Teams often default to 90-day timelines because it fits the quarterly business calendar, not because it's the actual time required. By simply asking 'How is it that every problem can be solved in exactly 90 days?', leaders can force more first-principles thinking about project scoping.
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CEO Dylan Field combats organizational slowness by interrogating project timelines. He seeks to understand the underlying assumptions and separate actual work from "well-intentionally added" padding. This forces teams to reason from first principles and justify the true time required, preventing unnecessary delays.
When a team presents a timeline that feels instinctively too long, trust that gut feeling. It likely signals an over-engineered solution. Complex systems never become simple; they only breed more complexity, causing timelines to expand endlessly. It's better to reset the team or the approach early on.
Combat the tendency for teams to ease into the new year by anchoring them around what must be completed in the first month. This creates a "fast start," builds early conviction in the annual plan, and prevents playing catch-up in February and March.
Before starting a project, ask the team to imagine it has failed and write a story explaining why. This exercise in 'time travel' bypasses optimism bias and surfaces critical operational risks, resource gaps, and flawed assumptions that would otherwise be missed until it's too late.
Instead of arguing for more time, product leaders should get stakeholder buy-in on a standardized decision-making process. The depth and rigor of each step can then be adjusted based on available time, from a two-day workshop to an eight-month study, without skipping agreed-upon stages.
