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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.

[00:00:42] Cheryl Dilley: Thanks so much, Sarah. Great to be here.

[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.

And when we met, we were talking about what would we do to fix healthcare with all the knowledge and years of experience we have, and you're like, we might need to burn it down and start over. [00:01:00] What did you mean by that?

[00:01:02] Cheryl Dilley: Well, Sarah, yeah. I've been doing transformations most of my life. You know, high tech and technology

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]

[00:01:52] Sarah Richardson: We keep hearing that technology is going to fix all of the years and years and years of policy. In fact, I was having this conversation with Bill [00:02:00] even today, where if you look at healthcare, like you look at application rationalization, you just keep piling things on top, and at some point there has to be a start over button.

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?

[00:02:23] Cheryl Dilley: Technology is amazing. When I started healthcare, I couldn't believe that I could buy a car. I could buy clothing, I could buy a house, and a better digital experience.

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.

I can't believe how much payers and brokers make versus it going towards healthcare and caring for others, right? So get rid of the middleman would save billions of dollars. I call it open marketplace. [00:03:00] So you would have total transparency on how much things cost and what competitors do. If you have a bad doctor, they get bad ratings and they don't exist to help, you know?

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.

Look like if it was all inclusive and it didn't, you know, bubble gun and paperclip wasn't part of it, and you could have a mobile. [00:04:00] Every other industry has figured this out, but healthcare seems to still be behind the curve versus leaping ahead, which would be amazing on all the innovation that could happen with people's health, with equity, and get healthcare to people that can't afford it.

Today

[00:04:13] Sarah Richardson: it almost sounds like we know what to do and yet. For myriad reasons, so many different structures in place. We choose maybe not to as a country and as different levels of providers. What level of bold leadership needs to happen to make a difference? Is it policy at the government level? Is it the funding to be able to open that type marketplace?

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

[00:04:43] Cheryl Dilley: I think it's someone that's stopped selling from mediocrity. It's almost like, well, yes, we have a bunch of technical debt. We know that our systems go down all the time, but literally someone's got to go in and just again, burn it down and start over.

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.

It should be just a basic [00:06:00] human, you know, thing that's provided.

[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?

[00:06:19] Cheryl Dilley: One of my very first rules is hire people that are smarter than I am. If I am assuming that I'm the smartest person in the room, you never get innovation, right? And the team isn't brought along for things. So as long as you can set the vision and strategy and empower those teams to figure out how to solve the problems, but you can't just let 'em loosen the field.

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

potential with full support behind them with air cover. and with that, I've just, I'm very proud of the teams that [00:07:00] I've worked with in the past.

[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.

[00:07:37] Cheryl Dilley: One of the things that I've always done is constant improvement, right? It's just the agile background and it's also like there, you know, my human nature is there's gotta be a better way to do this. Yeah, we did great, but is there something else we can do? And so I really do think the energizing the team when you have, and I've run across so many leaders that are either like super good with strategy but not good with tactical.

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.

[00:08:35] Sarah Richardson: There's an element to those things coming together. Well, that's about the psychological safety we bring to the table as leaders, but also about inclusivity, and it's not just the DEI component of it, it's really how you bring people together and make them feel like they matter. What have you seen that allows that to have teams thrive when there is so much change

[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.

[00:09:50] Sarah Richardson: And you've worked in some massive organizations.

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?

[00:10:09] Cheryl Dilley: I think the number one thing is you have to truly trust the leader that you work for.

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 you have to do that real time. So for me, that's really been. Success as well as my investment in the success of that leader, the success of the organization, who we serve [00:11:00] and the employees. And it can't just be one or the other. It has to be all of that.

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.

[00:11:13] Sarah Richardson: I always think about chief of staff is you get to be a little bit of everywhere all the time, and it's a pretty special place to be in an organization.

'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?

[00:11:44] Cheryl Dilley: It was interesting being at Intel as I always felt included, and I think I was always the non-technical girl in the technical world, so I brought a different lens Everybody would be like, I didn't think about that.

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.

[00:13:00] Speak with confidence, do your homework. and by the way, if you don't know the answer, just say, I don't know. I'll get back to

[Mic bleed]

[00:13:05] Sarah Richardson: I love that you share those perspectives. 'cause the thing, there are things that you and I have been fortunate enough to hear often in our careers, and we may be a bit of an anomaly because we're like, Hey, I'm the only one in the room.

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.

[00:13:32] Cheryl Dilley: Absolutely. And I, don't have an issue calling out one of my male peers if there's a micro inequity or something else. And, you know, my nirvana would be that they're aware of that themselves. 'cause I've taught thousands of employees on micro inequities.

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.

So having those male sponsors, having female mentors is really [00:14:00] what, I've always had a sponsor and I've always had a mentor and that's really what's helped me continue to progress as a leader. And again, not be afraid. and we, I've fallen on my face, I don't know how many times, but you have the support infrastructure to pick you back up and move you forward, and you learn

[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?

[00:14:46] Cheryl Dilley: I think I'm at a great pivot point. my role will be ending soon and it's just such a great opportunity,

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.

[00:15:44] Sarah Richardson: You made me think about, you know, we have scars from where we fall off our bike or didn't quite clear the fence when we were kids, whatever.

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.

[00:16:12] Cheryl Dilley: Definitely.

[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?

[00:16:24] Cheryl Dilley: I think, what's hilarious is you just mentioned it is humor. If you can't laugh at yourself and everything, seriously, why are we working so hard?

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.

[00:16:42] Sarah Richardson: What is a book podcast or a resource that's shaped your career?

[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.

[00:17:38] Sarah Richardson: I always once shared that as well. Leaders are always on stage. Pay attention to how you're showing up now with. Just the plethora of social media. I mean, you're never away from people paying attention to what you're doing, plus what you may put out there about yourself, and so always being aware of that aspect.

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

[00:18:02] Cheryl Dilley: I actually went to school for fashion. So I would love to do branding and my passion for women in STEM is really help women in their branding and their fashion and how they show up so they can do that with confidence like you and I are, get ready for this.

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.

[00:18:41] Sarah Richardson: I love that you say that, that whole perspective about dressing for the part as much as being educated or experienced for the part as far as what makes you feel your best self, and put that on, like put on the fancy earrings, put on the, the fluffy shirt, put on whatever makes you feel amazing.

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.

[00:19:17] Cheryl Dilley: I love that. Yes.

[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.

[00:19:48] Cheryl Dilley: Thanks so much, and I'll see you in a couple of weeks.

[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.