Meet Cat Miller, CTO of Flatiron Health

“Management should be as much about the long-term as it is the short-term. Not only because that’s the right way of building a company, but because there’s a huge financial ROI to doing so. I see Mandala as central in operationalizing a long-term strategy for companies like ours, helping us attract and retain talent.

Unlike other management programs I’ve been a part of, which can feel more like data dumps, Mandala is an experience. It’s given me a safe space for me and my peers to introspect, learn and connect. And it’s helped me show up to hard conversations in a more centered and grounded way.

Every session I attend with Mandala moves me from a stress level of 10 to a stress level of 4, and that itself is valuable. But on a subtler level, it’s given me the permission to check-in with myself, examine how I’ve been operating, and given me concrete tools to build more inclusive, resilient teams.”

 – Cat Miller

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Where did you grow up? And how do you think that shaped you today?

I grew up in Buffalo, New York. I grew up thinking I was going to be an English major and a philosopher until I got to my senior year of high school and was like, "Oh wow, we don’t have family money. I should earn money." And then that put me on a technology journey. I went to MIT, I got my degree in mathematics and computer science and have been doing some form of technology since then. I did take a year and a half off to be an actor in the middle there, but have been on a journey of largely startups and healthcare startups in my professional life since then.

You mentioned it as an aside, but how do you think growing up in a lower socioeconomic bracket affected the way you see the world?

I think about this through the lens of a paper I read at one point about class systems in the US and that our class systems are actually based on education rather than strictly money. So I actually think it made me a worse person for a while because I was like, "Well, I grew up poor and I got here, what's everyone else's problem?" 

And the key distinction is that my parents are educated. My father has a PhD and is a lawyer. My mother's a doctor. We had challenges when I was young and they were both in school but I think that they always valued education. 

And I came from a community that had certain advantages and it took me a long time to actually realize the number of advantages I had. And honestly, I also recognize in myself, there's so many things that I take for granted now that I can afford that when I visit my family, they can't necessarily. And it's actually a huge wake-up call and reminder of the differences between different economic situations.

Talk us through that evolution. How, and when did that shift take place for you?

I don't remember a particular moment. I do think that becoming a manager and being a manager now for a decade, I think pushed me to focus more on others. I started thinking about other people first. So I think there was a long journey of growth to being a better human being both at work and outside of work with that. 

This is not the time that it happened, but it reminds me a lot of the philosophy shift I went through very quickly, and I think a lot of white people went through very quickly around the murder of George Floyd, which is going from, yeah, there's something off about how we treat Black people in this country to a very clear understanding and realization that there are systems in place that are detrimental to Black communities, that there has been intentional directed racism in this country.

So I say that as I think that I'm not the only one whose view shifted from some recognition that there was something not great there to a very clear stark, oh, there's a huge problem that needs systemic fixing. And I would say that that happened over a short period of time in the summer of George Floyd, but it was a that experience, but over a longer time of just seeing more and more people and recognizing that my pain was not the only pain and that I didn't need to compare it to other people's.

Your journey mirrors the journey of so many others in this country. And in the world of work. How do you think the workplace has changed?

The workplace of 20 years ago, you didn't talk about religion, you didn't talk about politics, and unfortunately now politics includes will we have a planet to live on in 50 years? It includes Black individuals deserving equal rights. Politics has unfortunately expanded and it actually means that now it's much more important to me and I think much more important to other people that the place that I work aligns with my values and I'll call them political values, although I wish they weren't. I think they're just values. And so I do think that there's a big shift in terms of needing my organization to reflect that and to live the values that I live in my personal life. In a lot of ways that's the biggest shift for me.

How do you think the culture of work has changed?

This idea of professionalism that had separated work and personal life blew up during the pandemic because it had to. You saw people had their kids coming into meetings because, well, what are you going to do? And I'm worried that we're shifting back and we're getting into a little bit more of the old mode, but at least right now and for the last few years, I think there's been less of a work over here, life over here belief, it's been much more integrated and it's more okay if you're on a call and your kid comes in or your dog comes in or you have to deal with something. 

I know that there are some companies that are going back to the office, but I feel like the prevailing sentiment, including from leaders is like, hey, it's great to have some flexibility and the level of flexibility we have now and the recognition that you can work from lots of different places successfully is night and day from where it was five years ago.

And, as part of that change, people are not willing to tolerate the same things at work anymore. I genuinely think across the board, my industry, other industries, people have just had a reckoning of, "Oh, I don't have to do this job. If I don't like it, I can do something else." And that is, I think it pushes in a good way the emphasis on employers to have the job be something that is worth having and that people will actually want. And so they expect workplaces where you can bring your whole self to work. Which is why topics like well-being, belonging, and resilience matter.

Do you ever reflect on how you were managed, as you reflect on this change?

I think about my bosses, I had good bosses, so it's not a complaint about them, but I think about what they were thinking about and I don't think that my bosses of 15 years ago were thinking about my wellbeing, belonging or resilience. Or their own, for that matter.

