDING THEIR PREFERRED WORK STYLE: FOUNDER HITEN SHAH'S STORY NOTE: YOUR CEO MAY NOT BE AWARE OF ALL OF THEIR PREFERENCES (BUT THEY STILL HAVE THEM) GETTING TO KNOW THE BOARD BY CONNECTING DIRECTLY WITH AT LEAST ONE MEMBER ALWAYS BE CONCISE IN YOUR COMMUNICATION WITH YOUR BOARD NICK MEHTA'S ADVICE: FOCUS ON THE METRIC THAT THE BOARDS CARE MOST ABOUT MANAGE YOUR TIME WELL DURING THE BOARD MEETING UNDERSTANDING WHAT YOUR BOARD REALLY CARES ABOUT A WORD OF ADVICE: DON'T OVER‐PROMISE TO THE BOARD CHAPTER SEVENTEEN: When Things Go Pear‐shaped: Navigating Challenges, Setbacks, Failure, and Departures LEARN TO PRACTICE COMPASSION TOWARDS YOURSELF WHEN DIFFICULTY AND FAILURE HAPPEN (BECAUSE THEY WILL) PRACTICE SELF‐COMPASSION WHEN THINGS ARE HARD AT WORK UNDERSTAND THAT PEOPLE REACT DIFFERENTLY UNDER STRESS TREAT PEOPLE WITH RESPECT, ALWAYS WHAT TO DO IF A COLLEAGUE QUESTIONS YOUR IMPACT IF YOU FAIL AND GET LET GO, OR MESS UP IN A BIG WAY, YOU STILL BELONG IN THE STARTUP WORLD AND YOU'RE GOING TO BE OK WHEN YOU GET PASSED OVER FOR A PROMOTION OR A ROLE NORMALIZING SET‐BACKS AND GIVING YOURSELF PERMISSION TO FAIL AND LEARN IS IT TIME TO CALL IT QUITS? NO ONE GETS TO DECIDE WHEN YOU STOP BEING A STARTUP LEADER BUT YOU REFRAMING FAILURE AS ANOTHER LEARNING OPPORTUNITY OTHER TYPES OF SETBACKS OTHER THINGS THAT CAN GO WRONG AND HOW TO DEAL WITH THEM ADVERSITY IN THE STARTUP WORLD IS A FEATURE, NOT A BUG NAVIGATING PIVOTS SUCCESSFULLY AS A STARTUP LEADER TREAT PIVOTS AS A CHANCE TO BECOME A BETTER COMPANY IN TIMES OF CRISIS, UNDERSTAND YOUR CIRCLE OF CONTROL STAY AND ACCEPT, TRY TO CHANGE THINGS, OR LEAVE? IN TIMES OF MAJOR CHANGE, CONSIDER HAVING AN “ON THE BUS OR OFF THE BUS” CONVERSATION WITH YOUR TEAM IF YOU STAY, KNOW YOU WON'T AGREE WITH ALL DECISIONS TURNING A STARTUP PIVOT INTO A STARTUP LEADERSHIP ADVANCEMENT OPPORTUNITY: MINDY LAUCK, CEO OF BROADLY DON'T TRIANGULATE: IDENTIFY “YOU TWO” PROBLEMS ON THE FAME/BLAME CYCLE—WHEN THE HIGHS ARE HIGH AND THE LOWS ARE LOW DEPARTURES: WHEN IT'S TIME TO MOVE ON FROM YOUR ROLE DECIDING WHEN IT'S TIME TO MOVE ON QUESTIONS YOU CAN ASK WHEN DECIDING WHETHER TO LEAVE YOUR EXECUTIVE ROLE HOW TO LEAVE A ROLE LIKE AN EXECUTIVE HOW TO GIVE NOTICE WHEN YOU GIVE NOTICE: BE PREPARED TO BE ASKED TO CLOSE YOUR LAPTOP ON THE SPOT A WORD OF ADVICE: RESPECT THE COMPANY'S INTELLECTUAL PROPERTY (IP) AND DON'T TAKE IT UPON DEPARTURE ANOTHER WORD OF ADVICE: BE CAREFUL ABOUT POACHING EMPLOYEES (AT LEAST RIGHT AWAY) EXERCISING YOUR VESTED EQUITY AROUND YOUR DEPARTURE TAKING TIME OFF IN BETWEEN JOBS MAKE A COMMUNICATION PLAN KEEP IT POSITIVE BEWARE THE “DILBERT PRINCIPLE” AND LEAVE WITH GRACE ANYWAY NOTES