Sarah Richardson on Leadership, Humanity, and the Future of Healthcare Tech

Some interviews are so full of insight that editing feels impossible. This conversation with Sarah Richardson is one of them.

When we first connected, she didn’t really know me, but she still said yes to being my mentor. That yes became one of the most meaningful mentorships of my life. Sarah has been a guide, an anchor, and a reminder of the kind of leader I want to be, one who leads with clarity, compassion, and courage.

This interview is a masterclass in leadership and life. Every word carries wisdom and heart. Whether you work in healthcare, technology, or any space where people matter, you will walk away with lessons that make you pause, reflect, and grow.

Origins & Career Journey

You began in the hospitality and service industries, then made a transition into tech and healthcare IT. What was the move like, and what parts of your hospitality background do you still carry with you?

I love that question because I started my career in hospitality, and that will always be my first love. The focus has always been on creating exceptional experiences, and that translates directly and effectively into patient care and patient experiences.

That grounding has never left me. It’s how I approach technology, and it’s how I approach leadership. I always ask, what is the experience the person is having? Whether it’s an IT project, a coaching session, leading a workshop, or moderating a panel, I always put on the same lens: how do we make this experience better for the human being at the center of it?

That mindset is more important than ever because it’s harder today to get great patient care or even have a meaningful relationship with your primary care physician. I’ve also realized that when you put that hospitality or experience lens in place, it naturally brings an air of kindness. When things are rough and you are kind, those two things don’t have to be mutually exclusive. You can still get what you need, achieve what others need, and do so in a way that makes people feel good about the overall experience at heart.

Leadership & Change

You have led at the very top, from CIO to Chief Digital and Information Officer to board member and beyond. What has been the hardest transformation you have had to lead, and what did it teach you about guiding people through change at scale?

When I look back at the hardest transformations I’ve led, and it’s been more than once, I’ve typically been known for coming in to lead a turnaround or a complete redo of an organization.

It’s about shifting the mindset from seeing IT as a back-office or basement function to viewing it as a strategic enabler of patient care.

I’ve also realized that real change is rarely about the technology. It’s always about building trust, listening deeply, and showing people how their work connects to purpose. I’m a firm believer in organizational change management and in understanding the “why” behind the motivation that helps people embrace change rather than feel like it’s happening to them.

But transformation doesn’t happen in a vacuum. It’s layered on top of everything else going on in an organization. I’ve been through mergers and acquisitions, new system implementations, workforce reductions, expansions, leadership transitions, and of course, COVID-19. Each of those moments created a ripple effect that touched people at a very real and human level.

That’s why leading through change requires more than a strategy slide or a technical roadmap. It’s about being available, transparent, and willing to acknowledge the impact these shifts have on people’s lives, at home and at work.

As leaders, our role is to bring clarity when there’s uncertainty, consistency when things feel disruptive, and humanity when people are stressed. When people see that you’re walking alongside them, not above them, even the hardest transformation becomes an opportunity to strengthen trust and move forward together.

How do you, as a leader, maintain empathy and human-centered design even when pressure is up, deadlines are aggressive, or systems are rigid?

When pressure is high and the stakes are high, I always lean into empathy first. I remind myself and my teams that behind every deadline or system is a clinician, a patient, or a family who will feel the impact. That perspective keeps us grounded.

The other thing is, we are all patients. I often ask that question in different workshops and environments: who here is a patient at their own healthcare system? About half raise their hands. People have different insurance through spouses or employers, but when you experience care in real time, you become the best advocate for that environment.

It’s also important to be available and visible during times of change. Teams need to know they’ll get credit when they do a good job, and that I will take accountability when we fall short. That goes back to Jim Collins’ Good to Great and the concept of Level 5 leadership. That kind of transparency builds trust and signals that we’re in it together.

No one person should carry the weight alone. It’s not that Sisyphus moment of the rock constantly rolling back over you. When people feel recognized for their contributions and protected when things don’t go as planned, they’re more willing to take risks, to innovate, and to keep pushing forward even in tough moments.

Mentorship & Coaching

When you agreed to be my mentor, you didn't even really know me but you've given me so much. What makes you say "yes" to mentoring, even when you don't know where the relationship will lead?

Well, the first win you had in your court was Paul Connelly. If Paul Connelly asks me to do something, I’m going to say yes. He was so instrumental in shaping my career.

You always want to give back, but you also want to give back to the people who helped you get where you are today. There is always a special place for those leaders and those people in your life.

