Use a clear "stop-and-start" script and purposeful "why" framing to turn a teammate's endless devil's-advocate loop into decisive action, preserving empathy while driving progress.
When a teammate is stuck in endless questioning, the key is to frame the conversation around a clear "why" and a "stop-and-start" directive that preserves empathy while cutting indecision. The leader first identifies the business objective-forward progress on a critical delivery-and uses that as the north-star to avoid getting trapped in endless debate.
The article illustrates the approach with a fictional teammate, Janet, who constantly plays devil's advocate in planning meetings. By acknowledging her concern about missing edge cases, restating the shared goal, and then delivering a concise bottom-line message-"I need you to stop asking 'what if's' and start making decisions"-the leader shifts the focus from argument to action. If the softer approach fails, the leader escalates to the blunt stop-and-start phrasing, still anchored in the agreed "why".
Practical takeaways for technical leaders are: clarify the underlying purpose before the conversation, explicitly acknowledge the other person's worries, pivot to future-facing decisions, and keep the final directive to one or two sentences. This method reduces meeting waste, improves decision-making speed, and maintains team morale while keeping empathy intact.
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