Ethical Leadership Spotlights

10 Questions With Holy Cross' Next Generation Of Leaders

Holy Cross alumni are making a difference in a variety of industries, and many of the College's alumni have found themselves in professional leadership roles. We've spoken with over a dozen people who graduated from Holy Cross between 2003 and 2015 and asked each of them 10 questions. Here's how their time of The Hill shaped their worldview and their professional approach.

Mike Flanagan '15

Tell us about your job role and employer. What are you currently working on?

I am a Director on the Business Transformation team at Envision Healthcare. My role focuses on executing innovative strategies that strengthen our core business functions and improve the experiences of both providers and patients.

I am currently leading the implementation of AI Ambient Scribe products across our provider group to reduce documentation burden, improve physician satisfaction, and increase productivity. In addition, I am overseeing the rollout of AI Autonomous Coding technology within our Revenue Cycle Management operations to enhance medical coding accuracy, efficiency, and downstream process performance.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

Growing up in a healthcare family—my father a urologist and my mother a nurse—the industry always felt like a natural fit. I saw firsthand the challenges clinicians face as they try to focus on patient care while navigating administrative, financial, and technological pressures.

During my time in consulting, I spent several years traveling the country, working with both large academic health systems and small community hospitals. Those experiences taught me how collaboration across clinicians, administrators, and support staff directly impacts the quality of care patients receive.

My Holy Cross education provided a diverse intellectual foundation that helped me transition from finance to healthcare consulting and ultimately into leadership within a large physician organization. The emphasis on critical thinking, ethical decision-making, and serving others continues to guide how I approach challenges and lead in the healthcare space.

What has surprised you most about transitioning into a leadership role?

What has surprised me most is how much the core skills I relied on early in my career still matter—maintaining a learning mindset, solving problems, collaborating, and leading with emotional intelligence. Even as the challenges become bigger and more complex, those same qualities continue to make a meaningful difference.

I’ve also seen how powerful it is to cultivate a team culture where people feel supported and heard. When everyone feels part of something bigger, the sense of camaraderie and shared purpose elevates the work.

What is the most challenging aspect of your job? How do you navigate that challenge?

One of the most challenging aspects of my job is navigating the ever-changing healthcare landscape. This includes balancing clinical staffing challenges, adapting to evolving government regulations, and keeping pace with rapid technological advancements.

To manage that complexity, I focus on staying closely connected to our clinical teams and understanding what truly makes their work easier and more meaningful. Listening to their feedback and keeping a pulse on broader market developments ensures that the solutions we implement genuinely improve both their day-to-day experience and patient care overall.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

I’ve learned that leadership development is an ongoing process—one that requires curiosity, humility, and a commitment to continuous learning. I actively seek out leadership development opportunities and make it a point to learn from others in the organization whose styles I admire. I try to identify qualities in great leaders that I can integrate into my own approach.

Self-reflection plays a major role in that process. Being honest about my strengths and areas for growth, seeking candid feedback, and viewing constructive criticism as an opportunity rather than a setback have all helped me grow. Leadership takes time to build, and patience—with yourself and with others—is essential along the way.

What advice would you give to Holy Cross young alumni about developing as leaders?

My biggest piece of advice is to lead with care and empathy. Set the tone by supporting those around you and helping create a positive, collaborative environment. Be a sponge around the leaders you admire and seek out mentors who can help you grow.

It’s also okay not to have all the answers. Some of the best leaders I’ve worked with are those who lean on others’ expertise and ask great questions. Above all, use emotional intelligence to understand how you can make your teammates’ lives a little easier. Leadership often starts with that simple act.

We know that relationships are important for any kind of development. How do you build and maintain your network?

Holy Cross has provided a remarkable network that has supported me at every stage of my career—whether applying for internships, landing my first job, exploring new opportunities, or offering guidance to fellow alumni and students. I make a point to stay connected with classmates and other Holy Cross graduates, celebrating their successes and learning about the work they’re doing.

