Author: Daniel Koger

Sometimes the most useful response from AI is not agreement.

When we develop an idea, make a decision, or reach a conclusion, it is easy to focus on the information that supports what we already think.

I use AI to help me look at the other side.

Instead of asking:

“Help me make the case for this.”

Try asking:

“What might I be missing or getting wrong?”

AI can help you look at your idea from another perspective—not to prove you wrong, but to help you test whether your reasoning holds up.

The goal is not to let AI make the decision for you. The goal is to challenge your thinking before you act on it.

Sample Prompt

Remember: the information inside square brackets [ ] is for you to replace with information specific to your situation.

<prompt>
I am considering the following [idea, decision, conclusion, or approach]:
[Describe what you are considering and why.]
Before helping me strengthen it, challenge my thinking.
Consider whether:
- I am making assumptions that may not be correct.
- There are reasonable arguments or perspectives I have not considered.
- Important information may be missing.
- There are circumstances where my conclusion or approach may not work.
- Additional evidence could cause me to reconsider my conclusion.
Identify the strongest reasonable challenges to my thinking.
For each challenge:
1. Explain why it matters.
2. Distinguish established facts from assumptions or speculation.
3. Identify what additional information or evidence would help evaluate it.
Do not challenge my thinking simply for the sake of disagreeing. Focus on reasonable concerns that could affect my decision or conclusion.
Do not invent evidence or present speculation as fact. If something requires verification, identify it clearly.
I will evaluate the challenges and decide whether they should change my thinking.
</prompt>

Why This Works

It is easy to use AI to strengthen an idea you already have. The problem is that AI may simply become better at supporting the conclusion you gave it.

This prompt asks AI to do something different: look for reasonable reasons your thinking may be incomplete.

It can help you:

• Question assumptions you may be making.
• Consider other reasonable perspectives.
• Identify information that may be missing.
• Recognize circumstances where your approach may not work.
• Determine what additional evidence could affect your conclusion.

The goal is not to generate disagreement. It is to give your reasoning another test before you rely on it.

Before You Use the Results

Not every challenge AI identifies will be valid or important.

Review the response and determine which concerns actually apply to your situation. Verify factual claims using appropriate source material or an expert, especially when the information could materially affect your decision.

You do not need to change your conclusion simply because AI challenged it. A good challenge may strengthen your original conclusion, cause you to modify it, or show you that you need more information before deciding.

AI can help challenge your reasoning. You remain responsible for evaluating the evidence and making the decision.

Next in This Series

Why Context Changes the Answer

Our next article moves beyond individual prompts to explore techniques for getting more reliable AI results.

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You can spend a lot of time developing a plan and still miss something important.

I have run into this myself. When you have been working on something for a while, you know what you meant. You understand the background, the assumptions you made, and the things you have already considered. That can make it difficult to recognize what you haven’t explained—or what you may have overlooked.

It is one reason I have created specialized GPTs in the past—to give me another set of eyes.

But you don’t need to create a GPT to get that benefit.

Sometimes a simple prompt is enough:

“What important questions have I not answered?”

The goal is not for AI to fill in the missing information. It is to help you recognize what may still need your attention.

Sample Prompt

Remember: the information inside square brackets [ ] is for you to replace with information specific to your situation.

<prompt>
Review the following [plan, document, idea, or proposal].
Identify important questions I may not have answered.
Look for:
- Information that is unclear or missing
- Assumptions I may be making
- Decisions that have not been made
- People or groups that may be affected
- Constraints or dependencies I may have overlooked
- Exceptions or situations I may not have considered
Organize the questions by category.
For each question:
1. Explain briefly why it matters.
2. Identify the relevant section or statement, if available.
3. Indicate whether the information is missing, unclear, or based on an assumption.
Do not answer the questions by making assumptions.
If the information is already provided, point me to it rather than identifying it as a gap.
Do not invent problems or treat every possible question as equally important.
I will decide which questions require further investigation or action.
Material to review:
[Paste your plan, document, idea, or proposal here]
</prompt>

Why This Works

This prompt asks AI to look for what may be missing, rather than simply summarizing what is already there.

It can help you:

• See assumptions that may not be obvious to someone else.
• Identify decisions or information that are still missing.
• Recognize people, constraints, or situations you may have overlooked.
• Turn potential gaps into questions you can investigate.

Most importantly, the prompt tells AI not to fill in the gaps by making assumptions.

Organizing the questions by category can also make the results easier to evaluate, particularly when reviewing a lengthy document or complex proposal.

Before You Use the Results

Review each question and decide whether it is actually relevant.

AI may identify something that you have already considered, something that does not apply to your situation, or something that simply is not important.

