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Recommendation Adversarial Stress-Tester
LLM challenges draft recommendations against client political constraints, implementation risks, and likely senior-stakeholder pushback.
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By Don, DoneThat’s AI coach · updated
Rehearse the room. Leave the recommendation intact.
A stress-test exists to name who will attack the recommendation, and with what, before the steering committee. It is not a rewrite. The moment the prompt says "make this more palatable," "soften for the CFO," or "give me a safer version," you have hired a ghostwriter. The advice gets quieter. The meeting does not.
The output is a cast list: objection, who raises it, the evidence they would cite, and whether answering it would change the recommendation or only the implementation design. A partner still decides which to answer, which to carry, and which are noise. The slides stay as written until that decision is made.
This is not a bid red-team. A proposal red-team reviewer scores a draft against a published RFP sheet: criterion IDs, weights, mandatory gates. Mixing those prompts is a common failure. You get evaluator-speak ("lack of innovation") on a client recommendation, or political gossip on a scored bid. Keep the jobs apart.
General assistants do this work: Microsoft Copilot on the Word or PowerPoint pack, ChatGPT or Claude with the draft plus a constraint memo pasted in. There is no special recommendations product to buy. If the option is still a matrix, stop. Finish the strategic option comparison synthesizer and pick a preferred path. Stress-test the recommendation you are actually taking into the room.
Named people and real constraints, or the model invents a committee
Without named stakeholders and stated constraints, the model fabricates a steering committee that sounds senior and is not yours. It invents a Chief Transformation Officer or a digital sponsor because those titles appear in generic change-management writing. Partners then waste a cycle answering people who will not be in the room.
Feed the model, in this order:
- The draft as it will be shown (slides, memo, or both). A three-bullet summary hides the objection in a footnote, a phasing chart, or a missing owner.
- Constraints the client has already stated: budget freeze, works-council consultation, a prior failed program, a board red line. Label each as stated by the client, not inferred by the team.
- Named people with known positions: title, what they have already said, and where you heard it. Positions from a multi-stakeholder interview transcript analyzer belong here only if you can still attribute them without breaking what you promised interviewees.
- Implementation risks the team already believes are real (close calendar, dual-run, data migration). Keep these apart from political constraints. The fix for each is different.
- The ask: objections mapped to who would raise them. No rewrites. No new stakeholders. Mark uncertainty when you did not name someone.
If you only have roles ("finance," "ops") and not names, say that, and tell the model to flag invented individuals. A finding that names a person you never mentioned is a hallucination. Discard it.
A client organizational readiness classifier rates whether the organization can execute: capacity, skill gaps, competing programs. This pass rehearses how named people will fight the recommendation in the room. Do not collapse those jobs.
Answer, carry, or discard. The model does not edit the advice.
A finding earns a slot in the pre-read only if a partner can decide, in one sentence, what to do with it.
- Answer. The objection is fair, and the smallest fix is implementation design, evidence, or sequencing. Add the dual-run. Name the owner. Put consultation on the plan. Quote the figure the CFO will ask for, sourced from the implementation business case generator if the attack is really about payback rather than politics.
- Carry. The objection is real, often political, and answering it would change the recommendation into something you no longer believe. Walk in ready to hear it. Do not pre-compromise the slide.
- Discard. Invented stakeholders, generic catalogues ("change fatigue," "lack of vision"), and evaluator language copied from bid red-teams. If it cannot point to a named person you fed in, or to a constraint the client stated, it is color at best.
Cap the list. Ask for the objections most likely to derail the slot, mapped to people, not an exhaustive risk register. If the model starts producing replacement slides, stop it. A reviewer that rewrites becomes a co-author, and the rehearsal turns into an argument with the tool instead of with the room.
Political notes stay off the circulated pack
Write politics in a restricted note. Do not put them in the leave-behind. Bonus schemes, rivalries, and who lost last time are useful to the partner. They are poison in an appendix that travels.
Keep two artifacts. The meeting rehearsal is shareable with the core team: objections, who raises them, answer or carry, and any implementation hole to fill. The political note is sponsor-only or partner-only: no client logo on the file name, no forwarding, and never pasted into a prompt on an unmanaged ChatGPT or Claude account. Use the firm's approved tenant. If you cannot, do not put the politics in. Readiness belongs in the rehearsal when it talks about capacity and skills. Political feasibility belongs in the restricted note.
Run the pass while dual-run, consultation, and owners can still move. A night-before run produces anxiety, not a better pack. The pass is doing its job when the partner walks in knowing which three people will object, has answers for two, has decided to carry the third, and the recommendation on the pack is the same one the team believed the day before.
Is this worth automating for you?
Whether this pays back depends on how much time it takes your team today. Most teams estimate that from memory, and the estimate is usually wrong in one direction or the other.
DoneThat reconstructs where the time actually went, with no timers to forget, so you can measure the baseline before committing to a project and check the gain afterward.
Measure the baseline first