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Use Advanced Prompts for More AI Value

Last week I was at dinner with a group of executives, and of course, the topic of ChatGPT and AI came up. We went around and shared some of our favorite use cases for the technology, as well as ways w

David Cummings
See Profile
June 28, 2025

Last week I was at dinner with a group of executives, and of course, the topic of ChatGPT and AI came up. We went around and shared some of our favorite use cases for the technology, as well as ways we are experimenting with AI in our respective companies. Then I asked if anyone used existing prompts or more advanced context engineering. Not a single person did.

On the one hand, it is so powerful that you can ask questions, give it scenarios, upload documents, have it search the web, and with very little context, it quickly provides valuable answers and insights. So if you can do that with limited instructions, imagine what it can do with much longer, more detailed instructions.

That’s where prompt engineering templates come in. These are simply text—nothing more, nothing less—but by using these more comprehensive directions, you can get even more value from the AI.

Let’s look at a shared prompt example from Josh Kopelman for comparing board meeting decks. The prompt asks for two PDFs and does the following, with the output as a PDF document formatted and ready to go:

1 Snag the Numbers

Search every slide for hard metrics (ARR, revenue, burn, hires, NPS, runway, churn…).

Always show Prev (Actual) ➜ Curr (Target) ➜ Curr (Actual) ➜ variance.

2 What They Said vs. What They Did

List each commitment from the earlier deck (note slide). Under each, add status & note from the later deck,

3 Goal-Drift Radar

Call out any KPI whose name, definition, or cadence changed. List metrics that existed in the earlier deck but vanished in the later one.

4 Overall Verdict

• One-liner verdict with a traffic-light word (RED / YELLOW / GREEN).

• Follow with a breezy 4-to-6-bullet executive summary (≤ 150 words).

5 Rays of Sunshine & Storm Clouds

• Top 3 positives (good surprises, momentum).

• Top 3 concerns (lags, risks).

Cite slide numbers in parentheses.

6 Eight Smart Questions for the Team

Short, pointed follow-ups to close any info gaps.

Here’s the shared prompt board deck comparison prompt with the text for ChatGPT.

The overall idea is producing an experienced analyst report that might take a few hours and doing it nearly instantly with AI.

For entrepreneurs, the recommendation is to search for shared prompts online in the context of the work being done. If you’re analyzing term sheets, go online and find example prompts that do a much more detailed analysis than just a basic prompt. If you’re analyzing a partnership agreement, use the shared prompt that will give you more valuable insights. The AI results are great, and with a more advanced prompt, they’ll be even better.

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