The Complete Software Project Manager

FOREWORD xvii ACKNOWLEDGMENTS xix ABOUT THE AUTHOR xxi INTRODUCTION xxiii CHAPTER 1 Software Development Explained: Creativity Meets Complexity 1 A Definition of Software Development 1 Why Is Software Development So Difficult? Hint: It's Not Like Building a House 1 The Simple, the Complicated, and the Complex 2 Metaphor #1: Piles of Snow 3 Metaphor #2: The Ikea Desk 4 Metaphor #3: Heart Surgery 5 Using the Three Metaphors in Project Management 6 CHAPTER 2 Agile, Waterfall, and the Key to Modern Project Management 7 Agile and Waterfall 7 Waterfall 7 Waterfall's Problems 8 The Requirements Requirement 9 Inflexibility 9 Loss of Opportunity and Time to Market 9 Customer Dissatisfaction 10 Agile 10 Lack of Up-Front Planning 12 Lack of Up-Front Costs 12 Stakeholder Involvement 13 Extensive Training 13 Where Agile Works Best 14 The Need for Up-Front Requirements in Many Projects 14 The Real World 15 Agile Enough 15 The Software Development Life Cycle 15 CHAPTER 3 Project Approaches; Off-the-Shelf and Custom Development; One Comprehensive Tool and Specialized Tools; Phased Launches and Pilots 17 The Custom vs. Off-the-Shelf Approach 18 History 18 The Benefit of Off-the-Shelf 19 Off-the-Shelf Examples 19 Thinking You're Editing When You're Actually Creating 20 Common Challenges with Off-the-Shelf Software 20 Business Compromise 21 Discovering You Made the Wrong Choice with Packaged Software 21 Breaking the Upgrade Path 21 Locked into a Partnership and the Product Roadmap 22 Expense of Off-the-Shelf 22 Where Packaged Software Works Well 23 Frameworks and the Blurring Worlds of Custom and Packaged Software 23 Integrations vs. One Tool for the Job 24 To Phase or Not to Phase 25 Bigger Is Not Always Better 26 The Pilot Approach 26 Why Not Pilot? 27 CHAPTER 4 Teams and Team Roles and Responsibilities Defined 29 Teams and the Roles on Teams 29 Project Leadership 30 The Key Business Stakeholder 31 The Project Sponsor 31 The Program Manager 32 Project Manager 32 Multiple Project Managers 33 Confusion About the Project Manager Role; It's More Limited than You Think 34 Project Team 34 The Business Analyst 35 User Experience 35 Designer 35 The Programmers 35 Architect 36 Systems Administrator 36 Team Member Choice and Blending Roles 37 Getting All the Roles Covered 37 Real-World Examples for Role-Blending 38 Project Sponsor as Program Manager 38 Program Manager as Business Analyst 39 Front-End Programmer as User Experience 39 Design, UX, and Business Analysis 40 Back-End Programmer as Architect 40 SysAdmin as Architect 40 Professionals and Personalities 40 Programmers 40 Project Managers 41 Business Analysts and User Experience People 42 Architects and Systems Administrators 42 Insource or Outsource: Whether to Staff Roles with Internal People or Get Outside Help 43 The Myth that Insourcing Programming Is Better 43 Inexperience with Projects 44 How Knowledge Goes Stale 44 Outsourced Teams 44 When to Use Internal or External Teams 45 Roles Easiest to Outsource 46 Roles "in the Middle" 46 Roles that Are Usually Internal 47 Vendors and Hiring External Resources 47 Some Tech-Types to Avoid: Dot Communists and Shamans 47 The Shamans 48 Boundaries, Responsibilities, and Driving in Your Lane 49 Techies Who Don't Drive in Their Lane 50 Business Stakeholders Who Shirk Responsibilities 50 Business Stakeholders, Step Up! 51 Have a Trusted Technology Partner 52 How Best (and Worst) to Work with Your Technology Partner 52 Too Many Cooks 53 CHAPTER 5 Project Research and Technology Choice; Conflicts at the Start of Projects; Four Additional Project Delays; Initial Pitfalls 55 Choice of Technology, a Definition 56 The Project's Research Phase 56 Current State 56 Integrations and Current State 57 Data and