Lead Upwards

Lead Upwards
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In Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams , startup marketing leader Sarah E. Brown delivers an illuminating and accessible guide to maximizing your impact and delivering results in a startup leadership role. The author draws on over a decade of experience scaling SaaS companies as she explains how to prepare for, earn, and succeed in an executive role at a startup company. The book describes every step on the way to realizing your goals—and the goals of your startup—as you navigate the gap between a management role and the executive team. It covers what to do in your first 90 days, how to build and sustain a healthy team culture, and the art of communicating results to your leadership team and board. You’ll also learn: How to manage the challenges posed by leading a remote, distributed, or hybrid team Management strategies based on inclusive and diverse teambuilding, alignment with business objectives, and inspirational leadership Effective ways to level up your skills and stay current as your company grows A must-read book for current and aspiring executives at startup firms, Lead Upwards will also earn a place on the bookshelves of startup board members, founders, funders, and managers seeking a singularly insightful discussion of business leadership.

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Sarah E. Brown. Lead Upwards

Table of Contents

Guide

Pages

LEAD UPWARDS. HOW STARTUP JOINERS CAN IMPACT NEW VENTURES, BUILD AMAZING CAREERS, AND INSPIRE GREAT TEAMS

Introduction: Why Startup Leadership Matters at Every Level

NOTES

CHAPTER ONE What It's Really Like to Be an Executive at a Startup—and How It's Different from Being a Director or Manager

WHAT DOES A STARTUP EXECUTIVE REALLY DO?

A STARTUP EXECUTIVE'S SCHEDULE: A WEEK IN THE LIFE, AT A GLANCE

OTHER DIFFERENCES BETWEEN NON‐EXECUTIVE AND EXECUTIVE ROLES. Accountability at the Highest Business Levels

OWNING THE “WHY” OF THE WORK

DEPARTMENTAL UNDERSTANDING BEYOND ONE NARROW AREA

RESPONSIBILITY FOR BUILDING AND LEADING A HIGH‐PERFORMING TEAM

SIMPLY PUT: IT'S A BIGGER COMMITMENT

LESS COMPANIONSHIP AND CAMARADERIE WITH OTHER NON‐EXECUTIVE STARTUP EMPLOYEES

EXECUTIVES HAVE THE MOST CONTEXT OF ANYONE IN THE DEPARTMENT

WHO'S QUALIFIED TO BE A STARTUP EXECUTIVE?

NO ONE IS TRULY QUALIFIED TO BE A STARTUP EXECUTIVE BEFORE THEY'VE DONE IT BEFORE

WHAT QUALIFICATIONS AND SKILLS ARE ESSENTIAL ON THE JOB AS A STARTUP LEADER

MANY SCALING STARTUPS BRING IN LEADERS FROM BIG COMPANIES

EXECUTIVE COACH AND FORMER MICROSOFT NORTH AMERICA CFO JOHN REX: ADVICE FOR SCALING STARTUP LEADERS

SCALING IS HARD IN BOTH DIRECTIONS

LEARN TO DELEGATE WITH CAPABLE TALENT AS YOU SCALE

EARLY‐STAGE STARTUP VS. SCALE‐UP LEADERSHIP MINDSET

STARTUP LEADERS CAN'T GET STUCK AT 30,000 FEET

NOTES

CHAPTER TWO Bridging the Transition from Manager to Executive: How Leaders Got Their First Role

MAKING THE LEADERSHIP TRANSITION: YOU DON'T HAVE TO BE “FULLY READY” TO GO FOR IT

HOW THEY GOT THEIR FIRST EXECUTIVE ROLE: REAL STORIES FROM STARTUP EXECUTIVES

MINDY LAUCK ON BEING A NON‐FOUNDER STARTUP TEAM MEMBER PROMOTED TO EXECUTIVE, AND THEN CEO (TWICE!)

