The Accidental CIO - Scott Millett - E-Book

The Accidental CIO E-Book

Scott Millett

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Beschreibung

An indispensable guide showing IT leaders the way to balance the needs of innovation and exploration with exploitation and operational reliability Many books on modern IT leadership focus solely on supporting innovation and disruption. In practice these must be balanced with the need to support waste reduction in existing processes and capabilities while keeping the foundation operational, secure, compliant with regulations, and cost effective. In The Accidental CIO, veteran software developer-turned-executive Scott Millett delivers an essential playbook to becoming an impactful, strategic leader at any stage of your IT leadership journey from your earliest aspirations to long time incumbents in director and C-suite roles. You'll find a wealth of hands-on advice for tackling the many challenges and paradoxes that face technology leaders, from creating an aligned IT strategy, defining a target architecture, designing a balanced operating model, and leading teams and executing strategy. After the foreword from Simon Wardley, The Accidental CIO will help you: * Understand problem contexts you will face using the Cynefin decision making framework, and how the philosophies of agile, lean and design thinking can help manage them. * Design an adaptive and strategically aligned operating model by applying the appropriate ways of working and governance approaches depending on each unique problem context. * Organize a department using a blend of holacratic and hierarchical principles, and leveraging modern approaches such as Team Topology and Socio-technical patterns. * Develop and deploy an effective and aligned IT Strategy using Wardley mapping based on a deep knowledge of your business architecture. With this knowledge you'll be ready to create an empowered IT organization focused on solving customer problems and generating enterprise value. You'll understand the science behind what motivates teams and changes behavior. And you'll show your skills as a business leader thinking beyond IT outputs to impactful business outcomes.

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Table of Contents

Cover

Table of Contents

Title Page

Foreword

Introduction

Why Should You Care? The CIO Challenge

Taking Action: Becoming a Strategic Leader

What Will You Learn?

I A New System of Work

1 Why We Need to Change The System

The Age of Digital Disruption

Operating in a Volatile, Uncertain, Complex, and Ambiguous Business Environment

Leading IT in a Complex and Adaptive World

Summary

2 Philosophies for a New System

Philosophies vs. Methodologies

Discovering Value Using Design Thinking

Eliminating Waste with Lean

Managing Complexity in Software Development with Agile

Strategic Decision-Making Using Wardley Mapping

Summary

3 How to Change the System

Being Agile vs. Doing Agile

Why Only Adopting the Practices of Agile Won't Work

Use Systems Thinking to Change Behavior

Changing Leaders' Mental Models

Instilling Drive through Purpose, Mastery, and Autonomy

Summary

II Designing An Adaptive Operating Model

4 The Anatomy of an Operating Model

The Anatomy of an Operating Model

The Themes of an Adaptable Operating Model

Summary

5 How We Are Organized

Organizational Structure

Understanding the Influence of Conway's Law and the Cognitive Load Theory on Team Performance

Product-Centric Development Teams

Defining Product Team Boundaries

Evolving to Business and IT Fusion Teams

Managing Cross Team Dependency

Summary

6 How We Work

IT Management Frameworks

How to Solve Problems from Discovery to Delivery

Problem-Solving Methodologies

Discovery Tools for Understanding the Problem Space

Approaches to Manage the Solution Space

Summary

7 How We Govern

What Is Governance?

Alignment: Linking Work to Strategic Intent

Managing Demand: Visualizing Work

Prioritization: Focusing on the Things That Matter

Measurement: Defining and Cascading Value and Measures

Investment: Funding for Outcomes

Decision Rights: Empowering People

Performance: Monitoring Value

Summary

8 How We Source and Manage Talent

Sourcing Strategy

Recruiting

Developing

Retaining

Summary

9 How We Lead

Adopting New Leadership Behaviors

Embracing Servant Leadership

Instilling Intrinsic Motivation

Encouraging Growth and Development

Focusing on Improving the System

Summary

III Strategy to Execution

10 Understanding Your Business

Business Anatomy

Why IT Leaders Need to Understand the Anatomy of a Business

Purpose: Starting with Why and Understanding Your North Star

The Business Model: The System of Capturing Value

Operating Model: How We Do the Work

Business Context: Understanding What Can Impact Us

Business Strategy: The Choices We Make to Win

Summary

11 IT Strategic Contribution

Linking IT Execution to Business Strategy Using Enterprise Architecture

Creating an IT Strategy

Determining IT Contribution to Addressing BAU Challenges and Achieving the Strategic Objectives

Defining Principles to Guide Technical Solutions

Determining Strategic Actions for IT Capability Maturity Improvements

Measuring Contribution in Terms of Business Outcomes

Summary

12 Tactical Planning: Deploying Strategy

Planning Considerations

Following Hoshin Kanri to Deploy Strategy

Creating a Tactical Plan

Clarify the Business Needs: Where Do We Need to Focus Our Investment?

Review the Technology Landscape: What Do We Need to Optimize?

Review the IT Operating Model: What Do We Need to Change?

How Wardley Maps Can Help Inform Target Architecture and Operating Model Choices

Defining and Prioritizing the IT Initiatives

Communicating the IT Tactical Investment Road Map

Summary

13 Operational Planning: Execution, Learning and Adapting

Operational Considerations

Operational Planning

Feedback, Learning, and Adapting

Creating a Clear Line of Sight from Strategy to Execution

A Worked Example: From Strategy to Tactics to Operational Execution

Summary

Index

Copyright

Dedication

About the Author

Acknowledgments

End User License Agreement

List of Tables

Chapter 2

Table 2.1: Phase I: Stop self-destructive behaviour

Table 2.2: Phase II: become more context aware

Table 2.3: Phase III: Better for less

Table 2.4: Phase IV: Continuously evolve

Table 2.5: The various stages of evolution on a Wardley Map

Table 2.6: The difference between lean thinking and design thinking

Chapter 3

Table 3.1: The difference between linear and systems thinking

Table 3.2: Beyond budgeting's leadership and management principles

Table 3.3: The difference between Type X and Type I behavior

Chapter 4

Table 4.1: Managing by output, outcome, and goal

Chapter 5

Table 5.1: Different modes of operating to support an ambidextrous organizat...

