The Complete Software Project Manager Mastering Technology from Planning to Launch and Beyond

by Anna P. Murray

The Complete Software Project Manager Mastering Technology from Planning to Launch and Beyond

Publisher : Wiley

Author : Anna P. Murray

ISBN : 9781119161837

Year : 2016

Language: en

File Size : 1.32 MB

Category : Business Money

THE COMPLETE
SOFTWARE
PROJECT
MANAGER
MASTERING TECHNOLOGY FROM
PLANNING TO LAUNCH AND BEYOND

Anna P. Murray

Copyright © 2016 by Anna P. Murray. All rights reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.
Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in
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Library of Congress Cataloging-in-Publication Data
Names: Murray, Anna, 1966- author.
Title: The complete software project manager : mastering technology from
planning to launch and beyond / Anna P. Murray.
Description: Hoboken, New Jersey : John Wiley & Sons, Inc., [2016] | Includes
index.
Identifiers: LCCN 2015036771 (print) | LCCN 2015040806 (ebook) | ISBN
9781119161837 (cloth) | ISBN 9781119219910 (ePDF) | ISBN 9781119219903
(ePub)
Subjects: LCSH: Computer software—Development. | Software
engineering–Management.
Classification: LCC QA76.76.D47 M877 2016 (print) | LCC QA76.76.D47 (ebook) |
DDC 005.1–dc23
LC record available at http://lccn.loc.gov/2015036771
Cover Design: Wiley
Cover Image: © shuoshu / Getty Images
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1

To my partner in life and business, Chris Moschovitis.
Your support makes all things possible.

CONTENTS
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

v

vi

CONTENTS

The Need for Up-Front Requirements in Many Projects 14
The Real World 15
Agile Enough 15
The Software Development Life Cycle
CHAPTER

3

15

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

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

29

CONTENTS

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

vii

viii

CONTENTS

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
CHAPTER

5

53

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

CONTENTS

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
Search

82

82

Content Pages and Features
Integrations

83

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

ix

x

CONTENTS

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
The Math Part 109

109

CONTENTS

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
Customization

117
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

xi

xii

CONTENTS

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?
Making Decisions

148

147

CONTENTS

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
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
CHAPTER

157

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

153

xiii

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