Introduction xxv
Part I Become an Empathetic Leader 1
1 Hey, What Do You Know? 3
Build Your Skillset 3
Grow Through Listening 4
A Proactive Mindset 5
2 An Amazing IT Department? What’s That? 7
3 Conventional Wisdom Is Wrong 9
A Tale of Two Projects 10
The Downward Spiral of Micromanagement 11
Part II Four Steps to Innovate 15
4 The Right Foundation 17
Set Expectations 17
Build Trust 18
Share Your Values 19
5 The Laudato Hierarchy of IT Needs 21
6 Keep the Lights On (KTLO) 23
7 Lean and Efficient IT 25
8 Create Value 27
Cost Reduction 28
Increase Revenues and Enable Opportunities 28
Reduce Risk 29
9 Let’s Innovate 31
Develop the Mindset 32
Dedicate Resources 32
Embrace Risk 33
Idea Generation 33
Rapid Prototyping 34
10 CIO Report Card 35
Part III Develop a Winning Culture 37
11 Culture Eats Eggs and Strategy Eats Bacon, or Something to that Effect 39
The Wrong Way to Develop Culture 41
Building a Strong Culture 42
How Can a CIO Influence Culture? 42
The Blue Bloods 43
12 The Boxes, the Lines, and the Dashes 45
Step 1: Identify Your Functions and Business Needs 46
Step 2: Create an Org Chart 46
Step 3: Run Use Cases 46
Step 4: Identify Skills 47
Step 5: Review Your Team 47
13 Org Design—Just Show Me the Answer 49
Support 49
Cyber-Security 50
Portfolio Manager 50
HR Partner 51
Finance Partner 52
Executive Assistant 52
14 Organizational Design and Culture 53
15 It’s Not the Play, It’s the Player 55
16 Take Care of Those Peeps 57
Ask People What They Want from Their Career 58
Spend the Most Time with Your Best People 58
Provide Career Development Planning 59
Always Support Your Team, Even When They’re Wrong 59
Be a Diode 60
Have a Real Open-Door Policy 60
Listen 61
Only Make Changes that Are Necessary 62
Provide Fair and Timely Feedback 62
Be Kind Enough to Let Someone Go 63
17 Hire the Best 65
18 The Best Team Is a Diverse Team 69
19 Using Mercenaries—I Mean, Consultants 71
Management Consultants 71
Project-Based Consultants 72
Offshore, Nearshore, Onshore 74
Staff Augmentation 75
Boutique Firms 76
20 The Power of Experts 77
21 Build that Network 81
Formal CIO Networks 82
Navigating a Cocktail Party 83
Social Media 84
22 Good Advice Doesn’t Come Cheap; It’s Free 87
Part IV Deliver to Delight: a Collection of Usable Tips and Tools 89
23 The Written Word—a.k.a IT Strategy 91
Align Your Strategy 91
Create Your Strategy 92
Put Your Strategy into Action 94
24 It’s the Uptime, Stupid 95
Measuring Uptime 96
Nuances of Measuring Uptime 97
Information Technology Infrastructure Library (ITIL) 98
When You Have a Problem, Proclaim It Loudly 98
Troubleshooting 99
Let Them Eat Cake 101
Change Management 101
Daily Meeting 101
Annual Readiness 102
25 If It’s Important, You Better Get Two 103
Redundancy and Probability Math 105
The Only True Test 106
Does Any of This Matter in the Cloud? 106
26 Lock It Down 107
27 Lean and Efficient IT 109
Software 110
Legality 111
Cloud Services 111
Telcom 112
Professional Services 113
Capital Expenses Drive Operating Expenses 114
The Small Stuff 114
Reduction in Force 115
Less Is More 116
28 What Should I Work on First? 117
29 Limit Your Work in Process (WIP) 121
30 One List to Rule Them All 123
Create Your List 124
Rank Your List 124
Create a Standard Deviation Report 125
Communicate Priorities 126
Cumulative Total 126
Operationally Required Projects 127
Be Ready for Line Jumpers 128
Moving Forward 129
31 Portfolio/Program/Project Management 131
Consistency Creates Speed 131
Ranked Project List 132
A Unified Calendar 132
Big Room Planning 133
Project Charter 133
A Project Schedule Is Not a Project Plan 134
Kanban 134
Agile Mindset 135
Keep Teams Intact 135
Part V Develop Key Business Proficiency for Maximum IT Efficiency 137
32 Love Your HR Department, Just Don’t “Love” Your HR Department 139
Compensation 140
Employee Relations 141
Learning and Development 142
Payroll and Benefits 143
Organizational Design 143
Talent Acquisition 143
33 If I Wanted to Be a Lawyer, I Would Have Gone to Law School 145
Licensing Models 145
The Cloud 146
Indemnification 147
Limitation of Liability 147
Breach/Litigation 147
Force Majeure 147
Accounting Considerations 148
Data Ownership and Preservation 148
Cyber-Security 149
Unsavory Practices 149
End-User License Agreement (EULA) 150
Changing Terms on an Invoice 151
Virtualization 151
Hyperlinks 151
Relationships over Contracts 152
Software Audits 152
Other Involvement with the Legal Department 152
34 Let’s Make a Deal 155
35 Accounting, My Worst Subject 157
Chargebacks 158
Showbacks 159
Remedial Accounting Starts Here 159
General Ledger 159
Accruals 159
Balance Sheet 159
Income Statement 160
Statement of Cash Flows 160
Capital Expenses (CapEx) vs Operating Expenses (OpEx) 160
Capitalized Internal Labor 161
Depreciation 161
Write-Off 162
EBITDA 162
Return on Investment (ROI) 162
Lookback ROI 163
36 Learn Your Business, Inside and Out 165
Part VI Straighten Up and Fly Right 167
37 What You Should Have Learned in Kindergarten 169
38 Professionalism Isn’t Just Wearing a Suit 173
Complain the Right Way 174
Don’t Allow Gossip 174
Make Your Word Gold 174
Keep a Secret 175
Don’t Yell, Curse, or Pound the Table 175
Assume Everything Will Get Out 175
Remove Stress from Your Boss 176
Just a Little Bit Better 176
39 What You Do Matters—You’re Always on the Clock 177
40 Vendors and Frendors 179
41 A Word to the Vendors 181
42 Be a Cool Customer 183
43 Get Your Butt in Shape 185
Sleep 185
Weight Management 186
Nutrition 186
Exercise 187
Part VII Final Tips and Advice 189
44 When Something Goes Wrong 191
Step 1: Leap into Action 191
Step 2: Assess Things 192
Step 3: Plan Your Response 192
Step 4: Communicate 192
Step 5: Monitor the Situation 192
Step 6: Learn from It 193
45 When Others Come Knocking 195
46 What’s Wrong with Outsourcing? 197
47 Switching Jobs 199
Should I Stay, or Should I Go? 200
Make the Move 200
On-Board Yourself 201
48 Technology Matters 203
49 Conclusion 205
Notes 207
Index 213