I’ve also gained so much from colleagues across different phases of my career, from finance to healthcare consulting to my current role in strategy and transformation. Staying in touch with both current and former colleagues helps me learn from their experiences, understand the challenges they face, and find ways to support each other’s growth.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Throughout my career in healthcare, consulting, and finance, I’ve been fortunate to work with incredible individuals who have shaped how I think about growth and leadership. Many of my mentors stand out for their openness, honesty, and willingness to collaborate. I was drawn to them because of those qualities and learned a great deal—whether through their advice, their examples, or simply how they carried themselves during challenging situations.

Supporting mentees has become equally meaningful to me. I try to share the lessons I’ve learned to help colleagues and Holy Cross students or alumni navigate their own paths with confidence and perspective.

What advice would you give to Holy Cross young alumni interested in working in your industry?

For those interested in working in healthcare as a non-clinician, I encourage you to focus on how your work contributes to improving patient care and supporting those who provide it. Whether your role is in consulting, technology, operations, or finance, you can make a real impact on the patient experience and the overall delivery of care.

I’ve been fortunate to collaborate with physicians, nurses, and support staff and to spend countless hours in clinical settings, learning firsthand about the challenges they face each day.

Kristin Walker '10

Tell us about your job role and employer. What are you currently working on?

I’m the Senior Vice President of Merchandising at Tory Burch, based in New York City. My team and I are responsible for shaping the product strategy across categories—ensuring that what we bring to market reflects both the brand’s creative vision and our customer’s lifestyle.

Right now, we’re focused on refining how we infuse data-driven insights with our instinctive understanding of design and merchandising to build collections that feel both inspiring and trend forward.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

Holy Cross played an enormous role in setting me on my career path. As an Economics and Art History major, I learned to think both analytically and creatively—skills that are at the heart of merchandising.

My first experience in fashion came through a Holy Cross connection: an internship at Marc Jacobs with alumna Carolyn Risoli ’86. That opportunity introduced me to the industry and showed me how powerful the Holy Cross network can be.

The liberal arts education also instilled curiosity, empathy, and the ability to see connections across disciplines—qualities that have guided me throughout my career.

What has surprised you most about transitioning into a leadership role?

The biggest surprise has been how much leadership is about listening. Early in your career, you’re focused on proving yourself and delivering results. As a leader, your success depends on empowering others—creating space for different voices, guiding decision-making, and helping people grow.

It’s less about having all the answers and more about asking the right questions.

What is the most challenging aspect of your job? How do you navigate that challenge?

Balancing creativity with commercial performance is a constant challenge in fashion. It’s easy to lean too far to one side or the other.

I navigate that by fostering open dialogue between our design, merchandising, and planning teams, ensuring every decision reflects both creative integrity and business strategy. It’s a balance of intuition and data, art and science—and that’s what keeps it interesting.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

I’ve found that leadership development is a lifelong process. I make time to learn from peers and mentors, to listen to my team’s feedback, and to regularly reflect on what’s working and what’s not.

Self-reflection helps me stay grounded—it reminds me to lead with empathy, stay curious, and evolve alongside the people I work with.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job?

Leadership isn’t tied to a title—it starts with how you show up every day. Be curious, collaborative, and kind. Take initiative, but also listen and learn from those around you.

The best leaders are constantly learning, and Holy Cross gives you a great foundation for that kind of growth mindset.

We know that relationships are important for any kind of development. How do you build and maintain your network?

I approach networking as relationship-building. I stay in touch with people I’ve worked with by checking in, celebrating their successes, and finding opportunities to collaborate or support them.

I also make a point of mentoring younger colleagues—because so many people once did that for me. Authenticity and generosity go a long way.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Mentorship has been absolutely pivotal for me. My early mentors, including those I met through Holy Cross, taught me how to navigate challenges with confidence and integrity.