Current State 57 Business Needs 58 Possible Technology Solutions 58 Demos 59 Comparison Grids 59 Talk to Other People, a Journalistic Exercise 60 How Do You Know When Your Research Is Done? 61 Research Reality Check 62 You Can't Run the Control 62 Religious Wars 63 Passion over Reason 64 Business Stakeholders and Controlling Ego 64 How to Stop a Technology Religious War 65 Not So Easy 65 Preventing a Technology Religious War 65 Being Right 66 Stopping a War in Its Tracks 66 Détente and Finally Ending a Technology Religious War 67 Clarity 67 The Role of the CIO 68 Two Most Important Factors in Core Technology Decisions 69 Budget Constraints 69 The Team 69 Choosing Technology and What NOT to Consider: The Future 70 Other Conflicts that Delay the Start of Projects 71 Business Strategy and Organizational Authority 71 Design 73 Blue Sky 73 Overanalysis 74 The Project Charter, a Key Document 74 CHAPTER 6 Final Discovery; Project Definition, Scope, and Documentation 77 Budgeting and Ongoing Discovery; Discovery Work Is Real Work 78 Budgeting Final Discovery 78 What Discovery Costs 79 What Comes Out of Final Discovery: A Plan 79 Getting to a Plan 80 The Murk 80 Getting Out of the Murk 81 The Plan for the Plan--Company A 82 Hosting 82 Content Entry 82 Search 82 Content Pages and Features 83 Integrations 83 Back-end System 83 Data Migration 84 How Anyone Can Make a Plan for the Plan 84 Different Approaches to Elicit the Plan for the Plan 85 Exception to the Murk 86 Breakout Sessions 87 The Weeds Are Where the Flowers Grow 87 Not All Questions Will Be Answered 88 Agile, Waterfall, and Project Documentation 89 The Scope Document 90 Project Summary 90 Project Deliverables 90 Out of Scope 90 Constraints 91 Assumptions 91 Risks 91 Timeline 92 Budget, Scope, Timelining, and Horse-Trading 93 Metrics 93 What About "the List"? 94 Defining and Visualizing and Project Scope 94 What Usually Happens 95 The Chicken and the Egg 95 Common Questions 97 Where Does Design Fit In? 97 Working with Marketing Stakeholders 98 How You Know You're On the Wrong Track 98 A Word About Ongoing Discovery 99 CHAPTER 7 Budgeting: The Budgeting Methods; Comparative, Bottom-Up, Top-Down, and Blends; Accurate Estimating 101 An Unpleasant Picture 102 What Goes on Behind the Scenes; a Scene 102 Budgeting Type 1: Comparative Budgeting 103 Gotchas with Comparative Budgeting 104 Budgeting Type 2: Bottom-Up Budgeting 104 The Rub in Bottom-Up Budgeting 105 Budgeting Type 3: Top-Down and Blends 105 Why RFPs Don't Work 106 Accurate Estimating and Comparison Budgeting 107 Effective Estimating in Top-Down and Bottom-Up Budgeting 108 Establish a Base Budget for Programming, Ongoing Discovery, Unit Testing, Debugging, and Project Management 108 Percentages of Each 108 Programming Hours--Raw and Final 109 The Math Part 109 Additional Items to Consider 111 Budgeting and Conflicts 112 CHAPTER 8 Project Risks: The Five Most Common Project Hazards and What to Do About Them; Budgeting and Risk 115 Five Always-Risky Activities 116 Integration 116 Data Migration 117 Customization 118 Unproven Technology/Unproven Team 119 Too-Large Project 119 Want Versus Need 119 Want Versus Need: Programmers 120 Want Versus Need: Business Stakeholders 120 Optimism Is Not Your Friend in Software Development 120 Beware the Panacea Claim 121 Facing Risks 121 A Few Words About Fault 121 Identifying Risks Up Front 122 Embrace the Snow 122 Talking to Your Boss 123 Hidden Infections 124 Bad Technology Team; Wrong Technology Choice 124 Too Many Opinions and Lack of Leadership 124 The Contingency Factor 125 The Cost of Consequences 125 Contingency Percentage Factors 126 In the Real World 126 The Good News 127 A Common Question 127 Long-Term Working Relationships and Contingency 127 CHAPTER 9 Communication; Project Communication Strategy; from Project Kickoff to Daily Meetings 129 Project Kickoff 130 Project Kickoff Cast 130 Project Leadership 130 Company Leadership 131 Who Gives the Kickoff? 