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How to Confidently Ask for More Money: Proven Negotiation Strategies from Top CEOs

Negotiating for higher pay can feel intimidating, whether you're a Fortune 500 CEO closing a game-changing deal, a junior manager seeking a raise, or an entrepreneur in the YouEconomy aiming to boost profit margins. As business leaders, we constantly balance asserting the true value of our time and expertise against the risk of losing a client or opportunity. Often, the stakes loom larger in our minds than in reality.

So why don't we ask for more more often? Research reveals stark gender gaps. In a study of 78 graduate students by Linda Babcock, co-author of Women Don't Ask: Negotiation and the Gender Divide, only 12.5% of women negotiated their starting salary, compared to 52% of men. Women often fear damaging relationships or appearing too aggressive. Sheryl Sandberg, in her bestseller Lean In, highlighted studies showing women who negotiate are viewed as "harder to work with," reflecting persistent stereotypes.

A 2014 Australian study of 4,600 employees found women who ask for raises are 25% less likely to get them. Meanwhile, 15% of all participants hesitated due to relationship concerns.

In You've Got This: A Woman's Guide to Everyday Negotiation by Joanne Lipman, the author argues women often undervalue themselves due to socialization. "Men and women are wired differently," she writes. "Women are programmed from birth to value their contributions less."

Related: How to Ask for (and Get) More Money

Related: 6 Steps to Negotiating the Salary You Really Deserve

The reasons—societal norms, personal fears, biology—are multifaceted. The key? Control what you can. Whether negotiating your first salary or vendor contracts, these expert tips, drawn from decades of high-stakes deals, will empower you.

1. Start fresh. Don't anchor to past salaries, which may undervalue your current contributions. Base your ask on market value and your impact.

2. Prepare thoroughly. Schedule a dedicated meeting. Arm yourself with data: quantifiable achievements, metrics, and endorsements from supervisors, peers, and clients.

3. Own your wins. Project unshakeable confidence. Claim credit—say "I secured that major client," not "we." Ditch minimizers like "just" or "about." You landed 16 new customers and boosted efficiency by 5%—full stop.

4. Visualize success. Your mindset shapes outcomes. Rehearse the scene: your attire, setting, words, responses. Write your win in present tense, like "I now earn 12% more than last year." This primes your brain for achievement.

Related: 5 Things All Successful Negotiators Know

Real-world proof comes from these trailblazing CEOs who've mastered the art through triumphs and lessons learned:

Sarah Frey
CEO and Founder, Frey Farms; St. Louis.
From age 8, I've negotiated relentlessly. Costs rise; prices must follow. Spotting low cantaloupe stock, I pitched our fresh melons' premium value—and upsold volume. As a young woman sans degree in rooms of seasoned execs, pioneering sustainable agribusiness demanded boldness. Risk big, time it right, and align with the buyer's needs. Defend your worth fearlessly.

Maria Avgitidis
CEO, Agape Match; New York City.
Our matchmaking packages start at $25,000. Elite negotiations hinge on value: my costs, client budgets, my unique expertise attracting ideal matches, and their urgency for partnership. Frame discussions around shared value. Set expectations early, highlight your track record, and ask value-probing questions. Studies show women excel negotiating for others—channel that for yourself or a respected peer.

Angelica Terrazas
CEO and Founder, Launch LA; Los Angeles.
Corporate negotiation was my forte, but launching my entertainment venture exposed vulnerabilities sans corporate backing. Key lessons:

Maintain cool confidence. Fear is sniffed out—stay poised, articulate your unique value, and be ready to walk. No single deal defines you, but a bad one can.

Know your numbers cold. Run precise cost analyses. Present them calmly to depersonalize. If unviable, exit gracefully.

Negotiate like you sell. Pitch the 'why us' via:

  • Scarcity: "If you can't meet this, I'll explore vendors who can."
  • Dream-selling: "We're doubling revenue next year via a major contract. That unit discount is minor against your ballooning commissions."
  • Let them pitch you: "Your offering shines, but priorities X and Y loom. Help me solve them." Guide them to your ideal terms.

Related: 15 Negotiation Tips From People Who Always Get Their Way

This article originally appeared in the Summer 2019 issue of LadiesBelle I/O magazine.