I will say yes to mentoring when there is alignment, because I believe relationships can change the trajectory of a career and often people’s lives. Someone once gave me a chance beyond Paul, and I feel both responsible and joyful in paying that forward. In fact, it was a boss, so she was both a mentor and a boss, and I once asked her, “What can I do to repay you?” She said, “Always just pay it forward.”

You do not always know where the relationship is going to go, but if you lead with generosity, a little vulnerability, and the willingness to just be yourself as a leader, it usually goes somewhere meaningful. When we are in the boardroom, in the C-suite, or on stage, we are performing to a degree. But when you are with your mentees, you get to just be yourself. That helps them see the other side of what it really takes to do those other important parts of our careers.

And honestly, that is probably my favorite part at this point in my career, being able to say, “Here is where I screwed up. Here was the oops moment. Here are the things you probably should not do.” I probably have more scars and burn marks from the bad decisions than from the good ones, especially the times I did not listen because I thought I knew better. Those were rough lessons to learn. But that is exactly why mentoring matters, because it is about helping others learn the hard stuff a little easier.

BADdest Moment

Tell us about the ‘BADdest’ challenge you’ve taken on in your career—the boldest, most authentic, and driven moment you’re most proud of—and how it shaped you.

The boldest and most authentic moment for me was saying yes to becoming a CIO when I was still relatively young in my career. It was intimidating, but it also forced me to step fully into my capabilities, trust my team, and grow rapidly. That decision set the stage for everything that has come since.

It was not just about one role. For me, it has been a pattern of saying yes to opportunities that others have turned down. I took on assignments that were not always the most glamorous or the most obvious next steps, but they gave me invaluable experience and exposure I never would have gained otherwise.

At times, this meant literally packing up and moving across the country more than once. Rebuilding community, reputation, and trust in entirely new environments was humbling. It was sometimes exhausting. It was also always worth it.

What people do not always realize is that when you pick up your life for your job, you are also picking up your personal life, your family, your pets, your home, your entire community, and starting over every single time. While you are trying to be successful in your career, you are also making sure you are not leaving parts of your family behind in that journey.

Those choices taught me resilience. They reminded me that growth happens when you step into what is uncomfortable. Every time I said yes, I added another layer to my skill set, widened my perspective, strengthened my ability to lead with authenticity, and met incredible people along the way.

Now, as I travel to different cities across the country, I almost always have friends who live there because I have either lived there myself or we have all moved for similar reasons. That has become one of my favorite parts of this journey. Everywhere I go, there I am.

Innovation & Impact

In today’s healthcare and technology landscape, what innovations excite you the most, especially ones that aren’t widely talked about?

I get excited about innovations that create time and space for clinicians and improve patient experiences. That ties back to the hospitality mindset I’ve always carried.

Right now, ambient listening is one of the most promising. It’s already giving patients and providers more thoughtful time together, improving workflow, and strengthening connection in care moments.

I’m also drawn to patient engagement tools that may not grab headlines but quietly move the needle every day where it matters most.

Technology is advancing at leapfrog speed, but healthcare, by nature, adopts more deliberately because of our duty to do no harm. That’s right, but we also can’t afford to lag behind. The demands on clinicians and systems require us to pursue innovation while ensuring responsible governance.

Funding is tighter than ever, and many CIOs will tell you they get one shot to get it right. We talk about “fail fast,” but in healthcare, the runway for that is shrinking. With large system implementations, you have to make the right choice the first time. Leaders are taking longer to decide because they want to get it right, while still staying ahead of the game.

It’s a constant balance between being bold and being careful. You make the best choice based on what you know. If it doesn’t cause harm, it becomes part of the learning process. But not making a decision at all is worse than making a bad one.

How do you see the role of the CIO or technology leader evolving over the next 2-3 years? What new responsibilities or skills will be essential?

CIOs will continue to focus less on keeping the lights on and more on shaping enterprise strategy. As a leader today, you have to master communication, understand governance, and be aware of cultural influences just as much as the technology. You still want a technologist in the mix, but one who can do all of those other things as well.

Technology is no longer a support function. It is the engine that moves organizations and the industry forward. A successful CIO must understand how that engine works to guide the organization through constant change.

The role also requires fluency in operations, finance, and strategy. It demands living at the intersection of all of those disciplines. Not everyone is cut out for that, and not everyone wants to do it. It is one of the hardest jobs in any company right now. The margin for error is thin, the landscape is always changing, and the average CIO tenure is about three years.

