Learning from the Best: Scott Galloway & Kara Swisher on Negotiation Insights

Last week I (Alex) was listening to one of my favorite podcasts, Pivot hosted by Kara Swisher and Scott Galloway, and I did a double take when they shared a...

Hi there,

Last week I (Alex) was listening to one of my favorite podcasts, Pivot hosted by Kara Swisher and Scott Galloway, and I did a double take when they shared a question from a listener about workplace negotiations (though not specific to job offers).

As a huge fan of Scott Galloway and Kara Swisher, I was very keen to hear what they have to say about our favorite topic. In their October 25th episode, they dove into the art of negotiation on their podcast, and it was great to hear that the advice they gave largely echoes what we share with you! We want to unpack some of their best tips, add a few of our own insights, and bring them into the job-offer context.

🕶️ 1. Show you’re willing to walk (without announcing it!)

One of Scott’s most compelling points was about showing the other side that you’re willing to walk away. We generally agree, but when it comes to negotiating a job offer, it’s not about explicitly saying, “I’ll walk.” Rather, you want to tactfully demonstrate that you have options and that you’re desirable in the market.

This might look like sharing that you have other offers or are at least interviewing with multiple companies (but remember not to share anything about those companies, which we addressed in a previous issue). Building that quiet leverage speaks volumes—and often, it’s the key to landing a stronger offer without a standoff.

🤝 2. Negotiations as collaborative problem-solving

Kara and Scott both emphasized that a good negotiation doesn’t need to feel like a zero-sum game where one side wins or gets more than the other. Instead, approach it as a collaborative effort and you can make much faster progress. This is especially useful when negotiating salary or work flexibility. Opening with, “I’d love for this to be mutually beneficial; let’s find a way to make it work for both of us,” sets a positive tone and keeps the other side more open to creative solutions.

Companies also want to hire people who want to work there. So if you position the negotiation as being on the same side rather than strong-arming them into giving you what you want, it strengthens your candidacy (and yes, you’re still being evaluated, even after receiving an offer). On the other hand, when a candidate uses their upper hand (such as having another competitive offer) in an arrogant way, their offer is at risk even if they’re the top candidate.

🎧 3. Listening is underrated—especially as a technique to avoid oversharing

One of our favorite takeaways was the value Scott and Kara place on active listening. Just by listening well and reflecting back what you heard, you can build instant rapport. In practice, this could sound like, “I understand the budget is a concern—let’s explore some options that fit.” We’ve seen it time and time again: people respond well to feeling understood, and that understanding paves the way for better outcomes.

Our spin on this is to use what you hear during active listening to avoid oversharing information that may hurt your negotiation leverage. For example, the company may say, “We posted the salary range on the job description, does that range work for you?” Our advice is to avoid sharing a number or a range, and avoid even confirming that a number or range works for you. So a combination of active listening and not oversharing would look like, “I did see the salary range, thank you! What is your total budget for this role, not just for the salary?”

💼 4. Leave something for the other side

Scott shared that sometimes, it’s wise to leave a little “on the table.” While it might seem counterintuitive, small concessions build goodwill and set the stage for future opportunities. In a job negotiation, this could look like showing flexibility on start dates or adjusting a minor perk. You can figure out what concessions you’re willing to give by making a list of your personal priorities ordered in importance to you. Negotiate your non-negotiables and top priorities first, and consider offering up concessions lower down your list that are less important to you. In the end, your reputation as a fair and professional negotiator will make others want to work with you again.

Bringing it all together

Whether you’re negotiating a new role, a raise, or even making personal agreements, there’s much to take away from Scott and Kara’s negotiation advice, with a bit of adaptation.

If you’re looking to apply these strategies to an upcoming negotiation, we’re here to help with ideas that set you up for success. Reply back here if you have any follow-up questions or thoughts!

Best,
Gerta & Alex
Co-founders of YourNegotiations.com​