October 2, 2025: What if the only way to truly fix healthcare IT is to burn it all down and start over? Join me for a provocative conversation with transformation powerhouse Cheryl Dilley, who's spent 25 years leading enterprise-wide change across healthcare and high tech. We dive into why healthcare's technical debt has reached a breaking point, what Netflix can teach us about disrupting an entire industry, and the bold leadership required to stop settling for mediocrity. Cheryl shares her secrets for building resilient teams, succeeding as a chief of staff, and why humor might be the most underrated leadership trait in healthcare IT.

Key Points:

1. 00:00 Introduction to Flourish Soundbites 
2. 00:17 Meet Cheryl Dilley: Bold Leadership in Healthcare 
3. 01:07 The Need for Radical Change in Healthcare 
4. 02:08 Technological Solutions and Challenges 
5. 06:19 Building High-Performing Teams 
6. 11:47 Women in Technology: Career Growth Strategies 
7. 16:30 Speed Round and Closing Thoughts

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[00:00:00] Sarah Richardson: Welcome back to Flourish. I am Sarah Richardson and today's soundbite features powerhouse leader in transformation and strategy. Cheryl Dilley.

We're calling this episode Burning It Down to Build It Back. It's really about bold leadership and what we believe is necessary in healthcare today. Cheryl has more than 25 years of experience. She's driven enterprise wide change across healthcare and high tech, aligning strategy to execution, building resilient, high performing teams, and she is passionate about elevating women in technology, mentoring future leaders, and creating inclusive cultures that thrive through change.

And she has a bold hypothesis to truly fix healthcare in America. We're gonna have to burn it down and start over. Cheryl, welcome to the show.

[00:00:45] Sarah Richardson: I'm so grateful that you're here. We've met through Bluebird and we'll see each other at the conference in a couple of weeks.

There's a point when you just can't keep banding, bubblegum, paperclips and healthcare has been at that point for a couple of

[Mic bleed]

right? So we can't just keep gold plating things. There's companies out there with huge technical debt. When I start healthcare, I couldn't imagine. Small companies would have six to 700 applications and the amount of technical debt, I mean, it's almost like you need a new car and all you're gonna do is buy a new air freshener.

there's just a point in time where you really need to rethink and just completely renovate and start over again because there's so much. Technical debt over-engineering. healthcare doesn't need to be as complicated as the human body, and we can make it much simpler And affordable.

Humans deserve healthcare.

[Mic bleed]

How much do you really believe that? Technology can address things and what three to five things really need to change for it to be transformative?

And part of that is we just didn't invest. COVID like was a wake up call of, I don't wanna invest into technology. And these companies would rather. Fix, and this is probably a bad example, but toe fungus didn't actually fix the system, right? So for me, first thing, get rid of the middleman.

Cause health issues for other patients. So that for me is the first thing is just get rid of the things that cause raises healthcare costs. But that actually doesn't help with healthcare benefits or even healthcare, solving huge healthcare problems or even equity.

The second thing that I call it is Netflix it.

Right? I mean, you really need to come in and do a disruption, right? It's, for me, it's, as antiquated, as, you know, blockbuster was, you really need, and these companies are trying, Google's involved, Oracle's like all of these big companies, but it feels like they're just piling on, like you said, just more technology versus what would a healthcare system.

Today

You're talking about like what kind of leader needs to take the horns on this one?

You have to, you can't have a lapse with [00:05:00] care, so you have to have a transition plan to do that, All these companies are assimilating companies and creating a, we have it in everything else. We have it in human resource, right? Systems, we have it in financial systems, we have everything else, but companies that actually were into the healthcare, they're not even in the cloud yet.

Cloud's 15 years old, right? They could have actually modernized their systems and been more affordable. Right? We know the less technical debt you have. The better it is so, so stop selling for mediocrity or saying we can't, and start looking at what can we go do? Yes. Policies there, there are state and federal, you have to keep people safe.

AI is moving faster than the speed of light now. And so, we've gotta be able to look at what we can do and stop saying it's too broken, it's too expensive. We need to do X, we should do Y. And actually just get on it and get someone that is bold enough to, Leap ahead and make this worthy for humans, for healthcare.

[00:06:02] Sarah Richardson: Well, one of the things I love about your style is you are a bold leader and you have led global transformations, talent strategies across the continuum. What are some of the common threads in building these resilient, high performing teams that would need to be true for this endeavor?

