Home · The workbench · AI as a thinking partner
Drawer 04 The deepest pull

Use it to slow down — not just move faster.

Most reps use AI to produce more of the same, faster. This drawer is the other move: using prompts as a sparring partner. Pressure-testing an assumption. Steel-manning a "no." Preparing, not automating. The best reps don't type less — they think more clearly.

Think slower
🧠
Prepare, not automate
Three focus areas

What lives inside this drawer.

Three ways to use AI as a thinking partner instead of a content mill. Each one trades speed for clarity — on purpose.

🐢
01

Slow down assumptions

Ask the model to list what you're assuming — the ones you didn't notice you were making. Half of them are load-bearing. Half aren't.

  • Hidden buyer-side assumptions
  • Category norms you've stopped questioning
  • Timing and urgency you invented
  • What "obviously" hides
🥊
02

Pressure-test ideas

Feed the model your pitch, your discovery plan, or your proposal — and ask it to attack. A cheap sparring partner is worth more than a cheerleader.

  • Steel-man the "no"
  • Rehearse the toughest objection
  • Where the story falls apart
  • What a skeptical buyer sees
🎯
03

Prepare, not automate

Use the model to prep for the call — not to run it. Your prospect can smell an auto-generated email in three seconds. Prep is invisible; automation isn't.

  • Draft, don't send
  • Rehearse, don't recite
  • Plan, don't outsource
  • Your voice, sharpened
How to use it

Three prompts, one clearer head.

These aren't productivity hacks. They're twenty-minute conversations with a model before an important call.

01

Ask what you're assuming

Paste your call plan. Prompt: "List every assumption I'm making about this buyer. Rank by how much of my plan collapses if it's wrong." Read the list slowly.

"The load-bearing ones are usually invisible."
02

Steel-man the "no"

Ask the model to be the buyer. Tell it to say no — and to argue as intelligently as possible. Don't ask it to be nice. You want the real objection.

"If you can't beat the steel-man, you can't beat the real one."
03

Rehearse, then close the tab

Do the roleplay. Rewrite the opener until it stops sounding rehearsed. Then close the tab and get on the phone. The AI doesn't take the meeting — you do.

"The last sentence you rehearse is the first one that lands."
Keep it honest

When it helps — and when it doesn't.

✓ Reach for it

Reach for this drawer when…

  • You have a big call and want to stress-test the plan.
  • A deal stalled and you're too close to see why.
  • You keep hearing the same objection and your responses feel stale.
  • You want a second opinion at 9 PM when nobody else is on Slack.
✗ Put it back

Skip it when…

  • You're using AI to avoid a hard conversation with your manager or a peer.
  • You want to send the raw output as an email. Don't.
  • The model is telling you what you want to hear. Push back or move on.
  • You're substituting prompts for practice reps on the phone. That's a trap.
The point isn't to type less. It's to walk into the call knowing something you didn't know an hour ago.
— The house rule for drawer 04