Build Culture That Moves With Ambiguity

December 31, 2025 at 10:15 PMoperationalmedium

Situation

Committed to teaching the org to start moving with imperfect information rather than over-designing before committing. Will provide cover from Bjorn holding teams accountable for early SWAG estimates, enabling faster iteration and learning.

Reasoning

The current dynamic creates a vicious cycle: engineers over-design before committing because they fear being held to early estimates. This slows learning - you cannot learn alone in a room designing, you need to start moving. Creating psychological safety around early estimates enables a move fast and learn culture. Shielding engineering from premature accountability is one tactic to enable this broader culture shift.

Additional Context

Triggered by Portal estimate situation where Alex 25-hour SWAG was treated as hard commitment by Bjorn. Justin noted team hesitance stems from learned lack of trust from past experiences.

Source

reflection

AI Confidence

85%

Outcome

Partially successful - some traction on culture shift

Rating: 3/5

Decision ID: 9c348299-78df-42f8-a748-f863d29b5761