Evolving Digital Leadership (eBook)

James Brett describes himself as a digital leader who is passionate about developing people and organizations to create a positive future for humanity. Ultimately, he is a geek at heart. At the age of 11, he learned to code, and at 18, he had replaced the engine in his first car. His curiosity about how things work and his knack for fixing things continued into his adult work life. James studied micro-electronics and computing at university, spent the next 10 years in software development, and more recently has focused over 10 years on leadership and coaching. As a technology expert, he leads strategic thinking from the board level through to team implementations, covering digital strategy, organizational transformation, and product development.  He holds a global perspective on digital, having lived in the USA, UK, China, and Australia, which allowed him to understand the complex cultural and market dynamics that impact technology and product delivery across continents. James is well-respected in the tech industry, and has presented at several agile/digital conferences globally. As the ThoughtWorks Transformation Practice Lead, he had the privilege to work alongside his mentor, agile thought leader Jim Highsmith, on the global rollout of Adaptive Leadership. This started James down a path of ‘finding a better way' for teams and organizations. James is a certified Leadership Agility Coach, Integrative Enneagram Coach, NLP Master Practitioner, and Holacracy Practitioner. He leverages this unique combination of psychology and digital skills to grow high-performance teams, leaders and organizations. Ultimately, James wants to leave the world a better place for his children and our future generations, so it is no surprise that he donates his time to charities and not for profit organizations such as Redkite and Burn Bright. Outside of the office, you will find James enjoying time with his family, capturing photos, building and flying drones, or in his work shed constructing cubby houses.For more information on James, and the book, please visit his website: https://evolvingdigitalleadership.com/.

Contents 5
About the Author 7
Foreword 8
Acknowledgments 10
Part I: Digital Leadership 12
Chapter 1: Start Here 14
Our Journey 15
Yes, But… 16
This Book Isn’t an Agile Book 16
It Isn’t a Generic Leadership Book Either 16
How to Use This Book 17
Part I: Digital Leadership 17
Part II: Awareness 17
Part III: Intention 18
Part IV: Attention 18
Part V: Reflection 18
Self-Reflection Questions 18
Chapter 2: TL DR: Too Long
Becoming a Digital Leader (See Part I) 20
Digital Situational Leadership 20
Career Success Pyramid 22
Evolution of Leadership 23
Unnatural Selection 24
Awareness (See Part II) 26
Intention (See Part III) 28
Own: Our Career and Choices 28
Understand: What’s Important to Us 29
Four Things That Are Important to All Unnatural Leaders 30
Define and Set Intentions 30
Attention (See Part IV) 31
Managing Our State 32
Reflection (See Part V) 36
Ignite (See Chapter 20) 39
It’s Not Cheating (See Chapter 21) 39
Chapter 3: Becoming a Digital Leader 40
The Four Capacities 41
Tactical and Strategic 42
Delivery and Culture 42
The Four Modes 43
Mode 1 (Bottom-Left): Get Stuff Done 43
Mode 2 (Bottom-Right): Futurist 44
Mode 3 (Upper-Left): Friend of the Team 44
Mode 4 (Upper-Right): Utopian 44
From Technology to People 45
Technology 46
Process 46
People 47
Fork Me! 48
Thought Leadership Path 50
People Leadership Path 52
Deciding Which Path To Take 54
Other Shifts Required for People Leadership Success 56
From Personal Success to Team Success 56
Finite to Infinite 56
From Making the “Right” Decision to Making a Decision 57
From Solutions to Problems 57
These Leadership Shifts Cause Anxiety 58
Summary 59
Self-Reflection Questions 59
Chapter 4: Career Success Pyramid 61
Step 1. Own Your Career 62
Step 2. Get a Coach and a Mentor 62
Step 3. Redefine Personal Success 64
Step 4. Failure Happens, It’s How You Respond 65
Step 5. Balance Leadership and Technical 65
Leadership Styles 66
Size and Type of the Organization 67
Passion for Technology 68
Summary 69
Self-Reflection Questions 69
Chapter 5: The Evolution of Digital Leadership 70
Shift of the CTO Role Over the Last 10 Years 70
The Strategic Shift: Digital Enablement 71
The Culture Shift: Talent and Process 72
The Future Role of the CTO (or Digital Leader) 73
Accelerating Pace of Change and Sophistication 74
The Move to a Digital Society 76
End of the Office Block (and Cities) 76
Commoditization of Development 77
Extreme Competition for Talent (One Last Time) 77
