Ashley Haynes-Gaspar

Living each day to learn

Microsoft COO for U.S. Industry & Business Applications Ashley Haynes-Gaspar shares how a growth mindset informs her leadership.

For Ashley Haynes-Gaspar (BSBA ’99), learning wasn’t just something she did in school – it was woven into every day of her life. Growing up with a business-leader father, Haynes-Gaspar jokes that she was the only 5-year-old with a three-year plan.

“Growing up, my dad poured deeply into who I was,” she said. “His philosophy was that every day was meant to be lived to learn something.”

Haynes-Gaspar and her father would hold “nugget sessions” where they would discuss everything from leadership to the latest campaigns he was working on in his role in sales or marketing. It was in these moments that Haynes-Gaspar developed her passion for both life-long learning and marketing.

At the University of Florida, Haynes-Gaspar was able to further her knowledge in marketing while completing her bachelor’s degree in business.

“I enjoyed embracing the duality of marketing,” she said. “It’s both deeply analytical and creative.”

Choosing to attend UF was a “head and heart” decision for Haynes-Gaspar.

“I’m deeply biased, but I think that UF is the best university academically in the state of Florida and even in the South,” she said. “I grew up going to game days on Saturdays because my brother was a cheerleader. That intersection of academics and atmosphere was the perfect combination.”

As a student in UF’s business school, Haynes-Gaspar recalls the great friendships she made as a member of the business fraternity Alpha Kappa Psi and the impactful lessons from Professor Emeritus Joel Cohen, who she kept in touch with after graduating, and Huber Hurst Professor Robert Emerson, the business law professor many will recall for his costumes, as Haynes-Gaspar does.

“[Dr. Emerson’s] ability to walk so authentically in who he was, was deeply inspiring,” she said.

Beyond the great friendships and business insights she gained at UF, Haynes-Gaspar recalls the special magic of campus.

“It sounds cheesy, but I loved the way the wind whispers through the beautiful oak trees and the moss,” she recalled. “As someone who’s from the South but has since moved away, that is something that I truly miss.”

Moving away from Gainesville after she graduated from UF gave Haynes-Gaspar plenty of special, new experiences, though. Her non-traditional career path led her to live in 27 different countries and 15 states in roles that range from CMO to COO and in fields from marketing to finance to operations. Despite the constant change in her career, she has grown from every opportunity.

“I love each experience for what it taught me,” she said. “Each role made me the leader I am today.”

In her current role as COO of U.S. Industry & Business Applications at Microsoft, Haynes-Gaspar leads a team that drives growth for the technology company. Having served in this role for the past five years, Haynes-Gaspar notes that the most powerful thing that COOs can do to serve their team is to lead across three time horizons. She simply calls these the “Ts and Ds.”

First, is “time to dream,” which is a combination of disciplined thinking and dreaming of what could be.

“Over the next three to five years, what do we need to do to be successful?” she describes. “What should we start or stop doing today to meet the demands of tomorrow?”

Second, is “time to think,” which Haynes-Gaspar describes as contemplating what the COO can do this year to deliver results.

Lastly is “time to do,” which is focused on pure execution in the short term, like what needs to happen to accomplish goals by the end of the quarter or month.

“COOs and leaders can get trapped in the time to do,” Haynes-Gaspar warns.

As someone who has struggled with perfectionism throughout her career, Haynes-Gaspar understands that getting trapped in the “time to do” won’t lead the team forward.

“[Perfectionism] is an unobtainable yet deeply seductive goal,” she said. “But having a growth mindset helps you keep perspective. You have to think ‘Will this matter a day, week, month or year from now?’ Learn to let it go.”

The growth mindset has also helped Haynes-Gaspar through some of her most challenging career moments. One of her most significant pieces of career advice stems from what she describes as “a very tough 18 months of my life” working under a bad leader.

“I had a leader who was arrogant and deeply demanding,” she recalled. “While I am beyond grateful for the experience, I wouldn’t want to relive it. It was a moment in my life that was there to teach me about emotional boundaries.”

From the experience, Haynes-Gaspar learned not to let others influence how she feels.

“You have to learn not to metabolize others’ development opportunities as your own,” she said. “In my situation, I believed it was about me. It wasn’t. He had work he needed to do on himself. I don’t own that. I get to choose how I feel about who I am and what I bring to the table.

“It’s important to not let broken people make you play small.”

While she can freely share about the experience now, at one point, revisiting her period with the bad leader was hard. Over time, though, she learned that being vulnerable is one of the greatest expressions of courage.

“There was a point where the experience felt deeply personal,” she said. “I have found freedom in talking about it. Being vulnerable isn’t a weakness, it’s the greatest call to courage. Through the process of being vulnerable, you can help others grow.”

Haynes-Gaspar brings that mentality to her team at Microsoft through a program called “Practicing Us,” in which the team gathers to learn and practice principles around inclusion, self-development and growth.

“These can be tough sessions, but unless we make peace with the hard things in our lives, then they will continue to inform how we lead,” she said. “Our inside game runs our outside game.”

While many of the insights that Haynes-Gaspar has gained over the course of her career come from personal experiences, she also actively seeks out new advice on how to be a better leader. In her time outside of the office, the self-described Brené Brown superfan loves reading and listening to podcasts.

She’s also on a mission to learn from others through international connections. With a goal to travel to 60 countries by age 50, she’s getting close to reaching that objective with upcoming trips to Chile and Argentina, countries 57 and 58.

When she’s not continuing to expand her own knowledge, Hayne-Gaspar is doing roller-skating “jam sessions” with her daughter and likely sharing in their own “nugget sessions” along the way.