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Unleash Your Inner CTO!

Rob Crowley
February 24, 2021

Unleash Your Inner CTO!

The role of a technology leader has never been more challenging. We are in the midst of unprecedented technology change fuelled by the commodification of Big Data, IoT and Machine Learning. Yet keeping abreast of such technological advances alone will not be enough to guide your organisation to success. A successful technology strategy does not exist in a vacuum. Rather it supports and amplifies the delivery of your organisation’s core vision.

Join Rob on a tour of how to build feedback loops into your organisation’s technology decisions and enable a low-risk empirical approach to change. We will take an in-depth look at what it takes to create an adaptive technology strategy and explore and ensure that your organisation’s architecture is an accelerator rather than an inhibitor of business agility:

* How to identify and measure key business-aligned metrics and use these data points to pivot your technology strategy
* How to enable effective distributed technology decisions across your organisation
* How to build organisational memory surrounding technology decisions that can act as inputs into new decisions

By the end of the session, you will not only understand what is involved in creating a data-informed technology strategy but also have the knowledge to put it into practice. If you want to take to your expertise in crafting effective technology strategies to the next level, then this is the session for you. See you there!

Rob Crowley

February 24, 2021
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  1. UNLEASH YOUR INNER CTO!
    A PRIMER ON TECHNOLOGY STRATEGY
    @ROBDCROWLEY #DDDPERTH

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  2. PRIMER
    WHAT WE’LL BE COVERING
    GROWTH
    TECH
    STRATEGY

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  3. DEFINITION
    PURPOSE
    MAKING
    DECISIONS
    WHAT WE’LL BE COVERING
    TECH
    STRATEGY

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  4. ME
    PREV: PRINCIPAL CONSULTANT
    @TELSTRA PURPLE
    NOW: HEAD OF ENGINEERING
    @VIX TECHNOLOGY
    @DDDPERTH CO-ORGANISER
    TIME-POOR BIBLIOPHILE
    + = ROBDCROWLEY
    ARCHITECTURE TRAGIC

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  5. I ABSOLUTELY SHINY TECH
    WE WILL LEARN HOW TO GIVE THIS TECH PURPOSE
    @ROBDCROWLEY #DDDPERTH

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  6. @ROBDCROWLEY #DDDPERTH
    STRATEGY AND FRIENDS
    A (NOT SO) GENTLE PRIMER ON STRATEGY

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  7. So what is strategy?
    @ROBDCROWLEY #DDDPERTH

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  8. strategy
    noun
    a plan of action designed to achieve a long-term or overall aim.
    @ROBDCROWLEY #DDDPERTH

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  9. PURPOSE VISION MISSION
    | |
    THE WHY THE WHAT THE HOW
    A STRATEGY USES THE MISSION TO ACHIEVE THE VISION
    @ROBDCROWLEY #DDDPERTH

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  10. If we do not communicate with the outside world — to gain
    information for knowledge and understanding — we die out to
    become a non-discerning and uninteresting part of that world.
    JOHN BOYD
    @ROBDCROWLEY #DDDPERTH

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  11. Situational awareness is table stakes for
    effective strategy, it represents the ability to
    discover, communicate and learn about changes in
    the environment.
    @ROBDCROWLEY #DDDPERTH

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  12. As the environment changes, the ongoing value of
    previous decisions can decrease and perish
    @ROBDCROWLEY #DDDPERTH

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  13. COMPETITION ⇒ EVOLUTION
    @ROBDCROWLEY #DDDPERTH

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  14. DISRUPTORS VS FAST FOLLOWERS
    @ROBDCROWLEY #DDDPERTH

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  15. CASE STUDY: THE FIRST BROWSER WAR
    @ROBDCROWLEY #DDDPERTH

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  16. SATISFACTION
    DISSATISFACTION
    NOT
    FULLFILLED
    FULLY
    FULFILLED
    KANO MODEL
    OVER TIME ATTRACTIVE FEATURES
    BECOME MUST HAVES
    MUST HAVES
    PERFORMANCE
    ATTRACTIVE