You gotta roll up your sleeves and work with them, let their ideas rain, right? And again. We have diversity of thought because that's what drives innovation. So for me, I hire super smart people and then I unleash them to their

[00:07:01] Sarah Richardson: I bet you're one of those leaders that anyone who's ever worked for you comes back and says, oh man, I used to work for Cheryl or with Cheryl, and here's the things we used to be able to do. That's such a hallmark of your style, and it's important when you let people loose that are incredibly brilliant.

How do you help them balance strategy and operations? Because operations sometimes doesn't seem like the most fun aspect of what we do yet once you put something into place from a strategic perspective, by nature it gets operationalized. So how do you keep. Teams aligned and energized with those two in the mix.

A team that gets to do [00:08:00] both actually has accountability and pride that they've actually. Built a future model and then implement it and seeing it come to fruition, there is nothing more powerful for a team collaborating and getting to high performance when they not only have an idea, but they make that idea come true.

the transition from strategy to operation shouldn't be separate. It's one and the same. And even as you're going into operations, sometimes your strategy needs to change. So it's not just a single linear line of time. It repeats, it goes back, it goes forward, it goes up, it goes down, and sometimes it goes sideways.

[00:08:56] Cheryl Dilley: I'm probably the unicorn is I love ambiguity and [00:09:00] change, but I understand that all people aren't like that. So for me, I'm always very transparent with my team. Even when things are going to go sideways, Unanticipated change is I bring them along for the ride I help them understand the decisions that are being made, the trade-offs, consequences, cause and effect.

And we have that conversation as adults and as a team. And what I love about doing that is they actually have these wonderful ideas of like, Hey, did you think about this? Or did you think about that? And having that team. Cohesiveness. And diversity of thought.

It's not just DEI, but really allowing people at all levels of the organization help contribute, actually helps them be so much more invested and feel accountable for the outcomes that we achieve. And when we fail, we fail together. We give each other hugs, we stand each other up, and we move.

I mean, you were at Intel for a long time. You've been at Blue Cross Blue Shield. I mean, there's just, these aren't small endeavors, and you have been [00:10:00] described as the ideal chief of staff. What makes someone successful in that role and how do you approach it differently?

You have to be an extension of that leader, so that you can represent their brand. The other thing is you have to be very truthful to that leader. Don't sugarcoat things when things need to be told. Because a lot of times leaders at that level don't actually get honest feedback, right?

They don't actually get the human side of things, or they have been disconnected so long, they actually don't understand feet on the street. So for me, being a chief of staff is really, I should be able to step in for my leader and I can't do that unless. That there's a hundred percent trust.

Support each other and we're very honest each other on what's working and what's not.

And if you can do that holistic view, being a chief of staff is a great role because you actually help your peer staff, your boss, and the organization thrive.

'cause to your point, you can give your boss the tough feedback, but you can also share maybe their perspectives and help soften some of those things and help get people comfortable with what may be coming. And that can be tough for women. And when you consider being a woman in technology and for future leaders in tech, what career growth strategies do you recommend based on your own path?

And that's how I just gained my reputation. Even when I moved from sales to it, I [00:12:00] was like, you guys, you don't understand how the sales teams work. This technology does not work for them. And not just say it's wrong, but hey, let me make some recommendations, or from a curiosity perspective, which really helps ground me.

Have you thought about this? , Just being able to own your own career. Don't be afraid. you know, I had a great, mentor one time and she's like, what's the worst that's gonna happen? I'll be like, I'm gonna get fired. She's like, great. Go get another job. I'm not gonna be able to

Send my kids to school. Great. You know what, they can take out loans, right? So, you know, it's really just kind of settling into your comfort zone and your confidence and not being afraid to speak up. but speak up wisely. I always, especially with my male colleagues, I have to remind them we have two ears in one mouth and those should be used proportionally, right.

And it's not, shouldn't just be piling on. You should take a conversation to the next level. I was very lucky at Intel, as I always was, the only female in the room, but I, I've never, I never felt shut down or removed from the room. Healthcare is a little bit different, but you know, you've gotta know what you want.

