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Women's Financial Empowerment

Executive and Entrepreneur Dia Simms Tells Women to Flex Their Negotiation Skills

Photo: Courtesy of Dia Simms

Dia Simms started out as Sean “Diddy” Combs’ assistant and now she’s president of his company, Combs Enterprises, whose businesses and investments portfolio includes Bad Boy Entertainment and Cîroc Ultra Premium Vodka.

“I really encourage women to flex their negotiation skills. Get comfortable being uncomfortable,” she said, noting that, in her career, it’s men, not women, who come in most often asking to negotiate or renegotiate their salaries. “Negotiation is just a conversation. Women should feel confident to go in and negotiate their worth.”

Simms encourages women to treat themselves as an individual brand and to have a map-based approach of what they bring to the table.

“Be clear about your victories and be unabashed about sharing them,” Simms said. “Approach it as ‘here are my contributions, here’s what they’re worth.’”

Establishing rules

At 43, Simms is confident in herself no matter the situation.

“It’s daunting when you’re a woman in a room that is predominantly male,” she said. “When you are different in any room, for good or for bad, there’s a different level of attention.”

Her advice to women working in a man’s world: “Make it clear what your boundaries are and establish your economic impact as quickly as possible.”


Married for 12 years, Simms and her husband have a six-year-old daughter. She wants kids to know that entrepreneurship is a career option. She says women don’t talk about it enough and thinks the ongoing conversation should start in preschool.

Simms and Combs are committed to helping the next generation, including mentoring students Grades 6-12 at two Capital Prep schools — free, public charter schools that Combs founded in Connecticut and New York City.

Women supporting women

Simms knows it’s essential for women to support other women as well.

For example, when Simms was Combs’ chief of staff, they were hiring a chef. The top candidate was a female who didn’t ask for a large enough salary. Simms advised the chef to research a better rate and to ask for more money, which she did. The chef got the job and a bigger paycheck.

“Whatever side of the desk you’re on, we need to be thoughtful of how we can support each other,” Simms said.

Kristen Castillo, [email protected]

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