Table 5.2: The difference between project and product teams

Chapter 6

Table 6.1: IT frameworks

Table 6.2: When to favor each solution delivery life cycle

Chapter 7

Table 7.1: The processes that support doing the right things and doing the t...

Table 7.2: A balanced approach to governance

Table 7.3: Feedback loops applied at different levels of the organization

Table 7.4: Examples of leading tactical initiatives contributing to strategi...

Table 7.5: How bets and tactics contribute to and align with business outcom...

Table 7.6: Project vs. product funding

Table 7.7: Value- vs. plan-driven work.

Chapter 8

Table 8.1: The differences between coaching, mentoring, and training

Table 8.2: Using the continuous Improvement Kata for talent development

Table 8.3: Using the coaching Kata for talent development

Chapter 9

Table 9.1: The difference between a traditional and servant leader

Chapter 10

Table 10.1: How businesses adapted during the pandemic

Table 10.2: The difference in thinking in silos vs. thinking in value stream...

Chapter 11

Table 11.1: An example business strategy and measures

Table 11.2: An example of how IT actions relate to business strategy

Table 11.3: An example of the technical architectural and IT operating model...

Table 11.4: An example of how the IT tactical plans link to the IT action

Table 11.5: An example of how the strategic initiatives break down into prog...

Table 11.6: Terms used as the various levels of strategy deployment

Table 11.7: The case study business strategy

Table 11.8: An example of customer and business pain points mapped to capabi...

Table 11.9: The challenge we have with the capability

Table 11.10: Example of IT actions, and the dependency on other departments ...

Table 11.11: Examples of large operational risks that require IT strategic a...

Table 11.12: Principles based on observations of the business context

Table 11.13: Measuring the impact of IT strategic action in relation to the ...

Table 11.14: How to measure IT capability improvements

Table 11.15: Mapping an IT strategy template to the Pyramid Principle

Chapter 12

Table 12.1: Application inventory

Table 12.2: Application Analysis.

Table 12.3: Approaches to review security, data, infrastructure, and interfa...

Table 12.4: Analysis on filling technical gaps

Table 12.5: IT operating model capability gaps

Table 12.6: Using landscape analysis to identify solutions for IT initiative...

Table 12.7: IT initiatives to address IT capability needs

Chapter 13

Table 13.1: Gaps between knowledge, alignment, and effectiveness

Table 13.2: Mapping Wardley mapping techniques to the steps in the OODA loop...

Table 13.3: Questions to verify strategic alignment

Table 13.4: Customer and business pain points impacting NPS and Trustpilot s...

Table 13.5: IT strategic actions to contribute to improving customer NPS

Table 13.6: The state of the AS-IS Landscape

Table 13.7: Target architecture suggestions

Table 13.8: Tactical initiatives to move to the target state

Table 13.9: Operational projects distilled from the tactical initiative of i...

List of Illustrations

Introduction

Figure I.1: How this book is organized

Chapter 1

Figure 1.1: The Cynefin decision framework

Figure 1.2: IT needs to operate in both the ordered and unordered problem spa...

Chapter 2

Figure 2.1: The difference between philosophies, methodologies, and tools

Figure 2.2: The nonlinear and iterative five stages of design thinking

Figure 2.3: The Toyota House—the main concepts that make up the Toyota Produc...

Figure 2.4: The five-step thought process proposed by Womack and Jones in 199...

Figure 2.5: The Theory of Constraints

Figure 2.6: The Five Focusing Steps

Figure 2.7: Simon Wardleys Strategy Cycle

Figure 2.8: An example of a Wardley Map

Figure 2.9: How a Wardley Map can help visualise the appropriate method to us...

Chapter 3

Figure 3.1: The difference of doing ag...

Figure 3.2: The systems thinking icebe...

Figure 3.3: Where we have the greatest...

Figure 3.4: Linear vs. systems thinkin...

Figure 3.5: How mental models influenc...

Figure 3.6: How this book is structure...

Chapter 4

Figure 4.1: The operating model is the link between strategy and execution.

Figure 4.2: The interrelated five components of the operating model

Figure 4.3: The four themes of the adaptable operating model

Figure 4.4: The relationship of output to outcomes and impact

Figure 4.5: Multiple operating models are required to manage the spectrum of ...

Chapter 5

Figure 5.1: A hierarchy and the system of command and control

Figure 5.2: A holacracy and devolved decision rights

Figure 5.3: An organizational structure that balances a holacracy and hierarc...

Figure 5.4: An example of an organizational structure that balances holacracy...

Figure 5.5: A Wardley Map and the three modes of operating to support an ambi...

Figure 5.6: Team performance is greatly influenced by a combination of Conway...

Figure 5.7: An example of architectural design influences by teams organized ...

Figure 5.8: An example of architectural design influences by teams organized ...

Figure 5.9: How memory works and the three types of cognitive load on working...

Figure 5.10: How to optimize cognitive load

Figure 5.11: The characteristics of product-centric or product teams

Figure 5.12: Different examples of product teams

Figure 5.13: A product team based around a pricing capability

Figure 5.14: Different evolutions will suit different sizes of teams.

Figure 5.15: The comparison of the number of communication links between team...

Figure 5.16: Dunbar's numbers translated to team sizes

Figure 5.17: To keep teams small, distill them into smaller products.

Figure 5.18: The factors that can influence team boundary design

Figure 5.19: The three levels of the product taxonomy

Figure 5.20: Product portfolios are large and small to medium enterprises.

Figure 5.21: Product groups within a product portfolio

Figure 5.22: Examples of product groups at a large and small to medium enterp...

Figure 5.23: Product teams within a product taxonomy

Figure 5.24: Distilling product teams into smaller product teams

Figure 5.25: Team topology patterns

Figure 5.26: An example of a product team setup at a small retail e-Commerce ...

