Escaping_the_Kraken_-_October_2025.pdf

Transcript

1. Escaping the Kraken Maarten Dalmijn Why do easy things become nearly impossible as companies grow and what to do about 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. Statement: “I’ve Worked at a Company Where It Was Difficult to Build Great Products”
4. Product Management is Often Infuriatingly Difficult Why is this the case? Did I work at the wrong companies? Is something wrong with me?
5. 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.”
6. How Can You Make Impact As a PM The problem isn’t expertise Customer was mentioned once. Nobody talked about the competition or the market, vision or strategy. Almost all points related to struggles from within: organizational obstacles
7. 3rd State of Agile Culture Report, 2023
8. The Solution: Fire and Replace All Leaders?
9. Example: Sonos
10. Disaster Struck
11. Collaboration Collaboration Autonomy Autonomy Context Context Alignment Alignment Organizational System Organizational System 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 Plus: go public, restructure team to silos, launch more products, and get rid of QAs
12. Expertise Isn’t the Bottleneck Lack of expertise is not what makes Product Management difficult.
13. Interviewing for the Job Interviewing for the Job
14. Interviewing for the Job Interviewing for the Job Doing the Job Doing the Job
15. Why The Massive Delta? Interviewing for the Job Interviewing for the Job Doing the Job Doing the Job
16. The Problem is the System The Kraken
17. Counter-Productive Organizational System For Teams The Kraken Mindset Culture Organizational Structure Process Rules Bureaucracy Departments Leadership Policies
18. 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
19. Large Kraken = Brittle Teams Teams that are like circus animals busy jumping through hoops. Flexible and adaptable towards the kraken. Inflexible towards the work and the results we want.
20. Most Great Products Are Built By Small Teams with Trust and Psychological Safety Around 25 people Around 30 people Around 300 people
21. Leaders don’t trust their teams We create rules, processes and hierarchy to prevent having to trust our teams 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 breeds distrust
22. The Paradox of Control Leaders want to iterate quickly but they don't want to grant the trust necessary to iterate quickly
23. Distrust in Practice “Our job at Opendoor is to build the best platform possible to make selling, buying, and owning a home as delightful as possible. That's the mission and it matters because home ownership matters. Every week we don't make immense progress against this mission is a bad week for the world - the world is objectively worse and families are worse off if we don't make an insane amount of progress every single week. So we need to move faster - always. And we can't do that without being Al obsessed. So, starting today the first line in everyone's job expectation is simply this: Default to Al. (This applies to everyone, including me!) Starting with the next performance review, in addition to asking how much impact each employee delivered we will also ask ourselves how frequently does each person default to Al.”
24. 3 Reasons Why Leaders Often Create Brittle Teams 2. When you try to prevent sucking at predicting, you will guarantee to suck at adapting. 1. Not knowing what you WILL be doing is NOT the same as not knowing what you’re doing. Messiness is not necessarily incompetence 3. Better coordination doesn’t fix poor collaboration
25. Chocolate is Deadly for the Kraken CACAO CACAO Model for High- Performing, Empowered Teams
26. Elastic Teams Teams that are flexible and adaptable towards external obstacles that may come their way. Short feedback loops between team, the work and the results we want. Score high on CACAO.
27. Teams Do Work To Create Value Team Work Results We Want If the work is linear and predictable, dealing with internal obstacles is easy
28. Not Linear, But Messy Team Work Results We Want We need Elastic Teams that are flexible and adaptable
29. Context Context The 1 Obstacle st
30. One of the Easiest Things to Fix Understanding and remembering only improves significantly if context is provided before
31. #1. Obstacle: Missing Context Team Work Results We Want Self-referential: The goal of the work is to finish the work Result: Team unable to make decisions when they encounter mess surprises
32. #1. Obstacle: Missing Context The team needs lots of hand-holding and instructions (babysitting) The Product Backlog focuses on solutions. Talking to team members, they don’t know why they are working on something. Constantly asking for instructions and clarification Unable to reframe problems
33. Fixing the Missing Context The team needs to have all information available to them to make decisions. Every Product Backlog Item must include the relevant context Roadmaps cannot focus purely on features as you will lose context Whenever team comes to you with a question as a PM or PO, ask why can’t they answer this without needing me?
