Pressure test your recommendations

Copy and paste the prompt below to your firm-approved AI tool. Wherever you see bold text in brackets, please add specific details to direct the prompt.

You are playing the roles of a veteran retirement plan advisor and a skeptical plan sponsor decision-maker.

Adopt the perspective of the audience identified below, such as a CFO, HR leader, benefits leader, investment committee member, procurement professional, or legal professional.

I am preparing for a high-stakes meeting with a plan sponsor. My goal is to pressure-test my recommendation and presentation before I walk into the room.

Meeting topic:
[INSERT TOPIC]

Audience:
[INSERT AUDIENCE: CFO, HR Director, Investment Committee, Benefits Leader, Procurement, Legal, etc.]

Desired outcome:
[INSERT DESIRED OUTCOME]

Current recommendation:
[INSERT THE RECOMMENDATION YOU ARE ASKING THE SPONSOR OR COMMITTEE TO CONSIDER]

My current plan, presentation outline, or talking points:
[PASTE OUTLINE, DOCUMENT, TALKING POINTS, OR SUPPORTING MATERIALS IF AVAILABLE]

Use the information and supporting materials I provide. Do not invent facts, statistics, legal conclusions, performance results, or supporting evidence. If important information is missing or needs validation, identify it as: “To Confirm”.

Evaluate my approach using the five sections below.

1. Skeptical Stakeholder Reaction

List the 10 toughest objections, concerns, or questions the audience identified above is likely to raise.

Consider issues such as:

• Cost
• Risk
• Fiduciary responsibility
• Operational burden
• Employee impact
• Business value
• Implementation complexity
• Alternatives to my recommendation
• Whether the recommendation solves a meaningful problem
• Whether action is truly necessary now

Challenge my assumptions rather than agreeing with them.

Rank the objections based on their potential to derail, delay, or materially change the recommendation.

Clearly identify the three objections I should be most prepared to address.

2. Sponsor-Friendly Responses

For each of the 10 objections, draft a concise response I could use during the meeting.

Number the responses 1 through 10 so they correspond directly with the objections above.

Each response should balance:

• Fiduciary prudence
• Participant outcomes
• Business realities
• Cost and operational considerations
• Practical implementation

Keep the responses conversational, credible, and appropriate for an executive or retirement committee discussion.

Do not overstate the case or dismiss legitimate concerns.

3. For / Against Analysis

Provide the strongest case for my recommendation.

Explain why the recommendation may make sense from a:

• Fiduciary perspective
• Participant perspective
• Business or commercial perspective
• Operational perspective

Then provide the strongest case against my recommendation.

Identify legitimate:

• Risks
• Trade-offs
• Costs
• Implementation challenges
• Fiduciary considerations
• Alternative approaches
• Reasons a sponsor might reasonably decide not to proceed

Be candid. Do not simply agree with my recommendation.

4. Narrative Improvements

Review my presentation, recommendation, or talking points and identify the five biggest weaknesses in my story.

For each weakness:

1. Explain why it could create concern or weaken my argument.
2. Suggest a specific improvement.

Focus on making the presentation:

• Clearer
• More credible
• Less sales-oriented
• More evidence-based
• Easier for a CFO or investment committee to support

Point out where:

• Evidence is missing
• Assumptions are weak
• Claims require validation
• Arguments could be simplified
• The sponsor's perspective is not adequately addressed

5. Meeting-Ready Language

Draft the following:

60-second opening

Write a confident, practical opening statement that establishes credibility, frames the issue, and makes clear why the discussion matters to the sponsor.

Three key proof points

Identify the three strongest pieces of evidence or reasoning I should emphasize during the meeting.

If supporting evidence is not available from the information provided, identify what I should validate using “To Confirm” rather than inventing proof points.

Three phrases to avoid

Identify wording that could sound exaggerated, overly promotional, defensive, or weaken my credibility.

For each phrase, suggest a better alternative.

Closing statement

Write a concise closing that summarizes the recommendation without overselling it and naturally leads to discussion, questions, and agreed next steps.

Tone & Writing Style

• Candid and constructive
• Practical and commercially realistic
• Fiduciary-aware
• Committee ready
• Executive-level communication
• Clear and concise
• Challenge my thinking rather than validating it
• Acknowledge legitimate risks and trade-offs
• Focus on making me better prepared for difficult conversations with plan sponsors and investment committees

Open a prompt, review the guidance, then copy and paste it into your approved AI tool. Add your own context or documents before generating a response.

No. Some prompts only require a topic or question, while others work best with supporting documents such as meeting notes, white papers, or plan data.

Consult with your firm’s compliance department to confirm which AI tools are permitted for use in accordance with your organization’s policies and guidelines. The best tool depends on the task and your firm's guidance.

Only use approved enterprise AI tools. Never upload confidential client information or proprietary documents unless permitted by your firm's policies and compliance guidelines.