Figure 5.27: Projects are used to coordinate across product teams for complex...

Chapter 6

Figure 6.1: Methodologies put philosophies into practice.

Figure 6.2: Frameworks that are applicable to the various capabilities of IT...

Figure 6.3: The three main components of problem solving

Figure 6.4: Problem-solving methodologies mapped to the evolution stages on a...

Figure 6.5: The Double Diamond design process

Figure 6.6: The Double Diamond design process is based on continuous feedback...

Figure 6.7: W. Edwards Deming's PDCA cycle

Figure 6.8: The Six Sigma cycle

Figure 6.9: Problem discovery identifies the outcomes required to achieve a g...

Figure 6.10: A customer journey map

Figure 6.11: A customer journey map with a service blueprint, highlighting cu...

Figure 6.12: An event storming map

Figure 6.13: An example of mapping a value stream

Figure 6.14: Step 1, model the flow or the sequence of activities.

Figure 6.15: The updated value map with related applications

Figure 6.16: The updated value map with data on processing time

Figure 6.17: An updated value map, highlighted with opportunities for improve...

Figure 6.18: An example of applying five whys to root cause analysis

Figure 6.19: An example of a using a fishbone, or Ishikawa, diagram to highli...

Figure 6.20: Using a systems loop to model root causes

Figure 6.21: An impact map

Figure 6.22: Clarifying the goal

Figure 6.23: Actors that can influence the goal

Figure 6.24: The impacts actors can make to influence a goal

Figure 6.25: The outcomes required to achieve actor impacts

Figure 6.26: The tasks required to deliver an outcome

Figure 6.27: The anatomy of the solution space

Figure 6.28: The life cycle of a system can employ many solution delivery lif...

Figure 6.29: The project life cycles

Figure 6.30: Prince 2 and iterative delivery

Figure 6.31: The continuous delivery life cycle

Figure 6.32: Dual track development.

Figure 6.33: The lean start-up cycle

Figure 6.34: Design thinking and the lean startup

Figure 6.35: How to choose a delivery management approach

Figure 6.36: The waterfall, or BDUF, approach to delivery management

Figure 6.37: The scrum approach to delivery management

Figure 6.38: A Kanban board

Figure 6.39: The first way: Take a systems approach to the end-to-end deliver...

Figure 6.40: The second way: Ensure that there is constant feedback to optimi...

Figure 6.41: The third way: create an environment and culture that is always ...

Figure 6.42: CI and CD pipelines

Chapter 7

Figure 7.1: A goal tree

Figure 7.2: A Lean Value Tree

Figure 7.3: A revised “take” on the goal tree

Figure 7.4: Capturing demand at any level

Figure 7.5: The ideas pipeline

Figure 7.6: The A3 template follows the PDCA loop.

Figure 7.7: DIBB argument framework

Figure 7.8: Using a kanban board for project portfolio management

Figure 7.9: Teams pull work in when they have capacity.

Figure 7.10: Setting work limits

Figure 7.11: Lead time vs. cycle time

Figure 7.12: Define exit policies to govern the movement of work.

Figure 7.13: The demand on IT outside of the strategic initiatives

Figure 7.14: Using the tactical plan and target architecture to push back on ...

Figure 7.15: Using impact maps to visualize the priority of work

Figure 7.16: Teams employ demand shaping to manage smaller BAU work.

Figure 7.17: Visualizing highest value for lowest effort

Figure 7.18: Plotting initiatives to determine priority

Figure 7.19: Understanding priority using the cost of delay

Figure 7.20: Plotting IT capability initiatives to determine priority

Figure 7.21: Understanding value in terms of customer value, business benefit...

Figure 7.22: Where to use leading vs. lagging metrics

Figure 7.23: Linking business goal to operational action

Figure 7.24: Methods are designed to achieve measurements that are derived di...

Figure 7.25: Cascading purpose and measurements down the organization's level...

Figure 7.26: Framing goals in terms of customer value

Figure 7.27: Quantifying goals

Figure 7.28: Balancing measures for guardrails

Figure 7.29: Tactical initiatives, aka business outcomes, bridge strategic ob...

Figure 7.30: Tactical initiatives can be thought of as business outcomes.

Figure 7.31: Tactics produce the outcome and bets prove the outcome.

Figure 7.32: The four levels of investment strategy

Figure 7.33: Targeted levels of investment for strategic objectives

Figure 7.34: Initiatives are funded to contribute to achieving the strategic ...

Figure 7.35: Different initiatives will require different methods of funding....

Figure 7.36: Wardley Map showing how the evolution of an area can affect how ...

Figure 7.37: In product funding, investment is released based on value delive...

Figure 7.38: Product teams are funded based on strategic need.

Figure 7.39: Comparing how product teams are funded between large and small t...

Figure 7.40: Product teams “spend” their capacity on delivering the features,...

Figure 7.41: The areas of governance

Figure 7.42: Team roles

Figure 7.43: Strategic objectives are led by the exec group with support from...

Figure 7.44: Tactical initiatives are led by senior leadership and product gr...

Figure 7.45: Operational action is lead by product owners and teams.

Figure 7.46: Product teams are responsible for determining the best use of th...

Figure 7.47: Moving from project teams to product teams

Figure 7.48: Project, program, or outcome leaders can be required to coordina...

Figure 7.49: There is a responsibility at each layer of the organisation to f...

Figure 7.50: Fixed resource capacity can work on a plan driven, known scope, ...

Figure 7.51: Wardley Map showing how the evolution of an area can affect how ...

Chapter 8

Figure 8.1: T-shaped vs. I-shaped people

Figure 8.2: Simon Wardley's Explorers, Villagers, and Town Planners

Chapter 9

Figure 9.1: Moving leadership from command and control to empowerment, trust,...

Figure 9.2: Strive for autonomous teams that are completely aligned.

Figure 9.3: Maslow's hierarchy of needs

Figure 9.4: Influence your peers by changing beliefs, values, and attitudes....

