Negotiating Your Next Career Move: Leverage, Timing, and Strategy with Debra Osofsky

What do you do when you land the job you worked toward for years and realize it still doesn’t work for your life?In this episode of The Pivot Point, I sit down with Debra Osofsky, a deeply experienced negotiator, attorney, and negotiation trainer, for a grounded conversation about making thoughtful career decisions when the path you’re on no longer fits.With more than 35 years of experience and 15 years running her own consultancy, Debra has spent her career negotiating complex agreements, advising clients on how to prepare for negotiations, and teaching professionals how to think clearly under pressure. She shares what it looked like to leave a prestigious role intentionally, without panic or financial chaos, and why taking time to work through both the emotional and practical sides of a decision matters.We talk about what it really means to be ready to walk away, how to evaluate your options before making a move, and why exploring flexibility inside your current role is often the smartest place to start. This episode is about discernment, timing, and making career decisions you can stand behind later.If you’re accomplished, capable, and quietly questioning whether your current setup still makes sense, this conversation offers perspective, language, and a steadier way forward.✔️ What a BATNA is and why it matters when you are thinking about a career move✔️ How to approach a conversation with your current employer when you are considering a pivot✔️ What it really means to be ready to walk away, and why that clarity gives you leverage even if you stay✔️ How Debra transitioned out of a prestigious role without financial chaos✔️ Why being willing to say yes before you feel ready can open unexpected doors“You are in your strongest negotiating position when you’re genuinely prepared to walk away.”If this episode gave you language for conversations you’ve been avoiding, share it with someone who needs a smarter way to approach their next move.Grab your free Heart-Aligned Career Transition Starter at👉 https://www.leadintact.com/freebies/heart-aligned-careerAnd if you want support navigating your own pivot — strategically and sustainably — book a free 20-minute call here:👉 https://leadintactwithlaura.as.me/free-consultationTo connect with Debra Osofsky, find her on LinkedIn or email her directly at [email protected] You’ll Hear Success should feel good — and make sense.