What Coaches/Mentors Can Learn from Amusing Ourselves to Death
Fatima ran her mentoring sessions the way she ran everything else in her packed week, tight, energetic, full of quotable one-liners her mentees screenshotted and shared. Attendance was excellent. Feedback forms glowed. But when one mentee came to her with a genuinely tangled career decision, one with no clean answer and several competing tradeoffs, Fatima noticed she had no comfortable way to work through it out loud. Her usual mode was built for a crisp insight delivered fast, not for the slower back-and-forth a real dilemma required. Sitting across from a mentee who needed patience rather than a punchline, Fatima realized her own habit of packaging every piece of guidance as something quick and memorable might be leaving her least prepared exactly when the stakes were highest.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
The coaching format shapes the guidance given
The form advice takes, a punchy one-liner, a structured worksheet, a long unhurried conversation, shapes what kind of guidance can actually travel through it, regardless of how wise the coach is. Fatima's quotable lines traveled well, but the format itself could not carry the nuance a genuinely hard decision required.
Some situations really do call for a short, clarifying line, and turning every exchange into a long deliberation can overwhelm rather than help. Practice: keep at least one recurring session format built for slow, unhurried conversation, separate from your shorter, high-energy check-ins.
Keep at least one recurring session format built for slow, unhurried conversation, separate from your shorter, high-energy check-ins.
When insight becomes performance
Once a coaching practice rewards fast, memorable moments, even genuinely difficult guidance tends to get reshaped into something quotable simply to meet that expectation. Fatima's habit was not insincere, but it had trained her to reach for the crisp version before she had fully worked through the slower one underneath it.
Some mentees respond best to concise, energizing guidance, and a coach who abandons that entirely may lose an audience who needed it. Practice: before offering a quick insight on something genuinely complicated, name the tradeoff out loud first, so the compression is visible rather than hidden.
Before offering a quick insight on something genuinely complicated, name the tradeoff out loud first, so the compression is visible rather than hidden.
Losing practice in the slow, uncertain conversation
Coaches who mostly deliver fast, confident insight can lose comfort sitting with a genuinely uncertain conversation, since that skill rarely gets exercised in a practice built for quick wins. That comfort matters most exactly when a mentee brings a problem with no clean answer at all.
This comfort develops slowly through repeated practice, not through a single long session taken on faith. Practice: once a month, hold a session with no agenda and no planned insight, and let the conversation move at its own pace.
Once a month, hold a session with no agenda and no planned insight, and let the conversation move at its own pace.
A quieter risk than a mentee who stops listening
Postman's own argument, built around 1980s television, was that a public entertained into passivity is harder to notice and correct than one under open, visible control. For a coach, the equivalent risk is not a disengaged mentee, but one who stays enthusiastically engaged while quietly absorbing only the crisp lines and never actually building the slower reasoning those lines were meant to summarize.
The sharpest tension is between the energizing, memorable guidance mentees expect and the slower reasoning some of their real problems actually need, since the two rarely fit the same session comfortably. Fatima's workable path is not abandoning the quick insight but treating it as a doorway, using a memorable line to open a conversation and then deliberately staying in the room long enough for the fuller, less quotable reasoning to happen too.
Name one thing, honestly
- Which of your recent pieces of advice were genuinely well-suited to a quick line, and which deserved a slower conversation you skipped? - Do your mentees leave your sessions with a memorable phrase, a workable way of reasoning, or both?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Once a month, hold a session with no agenda and no planned insight, and let the conversation move at its own pace.