Imagine this: It’s 2 a.m., and you find yourself wide awake, mentally going over tomorrow's salary discussion for the fifteenth time. The thought of requesting more makes your stomach churn. “There are individuals who will lie awake at night anxious about asking for a raise,” says Bob Bordone, former negotiation instructor at Harvard Law School for 21 years. “What if they reject my request? Am I being overly ambitious? Maybe I don’t deserve it.” Meanwhile, someone else in the city sleeps peacefully, assured about making the same request tomorrow. The disparity between you and them isn’t about skill, experience, or contribution — it's your attitude toward difficult conversations. This difference can potentially cost you hundreds of thousands of dollars over your career. Many people miss out on significant earnings by shying away from negotiations. A modest 5 percent salary increase on a $75,000 income can accumulate to nearly $20,000 in added earnings over just five years, provided standard 3 percent annual increases are applied to your new baseline. (Specifically, it amounts to $19,909 in five years. And 26 cents.) The calculations clearly illustrate the compounding effect of avoiding negotiations.
What can we do about it? First, listen and learn. “One of the most counterintuitive yet vital skills of successful negotiators is being good listeners,” Bordone stated on the podcast. “To excel in negotiation, you need to present choices to the other party that are easy for them to agree to. The best way to do that is to understand their perspective.” This changes the way we perceive asking for a higher salary. Instead of an uncomfortable confrontation where one party wins and the other loses, you’re fostering a collaborative problem-solving environment. Excellent negotiators don't view negotiations as a zero-sum game; they seek creative solutions that meet everyone's essential needs. When you approach negotiations with this mindset, you’re not trying to “defeat” your boss or extract every last dollar from the company’s budget. You’re working to find a balance that values your contributions while considering the company’s priorities. This shift in mindset significantly boosts your likelihood of success.
So how can you effectively prepare for these high-pressure conversations? Bordone outlines a practical three-step system that has helped numerous professionals achieve larger paychecks:
1. Mirror Work: Recognize the different aspects of yourself in negotiations—such as the empathetic side that acknowledges company limitations, the assertive side that understands your contributions deserve recognition, and perhaps an anxious side concerned about finances.
2. Chair Work: Allow each side to express itself through role-playing exercises. “The physicality of it is quite impactful,” Bordone mentioned. “I’ll suggest setting up three chairs. I want you to move back and forth between these chairs and have them engage in conversation with each other.”
(In our developing course, Your Next Raise, we’ll incorporate many role-playing exercises and peer-to-peer practice sessions… more information on that below.)
3. Table Work: Bring these internal voices into the actual negotiation. By recognizing both your doubts and your confidence, you can create a nuanced and compelling argument.
Consider these tactical strategies when confronted with difficult discussions:
✅ Utilize the “Wizard of Oz tactic”: Be aware when bosses throw out phrases like “come back to me December 1st” to quickly close conversations. Don’t take these statements at face value.
✅ Reframe “company policy”: If your boss cites “that’s our policy,” challenge it instead of simply accepting it. Ask what issue the policy addresses, and then explore alternatives to achieve the same solution.
Your aim is to transform the dialogue from a deadlock into a problem-solving conversation.
✅ Recognize varying conflict thresholds: People have differing sensitivities to disagreement. What may seem like a healthy debate to you could feel like severe conflict to your boss. Bordone advises, “Are you going to apply this strategy to every negotiation in your life? Probably not. But for something significant like a raise that’s been bothering you, it may be valuable to prepare.”
Furthermore, the lessons learned from negotiating a raise extend beyond increasing your salary — they enhance every major financial discussion in your life:
🏠 Real Estate: Negotiating just 3 percent off a $400,000 home purchase saves you $12,000 upfront and significantly reduces interest costs over a mortgage’s lifespan.
💼 Business Deals: Whether you’re seeking investment for your startup or negotiating with vendors, improved negotiation skills can positively affect your bottom line.
🍽️ Family Dynamics: These same skills can assist you in resolving family inheritance disputes or managing household budget priorities, helping safeguard both your relationships and finances.
Beyond immediate financial benefits, honing negotiation skills cultivates “conflict resilience” — the ability to manage disagreements without resorting to avoidance or aggression. “If you find yourself thinking about it constantly, discussing it with friends often, or venting about it at your book club, then there's something significant
Imagine this: It's 2 a.m. and you're fully alert, going over tomorrow's salary discussion in your mind for the fifteenth time.