When I first met Ann Friedman, I had just locked my keys in my car. I underestimated L.A. traffic, parked 15 minutes after our meeting was set to begin, and spotted my keys between my driver's seat and the door as soon as it slammed shut. I couldn't think of anything else to do but laugh.
At the time, I was mostly an unpaid freelance writer, regularly steeling myself for an inbox filled with silence and rejection—so the car keys were the least of my problems. Ann, on the other hand, was and is a recognizable name in media. She's a longtime contributor to New York Magazine and a monthly columnist in The Los Angeles Times. Aside from her many other bylines, including in the likes of the New York Times Book Review and Elle, she hosts the popular podcast Call Your Girlfriend with Aminatou Sow and sends out a weekly newsletter that likely reaches every single cool girl you know. Somehow, given our two extremes, Ann became my mentor.
"It's another way of knowing about how my industry is evolving," Ann told me when I asked about what she's gotten out of mentorship. "Also, it feels really good to pass along the knowledge I've gained to people who can use it!" In the last three years, Ann has helped me polish pitches, edit drafts, navigate the corporate world, and return to freelancing with success. She's also introduced me to a tight-knit group of female creatives that I've leaned on for work and friendship.
Looking back on the car fiasco, I got lucky: It was the rocky but real start of my professional career. So, using a few of my experiences, I reached out to Ann to explain why some questions to ask a mentor may be considered "good" or "bad" based on how constructive they are to fostering this type of relationship. I posed five hypothetically "good" questions, five hypothetically "bad" questions, and a bonus question to help if ever you're lucky enough to meet Ann in person, too.
5 Good Questions to Ask
1. How do you want to approach this relationship, and what is the best way to reach you?
"I think it's good to set expectations for any relationship, but especially a professional one," she says.
2. I want to make sure that I accomplish this specific goal by next year. Is there a way we can work together to help me accomplish this?
"I love this question because it includes a concrete goal and a timetable," Ann says. "I think many mentees struggle to set goals, so you might want to back it up a step even further and ask for help in setting an achievable mid-range goal with your mentor."
3. I've run into a work issue, and here's a quick summary. What else should I do to solve it?
"It's fine to ask this, but if your mentor is not a fellow employee in your workplace, know that sometimes the answer has to be simply, 'Sorry, this sucks. I'm here to listen to you vent," she says. "Your mentor can provide advice but often isn't in control of the circumstances making things hard for you. Know that going in."
4. I've accomplished this goal, and now I want to strive for this project. Do you think that's the best way to build my career?
"This question is best asked of a mentor who has known you for awhile and is familiar with your aspirations," she says.
5. I have these strengths and these weaknesses. Where should I focus my time at this period?
"Maybe make it even more specific: 'How do I play to my strengths and account for my weaknesses to achieve my goal?'"
5 Bad Questions to Ask
1. How did you get where you are?
"This is so hard because many of the choices I've made and successes I've had were a product of the time and place. You can't re-create the media moment that was blogging in the early aughts or starting a podcast before Serial took off," Ann says. "Many of the choices I've made over my 10+ years as a journalist are not choices available to someone starting their career today. In general, it's impossible to reverse-engineer success."
2. Do you think I have any skills I should work on?
"It's always better to ask for specific feedback than general feedback," Ann says. "Ask, 'What about this specific piece of work could have been better?' instead."
3. Can you reach out to this important person that you don't know on my behalf?
4. I have a pressing issue that I need help with this very second. Where are you?
"Being a mentor is not an on-call role," Ann says. "Be attentive to their time constraints and schedule, and the feedback and responses you get from them will be of quality."
5. Let me tell you about this personal drama. Oh my god, right?
"Don't waste your professional mentor's time with questions that are strictly personal. Save those for your therapist."
Is there anything you wish people would ask you?
"More than anything, I wish they'd keep things concrete," she says. It's almost impossible to answer the super-general questions I sometimes get, like, 'How do I become a successful freelance writer?' That's a goal, not a question."
"But if someone says, 'I want to write an in-depth profile for a major magazine in the next five years,' that's something I might be able to help with. Specificity is powerful!"