0108 – How to Keep Copilot From Leading You Down the Wrong Path

Copilot is a fantastic thought partner—but it has a bad habit: it’ll often act like a cheerleader and agree with you, even when you’ve accidentally steered it the wrong way. In this episode, Annie shares a true story from Arnie (our founder) where one missing word flipped his idea on its head… and Copilot still praised it. That “yes‑man” tendency can push leaders and teams to run fast in the wrong direction if nobody—and nothing—pushes back. And here’s the good news: there’s a simple way to make Copilot stop clapping and start challenging—without turning every prompt into a big, complicated script. In the episode, Annie shares the exact phrase she uses to flip Copilot into “devil’s advocate” mode, plus a couple of easy tweaks (including a set-it-once option in some Microsoft 365 setups) that make the results noticeably sharper. If you use Copilot for strategy, planning, or decision-making, you’ll want to hear this before your next session.