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Slaying the Kraken

Avatar for Maarten Dalmijn Maarten Dalmijn
November 06, 2025
36

Slaying the Kraken

Avatar for Maarten Dalmijn

Maarten Dalmijn

November 06, 2025
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Transcript

  1. Slaying the Kraken Maarten Dalmijn Why do easy things become

    nearly impossible as organizations grow and how to fix it?
  2. Statement: “It’s Easy to Build Great Products at My Current

    Job” Easy peasy lemon squeezy: No difficult stakeholders Everyone is on the same page No useless planning rituals and roadmap ceremonies Teams have ownership over results No sudden work pushed to the teams
  3. Building Great Products is Often Infuriatingly Difficult Why is this

    the case? Did I work at the wrong companies? Is something wrong with me?
  4. Talking to Someone at One of the Most Admired Tech

    Companies in the World “Over here easy things are impossible and impossible things are easy.”
  5. Decided to rebuild their product New app must be finished

    before Ace headphones Managers yelled at developers when they said the app wasn’t ready Teams were organized around silos Ship it no matter the quality CACAO Model Organizational System Alignment Collaboration Autonomy Context Plus: go public, restructure team to silos, launch more products, and get rid of QAs
  6. Expertise Isn’t the Bottleneck Lack of expertise is not what

    makes delivering great products difficult
  7. The Problem is the System The Kraken The Kraken is

    what makes delivering value difficult by making simple things nearly impossible
  8. The Kraken: Counter-Productive Organizational System For Teams The Kraken Mindset

    Culture Organizational Structure Process Rules Bureaucracy Departments Leadership Policies
  9. Brittle Teams Feeding the Kraken Team A Team B Team

    C Busy fighting and feeding the kraken Customer Users Business Not busy thinking about customers, users and the business The Kraken
  10. The Paradox of Control Most leaders want to iterate quickly

    but are unable to grant the trust necessary to iterate quickly
  11. LACKING CONTEXT “Do teams have all information to make decisions?”

    INADEQUATE AUTONOMY “Can teams decide how to best do the work?” INSUFFICIENT ALIGNMENT “Are teams making decisions along a shared trajectory?” INEFFECTIVE COLLABORATION “Are teams making better decisions together?” SLOW Decision Speed Moving information to authority Operating at the Speed of Distrust LOW Quality of Decisions Decreasing collective competence ORG. SYSTEM
  12. INDIVIDUAL COMPETENCE LOW HIGH LOW HIGH COLLECTIVE COMPETENCE The Mighty

    Ducks The Avengers Pinky and the Brain Minions Collective Competence vs. Individual Competence
  13. CONTEXT “Do teams have all information to make decisions?” AUTONOMY

    “Can teams decide how to best do the work?” ALIGNMENT “Are teams making decisions along a shared trajectory?” COLLABORATION “Are teams making better decisions together?” ORG. SYSTEM Operating at the Speed of Trust High Speed of Decisions Moving authority to information High Quality of Decisions Increasing collective competence
  14. Leaders don’t trust their teams We create rules, processes and

    hierarchy to prevent having to trust our teams Brittle Teams struggle to make decisions and deliver The Cycle of Distrust When you don’t trust your people you will develop an organization where you can’t trust your people. Distrust fuels distrust
  15. Most Great Products Are Built By Small Teams with Trust

    and Psychological Safety Around 25 people Around 30 people Around 300 people
  16. Teams Do Work To Create Value Team Work Results We

    Want If the work is linear and predictable, dealing with internal obstacles is easy
  17. Not Linear, But Messy Team Work Results We Want We

    need Elastic Teams that are flexible and adaptable
  18. Ownership Elastic Team Work Results Decisions Deliver Feedback You can

    only have ownership with Elastic Teams: Teams can’t have ownership without the ability to make decisions
  19. CONTEXT AUTONOMY ALIGNMENT COLLABORAT- ION ORG. SYSTEM Elastic Team Work

    Results Decisions Deliver Feedback Ownership: Operate at the Speed of Trust If you want ownership together with better and faster decisions, operating at the speed of trust is mandatory
  20. CONTEXT AUTONOMY ALIGNMENT COLLABORAT- ION ORG. SYSTEM Brittle Team Work

    Results Decisions Deliver Feedback Orchestration: Operate at the Glacial Pace of Distrust The tentacles of the Kraken disrupt decision-making, delivering results and ownership.
  21. LACKING CONTEXT “Do teams have all information to make decisions?”

    INADEQUATE AUTONOMY “Can teams decide how to best do the work?” INSUFFICIENT ALIGNMENT “Are teams making decisions along a shared trajectory?” INEFFECTIVE COLLABORATION “Are teams making better decisions together?” ORG. SYSTEM
  22. CONTEXT AUTONOMY ALIGNMENT COLLABORAT- ION ORG. SYSTEM Constantly asking for

    instructions Teams with features to deliver Unable to reframe problems Many meetings Unable to make decisions Lots of coordination Many unresolved bottlenecks Working in silos Don’t get help when you need it Conflicts and escalation High WIP Technical Debt
  23. CONTEXT “Do teams have all information to make decisions?” AUTONOMY

    “Can teams decide how to best do the work?” ALIGNMENT “Are teams making decisions along a shared trajectory?” COLLABORATION “Are teams making better decisions together?” ORG. SYSTEM
  24. CONTEXT AUTONOMY ALIGNMENT COLLABORAT- ION ORG. SYSTEM Sufficient information to

    make decisions Given problems to solve Reframe problems when necessary Deep work Swift and decisive actions Few meetings Bottlenecks are swiftly resolved Teamwork not silowork Help each other as necessary Low tech debt unless intentional Conflicts quickly and quietly resolved High flow - works flows smoothly
  25. Why Fighting the Kraken is Difficult #1. The longer you

    are part of a system, the more blind you become to problems of the system. #2. When your organizational system makes it hard to make decisions, making changes to the system itself also becomes harder. #3. Organizational systems have evolved based on conditions from the past and are not designed for the future.
  26. Age of AI: Small Teams That Have Ownership Over Results

    No Longer Optional Don’t worry about your teams NOT adopting AI. Worry about your teams operating at the Speed of Trust.
  27. We Need Leaders With More Guts We need leaders who

    have the guts to chop off the tentacles of the Kraken to create an environment for Elastic Teams. Counter-Productive Organizational System Counter-Productive Organizational System
  28. Don’t Be Atlas Learn to let go of what you

    can’t influence. You can create high-performing teams in organizations with huge krakens... but you’ll bump into walls and your effort may not even be appreciated.
  29. Trust Distrust CACAO REMOVING - SLAYING THE KRAKEN Immediate Pain

    Difficult Scary Uncertain Risky Resistance ADDING - FEEDING THE KRAKEN Immediate pleasure Easy Comforting Certain Familiar No resistance
  30. CACAO to Fight the Kraken Easy, familiar and comfortable choices

    will gradually result in weak teams. Difficult, risky and uncomfortable choices are necessary for strong teams
  31. CONTEXT “Do teams have all information to make decisions?” AUTONOMY

    “Can teams decide how to best do the work?” ALIGNMENT “Are teams making decisions along a shared trajectory?” COLLABORATION “Are teams making better decisions together?” ORG. SYSTEM Kraken Tentacle Mapping High Speed of Decisions Moving authority to information High Quality of Decisions Increasing collective competence