Discover how empathy drives organizational performance and accelerates results. Learn why leaders who prioritize understanding over quick answers build stronger teams, faster decision-making, and sustainable success.
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I challenged the belief that leadership is about having all the answers. My greatest impact was helping people believe in themselves and become more than they thought possible.
Jacqueline R. Hollenbeck · In Her Own Words
In Conversation
Jacqueline R. Hollenbeck for Bold. Brilliant. Unstoppable.
Read the transcript
Jacqueline R. Hollenbeck: For me, influence starts with knowing who you are. Knowing what you value, knowing what you're good at, and what you still need to learn, and then having that courage to bring it all into the room. Over the course of my career. I've learned that influence isn't something you simply earn as you become more successful. It's something you build, one conversation at a time, one decision, and one relationship at a time. Sometimes, influence means having the courage to say, I see things differently. Sometimes it means asking the questions that change changes the conversation. And sometimes it means recognizing an opportunity in someone else, and giving them the encouragement to go after it. I've also learned that influence grows as your career grows. The more experience you gain, the more opportunities you have to shape decisions, challenge the way that things have always been done, and create opportunities for other people. And I think that's where influence becomes really powerful. It's when you stop thinking only about what you can accomplish for yourself and start thinking about when you can help make possible for other people and for the organization that you're part of. For me, that's influence what it really means. It's using your experience, your voice, your perspective to move something forward, and leaving things better than the way you found them.
What's one piece of advice you would give to younger women chasing their dreams?
Jacqueline R. Hollenbeck: Don't spend your career waiting for permission to become that woman that you know you can be. Take the opportunity, even if you don't feel ready. Ask the question nobody else is asking. Bring your perspective in the room, especially when it's different, and remember that confidence doesn't mean having all the answers. Some of the strongest leaders that I know are the ones who are comfortable saying, I don't know yet. And then figure it out. I think it's something I've learned throughout my career. You don't have to have everything figured out before you take that next step. You just have to be willing to take it. And one thing I've learned as my career has grown is that success becomes more meaningful when you think beyond what you could accomplish for yourself. Once you have that voice, a seat at the table, or some measurement of success, ask yourself, who will I encourage? What will I challenge? What doors will I hold open for someone coming in behind me? Because influence is something we have the opportunity to use. We can use it to make our workplaces better, our communities stronger, and ultimately lead people around us a little stronger than the way we found them. And if we can do that while staying true to who we are, I think that's a pretty powerful definition of success.
Full transcript available
Her Story
About Jacqueline
Jacqueline Hollenbeck is an award-winning Design Systems and UX leader with more than 25 years of experience helping organizations scale through thoughtful design, collaboration, and customer-centered solutions. Throughout her career, she has created digital experiences, established scalable design practices, and brought together design, engineering, and product teams to solve complex challenges and deliver meaningful impact.
Most recently, Jacqueline served as Design Systems Manager at Ford Pro, where she led the strategy, governance, and enterprise rollout of an award-winning design system and coded component library supporting global commercial platforms. Her leadership enabled more than 120 product teams to adopt a unified design framework, improving consistency, efficiency, and delivery across complex digital experiences. Under her guidance, the Ford Pro Design System earned both a 2025 Bronze Stevie Award for Women in Business and a 2026 Gold American Business Award for its innovation and impact.
Prior to Ford Pro, Jacqueline built her career at TIAA and Fidelity Investments, where she contributed to enterprise design initiatives, established UX standards and accessibility practices, and developed reusable solutions that improved customer experiences and strengthened collaboration across organizations. These experiences shaped the leadership approach that defines her work today: creating clarity in complexity, building strong partnerships, and helping teams achieve more together.
Known for leading with empathy, integrity, and collaboration, Jacqueline has a unique ability to bring people together around a shared vision. She believes successful organizations are built when people feel valued, empowered, and connected to a common purpose. While she is proud of the systems and products she has helped create, she considers her greatest accomplishment to be the growth of the people she has mentored and supported throughout her career.