Chapter 10

Figure 10.1: The five components of business anatomy

Figure 10.2: How business context changes can change strategy, business, and ...

Figure 10.3: The Business Model Canvas covers both the operating and business...

Figure 10.4: Value propositions, channels, relationships, and how revenue is ...

Figure 10.5: Components of the operating modelSource: The Business Model Canv...

Figure 10.6: The Operating Model Canvas

Figure 10.7: How value streams relate to business capabilities and processes,...

Figure 10.8: An example of a value stream

Figure 10.9: How value streams align to customer journeys

Figure 10.10: Core, extended, and supporting value streams

Figure 10.11: Value streams cross business units

Figure 10.12: Value streams require business capabilities to perform the acti...

Figure 10.13: Business capabilities are composed of people, process, and tech...

Figure 10.14: The factors in your environment that can affect your business

Figure 10.15: The growth-share matrix

Figure 10.16: The product lifecycle model

Figure 10.17: The attractiveness/advantage matrix

Figure 10.18: Michael Porters Five Forces model

Figure 10.19: The PESTEL model

Figure 10.20: The Strategy Choice Cascade

Figure 10.21: How strategic choices cascade throughout a business

Figure 10.22: The Value Disciplines model

Figure 10.23: The Value Proposition Canvas

Figure 10.24: Porter's activity system

Figure 10.25: Porter's value chain

Figure 10.26: An example of a Wardley map

Figure 10.27: The OGSM framework

Figure 10.28: An example of a strategy map

Chapter 11

Figure 11.1: The three levels of IT planning: strategic, tactical, and operat...

Figure 11.2: How Kotusev’s CSVLOD model and its artifacts relate to strategic...

Figure 11.3: The inputs, process, and outputs of creating an IT Strategy

Figure 11.4: The link between business demand and IT contribution

Figure 11.5: Use business capabilities to link IT to business success.

Figure 11.6: An example of an e-commerce business capability model

Figure 11.7: Mapping business capabilities from value streams

Figure 11.8: Mapping customer pains and linking to business capabilities usin...

Figure 11.9: Mapping business pain points and linking to business capabilitie...

Figure 11.10: Consolidating mapped business capabilities into the business ca...

Figure 11.11: Highlighting the maturity games on a business capability model...

Figure 11.12: The IT4IT reference framework.

Figure 11.13: The IT capability model based on the IT4IT reference framework...

Figure 11.14: The use of lagging vs. leading measures in strategy deployment...

Figure 11.15: The Pyramid Principle structure for effective communication

Figure 11.16: The structure of an IT strategy document based on the Pyramid P...

Figure 11.17: Highlighting key factors that will have a material impact on th...

Figure 11.18: A business strategy laid out using the OGSM template

Figure 11.19: The executive summary of IT strategic actions

Figure 11.20: Capability pain points highlighted on a customer journey map

Figure 11.21: Capability pain points highlighted on a value stream map

Figure 11.22: Linking IT strategic actions to improve business capabilities a...

Figure 11.23: Linking IT strategic actions to mitigate business challenges or...

Figure 11.24: Highlight key gaps in IT capability maturity.

Figure 11.25: The actions and how we will measure the key IT capability impro...

Figure 11.26: IT strategic principles

Figure 11.27: A one-page poster to communicate IT strategy

Chapter 12

Figure 12.1: Architecture abstraction from strategic to operational

Figure 12.2: The seven levels of Hoshin Kanri

Figure 12.3: Feedback and consensus for strategic cascade

Figure 12.4: The inputs, process, and outputs of creating a tactical plan

Figure 12.5: The three main processes of tactical planning

Figure 12.6: Creating a heat-mapped business capability model to highlight ar...

Figure 12.7: Define the target architecture to address business capability ga...

Figure 12.8: Define the target operating model to support bridging technical ...

Figure 12.9: Define initiatives to move to the target architecture and operat...

Figure 12.10: Prioritize initiatives into a tactical road map.

Figure 12.11: The output of the tactical planning process

Figure 12.12: A business capability model highlighted to show areas in need o...

Figure 12.13: Technical architecture layers to review

Figure 12.14: Mapping applications to business capabilities

Figure 12.15: Example of architecture diagram

Figure 12.16: Plotting applications on a matrix to determine life cycle decis...

Figure 12.17: Business capability categories

Figure 12.18: Choosing a method when bridging technical gaps based on the cap...

Figure 12.19: AWS Modern data architecture reference architecture

Figure 12.20: Thoughtworks technical radar

Figure 12.21: An example of a target state suggestion

Figure 12.22: The operating model is influenced by the strategy and the targe...

Figure 12.23: It is not obvious what method to use when using an application ...

Figure 12.24: It is easier to identify appropriate methods when using a Wardl...

Figure 12.25: Wardley maps deal with the entire value chain.

Figure 12.26: Start a Wardley Map by modeling user need.

Figure 12.27: Mapping the dependencies between capabilities on a Wardley map...

Figure 12.28: The evolution stages of components

Figure 12.29: Placing capabilities based on their evolution

Figure 12.30: An aggregated view of all the maps for each strategic outcome

Figure 12.31: Mapping where components related to Core, Supporting, and Gener...

Figure 12.32: Identifying weaknesses in the maps

Figure 12.33: The recommended methods for enabling capability based on evolut...

Figure 12.34: Organizing teams based on capability dependencies and evolution...

Figure 12.35: Complementing Wardley maps with a Boston matrix to determine pr...

Figure 12.36: IT initiatives address gaps in the technology architecture

Figure 12.37: An example of an initiative overview

Figure 12.38: Plotting initiatives to determine priority

Figure 12.39: The structure of an IT tactical plan document based on the Pyra...

Figure 12.40: The executive summary of IT strategic actions

Figure 12.41: An example of a tactical road map

Figure 12.42: Transformational target architecture with annotated pain points...

Figure 12.43: Transformational target architecture with annotated pain points...

