What if the key to unlocking better deals, stronger relationships, and greater confidence in negotiations was simply... asking better questions?
In this episode, we’re joined by Linda Swindling, internationally recognized negotiation expert and author of Ask Outrageously! The Secret to Getting What You Really Want. Linda brings a rare combination of legal insight, executive coaching experience, and practical negotiation wisdom to the table. Together we'll discuss why questions are your most underrated negotiation tool.
We begin by tracing Linda’s professional journey from a prospective lawyer to a negotiation professor and disucss how her legal training shaped her unique perspective on high-stakes communication. She shares the moment she realized that asking boldly, strategically, even outrageously, was the secret sauce behind successful negotiations.
From there, we dig deep into the psychology of asking: what makes certain questions effective, why some questions are avoided even when they could change the outcome, and how different types of questions: open-ended, probing, reflective, and more, can be used to guide conversations, diffuse tension, and uncover hidden opportunities.
Throughout the episode, Linda explains why questions are often more powerful than statements in negotiation, and how understanding the purpose and impact of a question can dramatically shift the direction of a deal. She reveals when and how to use specific types of questions at different stages of the negotiation process, helping you build rapport, uncover needs, and drive outcomes with intention. She also unpacks what it truly means to “ask outrageously,” not recklessly, but courageously and unapologetically, and shares how this mindset has helped her clients and audiences achieve unexpected wins.
Linda also highlights the common mistakes professionals make when crafting questions, such as asking too timidly, leading with assumptions, or failing to listen to the answers. She provides clear strategies to avoid these pitfalls and offers practical tools for developing stronger questioning techniques.
Reflecting on her career, she recounts one of the most challenging negotiations she ever faced and how the strategic use of questions became the turning point in its resolution. For those hesitant to speak up or afraid of asking the "wrong" question, Linda offers empowering advice to reframe their mindset and step into conversations with confidence.
To close the episode, Linda shares her top recommendation for anyone looking to level up their negotiation game: adopt one essential practice related to questioning that can make all the difference. She also suggests a few exercises and resources for professionals who want to refine their skills and start asking more purposefully today.
Whether you're negotiating a raise, a contract, or your next big career move, this conversation will equip you with tools to ask with more clarity, confidence, and courage.
Here are the links to free material on Linda's website (Code "TNC"):
- How well do you ask - https://www.lindasentme.com/ASK/quiz1/registerask.php
- What's Their DEAL Style? https://www.lindasentme.com/theirdeal/registertheirdeal.php
- What's My DEAL? https://www.lindasentme.com/deal/registerdeal.php