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November 25, 2025 19 mins

Episode Summary:

In this milestone episode host, Ann Pearson, introduces listeners to a fresh direction for the podcast! Spoiler alert: check out the new name of the podcast show.

She dives into a topic few paralegals admit out loud: the fear of asking questions on the job. Drawing from decades of experience and countless messages from paralegals who hesitate to speak up, Ann breaks down why this fear develops, how it limits professional growth, and what it costs you in your daily work.

She also reveals an exciting behind-the-scenes project: Ann AI, a private, secure AI tool trained exclusively on her teaching materials, built to give paralegals a judgment-free place to ask anything.

Key Takeaways:

Asking questions is a performance strategy not a weakness: avoiding questions leads to more guessing, rework, anxiety, and slower professional growth. Thoughtful question asking is part of being an effective paralegal.

Ann's five-step framework to ask better questions: Look for the answer first, provide context, offer your best guess, ask for the "why" when appropriate, and group non-urgent questions together.

There is now a safe space for paralegals to ask anything: Ann AI. Ann introduces a secure, private AI trained entirely on her courses, coaching, and frameworks to help paralegals navigate challenges they may feel uncomfortable asking a person.

Get more free paralegal resources:  https://paralegal-bootcamp.com/paralegal-resources 

For all of our paralegal podcast episodes: https://paralegal-bootcamp.com/

 

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