What Coaches and Mentors Can Learn from Save the Cat
In their first session, Deshawn's new mentee wanted a five-year plan, so Deshawn gave her one: milestones, skills to acquire, certifications to pursue, in a tidy document with dates in the margins. She nodded through the whole meeting, took notes, and never opened the document again. Three months later she admitted, almost apologetically, that the plan had felt like homework from a stranger, not something that had anything to do with her. What she actually remembered from that first session was an offhand comment Deshawn had made about his own second year in the field, when he'd nearly quit after a public failure and a colleague had talked him out of walking away over coffee that same week. She brought that story up unprompted, months later, at a moment when she was considering quitting herself. Deshawn realized the plan he'd built so carefully had done far less work than the ninety-second story he'd told without thinking about it at all.
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
Give your audience an early, concrete reason to root for your protagonist
Deshawn's five-year plan is the common failure — mentors lead with frameworks and milestones, before offering any human moment the other person can actually see themselves in. A coach who opens a first session with an assessment questionnaire, before sharing anything real about their own path, asks for trust before offering any reason to extend it.
Before your next first session, prepare one short, honest story about a specific moment you struggled, including how it actually felt, and share it early. Let your client respond to that moment before moving into any framework, plan, or assessment.
Stories tend to share an underlying structural shape
Mentors sometimes tell only the tidy, resolved version of their own story, skipping the actual struggle in the middle, so the story reads as a highlight reel rather than something a client can learn from. A success story with no real setback in it gives a struggling client nothing to map their own situation onto.
Next time you share your own experience, deliberately include the specific low point, not just the outcome, and describe what actually got you through it. That middle section, not the resolution, is usually the part your client needs most.
Know your story's core idea in one clear sentence before building anything else
A mentor who hasn't worked out the one thing they most want a client to internalize tends to offer scattered advice across many topics in a single session, none of which fully lands. Deshawn's original plan tried to cover five years of skills at once instead of anchoring around one core belief he actually wanted to pass on.
Before a session where you plan to share a formative story, decide in one sentence what you want the client to take from it. Tell the story so that sentence is the clear point, even if it means leaving out other true but distracting details.
Structure serves the idea, not the other way around
A well-told mentoring story cannot substitute for having genuinely useful judgment to offer. Some mentors lean on a strong personal narrative style while giving advice that doesn't actually fit the client's specific situation. Use story as a way to make real, situation-specific guidance land with more trust, not as a substitute for actually listening closely enough to know what that client needs.
A vivid personal story can pull a session away from the specific plan a client actually needs that day, and a carefully built plan can crowd out the human moment that would make the client trust it. When the two compete, let the client's immediate need decide: open with story when they need to feel understood, and hold the story for later when they need concrete next steps first.
Name one thing, honestly
What's the one story from your own struggles that you keep almost telling but never quite share, and what is it that stops you?
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
Before a session where you plan to share a formative story, decide in one sentence what you want the client to take from it. Tell the story so that sentence is the clear point, even if it means leaving out other true but distracting details.