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Challenge ideas with probing questions

Uncover blind spots and test reasoning with 2-3 critical questions.

Challenge ideas with probing questions preview

When to use this

  • Identify unstated assumptions before they undermine your argument
  • Test the strength of your reasoning before presenting
  • Explore implications and consequences you haven't considered

Quick guide

1.Select the text you want to challenge
2.Press ⌘⇧M → Question
3.Review the questions and insights provided
Challenge ideas with probing questions demo

Pro tips

Run it on your own drafts before sharing with stakeholders

Chain with Counter to get opposing viewpoints

Best for arguments and proposals that need stress-testing

Why questioning matters

Strong ideas survive scrutiny. The Question tool generates 2-3 thought-provoking questions that challenge the assumptions, reasoning, or implications of any text.

Each question comes with a concise answer that explains the challenge or offers insight, helping you think more deeply about your work.

Common use cases

  • Before presenting: Test your argument for logical gaps or weak points
  • Strategic decisions: Explore consequences and alternatives you haven't considered
  • Research review: Identify unstated assumptions in studies or papers
  • Draft feedback: Find blind spots in your writing before sharing

Question types you'll get

Assumptions: What unstated beliefs or biases does this rely on? Evidence: Is the logic sound? Is the data sufficient? Consequences: What are the implications, limitations, or alternative interpretations?

How the Q&A format helps

Unlike simple critique, each question includes a short answer explaining why it matters. This helps you:

  • Understand the challenge immediately
  • See what you might be missing
  • Decide which points need strengthening

Best practices

Use Question on content that makes claims or arguments. The more specific your selection, the more targeted the questions.

For comprehensive analysis:

  1. Start with Question to identify weak points
  2. Use Counter to see opposing viewpoints
  3. Follow with Evaluate for a full logical assessment

Run it on your own work before stakeholder review. It's better to find gaps yourself than to be caught off-guard in a meeting.

Related reading

Ready to try it yourself?

Download Criticly and start using this workflow today on your Mac.

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