Ask good questions, build better relationships

or, an interview with Chelsey Goodan, author of "Underestimated: The Wisdom and Power of Teenage Girls"

I talk a lot about the ways that parenthood and leadership are mutually reinforcing—as every working parent knows, there are several transferrable skills that lead to success at both work and home. As I read Chelsey Goodan’s new book, Underestimated: The Wisdom and Power of Teenage Girls, I was reminded of a big one: The importance of asking question—instead of making assumptions—and how it helps build trust and strengthen communication.

Asking good questions is at the core of what I do every day as a coach. It was also central in other chapter of my career when I was a therapist, professor, and administrator. And yet… I sometimes find myself lecturing my kids when I would be much better served approaching them from a place of curiosity. Why do I do this when I know better?!?

Chelsey is an academic tutor and mentor, with a particular emphasis on the empowerment of teenage girls. I’ll admit, when I first heard about this book, I wondered if I was the right audience—after all, my daughter is only 5 (although most days she thinks she’s 15 😵‍💫). But I found so much value in the book and in my interview with Chelsey. Thinking about these topics now allowed me to consider how I want to proactively address hard issues with my daughter (and my son). Even if your kids are super-young or you only have boys, I promise you will find something useful in this interview.

Chelsey regularly speaks to audiences about gender justice, conducts workshops, and coaches parents on how to better understand and connect with their daughters. She is the founder of The Activist Cartel and the mentorship director of DemocraShe, a nonprofit that guides teenage girls from historically underrepresented communities into leadership positions. As an activist, she advises public figures, galvanizes volunteers, and organizes large-scale events for national nonprofits, while also serving on the board of A Call to Men, a nonprofit working to end gender-based violence.

JW: One of your key messages is “seek to understand first”, which honestly sounds like a perfect principle for many relationships--parenting, marriage, work, etc. Tell us more about what you mean by this.

CG: Agreed, I use this in all my relationships! Most simply, I mean: Ask questions. With a curious, nonjudgmental tone. Don’t make assumptions and don’t project what you think or feel onto another person. With teenage girls in particular, they feel like adults are so quick to judge them, unfairly, because no one has even asked for their perspective. This makes them feel misunderstood. It can be as simple as, “What do you think about that?” or “How does that make you feel?” or “What do you think the solution is?” By asking questions, without pushing an agenda, trust develops. And then by repeating back what she shared, using the same words she used, a teenage girl will feel heard. That’s when understanding and deeper connections happen. 

JW: Your chapter on people-pleasing was thought-provoking. What kinds of messages can parents deliver that balance encouraging good citizenship with a recognition that boundaries are important?

CG: I find that girls get plenty of messaging on how to be nice, polite, and likable, and the point of focus is usually on how their actions impact other people. I think it’s rarer for a girl to learn how to check in with herself and see how actions might impact herself. Good citizenship doesn’t need to be self-sacrificial, and that’s where healthy boundaries can be formed. Women don’t need to be martyrs, trying to make everyone else happy. They can take a beat, check in with their inner voice, and ask what makes them happy. The messaging comes back to asking her simple questions like “Are you doing this to please other people, but you actually don’t like doing this at all?”

When I’m planning a dinner party, I’ve learned to ask myself if I want to cook lots of food or do I want to simplify it. People might love a more extravagant dinner, but it can be stressful, and my well-being doesn’t need to be sacrificed to do that. If people like me less because of the simpler dinner I cooked, then they weren’t my real friends in the first place.

I love when good citizenship comes from an authentic spirit of generosity, where the person giving also feels joy in the pure act of giving. I’ve learned that the more that girls are taught to connect with their authentic inner voice, the better they can decipher between those moments of genuinely wanting to give to others versus when a boundary is necessary to protect their own well-being. It can be very individualized, but without those types of boundaries, I see girls and women become completely drained and resentful. 

JW: I think for parents the transition from shielding younger kids from age-inappropriate information to radical honesty in the teen years can be confusing. How can parents manage this gradual shift with finesse?

