In early 2020, Katie spoke at the MAKERS Women’s conference, a global leadership event designed to empower women by making the space for vital conversation. During her time at the conference, Katie got a chance to catch up with various inspiring female leaders — including director Olivia Wilde.

Though known most recently for her work on Don’t Worry Darling, Wilde had just finished taking much-deserved victory laps for her work on the hilarious coming-of-age-story Booksmart (2019). After directing a critically acclaimed film, Wilde was brimming with advice about how to manage a large project using healthy communication skills — and how women are now beginning to share resources instead of hoarding their connections. If you struggle to communicate unapologetically and firmly in the workplace, this still-relevant throwback video is a helpful reminder that you’re not alone. Even after years spent in the spotlight, successful women leaders feel pressure to seem likable while also juggling (very valid) frustrations that they’re not given the same professional opportunities as their male counterparts.

And these quotes are fairly relatable and prescient given the state of Wilde’s most recent project. If you’ve been following the Don’t Worry Darling drama (from Spitgate to salad dressing), you know that Wilde has come under fire recently for tension onset — which, coupled with her dalliance with Harry Styles, was not exactly a good look. But still, comparing Wilde to some male directors who torment actors and crew only to be praised for their bad attitudes, it’s hard not to question the media’s perspective on women who don’t behave perfectly. In this short video, both Katie and Wilde sound off on the sad reality of discrimination — while also praising the evolving networking methods that women use to uplift each other.

Katie Couric: I feel like when women say something directly and they’re not being sweet or deflecting it with humor, they walk away and they’re like, Oh, I’m such a bitch. They think I’m such a bitch. I was so bad. I hope they don’t hate me. How have you, as a director, dealt with this likability issue?

Olivia Wilde: I think people appreciate clarity. It was easy to focus on being clear and to allow people to feel heard and then feel that my demands were warranted and fair. I wouldn’t regret having made that statement as long as I had listened and then been very clear about my point of view. I think where leadership can seem reckless, unpleasant, and aggressive is when people don’t feel heard. It’s a part of the film process that things move very quickly. Things become very chaotic. Things change constantly. But you never have to become a tyrant. You can be very clear and direct, but I think people really appreciate it because they feel those boundaries are in place and they’re being kept safe. I think you can always communicate why you’re asking them to work harder.

I remember a moment when a props person brought the wrong prop to set and we were under the gun for time. Everyone expected me to lose my mind and blow up because that’s what usually happens. People throw things and they yell. They think that seems powerful.

I said, “It’ll be more efficient if we just wait for the correct prop to come.”

Someone gave me directing advice the other night. They said, “Oh, Stanley Kubrick used to say the key to directing is to have at least five arguments a day on set so that everyone feels on their toes.” And I was like, That’s the most male philosophy of leadership I’ve ever heard. I can’t think of anything that would make people less efficient and less invested than perpetuating tension through arguments.

I went to the set of The Handmaid’s Tale and the director said, “It’s so hard [for women] to get their first break, and men just hire these guys because they have more faith or confidence in them.” And then they build up this list of credits, which helps them achieve more and more and more. But if you don’t get those first few things under your belt, it’s hard to succeed.

For a long time, for one woman to feel she was succeeding and breaking through the glass ceiling, there was this sense that, “I must go it alone because if I bring others with me, it’ll be harder to get through this small crack in the ceiling.”

Now I think that’s changing. I’ve benefited from people like Greta Gerwig, who is giving me crew members that she loves and relies upon. By recommending them to me, she’s making them unavailable for her projects. But she so wants to support me and my next endeavor that she’s like,” OK, you have to call these five people. They’re my trusted allies.” Sharing your brain trust and sharing what you’ve learned is something that has a huge effect. But for a long time people thought, OK, I’ve gotta protect these secrets for my own success.

I find it so gratifying to see women being much more generous with one another because I’m a little older than you are. I think that in my generation there wasn’t as much support among women. It was so intensely, fiercely competitive.

For so long I’ve even felt that it was about being a part of a boy’s club. Now it’s about proudly being a part of a girl’s club and feeling power in that.