Now, I try to pay that forward by mentoring emerging talent. It’s incredibly rewarding to watch others grow and to know you’ve played a small part in their journey.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

Be proactive, persistent, and stay curious. The fashion industry moves quickly, but it’s also built on relationships and trust.

Gain experience wherever you can—internships, retail roles, or smaller brands—and use those opportunities to understand how the business really works. Lean into the Holy Cross network; it’s an extremely powerful resource.

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

Be intentional. It’s easy to get caught up in career momentum, but balance doesn’t happen by accident. Prioritize your well-being, nurture relationships, and set financial goals early.

The values that Holy Cross instills aren’t just professional assets; they’re essential to building a well-balanced and fulfilling life.

Yarlennys Villaman Hale '14

Tell us about your role and employer. What are you currently working on?

I currently serve as the Director of Capital and Community Relations at the Massachusetts Bay Transportation Authority (MBTA), the oldest public transportation agency in the U.S. Our mission is to provide safe, reliable, and accessible transportation, and my work focuses on connecting the MBTA with the communities it serves, as well as with our more than 800,000 daily riders.

I lead the Public Engagement and Capital Engagement teams, driving initiatives that ensure both our riders and residents are informed, empowered, and able to provide meaningful input on the billions of dollars in capital projects across the system. By fostering strong community partnerships and strategically planning events and outreach, we create opportunities for the public to actively shape the future of transit in Massachusetts.

My vision is to make public engagement at the MBTA a model of transparency, collaboration, and impact—where every resident’s voice contributes to decisions that transform our transportation network and strengthen the communities it serves. At the same time, I work across departments to build cohesive, innovative projects that advance both capital development and community trust.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

I remember graduating from Holy Cross and thinking, “People say this degree will take me places, but I don’t know what’s next.” That uncertainty was scary. I reached out to the Holy Cross Alumni Office, which connected me with Trish Gannon, Class of 1987. At the time, she was working for the Boys & Girls Club of Boston. She took the time to meet with me, listened to what I enjoyed, and encouraged me to look into the MPA program at Suffolk University because it aligned with my goals. That conversation truly changed the course of my career.

I’ll never forget walking across the stage at my Suffolk graduation—Trish, who was serving on Suffolk’s Board of Trustees, stood up, and I gave her a big hug and said thank you. Moments like that remind me that life brings people into your path to guide you toward the purpose God has for you.

Through that journey, I began a career in public service at the state level. Along with my sister (Holy Cross ’15), I founded a 501(c)(3) nonprofit called Lazos Al Futuro in the Dominican Republic. Our mission is to support youth and help break barriers that might prevent students from finishing school. Today, we support 34 students, and 14 of them are attending top universities in the Dominican Republic.

All of these experiences—from Holy Cross to Suffolk, from mentors like Trish to launching my own nonprofit—remind me of the value of discernment at every stage of life. I’ve been fortunate to work in meaningful roles, and through it all, I try to live out the Holy Cross mission: to be a person for and with others.

What has surprised you most about transitioning into a leadership role?

Transitioning into a leadership role at the MBTA has been full of surprises. It’s such a busy agency, and learning a completely new field like transportation—with hundreds of acronyms and so many moving parts—can be overwhelming. Understanding how everything fits together takes time, but I’m determined to learn it all.

Starting a new job is always about taking baby steps, and as a working mom, it can feel like starting from scratch: learning a new field, meeting new colleagues, and finding my place. But every challenge has been a learning opportunity, and I’m excited for the growth that comes with it.

What is the most challenging aspect of your job? How do you navigate that challenge?

Working for the MBTA comes with its challenges—whether it’s community concerns about construction delays or complaints about how projects affect neighborhoods and daily rides. For me, the key is to take each challenge one step at a time and approach every situation with transparency and empathy.

