MEET Carol E.

Carol E. Reiley is the founder and CEO of a stealth health care startup and the co-founder and former president of the self-driving car company Often referred to as “The Mother of Robots,” she recently started a five-year term as a creative advisor for the San Francisco Symphony, where she looks forward to exploring how AI and other technologies can help shape the future of music.

What advice should first-time founders heed?

Your most precious resources as a startup are time and energy. Don’t be afraid to launch a crappy product in order to quickly test your key initial assumptions. We all know the mantra “fail fast.” We know getting something out there early is the best way to collect the feedback you need in order to know what to build. But it’s so much easier said than done. Your entire team has to get comfortable with releasing something they know isn’t perfect. And that can be particularly hard for younger people⁠—including younger founders⁠—because they’re afraid of what others will think or they’re closer to a background like school, where they may have never really failed. So you understand, intellectually, the value of speed, but there’s still a level of fear when you come to the reality of launch day about the less than ideal non-core issues, like the fonts on the website.

It’s something we struggled with at, but one thing that worked for us was to write down the milestones we wanted to hit so that the other team members ⁠could also understood the goals: “This is what 60% will look like, this is the 100% mark, this is 120%.” We openly acknowledged when some pieces weren’t the absolute best but still tested what we believed customers wanted. And once we’d actually released a non-final product, I think it became much less scary⁠—and much easier to see the benefits. It really helped us reprioritize. There were features that we didn’t think were important that our customers loved, and that actually unearthed new ways of delighting them. What really matters is how quickly you scramble to get the next version up.

What question are you asked more than any other?

Like most people, I’m often asked, “Where do you work?” I understand that it’s Silicon Valley shorthand for “Tell me about yourself,” but I really believe our jobs don’t define us⁠—especially as we move toward a gig economy where people are doing so many different things. A professor in graduate school once told me I should reinvent myself every 10 years (about the time it takes to become an expert and plateau on learning) and I think that was valuable advice. It’s empowered me to dive into a new field with fresh eyes and on a steep learning curve. Given the current pace of technology, many people are diving into new careers even more often than that.

I’m thankful that I happened to start working in AI and robotics when it was still a niche field. I didn’t have some big career plan or worry about trying to cater to the job market; I just did what interested me. And because of that, I’ve been able to play with so many different things, from aerospace engineering to medicine to deep-sea diving.

So rather than talk about what we do, I like to ask people, “What are you learning? What excites you? What worries you?” Hearing what someone is currently obsessed with, or what they would do if they had unlimited resources, is a springboard for a much deeper, richer conversation⁠—and might be the start of something new we can work on together.

What experience shaped who you are?

When I was 10, I started my first business⁠—which was based on my favorite books at the time, The Babysitters Club series. It was about girls who started a babysitting service for neighborhood families, and they had everything you’d see in a typical small business, from bylaws and meetings to financial woes and competitive threats. My friends and I copied their business model, and the experience taught me a lot of first principles⁠—how to get started, how to listen to your customers, employee morale, P&L, sales and good old fashioned hustle.

It also taught me the art of the pivot. Our business wasn’t like the one in the books, where customers were calling around the clock. We were barely breaking even. Then one customer asked me to walk their dog while I was babysitting, and that led to us eventually becoming the neighborhood dog walkers–a much more lucrative, repeatable business.

What’s the best interview question in your toolbox?

Some people get so good at interviewing that it’s hard to tell whether they would truly be a good fit⁠. So I like to ask a question they’re less likely to have a rehearsed answer for—“Describe your personality.” It helps me see how they think on the fly. But if we end up hiring them, it’s also really helpful to me as their manager. It gives me a head start on understanding what motivates them, what they value, how they think, where they want to grow.

For example, if someone is an introvert or likes to learn on their own, I can have a reading list ready for them. With someone else, I might block off more time early on to spend collaborating one-on-one. It just eliminates a lot of the initial friction of those first couple of weeks, when you’re still figuring each other out. If they can tell me about themselves, rather than me making assumptions or waiting until I know them better, I can do that much more to help them succeed.

What book should every company-builder read?

It’s extremely hard to pick—I try to read 100 books a year! I keep a library of fantastic books to share with my team, and we do reading groups to help us establish a shared language. One of my favorites is Carol Dweck’s Mindset, because so much of building a product or a startup is about failure. I love the way she talks about your brain as a muscle that needs to be exercised. It actually inspired me to write my own book on growth mindset, for kids, which is called Making a Splash.

Not All Those Who Wander Are Lost, by Steve Blank, is great as well—he talks about product-market fit from a sales and marketing perspective. It’s a little harder to find, but he has a blog that covers a lot of the same ideas on building a product, from idea generation to testing hypotheses to post-launch postmortems. He has lessons on things like getting all sides of your org working together and avoiding the blame game.

Another one is Talking to Humans, by Frank Rimalovski and Giff Constable. It’s very concrete and actionable—if you want to hold a focus group, for example, it gives you a list of questions to ask and tips on how to reduce bias. I think it would be helpful to anyone, regardless of their role. When you’re stuck on something, going and talking to customers is going to help you figure it out far more than sitting with your team in a room.

What’s a lesson you learned the hard way?

The right way to get buy-in. I have a very high tolerance for ambiguity and can distill lots of information to make quick decisions. People have a lot of opinions, and it’s good to hear them. They usually have a lot of valid points. But when everyone wants input on every single decision, that’s a slow and painful process. You have to find ways for people to feel comfortable trusting their teammates to make decisions on their own.

One thing that helps us is writing up decisions and key assumptions, so you don’t have to go through it all over again when someone new comes in. Sometimes assumptions change, and then the decision needs to be revisited. We also make sure that each new decision has one person who’s responsible for making it. But I think the most important thing is that whatever process you decide on, you make sure you’re respectful of it. You have to hold each other accountable to actually follow the plan.

What invention do you hope to see in your lifetime?

How can there be any answer besides immortality? Then I could see every possible invention in my lifetime! And I’d love more time to read more books, try more jobs, visit more places.

More realistically, though, I’m looking forward to seeing more advances in family planning. Right now, so many women have to balance higher education or building a career during some of the same years they’re most fertile, and that can be tough. Things like IVF are usually seen as answers to infertility, but I do love the idea of empowering women to choose when they want to have kids.

Hard-won advice