Coaching practices for I Have to Make an Ask That I Know is Going to Land as Self Serving or Unfair and I'm Dreading the Moment They Think it I Want to Get Ahead of Every Bad Thing They Might Be Thinking About Me Before They Can Say it

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Does this sound like the set of challenges you might be facing?

  • I have to make an ask that I know is going to land as self-serving or unfair, and I’m dreading the moment they think it
  • I’m dreading this talk because I know they’re already thinking the worst of me
  • I’m walking into this knowing exactly what they’re probably thinking about me
  • I have an ask I need to make of someone, and I hate the feeling of leading with my hand out
  • I want to lead with a bigger ask so my real request lands easier, but I keep second-guessing how high to go

Practices that may help

  1. Run an accusation audit before difficult asks
    Name the worst things the other person might think about you or your request — before they do.
    Labeling Emotions in Negotiation, Made Practical
  2. The accusation audit
    Pre-empt their worst objections by saying them out loud before they can.
    Tactical Empathy
  3. The accusation audit
    Say the worst thing they might be thinking about you — out loud, first — to defuse it.
    Never Split the Difference, In Practice
  4. Give genuine value before you make a request
    Lead with something useful — help, insight, attention — before any ask.
    The Rule of Reciprocity, Made Practical
  5. Open with a large but plausible request
    The initial ask must be large enough to likely be refused but not so extreme it looks absurd.
    The Door-in-the-Face Technique, Made Practical
  6. Investigate before escalating
    Ask one honest clarifying question before taking action on an assumed motive.
    Hanlon's Razor: Never Attribute to Malice What Stupidity Can Explain
  7. Assert your request or refusal directly and specifically
    Ask for exactly what you want or say no — without hedging, hinting, or burying the request.
    DEAR MAN: DBT’s Skill for Asking for What You Want Effectively
  8. Use the door-in-the-face technique to make the real ask seem small
    Make a large, reasonable request first; after it is declined, your actual (smaller) ask feels like a concession.
    The Contrast Principle, Made Practical
  9. Share advice with permission (ask–offer–ask)
    Ask what they know, offer information with consent, then ask what they make of it.
    Motivational Interviewing, Made Practical
  10. Apply door-in-the-face for prosocial or charitable asks
    The technique was originally tested in a prosocial context and works especially well when both parties share values.
    The Door-in-the-Face Technique, Made Practical

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