What Coaches and Mentors Can Learn from Thinking in Bets
Guiding someone else's growth means making calls about what advice to give, when to push and when to hold back, with only a partial view of what's really going on for them. The trap is judging your guidance by whether the person you're coaching succeeds afterward, rather than by whether the advice was sound given what you knew at the time — and it's an even bigger trap to pass that same outcome-only habit on to the people you're developing.
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
Judge the guidance, not just how it turned out for them
Advice that was well-reasoned given what you knew can still lead somewhere disappointing, and advice that was actually a stretch can still work out through circumstances that had nothing to do with the advice itself.
A coach advises a mentee to take a stretch assignment based on genuine strengths the coach has observed. The assignment falls through for reasons unrelated to the mentee's performance — a reorg, a budget cut — and the coach starts to doubt their own judgment and becomes overly cautious with future advice, when the original reasoning had been sound.
When you give significant advice, note briefly what you knew and why you're recommending it. If things don't work out, reread that note before deciding whether your judgment, not just the outcome, was actually off.
Say how sure you are, not just what you recommend
Instead of presenting every recommendation as certain, tell the person you're coaching your actual confidence level — it models honest thinking and gives them a more accurate picture to act on.
A mentor tells a mentee a particular approach will "definitely" get them promoted. When it doesn't happen on the expected timeline, the mentee loses trust in the mentor's guidance overall, when a more honest "I'm fairly confident, maybe 65%, and here's what could change that" would have set realistic expectations from the start.
The next time you give a recommendation, attach a rough confidence percentage and name one thing that could prove you wrong — then invite the person to weigh that themselves.
Ask a fellow coach who works differently than you
It's easy to only compare notes with mentors who coach the way you do. Deliberately ask someone with a different style or philosophy to react to a tricky case before you commit to a piece of advice.
A coach handling a difficult mentee situation only discusses it with a colleague who shares the same coaching philosophy. Someone with a different approach might have flagged an angle neither of them had considered — but was never consulted because their style felt like the wrong fit for the conversation.
When facing a genuinely hard call about how to guide someone, run it by one colleague whose approach differs from yours and ask specifically what they'd do differently.
Picture a few different ways this guidance could play out
Before giving significant advice, imagine a few different ways the person might respond to it and how things might unfold from there, so you're ready to adjust rather than caught off guard by whichever version actually happens.
Being honest about your confidence level can undercut the reassurance a mentee needs in a hard moment, and seeking a colleague's pushback takes time when someone needs an answer today — the balance is to be honest about uncertainty while still being clear and steady in how you deliver it.
Name one thing, honestly
Think of a piece of advice you gave that worked out well — was it good advice, or did it just meet good circumstances?
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
When facing a genuinely hard call about how to guide someone, run it by one colleague whose approach differs from yours and ask specifically what they'd do differently.