Deep industry knowledge and technical fluency are essential, along with the ability to stay a lifelong learner, adapt continuously, and maintain both team confidence and organizational trust. That is harder than ever because the rest of the C-suite is also changing rapidly.

Getting traction for the right roadmap is tougher while balancing the rapid pace of AI, constant cybersecurity threats, and evolving expectations. Finding balance inside all of that can feel like being a master juggler.

Technology now touches every department. Nothing is insulated from it or from the integrations that come with it. Once, we could install a point solution and walk away. Now, everything is connected through APIs and layered systems. Finding the needle in the haystack when something goes wrong has become more important than ever—and it is one of the things that keeps most executives awake at night.

AI, Ethics, & Governance

AI is reshaping healthcare rapidly, but not without risks. What does responsible use of AI mean to you in this context?

There are three things I always think about: transparency, equity, and governance.

First, transparency and explainability. Healthcare providers need to understand how AI reaches its recommendations. A black-box algorithm suggesting a treatment plan is not acceptable when people’s lives are at stake. Clinicians need to see the reasoning, not just the output, so they can validate and trust it.

If you have ever used AI, you know you can fight with it a little. I was playing with it just last night for my HIMSS post, and it pulled in references from SOAR. I thought, “No, wrong conference!” That is exactly why explainability matters in an EHR workflow.

Second, equity and bias mitigation. AI models are only as good as the data they are trained on. If that data does not represent diverse patient populations, we risk amplifying existing disparities. Healthcare is local, so responsible AI means actively testing for bias, ensuring models work across demographics, and being vigilant about who could be left behind.

When evaluating a vendor’s solution, it is not just about performance; it is also about equity outcomes. Think about it this way: you live in Atlanta, and I live near San Francisco. If we both need care in Chicago, and their large language models are trained only on local data, we could receive an inaccurate diagnosis because our demographics do not fit that profile. It can come down to the zip code or even the block.

That is why humans must stay in the loop. AI is not about replacement, it is about augmentation. The best implementations enhance what humans do—flagging potential sepsis cases, identifying care gaps or fall risks, or recommending follow-ups—while a qualified human still makes the final call.

Finally, governance. There must be clear policies around data privacy, patient consent, model validation, and ongoing monitoring. You cannot deploy AI and walk away from it. It is almost like it is alive; it needs to be cared for and fed.

Healthcare organizations need governance frameworks that define accountability, establish review processes, and continuously evaluate outcomes. The ones that get it right are not choosing between innovation and safety. They are structuring for both, and that is what makes them sustainable.

Where do you see the most urgent ethical or governance challenges with AI adoption in healthcare and beyond, and how do we start addressing them?

This came up in a panel I moderated just yesterday because there is a real gap right now. AI is being deployed faster than we can build the guardrails to ensure it is safe, fair, and explainable.

The governance gap is one of the biggest challenges. In a healthcare organization, who owns accountability when an AI model contributes to a clinical decision? How do we validate these tools before deployment, and how do we monitor them over time? Many health systems do not yet have clear answers.

Standardizing frameworks that establish expectations for safety, transparency, and oversight without crushing innovation is key. Legal and compliance teams need strong frameworks and audit procedures so that, if an event occurs, they can show the organization did everything it was supposed to do. In many ways, governance functions as an internal insurance policy.

We also have an education gap. The pace of AI evolution is outstripping our ability to educate the people who need to govern and use it. Board members must understand AI well enough to ask the right questions about risk. Clinicians need training on both the capabilities and the limitations. Patients should understand when AI is being used in their care and how it is being used.

That is not always easy. Many patients do not fully grasp what AI is. I have very intelligent family members in their eighties who stare at me when I explain that AI summarizes their notes and makes recommendations their doctor reviews. That tells you how much work we have to do.

To address this, organizations should establish AI governance committees embedded within existing structures that bring together clinical leaders, IT, legal, ethics, and data science. Build board literacy programs, staff training, and patient communication strategies. St. Luke’s in Boise is a great example. Under Reid Stephan’s team, Molly Zimmer runs an AI education program that has trained more than 2,500 people, from the history of AI to how it is used across the organization.

We must also demand transparency from vendors. Ask about training data, bias testing, failure models, and auditability. That is part of due diligence before entering any partnership. When we develop effective frameworks, we should share them widely. The best part about discussing AI right now is how much collaboration it sparks across the industry.

AI is not going to slow down, and we cannot either. We must accelerate governance and education to match the pace of innovation. The silver lining is that more healthcare leaders recognize this and are taking action. They just need to keep the gas on the pedal.

