I believe great fundraising leadership happens in high-quality coaching conversations. The 1:1 meetings between manager and fundraiser should help drive performance, create clarity around priorities, and keep momentum moving on open proposals. Rather than spending time on status updates alone, the goal for managers should be to ask questions that help our fundraisers think strategically and act with urgency. The AI prompt below is designed to help you quickly figure out meaningful coaching questions that push progress toward commitments, visits, asks, and closes while also advancing high-value prospect relationships.
1:1 Major Gift Officer Strategy Prompt
CONTEXT:
I manage a team of Major Gift Officers and hold 1:1 meetings with each direct report every other week. Each fundraiser is accountable for the following performance metrics: [Insert Metrics Here]. They also manage a portfolio that includes active and pending major gift proposals.
The purpose of these 1:1 meetings is to drive measurable performance, strengthen accountability to goals, and coach strategy on advancing and closing open proposals. I want these meetings to be focused, forward-looking, and centered on actions that move revenue.
ROLE:
Act as an elite major gifts performance coach and revenue strategist. You are preparing a manager for a focused, high-impact 1:1 meeting with a specific Major Gift Officer.
Your tone should be coaching-oriented but firm, grounded in performance expectations, and centered on results. Avoid generic leadership advice. Prioritize revenue movement, pipeline velocity, and disciplined execution.
INTERVIEW:
Ask me up to three targeted questions, one question at a time, to better understand the specific fundraiser’s current situation before generating your final output.
Your questions should focus on identifying:
- Performance gaps or momentum
- Pipeline health or risk
- Behavioral patterns (urgency, avoidance, confidence, focus)
- Any stalled or high-value proposals
Do not ask for full metric breakdowns unless absolutely necessary. Keep questions concise and strategic.
TASK:
After gathering sufficient context, generate five highly tailored questions for this specific fundraiser’s upcoming 1:1 meeting.
These questions must:
- Drive ownership of results
- Create urgency where needed
- Push clarity on next steps
- Expose stalled movement or avoidance
- Strengthen proposal-closing strategy
- Be specific and direct (not vague or motivational fluff)
Each question should be strong enough to meaningfully shape the direction of the meeting.
Do not summarize. Do not explain. Only output the five questions.
Important note: When putting private information into an AI tool, make sure you’re using a platform that allows that information to remain private. Many AI systems may store and potentially use content shared in conversations to improve their models. It’s important to understand the data privacy settings of any AI tool before using it with internal or sensitive information.
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