Can AI make you a better manager? with Hilary Gridley | from WorkLife with Molly Graham

Modupe (0:06)

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Today, we're sharing an episode of a podcast we think you'll love. It's been handpicked by the TED staff, and we think that as TED Business listeners, you'll come away with a fresh idea and a totally new perspective. Enjoy, and head to the link in the description for more.

Hilary Gridley (0:29)

If you are doing really thoughtful work, the AI can be an amazing amplifier for getting that thoughtfulness out at a bigger scale. But if you're just tapping a button and going in and saying, oh, we need a Q3 strategy, like, hey, Claude, write a Q3 strategy for me, that's what's going to be sloth.

Molly Graham (0:52)

I have one pretty strongly held belief when it comes to AI and all the stuff that's happening right now. That belief is that there are things about being human that aren't going anywhere. The messy, relational, judgment-heavy stuff, the art and taste and intangible stuff, the part of work and creativity that is almost impossible to teach or explain. That stuff, not going anywhere. My hope for AI is that it replaces all the like repetitive, menial work that humans should never have been doing in the first place. You know, like data entry or repetitive rule-based tasks or, you know, complex research and analysis that can take months and months and months. Things that aren't actually a good use of the power or the scope of a human brain. That's what I think AI should be for. And if it can take over that work for us, then I think it lets us, the human, focus on things that we're uniquely good at. I've told you that once in a while, I'm going to do an AI curiosity episode where I talk to someone who is deeply embedded in the AI world about a topic. And my goal with these episodes is to help us all learn what is real and what is not in all this AI chatter, and also what is worth our energy day to day. Today, I want to explore something deeply human at work. Management.

Managing people is relational. It requires judgment and taste, knowing and seeing the person sitting across from you. The best managers I've seen do something I've never believed you can systematize. They help people become better versions of themselves.

To be clear, there are a lot of bad managers out there. In fact, bad management is something you are almost guaranteed to experience in your work life. But in general, even though many of us are still learning how to be great at it, management is, I would say, the human kind of work that AI will never replace. Because we are talking about two complex human beings, and a lot of nuance and feelings and judgment. And yet, there are people who are making the case that AI should have a really big role in management. People I respect and whose judgment I trust.

Today, I'll be speaking with one of them, and I'm going to bring all my curiosity and all my skepticism. Can AI actually make you a better manager? Or does it just give you a faster way to do the job badly?

I'm Molly Graham, and this is WorkLife, where we untangle the messy human side of work. Hilary Gridley has spent years leading teams at companies like Whoop. More recently, she's known for her work helping managers use AI to coach people and give feedback and develop talent more effectively. In the process, she's found herself wrestling with questions that every manager eventually runs into. What is good judgment? Where does it come from? And is it something that you can teach? And can you teach it to AI?

Hilary thinks that the answers to all these questions are more complicated than I've been allowing for. So today, we're going to get her take on AI and management, but we're also going to talk about things like judgment and what might have become more valuable, not less, as machines get better at doing our jobs.

Hilary Gridley, welcome to WorkLife. I'm so happy you're here.

Hilary Gridley (4:46)

Oh, I'm so excited to be here. Can I tell you why I'm so excited to be here?

Yeah, totally. So your writing has obviously been so influential to managers working in high growth companies dealing with a lot of change. And so I've been a fan for a long time, but it wasn't until I read your waterline piece where I was like, oh my God, Molly was a wilderness instructor and I was a scuba instructor. And I feel like these are simpatico because back in the day, like my friends were going to get internships and I was like, I'm going to go teach scuba diving. And everyone was like, that's a stupid idea. And I believe to this day that that has informed so much of my own management style. And I'm like very much of the belief that the future belongs to people who take inspiration from unexpected places because all the unexpected places are kind of getting mined.