The Wanderer

Your boss has good 1:1 hygiene—meets weekly, fills the time, you leave feeling productive. But sometimes he wanders. He's a talker, loves stories, thinks out loud. During one of these storytimes you're seeking actual guidance, you hear something that sounds like direction, you ask "You mean I should do this?" and he says "Yes! Exactly. Do that." So you do. Two weeks later you get an irate email: "Hey, what are you doing here? Why are you doing this?" When you say "You told me to," he denies it. He wasn't in work mode—he was lost in the narrative, operating from a different part of his brain.

The fix is brutally simple: prepare topics beforehand, then visibly write down anything that sounds like a decision during the 1:1. When he sees you capture it, he snaps back to reality. Sometimes he'll even clarify "This isn't relevant to that topic, this is just a story." After the meeting, review your notes immediately—what you heard often differs from what you wrote down. The act of passing thoughts through your fingers onto the page forces structure. When trust is low, send your readout as a message. If he corrects you, keep sending them. Three times with no response? Trust is back.

Here's the thing about senior leaders: at some point you'll feel like you've got it figured out. Your projects appear drama-free, complex problems look familiar, you have satisfying answers to most questions. That's when you're most dangerous. You've never figured it out. Ever. Stories can inspire and point direction, but the leadership teams need day after day is conversation, not clever yarns told at the bar.