Unnatural Leaders: The Evolution of Digital Leadership 78
Deeply Understand People 79
Digital Organization 80
Drive and Integrate Key Technology Trends 80
Unnatural Selection 80
Summary 81
Self-Reflection Questions 81
Chapter 6: Unnatural Selection: Evolving Faster Than the Pace of Change 82
The Evolution Helix 83
Step 1: Awareness 86
Step 2: Intention 88
Personal Intention: Be Passionately Curious 89
Team Intention: Move from Performance Management to Growth 90
Stakeholder Intention: Build Long-Lasting, Mutually Beneficial Relationships 90
Step 3: Attention 90
Attention to Self 91
Attention to Team 91
Attention to Stakeholders 91
Step 4: Reflection 92
A Growth Mindset 92
Summary 94
Self-Reflection Questions 96
Summary of Part I: Digital Leadership 96
Part II: Awareness 98
Chapter 7: Humans as a Full Stack 100
Frontend 102
API and Microservices Layer 102
Backend 102
Human Frontend 103
Human API and Microservices Layer 103
Distortions 104
Deletions 104
Generalizations 104
Meta-Programs 105
Human Backend 106
Summary 107
Self-Reflection Questions 107
Chapter 8: Experts and Achievers 108
Stages of Development 109
Expert Stage 115
Experts as Team Members 116
Expert Leadership 116
Expert Stakeholder Management 117
Expert to Achiever Transition 117
Achiever Stage 117
Achievers as Team Members 118
Achiever Leadership 118
Achiever Stakeholder Management 119
Achiever to Catalyst Transition 119
Catalyst Stage 119
Catalysts as Team Members 119
Catalyst Leadership 120
Catalyst Stakeholder Management 120
So What Does All This Mean? 120
Assessing Our Stage of Development 123
Accelerating Our Development to Higher Stages 125
Summary 125
Self-Reflection Questions 126
Chapter 9: Preferences and Patterns 127
Frontend Communication Channel Preferences 127
Vr 129
Vc 129
Ar 129
Ac 130
Aid 130
Ki 130
Meta-Programs Layer 131
How Meta-Programs Are Configured 132
Convincer Meta-Programs 133
Relationship Comparison: Matching or Mismatching 134
Convincer Representation: Looks, Sounds, Feels, or Makes Sense 134
Convincer Demonstration: Number of Times or Length of Time 135
Authority Source: Internal or External 135
Meta-Programs for Evolving Faster Than the Pace of Change 135
Nature: Static or Process 136
Motivation Direction: Toward or Away From 136
Scenario Type: Pessimist or Optimist 137
Goal Striving: Skeptic-Optimization-Perfectionism 137
Tuning Meta-Programs for Success 137
A Meta-Program Tuning Example 139
Steps 1-3 140
Step 4 140
Step 5 140
Step 6 140
Being an Introvert Is Not an Excuse for Having Poor Social Skills 141
Summary 142
Self-Reflection Questions 143
Chapter 10: Personality Types 144
The Enneagram 146
The Enneagram Symbol 146
Type 1: The Reformer 147
Type 2: The Helper 148
Type 3: The Achiever 149
Type 4: The Individualist 150
Type 5: The Investigator 150
Type 6: The Loyalist 151
Type 7: The Enthusiast 152
Type 8: The Challenger 152
Type 9: The Peacemaker 153
Backend Processing 154
Common Technical Types 156
Which Balance of Types Makes a Great Team? 156
Common Leadership Types 157
Identifying Others’ Types 158
The Nine WIIFMs (or Nine Motivations) 162
Curiosity Is Key 163
Summary 164
Self-Reflection Questions 164
Summary of Part II: Awareness 165
Part III: Intention 166
Chapter 11: Intention: The Secret to Success 168
What Is Intention and How Does It Make Us Successful? 170
The Clarity Process 172
Owning Our Career and Choices 173
Choice 175
We Always Have a Choice 175
Four Powers 176
Owning Our Internal Thoughts 177
Owning Our Internal Feelings 177
Owning Our External Actions 180
Owning Our External Communications 180
Owning Our Four Powers Is Challenging and Empowering 181
Summary 181
Self-Reflection Questions 182
Chapter 12: Understanding What’s Important 183
The Challenge 184
Extrinsic Motivators 184
Intrinsic Motivators 185
The Midlife Crisis: The Painful Transition from Achiever to Catalyst 186
Human Full Stack 188
Backend Motivators: Enneagram Types 189
Three Meta-Programs That Impact What Is Important 190
Quality of Life: Be-Do-Have 191
Preference: People, Place, Things, Time, Activity, Information, and Systems 192
Attention: Self or Other 193
The Highest Frame Governs the Game 194
Purpose 195
Make a List 196
What Is Important to All Unnatural Leaders? 196
Purpose 197
Our Own Personal Growth and Evolution 198
The Growth of Our People 198
The Growth of Long-Lasting Stakeholder Relationships 198
Configuration of the Unnatural Leaders Full Stack 199
An Unnatural Leaders Backend Configuration 199
An Unnatural Leaders API Layer Configuration 199
Summary 200
Self-Reflection Questions 201
Chapter 13: Successful Intentions 202