[Mic bleed]

Awesome. What can I do with that? Because we never had to operate necessarily from that space of fear. And yet it is a very real thing and helping people overcome that. And so. For those listening to this conversation, if you don't have those people in your life, find them. Find people like you and I because we've been there and we get it.

But if they can't, you know, just giving a new perspective, not defensively, but just say, Hey, you know, let me, let me really tell you how that landed on me. and that gains that mentorship. Those male advocates are priceless. Right.

[00:14:14] Sarah Richardson: You do. And a recent conversation I had with Dr. Amber Tichenor, PhD, who wrote the book behind frenemy lines the Importance of Women as Advocates for women as well. And I'm hopeful that people see that just in our conversation, that it's also a responsibility to lift up other women, especially when there's so few of us in this industry and it's hard.

Be successful in healthcare IT with all the other pressures that we have in our careers, in our lives, and so I'm glad we're able to touch on that today too. But for you, looking ahead, what excites you most about what's next in your own career?

I can, you know, we'd be happy, like going and doing another massive transformation. Let's burn healthcare to the ground and start over. right, or [00:15:00] consulting or even, I still wanna keep my passion because I do believe. Mentoring women in stem, if they can boldly go where we've gone, would that help and avoid some of the skid marks, you know, that that's just helps in their career.

It also helps our industry because again, the theme today been like that diversity of thought. Is incredibly important. So for me, I'm really excited about going to soar, here at the end of the month, but also just really super excited about the opportunity and yeah, I don't think the percentage of women has changed in the 25 years I've been in.

They say it has, but it hasn't. So, just so much opportunity for that different lens can take you very far if you just have your support infrastructure and the confidence to go do it.

Almost use a separate section of, and this is the time that I choked in front of the board and this is the time that I didn't do so hot on that presentation. Like [00:16:00] there's all these moments where you're like, yeah, I got a lot of those battle scars I could share for sure. The sense of humor, I gotta believe is what gets us through some of those experiences because they're not funny while they're happening.

[00:16:13] Sarah Richardson: All right. Ready for speed round. Let's do it. I love speed round because you get like a couple sentences to answer these questions. What is a leadership trait that you believe is underrated?

Right? You actually have to love what you do and have a good time. And a little humor can sometimes bring a super tense situation just back into reality so you can actually have a human conversation.

[00:16:46] Cheryl Dilley: I think the best is actually a training that we took in my prior organization, and it was all about culture. And so I still live by those rules there's a, you know, An el mood elevator. So how are you coming into [00:17:00] a situation?

Are you coming at curiosity? Are you super angry? I used to call it, I'm in the basement today and I only need to get some help slam in the stairs. there's also the whole concept of being here now because we're so busy and with Zoom calls and emails and texts pending, I have a plaque that says, be here now so that when I'm in a conversation, a one-on-one with a co, anything in a meeting.

I'm actually present instead of distracted. it's also the shadow of the leader that you project, so you're always on stage, whether you know that or not. So that learning and that experience we did in intact teams really shaped me as a leader, especially at a pivotal point in my career.

That's a great reminder. If you were not leading transformations, what [00:18:00] career would you chase?

It just, it's how you feel and it sets the tone in tech. We see a lot of just jeans and t-shirts and everything else, but just really setting the brand and bringing back my fashion ranks. 'cause I still love fashion and still love doing all the color coordination and everything else. So I'd love to bring that into the current age and then actually use that experience to help women be their best.

Not just in leadership style, but in everything they do holistically.

Because when you have that confidence in yourself that you [00:19:00] believe you look good, then you feel better and you show up so confident. It's just really fun to plan. even today it was like, Hey, talking to Cheryl, like I'm gonna step it up a notch. I'm not gonna wear Lululemon today because we're on camera but I love the fact that we get to dress up just to have this conversation today.

[00:19:19] Sarah Richardson: Absolutely. Cheryl, thank you for joining me today and for sharing both your bold vision and your practical wisdom. Your perspective reminds all of us that transformation takes courage, strategy, and above all people.

First, leadership For our listeners, I encourage you to connect with Cheryl on LinkedIn, follow her insights on transformation leadership, and the future of healthcare. And if today's conversation has inspired you, please share this episode with a colleague who's ready to think differently about what is possible.

Cheryl, thanks again.

[00:19:50] Sarah Richardson: I'll see you in a couple weeks and to everyone who is listening, that's all for now and until next time, keep flourishing.