I think about an early manager who I love and respect and he taught me a lot of things including how to use humor to make the workplace better and to defuse stressful situations. But I have this memory of asking him if I can take this week off? And he just gave me this stunned look. And he was like, "Well, I guess as long as your work gets done."  

It was some answer that was just corporate and bad, and not reflective of him as an individual. More reflective of the training that he might have received around PTO. It’s funny, now, looking back to consider how much things have changed. 

How do you begin to adapt to the needs of today’s workplace? And what advice do you have for other managers in the same shoes?

Well, one thing that helps me is to think about managing for the long-term. Someone being here four years is a lot better than being here three years in terms of a lot of different factors. So if taking two and a half weeks…gives them that energy and interest and sparks them, or being told no would just make them sour and want to leave soon anyway, that's a worthwhile investment. And that's a basic example, because of course you can take a vacation, but I think that on a broader scale, I definitely think about what is the way to extend this person from three to four years? 

And then a gift that I got from my manager at my last company was he always talked about everything in terms of what my goals were, not just at the company. So he made it okay for me to always be talking about where do I want to go after? What is the pinnacle of my career? If you're talking to a 22-year-old and you want to talk about where do they want their career to go? It's frankly not going to be at your company. It's very unlikely that they're going to be there for 20 years and become CTO, right?

So I think this idea of, I want to invest in you as a person because I, I am the company, I'm investing in you long-term because I want to be someone you remember is lifting you up rather than pushing you down. I want to be someone who you would connect with in the future for opportunities for jobs, whatever. And I want you to say that Flatiron or wherever I'm working is a great company and recommend other people to it. Which is part of where programs like Mandala fits in. It helps managers think and build for the long-term.

How would you describe Mandala, in your own words?

Management should be as much about the long-term as it is the short-term. Not only because that’s the right way of building a company, but because there’s a huge financial ROI to doing so. I see Mandala as central in operationalizing a long-term strategy for companies like ours, helping us attract and retain talent.

I think it is a safe space for introspection, reflection, and connection. I think it solves the problem of–I'm not going to say this very eloquently–but things just keep going the way they're going. So someone has a behavior or they're going about their work, and the tendency is that they're going to keep doing it in the same way as they've done it before. And when the pressure turns on, they're probably going to get more stressed and everything's going to get a little bit worse. And so I think what Mandala solves is it breaks you out of that tomorrow is going to be the same as today, and I'm going to keep doing exactly what I'm doing. I think it gives an opportunity to change the routine and the default mode.

How has Mandala been valuable to you?

Every session I attend with Mandala moves me from a stress level of 10 to a stress level of 4, and that itself is valuable. But on a subtler level, it’s given me the permission to check-in with myself, examine how I’ve been operating, and given me concrete tools to build more inclusive, resilient teams.

And, I've said this before in another forum, but I feel like it's giving permission to say, actually it is worth it for you to work on yourself, or it is a business priority for you to work on yourself, and it's not taking something away from your job. But I think that what Mandala really tries to say is, if you don't take care of yourself, you'll be a bad leader. 

Before Mandala, I was operating on instinct in terms of my self-management. After Mandala, I feel I have permission and a few tools to handle it more consistently.

Why does that matter?

So I can't remember if I told you this story before, but a million years ago at Flatiron, I was on a semi vacation. I was on the West Coast, but I was at a hackathon for another company and I said something pretty spicy on Slack. 

There was some team that was delivering us something and they were late again and I was grumpy, and my manager was like, "Hey, Cat. So when you feel that way or when you act like that, other people can tell that you're frustrated." 

And that was just such a useful thing for me to know that even when I was trying to cover it up, or even when I wasn't trying to be grumpy, the fact that I was grumpy was intelligible to everyone around me, has been just an important fact in my life ever since. And I think if I hadn't had that, I think that's part of what Mandala's helping people realize and experience.

That when you’re not checking in with yourself, you’ll struggle to be inclusive and create healthy workplaces for others. After Mandala, I think the point would be that I am better able to show up to hard conversations in a centered and grounded way.

What makes it different from other programs you might’ve seen or been a part of?

Unlike other management programs I’ve been a part of, which can feel more like data dumps, Mandala is an experience. So Mandala doesn't give you information faster than you can process. Instead, it’s given me a safe space for me and my peers to introspect, learn and connect. And it’s helped me show up to hard conversations in a more centered and grounded way.

What makes it different from other programs you might’ve seen or been a part of?

Well, I mean, ideally, we're all playing a long game. We're all trying to take, at least in tech, I mean this is slightly different for other folks, but in a company where your risk is that your employees are going to turn over every two and a half years, changing up to every three and a half years has a huge business impact. So that's the business story. And the way you do that is you make it a better experience for everyone. You make people feel like they're growing, you make sure that they're not burning out, you make sure that their managers care about them. And that's I guess what I would say is, at the end of the day, the business rationale.

And the other argument, I would say, the less callous business argument is like, do you want your place to be a lovely place to work? Flatiron already was a lovely place to work, but I think something like this could actually impact the culture and the experience of places that maybe are not as far along or weren't built with the same empathy that Flatiron was built with from the ground up.

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