Oct. 31, 2025

🌓305. Consulting Trick or Treat feat. Alan Weiss (Weekend Rewind)

🌓305. Consulting Trick or Treat feat. Alan Weiss (Weekend Rewind)
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🌓305. Consulting Trick or Treat feat. Alan Weiss (Weekend Rewind)

On this Halloween live stream, Alan Weiss and I had a spirited chat about the ā€œtricksā€ consultants fall for and the ā€œtreatsā€ clients actually value. We riffed on wild promises vs. real outcomes, commodity work vs. initiating new value, carving people up vs. helping them grow, being a ghost vs. showing up with presence, and—my favorite—wearing masks vs. bringing the real you (including your voice, not AI slop šŸ™ƒ).

Alan shared early-career scars (including a disastrous pre-digital survey project) and the simple posture that got him through: learn the lesson, then move. We also touched on the true origin of Halloween, why low self-esteem—not AI—is the scariest trend haunting consultants, and how improv rules (ā€œyes, andā€¦ā€) make you unbeatable on your feet with clients. I briefly ā€œghostedā€ the stream (perfect timing) and Alan just kept rolling—proof that intellectual firepower + humor is the ultimate treat.

Takeaways

  • Don’t sell hope; sell outcomes. If you can’t deliver it, don’t promise it.
  • Stop accepting commodity requests; initiate higher-value conversations.
  • Grow people; don’t carve them. Change beliefs, not just behaviors.
  • Show up with presence—no ghosting, no masks. Let clients meet the real you.
  • Use AI as a tutor and pattern-maker, not a voice replacer. Keep your language yours.
  • Confidence > credentials: you can learn fast, but be honest about limits.
  • Self-esteem is the real monster under the bed. Build it; ship work; laugh often.
  • ā€œYes, andā€¦ā€ beats ā€œNo, butā€¦ā€ā€”in workshops, sales calls, and life.

Quotable

  • ā€œDo you want to be tricked, or do you want a treat?ā€ —Alan Weiss
  • ā€œAI should teach you how to fish, not hand you someone else’s fish.ā€ —Alan Weiss

Resources & mentions

  • Alan Weiss – Monday Morning Memo newsletter (QR mentioned on stream)
  • ā€œThe Whale Saleā€ Substack (Alan Weiss & Lisa Miller)
  • Improv principles (ā€œyes, andā€¦ā€) for facilitation & sales
  • My ā€œDamaged Goodsā€ idea on treating groups as ready to grow


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