How product teams operate, and why it doesn't work - John Cutler
In this episode of The Product Experience, host Randy Silver sits down with product veteran John Cutler to explore why creating great products remains one of the hardest things organisations do. They dive into why so many companies adopt off‑the‑shelf models (“Spotify”, “SAFe”, etc) and still struggle, and how the secret often lies not in what you build but how you build it—specifically the game you design for how you work.John shares his game metaphor for organisational design: how to see your team and company as playing two games — the political organisational game and the design‑game you craft for how you work. You’ll hear why behaviours matter more than titles and tools, why checkpoints and rituals matter more than frameworks, and how you can start tomorrow to define the behaviours you want, identify what’s blocking them, and change the rules of the game.
Chapters
00:00 — The stigma around “how you work”
00:54 — Introducing John Cutler (again)
01:25 — What John’s building at Dotwork
02:46 — From fun to formal: doing discovery at scale
04:04 — Why process became a bad word
05:10 — The “cavalier PM” mindset
06:28 — Empowered teams vs. harsh realities
08:00 — What great pockets of practice have in common
09:03 — Managing up vs. doing the right thing
10:24 — Playing the game vs. designing the game
11:20 — What makes a great internal game
12:33 — Defining success: thriving, surviving, progressing
13:46 — Environmental design: why leaders hesitate
15:10 — Making intentional design less intimidating
16:42 — Tools, rituals, and the power of checkpoints
18:23 — The behaviour design playbook
20:41 — Removing blockers: access, repetition, reflection
22:12 — Replayability and the value of feedback loops
23:29 — Fixing the finance game
25:20 — Creating local spheres of trust
26:27 — Starting with behaviours, not frameworks
28:01 — Diagnosing blockers with behaviour design
29:53 — Identifying anti-patterns with TRIZ
31:08 — The myth of corporate rationality
33:19 — When no complaints doesn’t mean no problems
34:13 — Closing thoughts: are you playing the right game?
Key takeaways
— Intentionally designing how you work (process, rituals, environment) is as important as designing what you build. John argues that the latter often gets all the attention while the former is treated as a dirty word.
— Use the metaphor of a game: good games have clear goals, balanced difficulty, feedback loops, social interaction, story‑elements. When companies design their internal work like this, teams perform better.
— Focus on behaviours not just tools or frameworks. What exactly does “empowered team” or “data‑driven” look like? Define the behaviours, identify blockers (competence, access, social reinforcement).
— Don’t assume that “no complaints = all good”. Organisations often get worse by stealth through people adapting or checking out. The absence of noise isn’t proof of health.
— Your personal radar counts: look around who is thriving in your company, and ask if you respect them. That may tell you if the “game” being played is one you want to join.
— Behaviour design and process design require constraint and ritual. Without checkpoints, loops close, or feedback cycles, the system decays.
— Macro headwinds (economics, AI, speed) mean continuous small improvements are under pressure; yet the fundamentals of “how we work” still matter.
— The relationship with support functions (like finance) can be changed: treat it as co‑designing the game, not battling a monolith. Receive SMS online on sms24.me
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