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  17. The novel becomes commonplace and in turn
    enables the creation of more complex innovations
    @ROBDCROWLEY #DDDPERTH

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  18. Use appropriate methods for the challenge at
    hand. A one-size-fits-all approach is suboptimal
    by definition.
    @ROBDCROWLEY #DDDPERTH

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  19. 3X MODEL – EXPLORE, EXPAND, EXTRACT
    PAYOFF
    SUCCESS
    EXPLORE
    EXTRACT
    ELIMINATE UNCERTAINTY ELIMINATE WASTE ELIMINATE VARIABILITY
    RISK APPETITE
    EXPAND

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  20. Large organizations die from a series of
    reasonable decisions.
    DR JASON FOX – HOW TO LEAD A QUEST

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  21. THINKING
    DOING
    OPERATIONAL
    (CERTAIN)
    PIONEERING
    (UNCERTAIN)
    QUEST-AUGMENTED STRATEGY
    DECISIONS
    EXPERIMENTS
    OPTIONS
    STRATEGY
    PROGRESS
    HYPOTHESES
    INSIGHTS
    MISSIONS
    QUESTS

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  22. Decisions without actions are pointless.
    Actions without decisions are reckless.
    JOHN BOYD
    @ROBDCROWLEY #DDDPERTH

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  23. OODA LOOP
    OBSERVE ORIENTATE
    DECIDE
    ACT
    Observe: Sense outside
    circumstances information
    Orientate: Analysis and
    synthesis of new information
    and previous experience to
    generate options
    Decide: Hypotheses, option
    selection and provide
    feedback
    Act: Test, probe and
    implement using doctrine
    @ROBDCROWLEY #DDDPERTH

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  24. Strategy is not a linear process but an
    iterative cycle
    @ROBDCROWLEY #DDDPERTH

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  25. § STRATEGY REQUIRES AN ITERATIVE APPROACH WITH HIGH CONTEXT FEEDBACK LOOPS.
    § COMPETITION IS DRIVING CONSTANT CHANGE ACROSS YOUR BUSINESS ENVIRONMENT.
    TODAY’S NOVEL IS DESTINED TO BECOME A COMMODITY (WHEN IS THE HARD PART!).
    § SITUATIONAL AWARENESS IS KEY TO RECOGNISING PATTERNS AND IDENTIFYING OPTIONS.
    § LEVERAGE MODELS SUCH AS THE OODA LOOP AND 3X TO PROMOTE DELIBERATE THOUGHT.
    § STRATEGIC THINKING IS A SKILL AND CONSEQUENTLY REQUIRES PRACTICE AND
    DEDICATION TO MASTER.
    STRATEGY AND FRIENDS TAKEAWAYS
    @ROBDCROWLEY #DDDPERTH

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  26. TECHNOLOGY STRATEGY
    AMPLIFYING YOUR BUSINESS OUTCOMES

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  27. technology strategy
    term
    a collective set of decisions created to guide the use of
    technology and related factors to achieve business or end user
    outcomes
    @ROBDCROWLEY #DDDPERTH

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  28. Write your technology strategy down and make
    it accessible. This is vital to building alignment.
    @ROBDCROWLEY #DDDPERTH

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  29. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    @ROBDCROWLEY #DDDPERTH

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  30. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    Describes the purpose, vision and mission of the business
    agnostic of technology. The technical strategy exists to
    amplify the delivery of business outcomes. Setting this
    business context with a clear articulation of the problems
    to be solved is vital to building alignment.
    @ROBDCROWLEY #DDDPERTH

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  31. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    Describes the current technology landscape along with the
    existing constraints and limitations. This section of the
    document aims to create a clear shared vision of the current
    limitations. This is key to managing stakeholder
    expectations around the delivery of strategic goals and the
    associated risks (legacy systems, environmental instability
    etc.).
    @ROBDCROWLEY #DDDPERTH

