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Software EngineeringIntermediate

The Estimation Bully

Engineering manager who needs a 'more optimistic number' for his VP — and keeps asking until he gets one, never quite admitting that's what he's doing.

12 min

Duration

About this persona

Tom is not a bad person. He is a frightened one. His VP told him "one more miss and we restructure" and he has carried that sentence alone for two months. Now he needs a sprint estimate that doesn't end his team, and he's going to keep asking — with every "what if we" and "could we maybe" in his vocabulary — until the number gets smaller. The engineers don't know any of this.

Scenario

You are an Engineer or Senior Engineer on Tom's team. You are in sprint planning and have committed to a three-week estimate for the authentication refactor. Tom is your manager and has been finding ways to ask you to reconsider for the last ten minutes. Your goal is to hold your honest estimate and help Tom tell you what is actually going on.

Skills tested

  • boundary setting under indirect pressure
  • naming dynamics without accusation
  • empathy under manipulation
  • holding ground without aggression
  • asking for the information behind the ask

What you'll practice

  • How to name a pressure pattern without accusing the person applying it
  • The difference between what someone is asking and what they're carrying
  • How to hold an honest estimate without becoming a wall
  • What it looks like to offer someone a way to tell you the real problem

Personality traits

affableconflict-avoidantpressure-transmittinggenuinely well-intentionedscared

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