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  1. Calling somebody up rather than out requires knowing what is being defended.

  2. Read the last one you sent and count what you asked for before you gave anything.

  3. Two things happened to me as a customer this month, and both are the kind of problem the company causing it will never find out about.

  4. Why You're Stuck Downstream

    Everyone says move upstream.

  5. The Uncertain Yes

    They said yes.

  6. A customer pays you real money and the first thing your company does is work out how to message them without a person involved.

  7. I took an objection at face value in a client meeting and got it wrong.

  8. The sales conversation holds everything Customer Success never gets.

  9. A personalized welcome email can be in the inbox seconds after signature.

  10. Two questions, asked right after you lay out what the customer is responsible for.

  11. Bad delivery makes Customer Success look like a drain.

  12. A customer who stops engaging usually gets filed as not invested.

  13. Two people can pull defensible retention numbers from the same data and reach opposite conclusions.

  14. Most companies hiring their first CS person write the scope before they meet anyone, which means there was never a bar to screen against.

  15. The Confidence Question™

    A leading indicator of customer success.

  16. When a customer says your work reads like AI, they are almost never pointing at formatting.

  17. Agentic workflows learn.

  18. For the individual contributor who can see a customer getting a bad automated experience and lacks the authority to halt it.

  19. Building customer-facing tools is close to free now, which is genuinely good.

  20. AI can deliver the appropriate experience at a scale we never had before.