Figure 12.44: Target architecture to show evolution for Data BI

Figure 12.45: Changes required to the operating model

Figure 12.46: Highlighting the challenges with the IT landscape

Figure 12.47: An example of why the phasing approach was taken

Figure 12.48: An example of an IT initiative.

Chapter 13

Figure 13.1: The three gaps that cause friction when de-losing strategy for e...

Figure 13.2: Leading through intent closes the knowledge, alignment, and effe...

Figure 13.3: An example of an OKR

Figure 13.4: An example of an OKR with child OKRs

Figure 13.5: Using OKRs to deploy tactical initiatives aka business outcomes ...

Figure 13.6: The process of operational planning

Figure 13.7: Distilling large initiatives into separate investments

Figure 13.8: Solution designs are at the operational level of the CSVLOD mode...

Figure 13.9: Product teams perform solution discovery to determine how best t...

Figure 13.10: Product team road maps get more abstract the further out they p...

Figure 13.11: A high-level operational plan covering what IT intends to deliv...

Figure 13.12: Feedback and review cadence based around Hoshin Kanri

Figure 13.13: Strategic, tactical, and operational feedback loops

Figure 13.14: Actual feedback loops depend on the project methodology being u...

Figure 13.15: The OODA loop

Figure 13.16: The Wardley strategic cycle

Figure 13.17: How the OODA and PDCA loops interrelate

Figure 13.18: Capturing information about the problem using an A3 template

Figure 13.19: A customer journey map and service blueprint highlighting the p...

Figure 13.20: A cause-and-effect diagram showing the root causes of issues

Figure 13.21: A diagram highlighting the state of the IT landscape in relatio...

Figure 13.22: A diagram highlighting the target architecture suggestions to s...

Figure 13.23: The organization structure based around value streams

Figure 13.24: Strategic objective A3 with tactical initiative countermeasures...

Figure 13.25: To demonstrate the operational level, we will focus on a single...

Figure 13.26: Root cause analysis of why OTIF is low

Figure 13.27: Linking operational projects to the tactical initiatives using ...

Figure 13.28: Tactical initiative A3 with operational project countermeasures...

Figure 13.29: Integrated strategic, tactical, and operational PDCA loops

Guide

Cover

Title Page

Copyright

Dedication

About the Author

Acknowledgments

Foreword

Introduction

Table of Contents

Begin Reading

Index

End User License Agreement

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The Accidental CIO

A Lean and Agile Playbook for IT Leaders

 

Scott Millett

 

 

 

 

 

Foreword

In the seminal “Manager's Theories about the Process of Innovation” (Journal of Management Studies, March 2002), Graeme Salaman and John Storey elegantly unravel the innovation paradox pervading contemporary organizations. They argue that the key to enduring success lies in the meticulous balance between survival today, which requires the efficient exploitation of existing competencies (marked by virtues of coherence, coordination, and stability), and survival tomorrow, which requires exploration and the dissolution of these very same virtues.

This intricate dance of dichotomies is further complicated by the axiom that today's breakthroughs morph into tomorrow's utilities. In an ever-evolving marketplace, the territories once charted in the name of exploration swiftly transition into arenas of exploitation. Furthermore, as innovations evolve into commodities, they lay the groundwork for venturing into new, adjacent domains, thereby perpetuating a cycle of renewal. In history, the standardization of simple mechanical hardware such as the nut and bolt enabled complex machinery. More recently, the transformation of bespoke computing into ubiquitous cloud services has catalyzed the emergence of Big Data and AI. This process underscores the relentless progression of technology and enterprise.

This dynamic interplay between the poles of exploration and exploitation underlines a perpetual motion, challenging the conventional understanding of management. Nothing stands still; everything is in motion; everything has a context. There are no simple solutions.

Into this turbulent landscape, organizations try to navigate and distinguish themselves with novel offerings while striving for operational excellence in commoditized domains. The constant motion and evolution from novelty to utility demands contextual agility in leadership and strategy. What works in one domain does not work in the other or even in the transition between the two. Amidst this maelstrom, leaders are tasked with decisions of monumental consequence, shaping the strategic direction, governance, talent development, and clarity with which their organizations communicate and survive both today and tomorrow. Missteps can precipitate misalignments with severe repercussions.

While many frameworks offer navigational aids in this environment, their applicability varies significantly across different contexts. The challenge of leadership lies in discerning the appropriate approach guided by the unique economic and technological contours of one's own organization. To do this, you have to understand the landscape that the organization operates within.

Dedicated to demystifying this landscape, The Accidental CIO comprehensively explores frameworks, methodologies, and techniques used by contemporary leadership and places them in context. From the strategic precision of the Hoshin Kanri process to the agility embedded in the OODA loop, from the creativity of design thinking to the adaptability of flexible planning horizons, this book weaves a rich tapestry of insights. It integrates strategic, architectural, and operational perspectives, offering a lucid understanding of the terrain leaders must navigate.

For executives championing innovation while managing commodity operations, fostering consensus, and driving strategic collaboration across all levels of the organization, The Accidental CIO emerges as an indispensable guide. In an era where adaptability and strategic foresight are paramount, this book is not just a resource but a beacon for the forward-thinking leader.

—Simon Wardley

Introduction

If there is no struggle, there is no progress.

—Frederick Douglass

Be yourself. Everyone else is taken.

—Oscar Wilde

How do you get to Carnegie Hall? - Practice, practice, practice

—Anonymous

We think too much and feel too little. More than machinery, we need humanity; more than cleverness, we need kindness and gentleness. Without these qualities, life will be violent and all will be lost.

—Charlie Chaplin

It was my first day on my new job, and it hit me like a bucket of ice-cold water. It wasn't that I had imposter syndrome. I just didn't know what to do.