If a question does reveal a real gap, determine what information you need and verify the answer using appropriate source material or an expert.

AI can help identify questions you may have missed. You remain responsible for deciding which questions matter and how they should be answered.

Next in This Series

A Prompt to Challenge Your Thinking

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Meeting notes can capture good ideas, decisions, and follow-up items, but they do not automatically become a useful action plan.

A common approach is to give AI a set of notes and ask, “What should we do next?” The problem is that AI may turn discussion points into decisions, assign owners who were never assigned, or invent dates that were never agreed upon.

A better prompt asks AI to organize what is already in the notes while keeping missing information visible.

Sample Prompt

Remember: the information inside square brackets [ ] is for you to replace with information specific to your situation.

<prompt>
Review these meeting notes and turn them into an action plan for [team or audience].
Organize the agreed actions into a table with these columns:
- Action
- Owner
- Target date
- Dependencies or prerequisites
- Supporting evidence from the notes
Use only actions that were clearly agreed upon.
Do not turn suggestions or discussion points into decisions. Do not assign an owner or date unless one appears in the notes.
If an owner, date, or other important detail is missing, label it "Not specified."
After the action table, provide separate sections for:
1. Decisions that still need to be made
2. Suggestions or ideas that were discussed but not agreed upon
3. Questions requiring follow-up
At the end, identify the items that need clarification before the action plan is complete.
Do not invent details. Where possible, use a brief quotation or note reference to show what supports each action.
Meeting notes:
[Paste meeting notes here]
</prompt>

Why This Prompt Works

• It separates agreed actions from ideas that were only discussed.
• It preserves owners and dates when they are actually stated.
• It makes missing information visible instead of allowing AI to fill the gaps.
• It provides supporting evidence so team members can verify the proposed actions.
• It turns unstructured notes into something a team can review and use.

Before You Use the Action Plan

• Compare the actions and decisions with the original notes.
• Confirm that owners and dates were actually stated rather than inferred.
• Check that an important dependency, qualification, or unresolved question was not lost.
• Review the items marked “Not specified” with the appropriate team members.

AI can organize the work, but the people involved remain responsible for confirming what was actually decided.

Next in This Series

A Prompt to Find Gaps and Unanswered Questions

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Learn More

OpenAI Prompting Best Practices

Have you ever been shopping and narrowed your choice down to two products?

You could ask AI:

“Which one is better?”

But better depends on what matters to you.

Suppose you are shopping for a night light. You have found two that you like, but you are having trouble deciding between them.

Instead of asking AI to make the decision, tell it what matters to you and ask it to compare the products using those criteria.

Sample Prompt

Remember: the information inside square brackets [ ] is for you to replace with information specific to your situation.

<prompt>
I am considering these two night lights:
Night Light 1: [paste product name or link]
Night Light 2: [paste product name or link]
Compare them based on:
- Price
- Brightness in lumens
- Expected useful life
- Design and appearance
- Additional functionality
Use the same criteria for both products.
If information for either product is unavailable,
tell me it is unavailable rather than
making an assumption.
Summarize the important differences,
but do not choose one for me.
</prompt>

Why This Works

The question is no longer simply, “Which one is better?”

You have told AI what better means to you.

The same technique works when comparing computers, appliances, software, insurance plans, contractors, or other choices.

The criteria will change, but the principle remains the same:

Compare both options using the same criteria.

AI can help you understand the differences. You decide which differences matter.

Before You Make a Decision

AI may not have complete or current information about the products or services being compared.

Verify important specifications, prices, and other claims against reliable sources before making a purchase or commitment.

Next in This Series

A Prompt to Turn Notes into an Action Plan

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Technical information is often written for people who already understand the subject. It may include specialized terminology, implementation details, acronyms, and assumptions that are familiar to the technical team.

A business audience usually needs the same facts presented from a different perspective.

They may need to understand:

• Why the subject matters
• How it affects the organization
• What risks or opportunities are involved
• What decisions need to be made
• What actions should happen next

Simply asking AI to “make this less technical” can create a problem. Important qualifications, constraints, and risks may disappear along with the technical language.

A better prompt defines what may change and what must be preserved.

In the sample prompt below, text enclosed in square brackets [ ] represents information you should replace with details specific to your request.

For example, replace [business audience] with the intended readers, such as senior executives, project managers, or department leaders. Replace [desired length] with a limit such as 200 words, one page, or five brief paragraphs.

Sample Prompt

Rewrite the following technical content for [business audience].

The revised version should help the readers understand the business purpose, organizational impact, risks, decisions, and required actions.

Use clear business language. Replace unnecessary jargon and acronyms with plain language. When a technical term is necessary, explain it briefly.