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  32. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    Describes the technology vision and details the primary
    decisions and intended actions to achieve this (embracing
    cloud to enable experimentation/innovation, expanding
    existing platforms, retiring costly legacy systems etc.).
    @ROBDCROWLEY #DDDPERTH

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  33. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    @ROBDCROWLEY #DDDPERTH

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  34. CASE STUDY: MYOB (BY @SIMONRAIKALLEN)

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  35. Takeaway: The MYOB platform manifesto
    encourages decisions and actions that are
    focused on the medium term view
    @ROBDCROWLEY #DDDPERTH

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  36. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    A visualisation of the technology landscape,
    outlining Platforms, Techniques, Tools and
    Languages - classified by appeal and
    relevance to the organisation (Experiment,
    Adopt, Hold, Retire)
    See: Build Your Own Radar by ThoughtWorks
    @ROBDCROWLEY #DDDPERTH

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  37. DEFINING A TECHNOLOGY STRATEGY
    § Executive Summary
    § Purpose
    § Business Strategy
    § Tech Landscape
    § Tech Vision (North Star)
    § Platform Principles & Guardrails
    § Tech Radar
    § Lightweight Architecture Governance
    Describes the approach to architecture and
    provides a framework for architectural decisions
    and direction. The framework covers guidance
    on:
    § Roles and responsibilities
    § Decision making process and autonomy levels
    § Decision tracking
    § Artefacts produced
    § Communicating architectural decisions
    @ROBDCROWLEY #DDDPERTH

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  38. Remember: Strategy is iterative.
    Do not aim for perfection on the first pass,
    timebox, seek feedback and repeat.
    @ROBDCROWLEY #DDDPERTH

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  39. Strategy is not static. Treat the technical
    strategy document as a living artefact.
    @ROBDCROWLEY #DDDPERTH

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  40. § TECHNOLOGY STRATEGY SHOULD AMPLIFY BUSINESS AND/OR USER OUTCOMES.
    § DEFINING A LONG FORM TECHNOLOGY STRATEGY DOCUMENT IS AN EXCELLENT WAY OF
    COMMUNICATING THE OBJECTIVES AND BUILDING ALIGNMENT.
    § STRATEGY IS AN ITERARIVE PROCESS. APPROACH DEFINING THE TECHNOLOGY STRATEGY
    DOCUMENT IN THE SAME WAY.
    § ENSURE THE TECHNOLOGY STRATEGY IS VISIBLE AND ACCESSIBLE ALWAYS. EMBED IT IN
    THE ONBOARDING EXPERIENCE FOR NEW STARTERS.
    TECHNOLOGY STRATEGY TAKEAWAYS
    @ROBDCROWLEY #DDDPERTH

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  41. METRICS
    HOW TO MEASURE WHAT MATTERS

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  42. Situational awareness is critical, but user needs
    cannot be met just by becoming aware of them
    @ROBDCROWLEY #DDDPERTH

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  43. metric
    noun
    a quantifiable measure of any component or process used to
    gauge the performance of the business and whose change
    informs if existing behaviour should be continued or adjusted.
    @ROBDCROWLEY #DDDPERTH

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  44. START
    END
    EVOLUTIONARY SYSTEM
    @ROBDCROWLEY #DDDPERTH

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  45. The only way to win is to learn faster
    than anyone else.
    ERIC RIES – THE LEAN STARTUP

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  46. The Core Principles of The Lean Startup:
    § Minimum Viable Product (MVP)
    § Continuous Deployment
    § Split Testing (aka A/B Testing)
    § Actionable Metrics
    § Pivot
    § Innovation Accounting
    § Build-Measure-Learn Loop

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  47. So how should good metrics be chosen?
    @ROBDCROWLEY #DDDPERTH

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  48. @ROBDCROWLEY #DDDPERTH
    DAVE MC CLURE’S PIRATE METRICS (AARRR!)
    ACQUISITION
    ACTIVATION
    RETENTION
    REFERRAL
    REVENUE
    Acquisition: How do users
    find you?
    Activation: How do users
    have a great first experience?
    Retention: Do users continue
    to return?
    Referral: Are users advocates
    and tell others?
    Revenue: How do you make money
    from your users?