Back in January of 2015 I received an offer from Iglu.com, an online travel agent for the cruise and ski markets, to become its first IT director. I wanted a change from Wiggle.co.uk, where I had been the first full time developer working along the founder, development manager, and most recently an enterprise architect. The new role was a step up, but I was confident in my technical ability. After all, it was only another form of e-commerce, and I was comfortable with that. But I wasn't prepared for a role as the most senior leader in IT and one that was part of the exec group—one that not only needed to lead and inspire an IT department, ensuring day-to-day reliable operational running, but one that had a pivotal role in contributing to the organization's digital transformation. It was a role that required me to be a business leader as well as a technical leader. I realized I had a lot to learn. Over the following years I studied and grew professionally. I learned both the theory and how to put it into practice. I had begun my journey to become a strategic CIO.

This book is the codification of all the knowledge I acquired, a playbook that I hope will be useful on your journey as you transition to a CIO or an IT leadership role. My context, like yours, is unique; the challenges you experience will differ from what I faced. However, if like me you have found yourself in an IT leadership position where you were unsure on your next move, then this book will provide you the guidance to help your orientation as you navigate the trials and tribulations of a life as a CIO.

Why Should You Care? The CIO Challenge

Becoming a CIO is a hugely rewarding role and one that is critical to nearly all modern businesses. Because of their unique position in the organization, CIOs understand the constraints and opportunities of the business as well as having knowledge of how to mitigate or capitalize on them. This makes them best placed to take a more active role in digital transformation projects, moving beyond implementing new technologies to spearheading organizational transformation and driving business value. However, it's still a relatively new role that's not very well understood by the rest of the business and the board; it is stressful and rapidly evolving. All of this is occurring within an environment of accelerated transformation, emerging technology, constant disruptions, rising customer expectations, against a backdrop of huge sociopolitical challenges. In short, a lot is expected from IT leaders and CIOs in this most turbulent of times.

The evolving expectations of the CIO to lead, disrupt and transform, run, mitigate risk, consolidate, and grow can appear to be contradictory based on the archetypes of IT leaders we have come to know. These contradictions form what Martha Heller calls the CIO Paradox as detailed in her book The CIO Paradox: Battling the Contradictions of IT Leadership (Routledge 2012):

The “Innovator's Dilemma” paradox refers to the conflict of having to manage the balance between the requirement to stay operationally stable, secure, reliable, and compliant with the need to innovate, experiment, and take chances.

The “Business-IT Alignment” paradox alludes to the need for CIOs to be technical experts as well as understand the business to ensure strategic alignment and coordination. This is difficult due to the complexity and rapid evolution of technology, the speed of business needs, and the time it takes to deliver technology.

The “Digital Literacy” paradox relates to the challenges that CIOs face caused by other executives' ignorance of the consequences of technology choices and how it affects the company.

The “Influence” paradox refers to the difficulty of acquiring authority to make decisions inside the business when they are often considered a service provider or an overhead.

The “Blame” paradox speaks to the difficulty of CIOs accepting accountability for the outcomes of technological projects when they don't have complete control over decision-making. This is chiefly caused by asking CIOs to deliver defined scope or output rather than outcomes.

This set of conflicting forces is deeply embedded in the operating and mental models of organizations that have been formed within contexts that are no longer relevant today. The problem is that the purpose the system (the IT operating model) was designed for has changed. The old system is based on archetypes of CIOs that are mutually exclusive in that either they specialize in running efficient operations (the service provider, order taking, stable, secure, process-oriented) or they are focused on innovation (the disruptor, adaptable, innovative, lightweight governance, and fast). CIOs don't need to be innovators or operational; they need to focus on innovation and operational stability. They need to manage digital transformation, digital optimization, and operation efficiency. A good CIO can make or break a company. However, boards hire or promote technologists. What they need are strategic leaders who specialize in technology.

Taking Action: Becoming a Strategic Leader

Great CIOs are sought after; they are partners, cocreators, consultants, and advisors. They are business leaders first, ones that just happen to be accountable for the technology within an organization. They report to the CEO, have a seat at the top table, contribute, and sometimes lead an organization to digital transformation and strategic success. They achieve this by balancing and adapting to meet the variety of challenges they face. These are the core behaviors that they exhibit:

Coauthor strategy.

Great CIOs are not order takers. They coauthor strategy and focus on what matters, namely generating enterprise value. They can achieve this because of their deep knowledge of the business and operating models. They understand the context that the business operates in and the material factors that can affect the organization. They know what the business needs to do to be successful—where it will play and how it will win. They interpret where technology contributes and where it can lead.

Focus on outcomes over output.

It doesn't matter what you do if it doesn't make an impact. Great CIOs bridge the gap between business impact and technology output by focusing on what business outcomes are required for success, how technology can be used to achieve them, and how best to organize teams to execute them.

Structure teams for intrinsic motivation.

Great CIOs know that they are only as good as their team. Great CIOs excel in recruiting, developing, and retaining talent. They do this by ensuring teams are motivated to solve complex problems and deliver value. They achieve this by designing an operating model to support people's need for purpose, autonomy, and mastery.

Focus on being agile, not doing agile.

Great CIOs know that to bridge the paradoxes, they need to be adaptable. There is no single way of doing something. Agile is appropriate for some problems, whereas big upfront design is suitable for others. Failure is expected when exploring uncharted problem spaces but not when working in well-known and understood areas. Sometimes it's best to buy and sometimes it makes sense to build. Great CIOs adapt their methods and team dynamics depending on context.

Manage the flow of work, not people.

Great CIOs work on the system, not in it. They leverage their power to remove impediments and inspire teams with an aligned vision, using their strategic, social, and relationship skills to influence and lead in change and innovation. They manage the flow of work; they lead the people.

CIOs that show aptitude in these areas will have an impact greater than any other exec on business success. However, to get there you will need the right attitude. You will need to embrace a growth mindset. You need to continuously learn, adapt, and develop. Picking up this book is your first step on that journey.

What Will You Learn?

I am going to show you how I became a strategic CIO. I'll walk you through, step-by-step, how to create an IT strategy and a tactical plan to execute it. I will show you how to design an operating model to deliver results. You'll discover how to create an IT organization that is empowered and focused on solving customer problems and generating enterprise value. You'll learn to adapt your methods depending on the context of the problem you are facing. You'll understand the science behind what motivates teams and how to change behavior. You'll be taught how to think like a business leader and focus on impactful business outcomes rather than IT output alone.

