Picture this: It’s 2 a.m. and you’re wide awake, mentally rehearsing tomorrow’s salary conversation for the fifteenth time.
Your stomach tightens at the thought of asking for more.
“There are people who will be up nights on end stressed about asking for a raise,” explains Bob Bordone, who taught negotiation for 21 years at Harvard Law School.
“What if they say no? Am I being too bold? Maybe I don’t deserve this.”
Meanwhile, across town, another professional sleeps soundly, confident about making the exact same request tomorrow.
The difference between you and them isn’t skill, experience, or contribution — it’s your approach to difficult conversations.
And this difference can literally cost you hundreds of thousands of dollars over your career.
Most people leave staggering amounts of money on the table by avoiding negotiations.
Even a modest 5 percent increase on a $75,000 salary compounds to nearly $20,000 in additional earnings over just five years, assuming standard 3 percent annual increases apply to your new baseline.
(Technically, it compounds to $19,909 in five years. Oh, and 26 cents.)
The math clearly shows the compounding impact of negotiation avoidance.
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So what should we do?
First, listen and learn.
“One of the most counterintuitive but critical skills for great negotiators are good listeners,” Bordone said on the podcast.
“To be a great negotiator, you need to frame choices for the other side that are easy for them to say yes to. And the best way to do that is to understand them.”
This flips the script on how we view asking for more money.
Instead of an awkward confrontation where someone wins and someone loses, you’re creating a collaborative problem-solving session.
Great negotiators don’t see themselves in a zero-sum game—they’re looking for creative solutions that satisfy everyone’s core needs.
When you approach negotiations this way, you’re not trying to “defeat” your boss or squeeze every last dollar from the company budget.
You’re finding the sweet spot where your contributions are properly valued while addressing the company’s priorities.
This mindset shift alone dramatically improves your chances of success.
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So how exactly do you prepare for these high-stakes conversations?
Bordone breaks down a practical, three-step system that’s helped countless professionals walk away with bigger paychecks:
Mirror Work: Identify the different sides of yourself in the negotiation — the empathic side that understands company constraints, the assertive side that knows your contributions deserve recognition, and perhaps an anxious side worried about finances.
Chair Work: Give each side a voice through role-playing exercises.
“The physicality of it is really powerful,” Bordone said. “I’ll say, let’s set up three chairs. I want you to go back and forth in each of these chairs and have the chairs have a conversation with each other.”
(In our still-under-development course, Your Next Raise, we feature many role-playing exercises and peer-to-peer practice sessions … more details on that below).
Table Work: Bring these voices into the actual negotiation. When you acknowledge both your hesitation and your conviction, you create a nuanced and compelling case.
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Try these tactical approaches when you face difficult conversations:
Use the “Wizard of Oz tactic”: Recognize when bosses use one-liners like “come back to me December 1st” to end conversations quickly. Don’t accept these at face value.
Reframe “company policy”: When your boss says “that’s our policy,” don’t just accept it. Ask what problem the policy solves. Then ask how else you might be able to achieve this same solution.
Your goal is to transform the conversation from a dead end into a problem-solving discussion.
Understand conflict recognition thresholds: People have different sensitivities to disagreement. What feels like healthy debate to you might feel like intense conflict to your boss.
“Are you going to do this for every single negotiation in your life? Probably not,” Bordone said.
“But if it’s something like a raise that’s been haunting you… it might be worth the prep.”
On top of that —
What you learn from negotiating a raise doesn’t just boost your paycheck — it helps with every big-money conversation in your life:
Real Estate: Negotiating just 3 percent off a $400,000 home purchase saves $12,000 upfront and thousands more in interest over the life of a mortgage.
Business Deals: Whether you’re pitching investors for your startup or haggling with vendors, sharper negotiation skills directly boost your bottom line.
Family Dynamics: From settling family inheritance questions to managing household budget priorities, these same skills help you protect both your relationships and your wallet.
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Beyond immediate financial gain, developing negotiation skills also builds “conflict resilience” — the ability to navigate disagreement without avoidance or aggression.
“If you’re thinking about it a lot, if you’re talking to your friends about it a lot, if you’re venting at your book club about it a lot, then there’s something there,” Bordone said.
“That probably says it is at least important enough to spend some more time strategizing on what you might do than just saying, ‘Oh, well, they suck.’”
And if you’re negotiating, then you’re in a position of power.
Bordone explains:
“The fact that they’re in that interaction with you means that you have some power in that, and you have some agency in that, and you have some ability to speak and persuade and be heard.
“And anyone who tells you otherwise is wrong.”
Watch the full interview on YouTube.
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