CHALLENGE FOR FIRST‐TIME EXECUTIVES: SAM MCKENNA SHARES HER STORY OF BEING PROMOTED TO VICE PRESIDENT OF SALES

MAKING THE TRANSITION BY LEARNING TO WORK DIFFERENTLY

FROM BIG COMPANY LEADER TO STARTUP EXECUTIVE: COO ERIN RAND'S STORY

NAIL THE LEAP: START AS A “HEAD OF” AND MAKE THE TITLE OFFICIAL ONCE YOU'VE PROVEN YOUR SUCCESS

CONSULTING AS A PATH TO DE‐RISKING YOUR FIRST EXECUTIVE ROLE

NOTE

CHAPTER THREE Understanding and Evaluating Your Fit at Various Startups

CHOOSING A STARTUP THAT'S RIGHT FOR YOU

WHY QUESTIONS MATTER

SOME SAMPLE QUESTIONS TO EXPLORE IN THE INTERVIEW PROCESS

OTHER CONSIDERATIONS. What's the Market and What's the Problem the Company Is Solving (and Do You Care?)

RESEARCH THE COMPETITION/MARKET

RESEARCH THE TEAM THROUGH YOUR CONNECTIONS AND/OR PUBLIC REVIEW SITES LIKE LINKEDIN AND GLASSDOOR

ASSESS THE CO‐FOUNDER RELATIONSHIP

UNDERSTAND THE STARTUP'S STAGE AND HOW IT ALIGNS WITH YOUR GOALS

DO YOU ALIGN WITH THE LEADERSHIP TEAM?

OTHER KINDS OF FIT TO LOOK OUT FOR

SOME EXAMPLES OF FIT

ASSESS THE MATURITY OF YOUR STARTUP'S DIVERSITY AND INCLUSION

WHAT'S YOUR STARTUP‐STAGE RISK TOLERANCE?

HOW MUCH EXECUTION AND “GETTING YOUR HANDS DIRTY” ARE YOU COMFORTABLE WITH RIGHT AWAY?

DETERMINING YOUR IDEAL STARTUP STAGE

NOTES

CHAPTER FOUR Landing Your Next Startup Executive Role: Leveling Up Within Your Current Organization or Seeking a Role Elsewhere

MY FIRST EXECUTIVE ROLE: JOINING AN EARLY‐STAGE STARTUP AND GETTING PROMOTED TO VP

HOW ANALIESE BROWN, VP OF PEOPLE AT CAMPMINDER, GOT PROMOTED INTO HER FIRST EXECUTIVE STARTUP ROLE

GENERALIST TO SPECIALIST: HOW TO “COME UP” AS AN EXECUTIVE IN YOUR AREA OF SPECIALIZATION

LEARN TO BALANCE THE TACTICAL AND THE STRATEGIC

UNDERSTAND BUSINESS AREAS OUTSIDE YOUR “COMFORT ZONE”

EMBRACE A LEARNING OR “GROWTH” MINDSET

HOW NICOLE WOJNO SMITH, VP OF MARKETING AT TACKLE, GOT HER FIRST EXECUTIVE ROLE BY LEVELING UP WITHIN HER THEN‐ORGANIZATION

HOW SMITH “LEVELED UP” BY BUILDING A PARTNERSHIP WITH THE C‐LEVEL TEAM

MASTERING DATA‐DRIVEN STORYTELLING AROUND BUSINESS OBJECTIVES

GAIN A DEEPER UNDERSTANDING OF CROSS‐FUNCTIONAL PARTNERS AND THEIR ROLES

PARTNER CLOSELY WITH YOUR FINANCE LEADERSHIP (UNLESS YOU'RE THE CFO; IN THAT CASE, PARTNER WITH EVERY OTHER EXECUTIVE TEAM)