Listening to people, acknowledging their concerns, and communicating honestly goes a long way in building trust and finding solutions that work for everyone. As our General Manager and Interim Secretary, Phil Eng, often reminds us, we want our riders to feel proud to ride—and we must ask ourselves how we meet the needs of today while building for the future.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

Right after college, I worked for a nonprofit supporting refugees and immigrants while completing my MPA in downtown Boston. I remember looking up at a tall building one day and visualizing myself working there—and not long after, I received an opportunity at the Attorney General’s Office, where I became the Director of Outreach. That role was a turning point for me. It made me realize that my education, experience, and perspective had real value—that I truly belonged in the room.

As a community organizer, I learned to meet people where they are and to think strategically about how to connect with different audiences. I led my first major initiative on Language Access, which was deeply personal to me as an immigrant from the Dominican Republic who once struggled with English. That project became a foundation for my leadership journey and shaped my future roles.

I’ve learned that leadership isn’t just about managing projects—it’s about being a team player, staying humble, and leading with empathy. Self-reflection has been essential. It reminds me of the Holy Cross motto: to be men and women for and with others. I try to live that out every day by treating people with respect, keeping my door open, and remembering where I came from.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers, industry, or job?

Don’t wait for opportunities to come to you—challenge yourself and take advantage of everything that comes your way. Whether it’s taking a leadership course, attending a conference, or simply getting to know the people you work with, every experience helps you grow.

Once you learn how to do your job, make your own mark so your work speaks for itself. It’s normal to have doubts or wonder “what if,” but in today’s world, you just have to take that first step and keep learning. Surround yourself with people who lift you up and who you can learn from. Little by little, you’ll climb higher—just remember to stay confident in who you are and never change what makes you, you.

We know that relationships are important for any kind of development. How do you build and maintain your network?

Relationships are everything. For me, building and maintaining my network often comes down to simple, genuine connections—grabbing coffee, making a quick call, or checking in. When I work in communities, I truly rely on those relationships.

I’m a bit old-fashioned: I love sending handwritten cards or thank-you emails to show appreciation. Your network and the people you surround yourself with help shape the leader you’re meant to be. In my line of work, reputation is everything, so I make a point of attending events and community meetings—but more importantly, I take the time to get to know people one-on-one.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

My mentors have truly changed my life. They’ve always pushed me to see more in myself, even when I couldn’t. Mentorship has helped me stay focused on what I want to do and where I want to go. I believe everyone needs a mentor at different stages in life—the guidance and encouragement make such a difference.

For me, mentoring others, especially Holy Cross students, is my way of giving back, just as my mentors did for me when I needed it most.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

If you’re interested in community engagement work, know that there are many paths you can take. Start exploring early—even volunteering for a local or statewide campaign can teach you a lot about working with people and seeing how communities come together.

If connecting with others excites you, there are meaningful opportunities in nonprofits, public service, and corporate roles that focus on community engagement, community affairs, or community relations. It’s impactful work, and every experience—big or small—helps you grow and make a real difference.

What advice would you give to Holy Cross graduates about developing personal life habits after college (finances, health, values, work/life balance)?

You’re still discovering who you are professionally, so challenge yourself while also taking care of yourself. Maintaining balance and caring for your mind and body is essential. For me, my faith moves mountains and reminds me to trust that God has a plan for me.

Since high school, I’ve written letters to myself at the end of each year to reflect on where I see myself and set goals for the future. Whether it’s journaling, going to the gym, or joining a group that aligns with your values, make space for what brings you happiness—don’t get lost in the busyness of life.

The second piece of advice is to never overlook the importance of spending time with friends and surrounding yourself with people who uplift you. Time is precious, and every moment matters when it comes to maintaining balance. Always remember: no matter where life takes you after Mount St. James, Holy Cross has your back. Don’t hesitate to ask for help when you need it. Life can feel like a rollercoaster, but you can rely on your Holy Cross network—a community that wants to see you thrive and will support you every step of the way.