Jacqueline continues to explore emerging technologies, including AI-assisted workflows, to improve accessibility, documentation, and operational efficiency while keeping people at the center of innovation. Beyond her professional contributions, she is passionate about mentoring others and volunteering with organizations such as Best Buddies in Massachusetts.
Today, through Hollenbeck Leadership, Jacqueline brings her experience in leadership, design strategy, organizational transformation, and team development to help leaders and organizations navigate change, strengthen teams, and create meaningful, sustainable impact.
Her Interview
Ten minutes with Jacqueline
01What do you attribute your success to?
I attribute my success to curiosity, empathy, and investing in people.
Early in my career, I realized that leadership isn’t about having all the answers. It’s about listening, asking thoughtful questions, and creating an environment where people feel supported, trusted, and empowered to contribute their best ideas.
I’ve also been fortunate to learn from incredible mentors who challenged me to think bigger, stay humble, and never stop learning. Those lessons shaped the leader I am today.
Throughout my career, I’ve found that when people feel valued and connected to a shared purpose, amazing things happen. Teams become more collaborative, innovation accelerates, and the results often exceed what any one person could accomplish alone.
The awards and successful products are wonderful milestones, but I measure success differently. I measure it by the people I’ve helped grow, the trust I’ve built, and whether I leave every team stronger than I found it.
02What’s the best career advice you’ve ever received?
The best career advice I ever received was, ‘Your job as a leader isn’t to be the smartest person in the room. It’s to create a room where everyone else can do their best thinking.’ That advice changed my perspective on leadership. I realized leadership isn’t about having all the answers. It’s about listening, asking thoughtful questions, removing obstacles, and creating an environment where people feel safe to contribute. Looking back, every meaningful accomplishment in my career, including leading an award-winning design system, was made possible because incredible people felt empowered to do their best work.
03What advice would you give to young women entering your industry?
Don’t underestimate the value of your voice.
Early in your career, it can be easy to think you need to have all the answers before speaking up. The truth is that curiosity, thoughtful questions, and a willingness to learn often create more impact than having the perfect answer.
Seek out mentors who will challenge and encourage you, but also remember to become that mentor for someone else as your career grows.
Most importantly, don’t try to lead like someone else. Your empathy, perspective, resilience, and authenticity are strengths, not weaknesses. The leaders who make the greatest impact aren’t the loudest in the room—they’re the ones who help others succeed.
Build relationships, stay curious, embrace change, and never stop learning. Those qualities will carry you further than any title ever will.
04What are the biggest challenges or opportunities in your field right now?
Artificial intelligence is transforming the way we design and build digital experiences, and I believe that’s one of the greatest opportunities our industry has ever seen.
AI can automate repetitive work, accelerate research, improve accessibility, and help teams move faster than ever before. But technology alone isn’t enough. The real opportunity is using AI to free designers to focus on what humans do best: understanding people, solving meaningful problems, and creating experiences that build trust.
Another exciting opportunity is the growing recognition of design systems as strategic business assets. They aren’t just component libraries—they’re the foundation that helps organizations deliver consistent, scalable, and accessible experiences while enabling designers and engineers to collaborate more effectively.
The future belongs to organizations that combine emerging technology with human-centered leadership. That’s where the greatest innovation will happen.
05What values are most important to you in your work and personal life?
The values that guide me are empathy, integrity, curiosity, and kindness.
Empathy helps me understand people beyond their job titles. Integrity means doing what’s right, even when it’s difficult. Curiosity keeps me learning, adapting, and growing, while kindness reminds me that every interaction is an opportunity to make someone else’s day a little better.
These values aren’t separate from leadership, they define it. I’ve always believed that people do their best work when they feel respected, heard, and supported.
Whether I’m leading a team, mentoring someone early in their career, or simply collaborating with colleagues, I want people to leave our interactions feeling more confident than when they arrived.
If I can help people believe a little more in themselves, then I’ve done something worthwhile.