This book is organized into three parts, as illustrated in Figure I.1.

Part 1

: “A New System of Work”

I explain the underlying factors that require us to change the system, the philosophies that we need to embrace for a new way of working and thinking, and the science of how we can change the system and inspire our teams.

Part 2

: “Designing an Adaptive Operating Model”

We examine each component of the operating model, from ways of working to governance, leadership, talent, and organizational structure. I'll show you how each component relates to the others, and how they can adapt to the problem context they are addressing.

Part 3

: “Strategy to Execution”

Where I show you how you to understand your business at a deeper level so that you can interpret business needs and define an IT strategy that will contribute to business success. Then how to deploy and execute that strategy, ensuring alignment across the organization at both a tactical and operational level.

Each chapter revolves around a central argument that we need a balanced and adaptive way of working across all of IT to manage the paradoxes and the extremes of being a CIO.

Feel free to read this book from beginning to end, or if you wish, dip into any chapter that is of interest. I do suggest, however, that you read Part 1, “A New System of Work” first. Part 1 lays the groundwork and context for the philosophies that underpin much of Part 2, “Designing an Adaptive Operating Model,” and Part 3, “Strategy to Execution.”

Figure I.1: How this book is organized

Why Should You Listen to Me?

This book is based on more than 20 years of experience in IT, from an operational level as engineer, to a tactical level as a development manager and solution architect, to most recently at a strategic level as an enterprise architect and CIO. I have worked for large multinational companies, startups, and high-growth organizations. I have worked with many brilliant CIOs, CTOs, IT directors, enterprise architects, CEOs, founders, and experts across many fields in IT and the wider business. When I stepped up to IT director, I looked for a book that would support me to become an IT strategic leader, one that would help me design the IT organization to address the paradoxes and challenges covered earlier, one that would show me how to effectively build and execute strategy. But there was no book. No manual. No holistic view of how to build a system for success. I had to learn the hard way. I attended many CIO/CTO events, I read anything I could get my hands on, I watched all the videos, I listened to the podcasts, I read blog articles, I spoke to other IT leaders, my old bosses, and new friends. I learned through trial and error. Many errors. Over time I was able to put the puzzle together piece by piece.

I wrote this book because I wanted to codify my knowledge and help refine my own understanding of how to be an effective CIO. I wanted to demystify the problem space and help others who will be going through a similar experience. This book shows the end of my journey, or rather the end of the beginning. The format of this book, the diagrams and content, will appear structured and polished. My journey to get here wasn't as black-and-white as the text in the book. It was never as neat and tidy, or as lined up as I might like it to have been. My journey was full of messy white boards, notebooks full of ideas, trials, and errors. The breakthroughs were made collaboratively with my team, usually over a cup of tea. I am sure your experience will be just as challenging and chaotic, but I hope ultimately fun. My intention with this book is that by sharing my knowledge, it will help you on your journey.

The Start of Your Journey

As with all good stories, we will begin at the beginning. In Chapter 1, “Why We Need to Change the System,” we will examine the underlying factors behind digital disruption that have converged to create a volatile, uncertain, complex, and ambiguous business landscape. We will look at why this has driven the need for new ways of working: the need to embrace collaboration, customer centricity, and fast feedback cycles and the ability to quickly adapt, while at the same time ensuring operational security, stability, and cost control.

The rest of the story goes like this:

Chapter 2

: Philosophies for a New System

.

Where I introduce you to lean, design thinking, agile, and Wardley mapping. These underlying philosophies will be used to shape your strategic thinking.

Chapter 3

: How to Change the System

.

Where I explain systems thinking as a way of making sense of complexity and how mastery, purpose, and autonomy can instill intrinsic motivation in teams.

Chapter 4

: The Anatomy of an Operating Model

.

Where I examine the various components of an operating model that work together to determine “how things are done.”

Chapter 5

: How We Are Organized

. Where I delve into the how and why of structuring a department and the development teams within it.

Chapter 6

: How We Work

.

Where I cover the many approaches to understanding and solving problems and how to choose the most appropriate method.

Chapter 7

: How We Govern

.

Where I discuss how the various elements of governance can adapt and complement the ways of working depending on unique problem context.

Chapter 8

: How We Source and Manage Talent

. Where I detail perhaps one of the most important responsibilities of a CIO succeeding. How we can attract, develop, and retain talent.

Chapter 9

: How We Lead

.

Where I introduce you to the notion of servant leadership and how, by support and leading rather than managing teams, you can get the best out of them.

Chapter 10

: Understanding Your Business

. Where I enable you to understand your business at a deeper level.

Chapter 11

: IT Strategic Contribution

. Where I show you how to interpret business need and create an IT strategy.

Chapter 12

: Tactical Planning: Deploying Strategy

.

Where I explain how to deploy strategy and define the tactical initiatives that will bridge between strategic intent and operational action.

Chapter 13

: Operational Planning: Execution, Learning, and Adapting

. Where I examine operational execution and how to review and adapt strategic, tactical, and operational planning based on feedback.

IA New System of Work

 

Chapter 1:

Why We Need to Change The System

Chapter 2:

Philosophies For A New System

Chapter 3:

How To Change the System

1Why We Need to Change The System

It is not the most intellectual of the species that survives; it is not the strongest that survives; but the species that survives is the one that is able best to adapt and adjust to the changing environment in which it finds itself.

—Leon C. Megginson on Darwin's On the Origin of Species

It is not necessary to change. Survival is not mandatory.

—W. Edwards Deming

The techniques that worked so extraordinarily well when applied to sustaining technologies, however, clearly failed badly when applied to markets or applications that did not yet exist.