34. Teams With Context Characteristics: Rarely ask for instructions and make decisions Moving authority to information: Decentralized Decisions If they encounter problems, they can come up with different ways to solve them Can challenge their PM/POs
35. Expertise Matters For Context
36. #2 Obstacle: Inadequate Autonomy Team Work Results We Want Other Teams Experts Outside the Team
37. #2 Obstacle: Inadequate Autonomy Team Other Teams Experts Outside the Team The team lacks the expertise or trust to make decisions without involving others outside of the team The Real Team
38. Lots of waiting, high WIP and way too many meetings: Teams must coordinate with many other teams #2 Obstacle: Inadequate Autonomy Team can’t make decisions because they depend on others outside the team Teams scared to make decisions due to culture or environment
39. Overcoming the 2nd Obstacle: Conditions for Autonomy Characteristics: Teams can ship features to production independently Waiting and inaction Decisive Action Team has trust and psychological safety Team can mostly make decisions without depending on others
40. #3 Obstacle: Lack of Collaboration Work Results We Want Subteam Subteam Subteam Subteam Subteam Subteam Subteam Subteam Subteam
41. #3 Obstacle: Lack of Collaboration Silos everywhere all at once. Even simple things become difficult: Teams work in silos and horizontal slices. When you need help from another team, you don’t get it Bottlenecks within and between teams, e.g. QA is slow
42. Effective Collaboration Collaborative Teams of Teams: Teams collaborate as necessary to produce vertical slices of value Sluggish Silos Collaborative Teams of Teams Receive help as necessary from other teams Bottlenecks within and between teams are swiftly resolved
43. 3Cs: Chaos, Cannibalization and Conflict Teams have no clue what other teams are working on #4 Obstacle: Insufficient Alignment When teams need help, there is a big fight Teams are working on too many different things at once
44. Moving Along a Shared Trajectory Characteristics Teams know what other teams are working on 3Cs: Chaos, Cannibalization and Conflict Focus and Clarity When teams need help from each other, it’s quietly and quickly resolved Feels like teams are pulling in the same direction
45. 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 also becomes harder. #3. Organizational systems have evolved based on conditions from the past and are not designed for the future.
46. 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 not being able to operate as an elastic team. AI will take care of itself.
47. Feeding and Fighting the Kraken Counter-Productive Organizational System Counter-Productive Organizational System Like the bottom of the pyramid constrains the top of the pyramid, our organizational kraken constrains the context, autonomy, collaboration and alignment of your teams.
48. 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
49. 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.
50. The goal is to create a small little oasis - a small pocket of product management excellence. Start with providing Context. Strategy for Slaying the Kraken
51. Strategy for Slaying the Kraken As you move down, you will begin to notice systemic problems Fixing inadequate autonomy often means: Changing team structure Moving individuals around Fixing cultural issues (trust, psychological safety)
52. Strategy for Slaying the Kraken Lack of Collaboration is one of the toughest nuts to crack. It’s impacted by all dysfunctions above and below.
53. Strategy for Slaying the Kraken Lack of Alignment usually indicates organizational and leadership problems. OKRs don’t fix insufficient alignment, start with: Vision Strategy Removing Institutionalized Competing Interests Reducing WIP Collaboration Collaboration Autonomy Autonomy Context Context Alignment Alignment Organizational System Organizational System
54. Strategy for Slaying the Kraken Fixing broken organizations is like fixing spaghetti code. When you touch one area, you might be touching ten other areas at the same time. This is why most organization settle for short-term surface-level success like the Spotify model or OKRs
55. CACAO to Fight the Kraken Do you want Brittle Teams or Elastic Teams? CACAO
56. If You Remember Two Things... “A bad system will beat a good person every time.” - W.E. Deming #1. Changing complex systems is much harder than developing Product Management expertise. This is why Australia is still plagued by 200 million rabbits. It’s also why we still don’t know whether eggs are healthy or not.
57. #2. Use CACAO to Create Elastic Teams with Short Feedback Loops to The Results We Want Context Autonomy Collaboration Alignment Organizational System Feel free to send any questions you might have to maarten@dalmyn.com
58. Collaboration Collaboration Autonomy Autonomy Context Context Alignment Alignment Organizational System Organizational System 2. swiftly make decisions and act? 3. make better decisions together? 4. Move along a shared trajectory? 5. Work in an Organizational System that supports Context, Autonomy, Collaboration and Alignment? CACAO: Do We Have Brittle or Elastic Teams? Do Teams: 1. have all information to make decisions?