Design prompts that generate genuine counter-arguments and alternative viewpoints rather than agreeable summaries.
Leadership & Management
Using Generative AI to Stress-Test Strategy and Management Decisions
Trains leaders to use generative AI deliberately to challenge strategic assumptions, generate alternative scenarios and surface blind spots before major decisions are finalised.
🗓️Duration5 training days
📚Content4 modules · 8 sessions
🎓On completionAccredited attendance certificate
About the programme
Course Overview
Groupthink and confirmation bias can narrow strategic options before a decision is finalised, and generative AI, used deliberately, can generate counter-arguments, alternative scenarios and stakeholder perspectives a management team would not surface alone, but only if prompted well and checked for the model's own biases and confident-sounding errors. This course covers structured prompting techniques for generating genuine counter-arguments rather than agreeable summaries, using AI to construct multiple future scenarios for stress-testing a plan, running an AI-assisted pre-mortem to surface failure modes before launch, and critically evaluating AI-generated challenge rather than accepting it uncritically. Teaching uses live prompting exercises on a real strategic decision each participant brings, comparative exercises showing how prompt design changes the quality of challenge produced, and a facilitated pre-mortem session. Participants leave with a set of tested prompts and a pre-mortem output ready to use in a real strategy session.
Expected Learning Outcomes
Use generative AI to construct multiple plausible future scenarios for stress-testing a strategic plan.
Run an AI-assisted pre-mortem exercise that surfaces failure modes before a major decision is finalised.
Identify where AI-generated challenge reflects genuine insight and where it reflects the model's own training biases.
Combine AI-generated alternatives with human expert judgement rather than treating AI output as a final answer.
Facilitate a management team discussion that uses AI-generated challenge without letting it dominate the conversation.
Document which strategic assumptions were tested, by what method, and with what outcome, for later review.
Who Should Attend
Executive teams and strategy directors preparing major investment or market-entry decisions.
Chief executives seeking structured challenge before board-level strategic proposals.
Strategy and corporate development managers responsible for scenario planning.
Programme boards approving significant transformation or capital allocation decisions.
Consultants and facilitators running strategy workshops for client leadership teams.
Risk committees seeking additional independent challenge on strategic assumptions.
Course Modules
Select any module to see its sessions and points.
01Prompting for Genuine Challenge
2 sessions · 8 points
Session 1Why Default AI Responses Tend Towards Agreement
- Recognise why an unprompted AI response often mirrors and validates the framing given to it rather than challenging it.
- Compare a neutral prompt with a deliberately adversarial prompt on the same strategic question to observe the difference.
- Identify prompt phrasing that unintentionally signals a preferred answer and biases the AI response towards it.
- Draft a prompt instructing the AI to argue explicitly against the proposed strategy before summarising for it.
Session 2Building a Reusable Challenge Prompt Set
- Develop a library of prompts for generating counter-arguments, stakeholder objections and worst-case interpretations.
- Test prompts for consistency by running them multiple times and comparing the range of challenge produced.
- Adapt challenge prompts to reflect the specific sector, regulatory context and competitive position of the decision.
- Share a tested prompt set with the wider team so challenge quality does not depend on one person's prompting skill.
02Scenario Generation and Pre-Mortems
2 sessions · 8 points
Session 1Generating Alternative Futures
- Use generative AI to construct several plausible future scenarios that could affect a strategic plan's success.
- Vary key assumptions systematically to see how sensitive the strategy is to each one.
- Compare AI-generated scenarios against the management team's own scenario set to identify blind spots.
- Select the scenarios most useful for testing the plan's resilience rather than the most dramatic or unlikely ones.
Session 2Running an AI-Assisted Pre-Mortem
- Facilitate a pre-mortem exercise where the AI is prompted to explain, in detail, why the strategy failed a year later.
- Cluster AI-generated failure modes by root cause to identify the highest-priority risks to address before launch.
- Compare AI-generated failure modes against the team's own pre-mortem output to catch gaps in either source.
- Translate identified failure modes into specific mitigating actions owned by named individuals.
03Evaluating AI-Generated Challenge Critically
2 sessions · 8 points
Session 1Distinguishing Insight from Model Bias
- Assess whether an AI-generated objection reflects genuine strategic risk or a common pattern in its training data.
- Cross-check AI-generated market or competitor claims against verified external sources before acting on them.
- Identify confidently worded AI output that lacks supporting evidence and treat it with appropriate scepticism.
- Recognise when a strategic question is too novel or context-specific for generic AI-generated challenge to be reliable.
Session 2Combining AI Challenge with Expert Judgement
- Position AI-generated challenge as one input alongside expert judgement, data analysis and stakeholder consultation.
- Assign a named person to independently verify significant claims or risks raised by AI-generated challenge.
- Avoid over-weighting AI-generated challenge simply because it is available quickly and at low cost.
- Decide which AI-raised issues merit further investigation and which can be reasonably set aside with documented rationale.
04Facilitating AI-Assisted Strategy Sessions
2 sessions · 8 points
Session 1Running the Session with a Management Team
- Structure a strategy session that introduces AI-generated challenge at a specific point without derailing the discussion.
- Manage a team's tendency to defer to AI-generated output as more objective than colleagues' opinions.
- Keep the discussion focused on decisions and actions rather than debating the AI tool's output indefinitely.
- Close a session with a clear record of assumptions tested, challenges raised and resulting decisions.
Session 2Governance and Documentation
- Document which strategic assumptions were tested using AI-assisted methods and with what result.
- Set a policy on how AI-assisted challenge is recorded in board or committee papers for audit purposes.
- Review, after key decisions play out, whether AI-generated challenge anticipated the issues that actually arose.
- Refine the organisation's approach to AI-assisted strategy testing based on accumulated experience over multiple cycles.
What the participant receives
4 course modules
A structured syllabus
8 training sessions
across 5 days
32 detailed points
Applied, detailed content
Accredited attendance certificate
On completing the programme
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