Clayton M. Christensen, The Innovator's Dilemma: When New Technologies

—Cause Great Firms to Fail

The strategic role of IT has increased greatly in the last number of decades due to the impact of digital technologies at both a business and a social level. The old model of IT as a support center or an order taker is outdated in today's complex digital business world, where pace, adaptability, creativity, innovation and collaboration are fundamental to succeed in both existing and new business endeavors. This requires a new IT operating model. One that can contribute to digital exploration and the discovery of new opportunities but at the same time can maximize and exploit the performance of an incumbent business model.

This chapter begins with an examination of the impact that new technology, rising customer expectations, and an adaptive competitive set have had on the business landscape and why it is now often characterized as a volatile, uncertain, complex, and ambiguous environment. This context explains the complex and unpredictable challenges the business, and therefore IT leaders, will face. This uncertainty requires a change in how we operate, as the characteristics and approaches to these new problems are very different to the traditional ways of working formed many decades ago. But at the same time, we must understand what has not changed. IT leaders still face the same problems of supporting an organization’s need to scale in a cost effective and secure manner.

To understand how best to manage challenges in support of these two extreme ends of business need, and everything in between, we will leverage the Cynefin decision framework. The framework will aid your situational awareness, helping you to categorize problems based on observable characteristics. Through this categorization of problems, you will learn of the most appropriate methods of approaching them, which will give you a greater chance of succeeding in solving them.

The bottom line is that we need an adaptive IT operating model that is fit for purpose for today's complex and volatile business environment, one that can innovate and cocreate but at the same time provide scalable and efficient solutions to exploit the organization’s current model and maximize value.

The Age of Digital Disruption

Software is eating the world, it is the rise of the knowledge worker, and according to Davos World Economic Forum, we are in the Fourth Industrial Revolution. Call it what you will, but the speed at which technology has impacted our lives, from both a business and social context, has focused the need for a more strategic IT leadership. This digital disruption is important to understand as it is the fundamental reason IT leaders, and businesses, need to change the way they lead and make decisions. The factors causing this disruptive business landscape are faster and cheaper technology, evolving customer expectations, adaptive organizations, and new business models.

Disruptive Technology

Access to cheap, pay as you go, infinite cloud computing power and storage, means low cash flow startups that can't afford large capital investments are no longer prohibited from launching into, and disrupting, established markets with speed. Managed cloud services for databases, infrastructure, and machine learning allow companies to focus on value-add activities such as innovation and experimentation by building upon a rising platform of leading-edge capabilities rather than focusing on keeping the lights on. The adoption of mobile technologies, voice-activated assistants, and connected homes has meant that technology is penetrating every aspect of our lives, and businesses have been keen to capitalize on being able to reach customers 24/7.

As technology became cheaper and more powerful, so did data storage and the tools to analyze it. This, coupled with the explosion in the amount of data that was available on customer behaviors due to the always-on connected devices and IOT, enabled companies to start creating powerful and relevant experiences for end users. Digital companies are now able to make better choices on how to evolve their products and services by analyzing the mass of information gained from customer behavior. Data visualization and analytics platforms are easier to use than ever before to gain deeper insights and understanding; furthermore, these platforms are made directly available to the teams that run business departments and make decisions, vastly reducing the lead time from insight to action.

The Rise of Customer Expectations and Influence

Perhaps the single biggest impact from the advances in technology and new value propositions is that of the shift in expectations and the influence of customers on today's business environment. Customers have high expectations for an immediate response to service requests and the fulfillment of purchases 24 hours a day and seven days a week. Personal time by end users is increasingly spent in the cloud on highly polished user experiences with high levels of customer service. This results in customers, both internal and external, having much lower tolerances and higher expectations, when it comes to user experience than before.

Consumer influence is now greater than ever due to the wide adoption of social media platforms, which enable customer networks to have a direct impact on brands. Because of the power of customers, there has been a shift to how organizations are selling and positioning themselves. Customer-first and customer-centered strategies are now the norm due to the value customers place on service and product experience. This is heavily influenced by the large tech companies such as Amazon and Google.

Adaptive Organizations

Companies that have thrived in the digital era have been those that have been able to adapt their ways of working. Highly collaborative, customer focused businesses who learn and adapt at pace, are far better positioned to remove constraints and exploit opportunities. Traditional methods of having a strategy with a fixed three-year detailed plan is no longer as useful as they once were due to the rapid pace at which competition and customer expectations are moving. Companies that have embraced and pushed down a learn-and-adapt feedback cycle to employees versus a command-and-control mentality are finding that they can innovate far more effectively. Pushing down accountability and autonomy to highly skilled and talented employees that are close to the problem, and aligned to the company strategic need and vision, is proving to be an effective way of working. Empowering workers to analyze data to identify patterns and trends to make more informed choices and better decisions when determining what to do to achieve goals is reaping rewards. Embracing the reality of the sometimes-chaotic rate of change and unpredictability in the business context rather than trying to control it is really the only strategy.

Innovation has proved to be ever more essential for businesses to adapt and transform. Because of the art of the possible that new digital technologies afford, organizations should challenge long-held assumptions around business model propositions, test hypotheses through fast and inexpensive experimentation, and be comfortable with making mistakes along the way to learn. Cloud-based technology has made it much faster to test ideas without committing to large upfront costs. To avoid being disrupted, progressive businesses are disrupting their own business models. This ruthless focus on innovation and self-disruption through continuous learning, all enabled by a culture that values experimenting and not being afraid to fail, is now a fundamental capability that is needed to succeed.

New Business Models

The convergence of technology, shifting customer expectations, and the rise of highly adaptive organizations has led to a tremendous amount of business model change, not only through the digitalization of existing value propositions but also through the creation of new business models. This evolution has been powered largely by a move from products to services and platforms. Products are increasingly moving from an ownership model to an access model, and customers are valuing experiences that evolve daily over waiting for the next version of a product. We no longer buy music; we rent it. We don't own films; we stream them. We buy smart devices connected to the Internet along with subscriptions to services. Free models, subscription, on-demand, and freemium are just some of the new ways to sell products as services that have helped to disrupt the incumbent business models.