CG: My experience has been that girls are ready for radical honesty earlier than their parents usually think. But I think there are ways to test the waters over time. Watching a TV show together and asking her questions about some of the more mature storylines can be a helpful way to gauge what she’s ready to talk about. Romantic storylines in shows are helpful, asking questions in a really easygoing tone: “Why do you think he likes her?” and “Why do you think she likes him?”

The more I ask questions about her thoughts on things, the more I can attune to where she’s at in her development. I think it’s great to set a foundation for those types of conversations at an early age, so it doesn’t feel like it’s coming out of nowhere when she’s 16. I always make sure to affirm her thoughts on things, calling them specifically “smart.” This helps her feel good about sharing more and thinking about it more, because she feels respected. If a girl feels like you respect what she has to say, that also builds trust.

I would also test the waters by sharing something about yourself with radical honesty and see how she receives it. Something small, like an insecurity that popped up in a social environment, and then find a way to laugh about it together. Moments like those make a girl feel like you trust her with your own vulnerability and that also builds trust and mutual respect.

JW: You talk about how worrying is perceived control (so true), and yet worrying is also baked into most aspects of modern parenthood. How can parents manage their own worry--and why is this important?

CG: Worry is based in fear. And when teenage girls feel a lot of fear being projected at them, they don’t respond well. Anything rooted in fear will naturally lack trust. Building trust between you and your girl is of course important, but I also think it’s so important to empower a girl to trust herself. If a parent is constantly worrying about and second-guessing her choices, then she’s not going to feel like she trusts herself. Trusting herself is at the root of empowerment. I always recommend vocalizing to a girl at any age: “I trust you.”

By worrying, we think that can help create a desired outcome, but in reality, that’s perceived control. At the end of the day, we can’t control other people’s thoughts and actions. One way that I help manage this (very human and normal) inclination to worry is to first: Become aware of it. I’ve gotten better and better at catching myself spiraling into a state of worrying. And with that awareness, I stop, and ask myself: Is this in my control? Or is this me trying to control someone else’s behavior? If it’s about someone else, then I have to do whatever I can to let it go and trust. That worry will just burn up my energy otherwise. I’ve found that when I make a choice inside of my brain—to choose trust—then it grows from there. Trust generates more trust, and the people around me really appreciate when they feel trusted.

JW: One of the things I kept thinking when I was reading this was “I hope my kids have a Chelsey in their lives when they're teenagers!” I recognize that as much as I try to instill a sense of openness and partnership, there will inevitably be things that they don't want to tell me--and that's developmentally appropriate! So, what advice do you have for how parents can help foster relationships between their kids and other trusting adults?

CG: Aw this means so much to me! Thank you. I’ve found that it’s important that the kid feels like the adult isn’t forced upon them by a parent. When a parent would call to hire me for tutoring, the first thing I would ask is: “Did she request a tutor?” Any time that a girl can be offered a choice in the matter, the better. It’s also important that she feels like this adult is on her team, rather than her parents’ team. Not that there needs to be different teams, but it naturally happens, and I always tell a girl that I will be advocating for her. I don’t go to the girl to advocate for something the parent wants. This helps her feel safe because she knows that I have her back.

One way this can play out is when the parent is putting pressure on her grades. Rather than telling the girl she needs to do better, I talk with the parents about reducing pressure. Girls are so thankful when I do that, and it reduces stress for the girl in a way that usually helps her do better work. Her grades naturally improve because the anxiety around performance is lifted. When parents see the positive impact, then more trust is built. Overall, parents help foster this dynamic through verbalizing trust, and telling their daughter that they’re glad she has someone to talk to. This is helpful to communicate when a kid has a therapist as well.

Lighting Round

Best book you read lately... The Creative Act: A Way of Being by co-authors Rick Rubin and Neil Strauss

When I was a teenager, I was obsessed with... The Christopher Guest movies Waiting for Guffman & Best in Show

What is the best piece of advice you have for parents?... Phrase everything as a question. A tone of curiosity helps a kid not feel judged. They shut down and close off when they feel criticized, which happen when things are said as a statement rather than a question.

What do you wish someone told you when you were a teenage girl?... “You don’t need to be perfect to feel worthy. It’s also a futile goal because perfection doesn’t exist.”

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