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Roadmap decisions rather than dates.

by management (220)11 Aug 2026

One thing that bothered me about Imprint’s product after joining was our lack of passkey support.Passkey support is a rare opportunity to increase resiliency to phishing attackswhile simultaneously reducing login friction. If it’s good for our members, our partners, and our product,it felt like something we should have already shipped.Nonetheless, it was hard to get it onto the roadmap alongside everything else we were working on.

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  • Software is not, as some argue today, free, but it’s no longer constrained on implementation weeks but instead on correct decisions.
  • But we were never constrained on calendar time, what mattered was accelerating the pace of high-quality decision-making.
  • In my experience, calendar discussions are another way that folks deliberately get stuck, because no company ever has a central list of the true priority of every task. Asking for that non-existent list shifts accountability for forward progress off the asker, but it’s a fundamentally unreasonable thing to ask for. Thinking about things from a CPU scheduling perspective: any scheduler that tried to centrally orchestrate priority within every thread would be extraordinarily slow and stuck all the time; it’s only by locally determining priority–often through extremely crude methods–that things move quickly overall.
  • Combining all of these ideas, the world we live in is increasingly constrained by access to high-quality decisions. Rather than talk about scheduling software around software, we should be fixated on the idea of accelerating making high-quality decisions. Every hour we spend deciding priorities or timelines is a distraction from making the next decision.
  • As an ending caveat, this isn’t an argument that we shouldn’t have dates on projects. Dates are the external interface for coordinating across companies, so you still need dates. However, I think teams are better picking a plausible, slightly conservative external date and then entirely ignoring that date internally. Instead, they should focus on the list of decisions to be made, and work through them directly. Dates, global priorities, stack ranked items… An engineer who doesn’t know the release date can still ship.

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In summary, the most compelling insight is that modern software delivery is no longer constrained by calendar time or staffing, but by the pace of high-quality decision-making, which can be dramatically accelerated through empowered teams, automated cross-functional harnesses, and rapid prototyping.

  • Empower teams to absorb cross-functional handoffs and own architectural decisions, reducing bottlenecks from strict boundaries and the mythical man-month trap.
  • Leverage AI to build centralized context and function-specific approval harnesses, enabling decentralized teams to operate with minimal dependencies.
  • Replace calendar-driven planning with rapid prototyping to iteratively resolve ambiguity, turning complex problems into fast, low-risk experiments.
  • Shift roadmaps from date-based scheduling to decision-based tracking, using conservative external deadlines while internally focusing on unblocking critical decisions.

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