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  49. DATA ↦ INFORMATION ↦ INSIGHTS
    @ROBDCROWLEY #DDDPERTH

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  50. Most companies do not capture the data
    required to make effective informed decisions
    @ROBDCROWLEY #DDDPERTH

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  51. Make your users’ needs your north star
    @ROBDCROWLEY #DDDPERTH

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  52. Doctrine are the basic universal principles that are applicable
    to all industries regardless of the landscape and its context.
    SIMON WARDLEY
    @ROBDCROWLEY #DDDPERTH

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  53. Software delivery is an exercise in
    continuous improvement, and our research
    shows that year over year the best keep
    getting better, and those who fail to
    improve fall further and further behind
    DR NICOLE FORSGREN, JEZ HUMBLE & GENE KIM – ACCELERATE

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  54. DevOps
    term
    a set of practices that works to automate and integrate the
    processes between software development and IT teams, so
    they can learn faster.
    @ROBDCROWLEY #DDDPERTH

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  55. STATE OF DEVOPS
    DEPLOYMENT
    FREQUENCY
    LEAD TIME FOR
    CHANGE
    FAILED CHANGE
    RATE
    SPEED FOCUSED
    STABILITY FOCUSED
    @ROBDCROWLEY #DDDPERTH
    MEAN TIME TO
    RECOVER

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  56. METRICS AS A MEANS FOR BALANCED BEHAVIOUR
    SPEED (PRODUCTIVITY)
    QUALITY (STABILITY)
    THE (NON SCIENTIFIC) CONE
    OF BALANCED BEHAVIOUR
    FAILED CHANGE RATE + MTTR
    LEAD TIME FOR CHANGE
    +
    CHANGE FREQUENCY

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  57. SPEED AND QUALITY
    @ROBDCROWLEY #DDDPERTH

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  58. ANTI-PATTERNS TO AVOID WHEN USING METRICS
    METRIC MISSTEPS

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  59. Achieve excellence, don’t just avoid errors
    L. DAVID MARQUET – TURN THE SHIP AROUND

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  60. @ROBDCROWLEY #DDDPERTH
    The more any quantitative social indicator is used for social
    decision-making, the more subject it will be to corruption
    pressures and the more apt it will be to distort and corrupt
    the social processes it is intended to monitor
    CAMPBELL’S LAW

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  61. CASE STUDY: US HOSPITAL REPORT CARDS
    @ROBDCROWLEY #DDDPERTH

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  62. Vanity metrics depict the rosiest picture
    possible but do not accurately reflect the key
    drivers of your business
    VANITY METRICS
    @ROBDCROWLEY #DDDPERTH

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  63. Using the same metrics as successful companies
    without understanding if they align to your
    business drivers
    CARGO CULT METRICS
    @ROBDCROWLEY #DDDPERTH

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  64. CARGO CULT METRICS
    @ROBDCROWLEY #DDDPERTH
    Substituting imitation for understanding is a
    beguiling shortcut but is suboptimal at best

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  65. There is nothing so useless as doing efficiently that which
    should not be done at all
    PETER DRUCKER
    USELESS METRICS
    @ROBDCROWLEY #DDDPERTH

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  66. Using metrics for comparison and punishment
    rather than for continuous improvement purposes
    WEAPONISED METRICS
    @ROBDCROWLEY #DDDPERTH

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  67. @ROBDCROWLEY #DDDPERTH
    Any observed statistical regularity will tend to collapse once
    pressure is placed upon it for control purposes
    GOODHART’S LAW

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  68. When a measure becomes a target, it ceases to be a
    good measure
    @ROBDCROWLEY #DDDPERTH


