
In Confidence with Lisa Sun: A Gravitas Podcast Episode 59: How to Ask for Anything Without Sounding Difficult with Dethra Giles
Mar 31, 2026
33:46
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
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
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