131 Kickoff Presentation 131 High-Level Project Definition 132 Business Case and Metrics 132 Project Approach 133 Team Members and Roles 133 Project Scope 134 Out-of-Scope 134 Timeline 134 Budget 135 Risks, Cautions, and Disclaimers 136 Monthly Steering Committee 137 Monthly Steering Committee Attendees 137 Monthly Steering Committee Agenda 137 Weekly Project Management Meeting 139 Weekly Project Management Attendees 139 Weekly Project Management Agenda 139 Daily Standup Meeting 140 Well-Run Meetings 140 Insist on Attention 140 Timeliness 140 Getting "into the Weeds" 141 Needs to Be Kicked Upstairs 141 Poor Quality Sound--Speakerphones and Cell Phones 142 Too Much Talk 142 Agenda and Notes 143 CHAPTER 10 The Project Execution Phase: Diagnosing Project Health; Scope Compromises 145 What Should Be Going on Behind the Scenes 145 The Best Thing You Can Ever Hear: "Wait. What Was It Supposed to Do?" 146 Neutral Corners 147 What If Things Aren't Quiet? 147 Making Decisions 148 How to Listen to the Programmers 149 The Programmer's Prejudice 149 SneakerNet and the Fred Operating System 150 SneakerNet Integrations 150 The Fred Operating System 151 The Hidden Benefits 151 Demos and Iterative Deliverables 151 Why Iterative Deliverables Are Important 151 Why Iterative Deliverables Are Hard 152 What You Can Do to Achieve Iterative Deliverables Even if It's Hard 153 Demos 154 Scope Creep 154 Dealing with Scope Creep; Early Is Better 155 Scope Creep and Budgeting 155 Scope Creep and Governance 155 Types of Scope Creep 156 Scope Creep and the Team 157 CHAPTER 11 First Deliverables: Testing, QA, and Project Health Continued 159 The Project's First Third 159 The Second Third 159 A First Real Look at the Software 160 The Trough of FUD 161 Distinguishing a Good Mess from a Bad Mess 163 An Important Checkpoint 163 Getting to Stability 164 First Testing and the Happy Path 164 Quality Assurance 165 Bug Reporting 165 Regression Testing 166 Bugs: Too Many, Too Few 166 Testing: The Right Amount for the Job 166 Too Much Testing? 167 Bug Cleanup Period 167 Timeline So Far 168 CHAPTER 12 Problems: Identifying and Troubleshooting the Three Most Serious Project Problems; Criteria for Cancellation 169 A Rule About Problems 169 Additional Resources 170 Fault--A Review 172 Common Late-Stage Problems 172 Business User Revolt: "We Talked About It in a Meeting Once" 172 Managing Business User Revolt 173 What If No or Little Documentation Exists? 174 Risk Chickens Come Home to Roost 175 Managing the Risk Chickens 176 When Programmers Ask for More Time 178 Lurking Infections 178 Bad Technology Team 179 How to Manage a Bad Technology Team 179 Wrong Technology Choice 180 Managing a Wrong Technology Choice 180 The Sunk-Cost Bias 181 Lack of Leadership 181 Managing Lack of Leadership 181 CHAPTER 13 Launch and Post-Launch: UAT, Security Testing, Performance Testing, Go Live, Rollback Criteria, and Support Mode 183 User Acceptance Testing: What It Is and When It Happens 183 Controlling UAT and "We Talked About It in a Meeting Once," Part Deux 185 Classifying UAT Feedback 185 Bugs 186 Not Working as Expected--The Trickiest Category 186 Request for Improvement 187 Feature Request 188 Conflict Resolution and Final Launch List 188 Load Testing 189 Performance Testing 189 Security Testing 189 Sign-Off 194 Questions to Ask Regarding Launch Readiness 195 Not Knowing Is Not Acceptable 195 Criteria for Rollback 196 Singing the Post-Launch Blues 196 Was It All a Big Mistake? 198 Metrics 198 Ongoing Development 198 Surviving the Next One 199 APPENDIX 201 GLOSSARY 215 INDEX 223