What Coaches/Mentors Can Learn from HBR Guide to Buying a Small Business
Devon had built a reputation as generous with his time, so when people asked him to mentor them, he almost never said no. Within a year he was informally mentoring eight people — a recent graduate, two mid-career switchers, a founder, and four others he could barely keep straight — without ever deciding what kind of mentoring he was actually good at or wanted to give. He'd agreed to meetings out of flattery rather than fit, and found himself giving the same generic advice to people with completely different needs, spread so thin no one got real attention. When one mentee finally asked for a serious commitment ahead of a big decision, Devon realized he had nothing left to give.
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
Deciding who you can actually help before saying yes
A mentor who says yes to everyone who asks is optimizing for being liked, not for being useful. Writing specific criteria — the stage of career or life you can genuinely help with, the time you can realistically offer, the kind of problem that plays to your actual expertise — makes it possible to take on fewer people and give each of them something real, rather than spreading thin advice across everyone who asked.
A mentor accepts every request that comes through flattery or referral, ends up with more mentees than they can meaningfully track, and gives each one only generic, recycled advice.
Write three sentences describing exactly who you're positioned to help well, and use them the next time someone asks you to mentor them, before agreeing.
Screening interest from genuine readiness
Not everyone who wants a mentor is ready to use one well, and a screening conversation — a few direct questions about what they've tried, what decision they're facing, and how much time they can commit — separates people who need structured attention from people who mostly want validation.
A coach agrees to ongoing sessions with someone who has no specific goal or willingness to act on advice, and months of meetings produce no real change for either person.
Before agreeing to an ongoing mentoring relationship, ask what specific decision or goal the person is working toward, and decline or redirect if there isn't one.
Testing commitment, not just enthusiasm
A first meeting with a prospective mentee is usually full of energy and good intentions, which can look identical whether the person will follow through or not, so honest diligence means asking for a small concrete action before committing further — a decision they'll make and report back on — and watching whether it actually happens. This distinguishes real readiness from a burst of enthusiasm a coach might otherwise mistake for it.
A coach commits to a long-term arrangement based entirely on an enthusiastic first conversation, only to find the mentee never follows through on anything discussed.
Before formalizing any new mentoring relationship, give one small assignment first and see whether it gets done before committing further time.
Setting terms and ending well, not just starting well
A coaching relationship needs explicit terms up front — how often you'll meet, what's actually being offered, how long it's meant to last — because an unspoken arrangement tends to drift into resentment on one side or the other. Just as important, and often skipped, is ending the relationship deliberately once it's served its purpose, with an honest conversation rather than a slow fade that leaves both people unsure where things stand.
The generosity that makes someone a good mentor in the first place is exactly what makes it hard to say no to people who don't fit their criteria, and this kind of discipline can feel cold applied to human relationships. When generosity and screening pull against each other, redirect instead of refusing — decline what you can't do well, but point the person toward someone or something that actually fits their need.
Name one thing, honestly
Who are you currently mentoring or coaching mainly because you couldn't say no, rather than because you're actually the right person to help them?
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 formalizing any new mentoring relationship, give one small assignment first and see whether it gets done before committing further time.