Her Content Hub
Articles by Jacqueline
Empathy Is Leadership: The Advantage of Leading with People in Mind
Why understanding people is the key to driving results and building high-performing teams.
Empathy Isn't the Opposite of Performance. It's Often the Reason Performance Happens.
Empathy is often treated as something separate from performance.
I've found that it's deeply connected to it.
For years, I've heard empathy described as a personality trait—something nice to have if compassion comes naturally. I've come to see it differently. Empathy is one of the most practical leadership skills a person can develop.
Empathy isn't about lowering expectations. It's about understanding what people need so they can meet, and often exceed, them.
Throughout my career, I've led teams responsible for large-scale digital transformation, enterprise design systems, and cross-functional initiatives involving designers, engineers, product managers, researchers, and business leaders. In each of these environments, success depended on more than having the right strategy or process. It depended on people being willing to speak up, challenge ideas, collaborate, and take ownership.
The strongest teams I've led weren't the ones that made the fewest mistakes. They were the ones where people felt safe enough to surface them.
When people know they're trusted, respected, and supported, they're more willing to ask difficult questions instead of hiding problems. They share ideas earlier, collaborate more openly, and take ownership because they know they're working toward a shared goal rather than protecting themselves.
Empathy Accelerates Better Work
I saw this firsthand while leading a design system team. Upper leadership wanted us to move faster, so an outside agency was brought in to work alongside my team.
At first, the dynamic felt awkward. We had two groups of talented designers who didn't yet know how to work together.
I started meeting one-on-one with the agency designers. My goal wasn't to tell them how to contribute. It was to help them feel confident enough to bring forward the expertise they already had.
Something changed.
As they became more comfortable speaking up, the two teams began learning from one another. The awkwardness disappeared, and what emerged was a remarkably collaborative, well-oiled team.
Designers began mentoring one another, sharing knowledge, and lifting each other up. Everyone was growing.
And we delivered the design system faster.
What I remember most, though, isn't the speed. It's the joy I felt walking into those morning team meetings and watching what they had become. I could see the pride they took in their work and in one another.
People who had started as two separate groups had become one team. Each person was more confident, more capable, and more knowledgeable because of the people around them.
That experience reinforced something I've learned throughout my career: sometimes a leader's most important contribution isn't having the answer. It's creating the conditions where other people can bring their best answers forward.
That doesn't mean lowering the bar. In fact, I believe empathy allows leaders to raise it.
Empathy Can Make Organizations Faster
When trust exists, communication improves. When communication improves, decisions happen more quickly. When people collaborate instead of competing, fewer problems reach crisis level.
Organizations often invest heavily in new technology to improve efficiency. Those investments matter, but technology delivers its greatest value when people are willing to work together. The strongest systems I've helped build weren't successful because of the software alone. They were successful because the people behind them trusted one another.
One of the practices I value most is listening before solving.
Leaders often feel pressure to have the answer immediately. I've learned that asking thoughtful questions usually leads to better solutions than offering quick ones. People don't always need a leader with all the answers. They need a leader who is willing to understand the problem before deciding how to solve it.
Empathy and Accountability Can Coexist
Perhaps the greatest misconception about empathy is that it conflicts with accountability.
My experience has been exactly the opposite. When people know you genuinely care about their success, difficult conversations become easier. Feedback feels like coaching instead of criticism. Accountability becomes something you do with people, not to them.
The result isn't just stronger relationships. It's stronger performance.
Looking back, the projects I'm most proud of aren't memorable because of awards or recognition. They're memorable because of the people who grew while we were accomplishing them together.
- Some became mentors.
- Some accepted leadership roles.
- Some discovered confidence they didn't know they had.
That, to me, is the legacy every leader has the opportunity to create.
Technology will continue to evolve. Organizations will reorganize. Strategies will change.
But the leaders who leave the greatest impact will be the ones who remember that business has always been, and will always be, about people.
Because empathy isn't the opposite of performance.
It's often the reason performance happens.
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