START UNOFFICIALLY RECRUITING YOUR “BENCH” DREAM TEAM FOR YOUR DEPARTMENT

LEVELING UP IN THE ENGINEERING SIDE OF THE BUSINESS: JEFF AMMONS

LEARNING TO LET GO OF BEING THE ONE TO WRITE CODE AND SHIFTING TO EMPOWERING HIS TEAM

ON INTERNAL PROMOTIONS: NICK MEHTA'S PERSPECTIVE AS CEO OF GAINSIGHT

GETTING HIRED: LANDING THE ROLE

INTERNAL PROMOTIONS TO EXECUTIVE ARE POSSIBLE, BUT NOT AT EVERY COMPANY

CHAPTER FIVE Get the Offer and Secure Your Executive Seat

FIND YOUR FIRST (OR NEXT) EXECUTIVE ROLE

INTERVIEWING FOR YOUR EXECUTIVE ROLE

NAVIGATING THE OFTEN BYZANTINE STARTUP HIRING PROCESS

THE INTERVIEW PROCESS

UNDERSTAND THE PRESENTATION TECH STACK AND PRACTICE YOUR PRESENTATION WITH FRIENDS

MEETING WITH THE CEO: UNDERSTAND THEIR VISION

WHEN THE STARTUP'S HIRING PROCESS GOES AWRY

GETTING THE OFFER

COMPENSATION BREAKDOWN

NEGOTIATING THE OFFER

DO YOUR RESEARCH

RISK VS. REWARD: A NOTE ABOUT EQUITY

FIND OUT THE PERCENTAGE OF EQUITY BEING RECEIVED AND ITS CURRENT VALUE

UNDERSTAND YOUR VESTING SCHEDULE IN YOUR OFFER

FIND OUT THE TAX IMPLICATIONS OF YOUR EQUITY

HIRE AN ACCOUNTANT AS SOON AS YOU ACCEPT AN OFFER

A NOTE ON EARLY‐STAGE EQUITY

HIRE A LAWYER TO REVIEW YOUR OFFER LETTER AND CONTRACT

NEGOTIATING YOUR TITLE

CASH VS. EQUITY: FOOD FOR THOUGHT

MORE ON EQUITY AND CAP TABLES FOR UNDER‐REPRESENTED STARTUP LEADERS

A WORD: IF THE DEAL GOES SOUTH WHILE YOU'RE IN NEGOTIATIONS

AFTER YOU SIGN THE DEAL

NOTES

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”

Exercise: Personal Retrospective, by April Wensel

Exercise: Happiness and Fulfillment Timeline by Dave King (Adapted from Stanford Graduate School of Business)

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

CREATING A HIGH‐PERFORMANCE, SUPPORTIVE CULTURE ON YOUR TEAM

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

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. When It's a Temporary Thing

When the Performance Issue Doesn't Improve Over Time

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

Move It!

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

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. Not Growing Fast Enough

Your Department Is Underperforming (As a Whole)

Someone or Some Area of Your Team Specifically Is Underperforming

The Business Isn't on Track to Hit Goals and You're Not Responsible

The Business Isn't on Track to Hit Goals and You're Responsible

You Missed an OKR

OTHER THINGS THAT CAN GO WRONG AND HOW TO DEAL WITH THEM. Your Cross‐functional Department Head Fails

What To Do When a Failing Executive Tries to Take Down Your organization With Them

Your Organization and/or Business Is Going Well But You're Burnt Out or Facing Another Personal Challenge That's Difficult

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

CHAPTER EIGHTEEN Measuring Success: How to Know If Things Are Working

WHO CARES ABOUT LEADING AND LAGGING INDICATORS?

UNDERSTANDING THE METRICS THAT SET UP YOUR DEPARTMENT FOR SUCCESS

FOCUS ON MEASURES THAT SHOW OUTCOMES VS. ACTIVITY

GETTING COMFORTABLE WITH QUANTITATIVE MEASUREMENT TOOLS

HOW THE BOARD THINKS ABOUT YOUR INDICATORS

MEASURE WHAT COUNTS AT A REGULAR CADENCE

OTHER “SUCCESS” MEASURES

LETTING LEADING INDICATORS GUIDE YOUR EARLY‐STAGE STARTUP GROWTH

RAND FISHKIN'S ADVICE FOR METRICS: KEEP IT SIMPLE

HOW TO WORK WITH YOUR CEO ON MEASURING YOUR PERFORMANCE

BUILDING ACCOUNTABILITY INTO YOUR TEAM REPORTING

CHAPTER NINETEEN Communicating Your Results to Your CFO, CEO, Company, and Board

WHY BOARD MEETINGS EXIST (AND NO, THEY'RE NOT JUST TO TORTURE STARTUP FOUNDERS AND EXECUTIVES!)

