What Coaches and Mentors Can Learn from Pitch Anything
Marcus had a genuinely good idea for a mentee: switch majors before another semester of misery. He built his case like a lawyer, walking through every grade, every miserable Tuesday the kid had complained about, then delivered his conclusion like a verdict. The kid nodded along and did nothing for six months. A colleague pointed out what had gone wrong: Marcus had built the case for himself, not for the version of the conversation his mentee could actually hear. Next time, Marcus opened by asking what a good Tuesday would even look like, and let the mentee talk himself most of the way to the same conclusion. The advice hadn't changed. The order, and who got to arrive at the answer, had.
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
Let them arrive at the destination themselves
A mentee evaluates advice differently depending on whether they feel they reasoned their way to it or simply received it from an authority, even when the content is identical. Structuring a hard conversation around questions that lead toward a conclusion, rather than stating it first and defending it, respects how people actually change their own minds.
Over-relying on questions when someone is in genuine crisis can read as evasive when they need direct, clear guidance.
Before your next hard conversation, write the conclusion you want them to reach, then draft three questions that could lead them there.
Use your authority sparingly, on purpose
Your credibility is a resource, and spending it on every point, rather than saving it for moments that truly need it, teaches the person to wait for your verdict instead of doing their own thinking. This is not withholding help; it is trusting the relationship enough to let genuine engagement do the work assertion would otherwise do.
Withholding expertise on a genuinely urgent matter to preserve their sense of ownership can leave real harm unaddressed.
In your next session, identify one point where you'd normally just tell them the answer, and ask their view first.
Sit with real discomfort instead of resolving it for them
Coaches often rush to resolve tension the moment it appears, offering reassurance or a quick fix before the person has felt the weight of their own situation. Letting a genuine, uncomfortable question sit unanswered a beat longer than feels natural often produces more honest reflection than immediately smoothing the discomfort away.
Letting real distress sit too long without support can feel like abandonment rather than a deliberate pause.
The next time you feel the urge to fill an uncomfortable silence, count to ten before speaking again.
Read the actual person in front of you today
The same client who wanted direct challenge last month may need patience today, and delivering your usual style regardless of what they bring into the room ignores real signals about what this specific conversation needs. Adjusting your approach session to session, rather than running the same method regardless of their current state, treats coaching as a responsive relationship rather than a fixed technique applied uniformly.
Letting someone arrive at their own conclusion can collide with a moment that genuinely calls for direct authority, a safety concern, a deadline they don't realize is real; let authority speak plainly, then return to open questions once the concern is addressed.
Name one thing, honestly
Think about your last hard conversation with a mentee: did they arrive at the conclusion themselves, or did you hand it to them and hope it stuck?
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
The next time you feel the urge to fill an uncomfortable silence, count to ten before speaking again.