    MARILYN STRATHERN

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  69. § PIVOT! BASE CONVERSATIONS TO METRICS RATHER THAN NON-ACTIONABLE OPINIONS.
    § USE CUSTOMER NEEDS AS THE BASIS FOR YOUR INITIAL SET OF METRICS.
    § CAVEAT EMPTOR! INCENTIVE STRUCTURES WORK, MEASURING THE WRONG THING CAN
    LEAD TO UNANTICIPATED CONSEQUENCES.
    § EFFECTIVE METRICS OFTEN WORKS IN UNISON TO DRIVE BALANCED BEHAVIOUR.
    § METRICS ONLY DELIVER VALUE IF THEY INFLUENCE BEHAVIOUR.
    METRICS TAKEAWAYS
    @ROBDCROWLEY #DDDPERTH

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  70. GETTING STARTED
    TIPS TO BUILD YOUR STRATEGIC ACUMEN

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  71. Disclaimer: The transition between delivery and
    strategic focuses is non-trivial and requires
    dedication and commitment
    @ROBDCROWLEY #DDDPERTH

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  72. Technical ability is unlikely to be the constraint
    on your career progression
    @ROBDCROWLEY #DDDPERTH

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  73. Invest in truly learning your business and
    industry. This is vital to growing your
    situational awareness.
    @ROBDCROWLEY #DDDPERTH

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  74. Build your network both inside and outside
    work. Hallway tracks at conferences afford
    incredibly valuable learning opportunities.
    @ROBDCROWLEY #DDDPERTH

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  75. Know and share the context always
    @ROBDCROWLEY #DDDPERTH

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  76. As a leader your focus should be on growing an
    environment that encourages the behaviour you
    want to see
    @ROBDCROWLEY #DDDPERTH

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  77. Corollary: Attempting to embed behaviours
    that run contrary to the incentives defined by
    the environment is a Sisyphean endeavour
    @ROBDCROWLEY #DDDPERTH

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  78. You may not always have the authority to
    make a decision but you can always champion a
    cause
    @ROBDCROWLEY #DDDPERTH

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  79. Embrace empiricism, base conversations on
    metrics instead of non-actionable opinions
    @ROBDCROWLEY #DDDPERTH

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  80. You can achieve amazing things if you do not
    need to take credit for it
    @ROBDCROWLEY #DDDPERTH

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  81. Live, operate and think in a world of ambiguity
    and be able to context switch dramatically
    across delivery and strategy
    @ROBDCROWLEY #DDDPERTH

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  82. TAKEAWAYS
    @ROBDCROWLEY #DDDPERTH

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  83. RESOURCES
    @ROBDCROWLEY #DDDPERTH

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  84. § Defining a Tech Strategy | Sarah Taraporewalla:
    https://sarahtaraporewalla.com/agile/design/architecture/Defining-
    a-Tech-Strategy
    § Tech Strategy: You need it, but what is it? | Nick Tune:
    https://medium.com/nick-tune-tech-strategy-blog/tech-strategy-
    you-need-it-but-what-is-it-af292421e422
    § Build Your Own Rader | ThoughtWorks:
    https://www.thoughtworks.com/radar/byor
    § Cargo Cult Analytics | Stijn Debrouwere:
    http://debrouwere.org/2013/08/26/cargo-cult-analytics/
    RESOURCES
    @ROBDCROWLEY #DDDPERTH

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  85. § The Lean Startup | Eric Ries
    § Turn the Ship Around | L. David Marquet
    § Accelerate | Dr Nicole Forsgren, Jez Humble & Gene Kim
    § How to Lead a Quest| Dr Jason Fox
    § Wardley Maps | Simon Wardley
    § Team Topologies | Matthew Skelton & Manuel Pais
    READING LIST
    @ROBDCROWLEY #DDDPERTH

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  86. QUESTIONS
    @ROBDCROWLEY #DDDPERTH

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  87. @ROBDCROWLEY | ROBDCROWLEY
    THANK YOU!

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  88. § Images sourced from www.pexels.com
    § Browser war from medium.com/@traciemasek/a-brief-history-of-
    the-original-browsers-and-the-first-browser-war-7823fdf756fe
    ATTRIBUTION
    @ROBDCROWLEY #DDDPERTH

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