The Three Intentions of Unnatural Leaders 203
Intention 1: Passionately Curious 203
Intention 2: From Performance Management to Growth 205
Caring for People Doesn’t Mean We Are Doormats! 208
We Can’t Fake It Well! 208
Intention 3: Build Long Lasting, Mutually Beneficial Relationships 208
We Like People Like Us 210
Frames of Mind 211
Define Your Own Intentions 212
Setting Intentions 213
Summary 215
Self-Reflection Questions 215
Summary of Part III: Intention 216
Part IV: Attention 217
Chapter 14: Attention: Self 220
Choose 221
Choosing to Own Our Time 221
Frame 224
Perform 227
State Management 228
The TEA Model 229
Method 1: Changing State by Changing Our Thoughts 231
Method 2: Changing State by Changing Our Actions 232
Summary 233
Self-Reflection Questions 234
Chapter 15: Attention: Team 235
Building a Great Tech Brand 235
Innovative and Interesting Products 236
Impact on People, Industry, and /or Society 236
Commercial Sustainability 237
Working with Smart People 237
Solving Big and Interesting Problems 237
Using Interesting Technology 237
Collaborative, Empowering, Contemporary Culture 238
Where Should We Focus Our Attention When Growing Our Teams? 239
1. Hiring 239
2. Onboarding 239
3. Growth and Execution 239
4. Exit 239
The Two Phases of Team Attention 240
Deep Understanding of the Individual 240
Establish Effective Communication Patterns 241
Co-Create Their Profile 242
Co-Creating a Personal Growth Plan 243
Coaching and Support 244
Focus on Learning 248
The Challenge of Leading and Coaching 250
Summary 251
Self-Reflection Questions 251
Chapter 16: Attention: Stakeholders 252
Step 1: Identifying Stakeholders 253
Stakeholder Relationship Map 253
Upper-Left Quadrant: Fix 254
Upper-Right Quadrant: Maintain 255
Lower-Left Quadrant: Monitor 255
Lower-Right Quadrant: Leverage 255
Step 2: Understanding the Stakeholder 256
Getting Specific 256
Never Ask Why? 258
Get Clear On What Success Means (To Them!) 259
Step 3: Positively Influencing Stakeholders 260
Why the Business Needs to Support the Initiative 261
How We Plan to Address the Business Need 261
What We Require to Execute and Enable the Business 262
Gaining Buy-in to Reduce Technical Debt 262
When It All Goes Wrong 265
Summary 265
Self-Reflection Questions 266
Summary of Part IV: Attention 266
Part V: Reflection 268
Chapter 17: Reflection 271
Gaining Perspective 272
Levels of Perspective 273
Individual and Team 274
Teams 274
Department, Region, Organization 275
Industry 275
Technology 275
Society and Economy 276
Mankind and the Planet 276
The Reflection Framework 276
Embracing Change 277
Evolutionary Belief System 279
Reflection Methods 280
Method 1: Journaling 281
Method 2: Feedback 281
Method 3: Coaching 281
Method 4: Mentoring 281
Method 5: Meditating 282
Method 6: Levels of Perspective 282
Reducing the Learning Delay 282
Reflection Is a Lot like Software Testing 283
Summary 283
Self-Reflection Questions 284
Chapter 18: Reflection Methods 285
Journaling 286
Reflecting and Journaling on Critical Events 287
Looking for Patterns 289
Feedback 290
Practices 290
Future Reflection 291
Reflecting on the Future of Technology 293
Reflecting on 3D Printing Technology 293
The Importance of AI 295
Reflecting on the Future of Society 297
End of the Office Block 297
Sharing Economy 297
Smart Homes, Smart (Driverless) Cars, and Smart Cities 298
Virtual Societies 299
Facilitating Reflection 299
Summary 300
Self-Reflection Questions 301
Chapter 19: Reflecting Together 302
My Reflections on Writing Evolving Digital Leadership 303
Focusing Considerable Time and Energy on One Thing Has an Incredible Amplifying Effect 303
State Management Is Critical to Completing a Book 304
Early Feedback Has Been Exciting! 304
Taking a Lean-Startup Approach and Interviewing 40 Digital Leaders Was Invaluable 304
Not Enough People Are Thinking Far Enough Into the Future 304
Build, Measure, Learn: Getting Feedback Is Essential 305
The Book Writing Process Is Way More Than “Just” Writing 305
Summary of Reflection 305
Facilitating Your Reflection on Evolving Digital Leadership 305
Evolving Digital Leadership Self-Reflection Questions 306
Chapter 20: Ignite 308
Ignite 308
Ignite Yourself 309
Ignite Your Teams 309
Ignite Our Community 310
What If? 311
What If Artificial Intelligence Takes Over? 311
What If We Prepare Our Children for the Digital Future? 313
What If We Genuinely Believed Every Challenge (or Failure) We Faced Was a Gift? 314
Chapter 21: It’s Not Cheating 316
Online Companion Website and Community 316
Visuals 317
Self-Reflection Questions 317
Quotes 317
Feedback 317
Index 318