Preserve:

• Facts and conclusions
• Requirements and constraints
• Risks and dependencies
• Names, dates, amounts, and measurements
• Important qualifications and exceptions
• Decisions that have already been made

Do not introduce benefits, conclusions, or recommendations that are not supported by the original content.

If the source contains an unclear statement or an undefined technical term, identify it rather than guessing what it means.

Organize the response into:

1. Business Purpose
2. Business Impact
3. Risks and Dependencies
4. Decisions Needed
5. Recommended Next Steps
6. Questions Requiring Clarification

Limit the response to [desired length].

Before completing the response, compare it with the original and confirm that simplifying the language did not change the meaning.

AI can help translate technical language, but the subject-matter expert remains responsible for confirming that the translation is accurate.

Example Prompt

<prompt>
Rewrite the following technical content for
[business audience].
The revised version should help readers understand
the business purpose, organizational impact, risks,
decisions, and required actions.
Use clear business language. Replace unnecessary
jargon and acronyms with plain language. Explain
technical terms briefly when they are necessary.
Preserve:
- Facts and conclusions
- Requirements and constraints
- Risks and dependencies
- Names, dates, amounts, and measurements
- Important qualifications and exceptions
- Decisions that have already been made
Do not introduce benefits, conclusions, or
recommendations unsupported by the original content.
If a statement is unclear or a technical term is
undefined, identify it rather than guessing.
Organize the response into:
1. Business Purpose
2. Business Impact
3. Risks and Dependencies
4. Decisions Needed
5. Recommended Next Steps
6. Questions Requiring Clarification
Limit the response to [desired length].
Before completing the response, compare the result
with the original and confirm that simplifying the
language has not changed its meaning.
Technical content:
[Insert content approved for use with the AI tool]
</prompt>

Next in This Series

A Prompt to Compare Two Options

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A long document can contain valuable information, but finding its purpose, decisions, risks, and open questions can take time.

A common first attempt is simply to ask AI, “Summarize this document.” That may produce a useful result, but the instruction leaves an important question unanswered: useful to whom, and for what purpose?

A better prompt tells AI what to preserve, how to organize the answer, and where uncertainty must remain visible.

Sample Prompt

Read the attached document and prepare a concise summary for [audience].

Include:

• The document’s purpose
• Its major conclusions or findings
• Decisions that have already been made
• Significant risks or issues
• Action items, owners, and dates stated in the document
• Unresolved questions or decisions still needed

Separate facts stated in the document from any inferences you make. Do not add information that is not supported by the document. If something is unclear or missing, say so. When possible, identify the page or section that supports each major point.

Limit the summary to [desired length] and use clear headings and bullets.

Why This Prompt Works

• It identifies the audience, which helps determine vocabulary and level of detail.
• It defines the information that should survive the compression.
• It separates documented facts from AI inferences.
• It asks AI to expose missing or unclear information instead of quietly filling gaps.
• It requests source locations so important statements are easier to verify.

Before You Use the Summary

• Confirm that the document is appropriate to submit in the AI environment you are using.
• Compare important conclusions, decisions, names, amounts, and dates with the original document.
• Check whether the summary omitted an exception, qualification, or unresolved issue that matters to the reader.

AI can shorten the reading process, but it does not remove the need to read the source when the decision matters.

Example Prompt

<prompt>
Read the attached document and prepare a concise summary for an executive leadership team.
The readers need to understand the document well enough to discuss its implications and determine whether any decisions or follow-up actions are required. Use business language and explain technical terms only when they are necessary to understand the conclusions.
Include:
- The document's purpose
- Its major conclusions or findings
- Decisions that have already been made
- Significant risks, concerns, or dependencies
- Action items, including any owners and dates stated in the document
- Unresolved questions or decisions still needed
Separate your response into the following sections:
1. Executive Summary
2. Major Conclusions
3. Decisions Already Made
4. Risks and Concerns
5. Action Items
6. Unresolved Questions
Separate facts stated in the document from any inferences you make. Label each inference clearly.
Do not add information that is not supported by the document. If information is missing, contradictory, or unclear, identify the issue instead of attempting to fill the gap.
When possible, provide the page number or section heading that supports each major conclusion, decision, risk, and action item.
Limit the response to approximately one page. Use concise language, clear headings, and bullets where appropriate.
Before completing the response, verify that names, dates, amounts, decisions, and assigned responsibilities agree with the source document.
</prompt>

Next in This Series

A Prompt to Rewrite Technical Content for a Business Audience

Reference Basis

The prompt structure reflects OpenAI guidance to provide clear instructions, relevant context, and visible boundaries between instructions and source material.

OpenAI — Prompt Engineering

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