What Coaches and Mentors Can Learn from The Hard Thing About Hard Things
Assuming a mentee's genuinely hard problem has a known trick that makes it manageable, rather than requiring them to face their specific situation directly, is the trap The Hard Thing About Hard Things names, and it's an easy one to fall into when generic advice feels like a safe, comfortable answer 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
Face the struggle directly rather than looking for an easy way out
The hardest periods a mentee goes through rarely have a trick that makes them easy; they require confronting the actual problem instead of searching for advice that avoids it.
A mentor offers a mentee facing a serious problem the same standard advice given to everyone, instead of helping them sit down with the specific facts of their own situation.
Help your mentee name the actual hard problem they're facing in one sentence, and identify the first real step toward it rather than the next piece of advice to give them.
Tell the truth, especially when the news is bad
Communicating clearly and honestly with a mentee about difficulty, even when it's uncomfortable, keeps their trust intact and helps them actually improve instead of receiving only comfortable feedback.
A mentor softens honest feedback about a mentee's serious blind spot, and the mentee continues making the same costly mistake because no one told them directly.
Identify one piece of honest feedback you've been softening with a mentee, and deliver the direct version of it this week.
Help them make the hard decisions their situation actually requires
Delaying a necessary difficult decision, out of discomfort, usually makes the eventual outcome worse for a mentee, including in ways that show up well after the mentoring relationship has ended.
A mentor avoids pushing a mentee to address an ongoing problem they've been putting off, and the mentee continues to absorb the cost of the delay.
Identify one decision your mentee has been delaying, and ask them directly what's stopping them from addressing it this week.
Build the approach their specific situation needs, not a generic playbook
The right guidance for a mentee varies by their actual circumstances, and handing them someone else's exact path wholesale often fails to fit the problem they actually have.
Offering established guidance and tailoring it to a mentee's specific situation aren't opposites — the strongest mentors offer structure where it fits and adapt it the moment it stops matching what their mentee actually needs.
Name one thing, honestly
Is there a hard problem your mentee is facing that you've been treating as a search for the right advice, rather than a decision only they can make?
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
Identify one decision your mentee has been delaying, and ask them directly what's stopping them from addressing it this week.