Episode 59: How to Ask for Anything Without Sounding Difficult with Dethra Giles episode artwork

EPISODE · Mar 31, 2026 · 33 MIN

Episode 59: How to Ask for Anything Without Sounding Difficult with Dethra Giles

from In Confidence with Lisa Sun: A Gravitas Podcast · host Lisa Sun

Have you ever stayed quiet in a meeting because you were worried about how your pushback would land? Or stayed silent about something you deserved because you did not want to rock the boat? That fear of being labeled difficult is costing you more than you think.   In this episode of In Confidence, Lisa sits down with HR expert, four-time TEDx speaker, and author Dethra Giles to solve one of the most requested challenges from our community: how to ask for more at work without sounding difficult.   Dethra shares her D.A.R.E. model, a four-step framework for conversational intelligence that works whether you are making a big ask, disagreeing in a meeting, or negotiating your way through a no. In this episode you will learn: Why capable, accomplished people shrink instead of speak up How to push back and disagree at work without blowing up the relationship Why no is not the end of the conversation, it is the start of a negotiation How to ask for a promotion, a project, or an opportunity by leading with value The one thing you should build right now to ask for anything with confidence If self-advocacy, workplace communication, and conflict management are areas you are working on, this episode will change how you show up tomorrow.   Download our free PDF: How to Ask for Anything Without Sounding Difficult   Learn more from Dethra Giles: https://www.dethragiles.org/   Get That's Not What I Said: https://www.dethragiles.org/book-me   00:00 Intro 02:04 Meet Dethra Giles 07:39 How to Ask for Something Without Sounding Difficult 11:09 Dethra's D.A.R.E. Model 12:07 How to Push Back Without Starting an Argument 13:07 Live D.A.R.E Walkthrough 18:47 How to Ask for Something Without Sounding Entitled 25:23 When You Hear No 28:15 Three Things to do Tomorrow 31:34 Lisa's Power Move and Shoutout   Connect With Us So You Never Miss a Moment of Inspiration:      Visit Our Website      Get Our Best-Selling Book in Paperback      Follow Gravitas on Instagram      Follow Lisa on Instagram      Connect with Lisa on LinkedIn      Follow Gravitas on TikTok    Follow Gravitas on Substack    Suggestions or Questions? Email Us.   

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Episode 59: How to Ask for Anything Without Sounding Difficult with Dethra Giles

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