I believe the role of a chief AI officer can be valuable in some settings, but what matters most is shared accountability. I’d rather see a committee or educator focused on ensuring AI is applied responsibly. It is not about how we will use AI; it is about how we are using it and keeping that oversight in place. Shutting it down out of fear would only leave us further behind.

Representation & Advocacy

You’ve been such a champion of representation and uplifting others, from supporting Tech She Secures since the beginning to serving on boards like Bluebird Leaders and beyond. Why do you think platforms and communities like these matter for women in tech and leadership?

A platform like Tech She Secures or a community like Bluebird Leaders, and for me also Women’s Business Leaders of the U.S. Healthcare, matters because they create visibility, support, and belonging. Those three things are still far from guaranteed for women in tech and leadership.

Visibility is critical. When women see other women leading in cybersecurity, healthcare IT, or executive roles, it shifts the art of the possible. Representation is not just symbolic; it is proof. It tells emerging leaders that they belong here and that there is a path forward. Without that visibility, talented women may never see themselves in these roles. I have always said that when you look up and see yourself reflected somewhere in the mix, you believe it is possible. You can still believe when you do not see it, but it is harder because there is not always that arm reaching out to help you get there.

Support accelerates growth. Communities like these provide what many corporate environments still do not: genuine mentorship, honest conversations about life and challenges, and networks that open doors. Women supporting women is not just nice; it is strategic. We share opportunities, make introductions, and advocate for one another in rooms where decisions are made, even when the person is not in the room.

Think about the impact of someone speaking positively about you when you are not there, saying, “That does not sound like her,” or “She can handle that.” My friend Amber Tichenor, who wrote Behind Frenemy Lines, talks about the harm caused when women do not support each other and the importance of building mutually supportive bonds. I have had my share of mean girl experiences in my career, so I am especially passionate about helping other women get where they need to go.

Belonging drives innovation. When women feel like they truly belong, not just tolerated but valued for their ideas, they bring their full selves and their best thinking to the table. Research shows that diverse leadership teams make better decisions because they see problems from multiple perspectives. Communities like these help women build confidence and connections so they can claim their seat at the table.

Boards with two or more women are more effective. Women make most healthcare decisions in their families and approach problem-solving and conflict differently. When we collaborate, the effect is exponential. When you uplift one woman, there is a ripple effect. Women do not keep that to themselves. They mentor others, hire differently, and advocate for inclusive policies. This goes beyond DEI initiatives; we have been doing this for years because it is the right thing to do. And it is not just about being fair, even though that matters a lot, it is about building stronger, smarter, more innovative organizations.

Healthcare IT especially needs every perspective it can get. We cannot afford homogenous thinking. I love hearing stories from people who came from other industries because there is always something new to learn. That is why I created the Flourish Podcast. The most important question you can ask anyone is, “What did it take to get here?” Everyone’s story is different, and there is always something special in each one.

For young women or anyone entering tech and healthcare leadership, what is one belief you wish them to carry, one skill you wish they develop early, and one support or mindset you wish more organizations provided?

Number one is to believe in yourself. You are capable, even when the room makes you question it.

Second, know your skill set. Learn to communicate with clarity and confidence, because it will open doors for you. I went through the entire Toastmasters program to become a Distinguished Toastmaster. It took me seven years to complete, which is a long time. I do not know if it takes everyone that long, but one of my mentees just joined Toastmasters and is already building her confidence through it.

That is important because you can walk into a room and think, “Wow, I am overwhelmed. There are so many important people here. What am I going to say?” It teaches you that less is often more. I am still learning that, by the way. But when you know how to communicate clearly, it helps you find your footing in any space and opens new opportunities.

And then there is support. Find communities that lift you up, like the Tech She Secures platform, Bluebird Leaders, or WBL. Not just organizations that pay you, but places that give you energy and growth. Volunteer your time, spend time with people you can learn from, and create community everywhere you go.

If you are introverted, that can feel tough. People say, “I am shy; I do not know how to connect.” My advice is to start small. Go to a Bluebird event. I promise, even if you are the most introverted person on the planet, you will walk away with new friendships and people who are genuinely happy you came. They do not care what your title is; they are just glad you are there.

Those are the spaces where you can build confidence, thrive, and connect. Find your tribe. It is one of the Blue Zone theories from Dan Buettner’s work, and I believe it applies both personally and professionally. Having your tribe—people who encourage and inspire you—is one of the things that truly contributes to longevity, in life and in leadership.

The Road Ahead

You’ve had such a dynamic career, CIO, executive coach, community builder, board member. What’s next for you? Where do you see your journey heading in the next chapter?