COMMUNICATING AT THE BOARD LEVEL

COMMUNICATING AT THE “ALTITUDE” OF THE BOARD

HOW IS YOUR BUSINESS PERFORMING WITHIN THE CONTEXT OF THE GREATER MARKET (OR THE VC'S PORTFOLIO?)

DO YOUR HOMEWORK

BUILD RELATIONSHIPS WITH THE BOARD PRIOR TO YOUR FIRST MEETING

TAKING A STORYTELLING APPROACH TO BOARD PRESENTATIONS

COMMUNICATE WITH YOUR DEPARTMENT TEAM TO GET WHAT YOU NEED FROM THEM

CREATING YOUR BOARD SLIDES: THINK AT A HIGH ALTITUDE

HOW TO CREATE YOUR BOARD SLIDES

EXAMPLE DEPARTMENT OKR SNAPSHOT SLIDE REPORTING RESULTS WITH R/Y/G

OTHER TYPES OF SLIDES TO INCLUDE IN YOUR BOARD DECK

THE PURPOSE OF YOUR APPENDIX AND/OR PRE‐READ MATERIAL

TIP: ENSURE EVERY SLIDE HAS A NARRATIVE‐DRIVEN TITLE

PRESENTATION TIPS: BEFORE, DURING, AND AFTER THE BOARD MEETING. Before the Meeting

Practice Helps You Succeed

During the Meeting

After the Board Meeting

CHAPTER TWENTY Mentorship: How to Further Grow Your Career by Networking and Giving Back

MENTORSHIP POWERS THE STARTUP ECOSYSTEM

MENTORSHIP'S ROLE IN SUPPORTING DEVELOPING LEADERS

MENTORSHIP IS ABOUT KNOWLEDGE AND CHEMISTRY

MENTORS DON'T HAVE TO KNOW ALL OF THE ANSWERS

ENLISTING YOUR OWN MENTORS: DEVELOPING A GROUP OF PERSONAL ADVISORS

MENTORS CARE ABOUT YOU PERSONALLY AND CAN KEEP YOUR PRIORITIES STRAIGHT

SEEK MENTORSHIP THAT PROMOTES EQUALITY

SIGN UP TO MENTOR AT AN ACCELERATOR

MENTOR THROUGH AN OFFICIAL ORGANIZATION

FIND COMMUNITY AND SHARE MUTUAL SUPPORT AS A “PEER MENTOR”

AFFINITY ORGANIZATIONS

OTHER TYPES OF SUPPORT: SPONSORSHIP AND COACHING. Sponsorship

Coaching

DON'T DISCOUNT INFORMAL MENTORSHIP

TAKE MENTORSHIP TO THE NEXT LEVEL: SCALE YOUR IMPACT

AFTERWORD

ACKNOWLEDGMENTS

ABOUT THE AUTHOR

INDEX

WILEY END USER LICENSE AGREEMENT

Отрывок из книги

SARAH E. BROWN

The venture capitalist's remarks were part of his due diligence in determining whether the early‐stage startup he invested in should hire me for a marketing leadership role. But upon hearing his backhanded compliment, my heart sank. While I was grateful for his affirmation that I was qualified to be considered for the position we were discussing, it made me wonder: why had I waited when my resume suggested I had enough experience for a startup executive position years earlier?

.....

Harvard Business School author and leadership coach Anne Morriss says that, based on her and her partner Frances Frei's research, demographics bear no weight on who succeeds in a leadership role.

“Our research shows there aren't major demographic differences in who ends up ‘killing it’ at a startup in a leadership role,” says Morriss.

.....

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