65: Unrealistic Planning, Broken Collaboration — and How to Fix Both

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Are you optimizing for starting work instead of finishing?



In this episode, I’m joined by Joakim von Prónay, an engineer and psychologist by education and a coach by passion.

We break down how fake roadmaps and a “Global Roadmap Owner” role turn planning into a Gantt chart exercise. We make planning useful with a simple rule: it’s better to be roughly right than precisely wrong. Predictability becomes the lever for real accountability, measured by “did we do the things we said we were gonna do.” Escalation culture gives way to real collaboration, not the default “ask the boss” reflex.

You’ll Learn:

• The reason long-term planning works when it’s roughly right instead of precisely wrong
• What happens when teams are incentivized to start work instead of finish it
• The link between delivery predictability and real prioritization and accountability
• The damage of treating roadmaps like a Gantt chart exercise
• What it feels like when every question defaults to “ask the boss” instead of talking directly
• The reason fragmented steering creates conflicting directions
• The link between a single “central rule” and measurable goals

Timestamps:

[00:00] Introduction

[06:14] Why high-performing teams are so rare

[09:27] The danger of planning for perfection

[15:46] Why teams start work instead of finishing it

[19:32] The power of predictability and real accountability

[25:40] When collaboration breaks down into escalation

[31:58] What fragmented steering really looks like

[38:45] The rule that defines true strategy

[46:23] A Spotify story and the engineer’s warning

[51:17] How alignment turns insight into action

Connect more with Joakim on LinkedIn.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.