I am focused on building, maybe you could say platforms to a degree, but not in the technological sense. I am focused on building platforms that scale leadership impact. I have never felt more energized about how important that is right now.

If you can multiply impact, that is what matters. I want to do that through media with This Week Health and Community. We are so much more than podcasts. Our company is about creating a platform and a community where healthcare leaders learn from each other, share challenges openly, and build relationships that drive real change. Through This Week Health and through Flourish, I get to amplify voices, talk about real problems, and facilitate conversations that move the industry forward.

I am also deeply committed to developing the next generation. Through executive coaching and the programs I teach in, I get to help leaders navigate complexity, find their voice, and step into bigger roles. I have had incredible mentors throughout my career, and paying that forward is both a joy and a responsibility.

I like to say transformation happens one leader at a time. I grew up in corporate America, and with hybrid and remote work environments today, I don’t know that the newer workforce gets to go into an office and learn all those unspoken cues of success, the nonverbal signals, the side conversations after meetings, or those “big kid” meetings where you just sit, observe, and later ask your boss, “Why did that happen?” I had leaders who gave me that space to learn. I do not know how you replicate that fully in a virtual world, but I want to help figure it out.

Some of my strongest relationships came from those in-person moments, the hallway conversations, the snow days when everyone was stuck in the office together. Those were formative experiences, and I want to help people find that same sense of connection, even in a changing environment.

I also love serving on boards like Bluebird Leaders and FortyAU and doing advisory work for Otis Health and Reveal Health. Those roles let me contribute strategic perspective and stay close to innovation across healthcare. Whether it is leadership development, a new healthcare solution, or an inclusive workspace, all of those efforts come together to create stronger, more human organizations.

There is a common thread through everything I do. It is not about doing more, though my boss Bill would tell you otherwise. He’ll call me out of the blue and ask, ‘Where are you? Are you traveling too much?’ And you have to love a boss who asks that, because he genuinely means it. He wants us to have the space to say yes to the things that matter most while still keeping balance.

He is one of the best mentors I have ever had because he always makes you think differently. He will ask a question even when he knows the answer, just to make you consider another angle. And he will remind me, “There are only 24 hours in a day.” I am a big believer in rest, hydration, and self-care, though I will admit that exercise is usually the first thing I give up. I am working on that.

It is tough because I am wired to be altruistic. You see something unjust or something you could make better, and you want to jump in. But there is a point where you have to know your own boundaries. I always joke that I would have ten cats if I could, but just because you can does not mean you should. That applies to projects too, because you cannot do everything at once and still do it well.

For me, it is about structuring for deeper connection with people, with purpose, and with myself. Whether it is building a platform, coaching leaders, or advising organizations, my goal is to help people truly flourish. That is not just a play on words. When we create workspaces where people can flourish, we are advancing humanity, promoting digital responsibility, and making good decisions for our environment.

My favorite part of all of it is the human connection. I truly believe we transform healthcare one relationship, one conversation, and one introduction at a time. When I connect the right people who go on to solve problems together, that impact scales far beyond anything I could do alone.

So, what is next for me? More of that, going deeper, being more intentional, and focusing on what truly matters, and continuing to make human connection the hallmark of my career and my life.

Closing Reflections

When I think back to how this connection began, I still smile. Sarah didn’t know me, but she said yes, and that yes changed everything. It opened the door to one of the most meaningful mentorships of my life, one that has shaped not only how I lead but who I am becoming.

Every conversation with her leaves me better, and this interview was no different. It reminded me that leadership is not a destination but a continuous practice of awareness, empathy, and courage. Sarah has this rare ability to make you pause, reflect, and see things through a lens of both wisdom and warmth.

As I was putting this feature together, I found myself re-reading her words not just as an editor but as a student of leadership. There is something deeply grounding about the way she leads with clarity, grace, and purpose. It is the kind of leadership we need more of in this world.

I will always be grateful to Paul Connelly for making that introduction because it brought someone into my life who has become both an incredible mentor and a lifelong friend. And to Sarah, thank you for every lesson, every moment of encouragement, and for reminding all of us that the best leaders lift others as they rise.

Maliha

Disclaimer: The content on this blog and website reflects a combination of my personal experiences, perspectives, and insights, as well as interviews and contributions from other individuals. It does not represent the opinions, policies, or strategies of any organization I am currently affiliated with or have been affiliated with in the past. This platform serves as a personal space for sharing ideas, lessons learned, and meaningful reflections.