At this year’s 2025 Leadership Retreat in Washington, DC, NeW was honored to host May Mailman, Deputy Assistant to the President, mother, and attorney as the first guest speaker of the weekend. 

She offered a behind-the-scenes look at working for the Trump Administration and what it means to be a conservative woman in politics today. 

A Day in the Life at the White House 

During her speech, Mailman described Day 1 in the White House as pure chaos. “This is the craziest first day of a job you’ll ever have because the entire place quits, and an entire other [team] starts.” 

Her office, responsible for all paper going to and from the President, was printing policy drafts from the Capitol Building while also trying to organize the new staff in the West Wing. Later, she helped to create the Policies and Coordination Office to streamline this process. 

She worked on a range of executive orders and policy initiatives, highlighting her recent and most meaningful accomplishment of helping ensure the International Olympic Committee respects biological sex in its policies and protects women’s sports. 

On Being a Conservative Woman in Politics 

Mailman shared what it was like to be “out” as a conservative woman in Harvard law school before it was “acceptable.” 

“It used to be quirky,” she said. “Now it’s treated like a hate crime.” But she urged students not to retreat. “As women, you are the ambassadors for conservatism.” 

Her 6-point advice to the future leaders was inspiring and very practical: 

1. Speak up or don’t go to the meeting.
   • If you plan to contribute, you’ll stay engaged. If you don’t intend to participate, why are you even there? 
2. Be outside your comfort zone.
   • Mailman acknowledged that Covid made it easy to stay isolated but encouraged women to say yes to social settings. Networking in person often opens unexpected doors. 
3. Get advice from risk-takers.
   • Most of Mailman’s biggest opportunities often came after men encouraged her to step up. They were the ones who pushed her to try something she never considered before. 
4. Do interesting things.
   • Mailman structured her life to prioritize meaningful work, not just money. Find a supportive partner and build a life that lets you pursue purpose.” 
5. Let your work quality do your networking.
   • Don’t ask to grab coffee, Mailman said. Just be present, do great work, and people will notice. That’s how networking really happens. 
6. Fill a vacuum and be useful.
   • Rather than asking what needs to be done, be intuitive. See where something might be lacking and take charge on filling that gap.
      

Can You Really Have It All? 

When asked about balancing work and family, Mailman didn’t sugarcoat it. “It’s not easy,” she said. “But people have kids all the time. You figure it out.” 

She married later in life when she was 34, now has two kids (with one on the way!), and emphasized the importance of choosing a spouse who gives you the flexibility to work how you want. Whether you want to work full-time, part-time, or not at all, Mailman told the women that having a husband with a steady income made it possible for her to pursue her “interesting things.” 

Her Final Encouragement to Young Women 

Mailman reminded the women that being the only one in the room with a different perspective can be isolating but also empowering. “If you’re the only one with that view, you’re memorable. Be smart, be kind, and be bold.” 

Mailman’s message was clear: leadership isn’t about waiting. It’s about showing up, speaking out, and doing the work that matters. 

This blog was written by NeW Media Relations Coordinator, Colleen Dean.