Critical Thinking Prompts

(stress-testing assumptions, exposing blind spots)

1. Objective Validity Test

• Purpose: To interrogate whether a project should exist at all by attacking problem legitimacy before solution quality, preventing the high cost of "successful" projects that deliver no value.

• Prompt: “Evaluate whether the following project should exist at all:
  
  [PROJECT OR INITIATIVE]
  
  Analyse from five perspectives:
  1. Strategic alignment
  2. Opportunity cost
  3. Organisational incentives (who benefits politically)
  4. Alternative ways to achieve the same outcome
  5. Evidence the problem is real rather than perceived
  
  Then provide:
  - the strongest argument FOR the project;
  - the strongest argument AGAINST the project;
  - the conditions under which the project becomes irrational”

• Technique:
  Premise Interrogation
  - Forces a "Go/No-Go" interrogation from five angles to test whether the problem itself is legitimate.
  Exit Ramp Creation
  - Defines the conditions under which the project becomes irrational, giving leadership permission to cancel before major sunk costs accumulate.

2. Pre-Mortem Architect Prompt

• Purpose: To dismantle organisational optimism and sunk-cost bias by constructing specific, actionable failure narratives and early warning signals.

• Prompt: “I am about to execute the following plan or decision: [plan summary / decision].
  Assume it is now [6 / 12 / 18] months from today and this initiative has failed.
  
  Your task is not to evaluate whether it will fail, but to construct the three most plausible failure narratives - each with a different root cause (one technical, one organisational, one external).
  
  For each narrative, identify:
  the earliest leading indicator that would have been visible in weeks 1-4, and
  what assumption in the original plan made the team blind to it.”

• Technique:
  Domain Locking
  - It forces three distinct failure categories (technical, organisational, external) to prevent the analysis from collapsing into a single, vague narrative.
  Evidence Orientation
  - It demands early leading indicators (weeks 1–4) to move the failure from a hypothetical future to a detectable, actionable present.

3. The Red Team Brief

• Purpose: To expose vulnerabilities and attack logic by bypassing the AI’s default politeness and preventing critique from being diluted by premature solutions.

• Prompt: “You are a senior adversarial reviewer: your job is not to improve this plan but to defeat it.
  Here is the plan: [paste plan or proposal].
  
  Your audience is a sceptical investment committee / steering board / client who will challenge everything.
  
  Produce a Red Team brief structured as:
  (1) the three strongest objections to the strategic logic,
  (2) the two data gaps that most undermine confidence in the projections,
  (3) one scenario under which this plan actively makes things worse than doing nothing, and
  (4) the single question that, if asked in a board meeting, would expose a weakness the sponsor cannot currently answer.
  
  Do not offer solutions - only expose.”
  
  [Optional Extension – Cultural Failure Probe: ] "Act as a cynical Red Team Lead. Everyone is nodding and saying [PROJECT] looks good - which is a red flag. Identify 3 'Silent Killers' that have nothing to do with budget or tech (e.g., cultural rejection, ego-driven sabotage, or malicious compliance). Tell me exactly which 'confident' assumption is most likely to be [PROJECT] undoing. Next, it is one year from now, and this project has failed catastrophically. Ignore obvious reasons like 'budget' or 'resource constraints.' Identify 5 'silent' or cultural reasons why this failed."

• Technique:
  Adversarial Constraint
  - By explicitly forbidding the AI from offering solutions, it suppresses the "reassurance reflex" and forces the model to remain in a state of pure, undiluted critique.
  Structured Attack Brief
  - The fixed deliverables (3 objections, 2 data gaps, 1 adverse scenario, 1 unanswerable question) force the analysis into a board-ready format.
  Operational Precision
  - The "unanswerable question" prepares the sponsor for the most damaging challenge likely to emerge in a board or steering meeting.

4. Assumption Audit

• Purpose: To identify load-bearing assumptions within an objective and assess how fragile they are.

• Prompt: “The following objective has been set for this project or initiative: [state objective exactly as written]. Do not accept this objective at face value.
  
  Identify every load-bearing assumption embedded in it:
  assumptions about user behaviour,
  market conditions,
  organisational capability,
  technology readiness, or
  stakeholder alignment.
  
  For each assumption:
  rate its fragility (high / medium / low),
  identify what evidence would be needed to validate it, and
  flag which assumptions are being treated as facts in the current plan.
  
  Then rewrite the objective in a form that is more epistemically honest about what is actually known vs. assumed.”

• Technique:
  Honest Reframing
  - It forces the team to rewrite goals based on uncertainty, transforming a plan from "We are doing X" to "We are testing if X is possible."
  Fragility Triage
  - By rating assumption fragility (High/Med/Low), it provides a clear triage signal for PMs to prioritise their attention toward the most brittle parts of the strategy.

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