The QuestionAble
Strategy Podcast
“To be honest, I thought it was going to be boring. But it wasn’t! It was actually really interesting!”
-Steve Hellman (my own father)
There’s nothing questionable about it. Learn from pioneers in different fields about how asking questions helped them become the best at what they do.
Latest Episode
Episode 12: An Education Technology Founder Asks… with Audrey Wisch
What sparks a genuine love of learning? How can curiosity be nurtured in students? In this episode, Antonia talks with Audrey Wisch, founder and CEO of Curious Cardinals, about launching a company that connects high school students with college mentors to bridge passions and academics. Audrey shares how asking thoughtful questions drives engagement, builds confidence, and ignites lifelong curiosity. They explore mentorship, share founder insights, and discuss how parents can use AI to support meaningful learning in a rapidly changing tech landscape.
Episode 9: A Communications Expert Asks… with Matt Abrahams
How can asking the right questions change the way you communicate? What if overcoming social anxiety is just a matter of mastering your listening skills? In this episode, Antonia speaks with Matt Abrahams, Stanford lecturer and host of the "Think Fast, Talk Smart" podcast, about the transformative power of effective questioning. They dig deep into fundamental patterns and practices that enhance communication. This conversation about how curiosity and connection can elevate your interactions, both in casual conversations or high-stakes situations, has important lessons for everyone.
Episode 8: A Mentalist Asks… with Jason Suran
How does a mentalist read your thoughts without you even realizing it? What role do questions play in creating an unforgettable performance? What behavioral cues are dead giveaways for mind-reading? In this episode, Antonia dives deep with Jason Suran, a master mentalist renowned for his mind-reading performances in NYC and beyond. Jason reveals the fascinating techniques he employs to engage his audience, including how he uses questions to unlock hidden thoughts and create a captivating atmosphere.
Past Episodes
Episode 11: An Architect Asks… with Mark Harris
What shapes the spaces we live in? How do the questions we ask reveal what truly matters to a community? In this episode, Antonia sits down with acclaimed architect Mark Harris to explore the interplay of curiosity, design, and human stories behind every building. Mark, a featured artist at the Venice Biennale, shares how asking unconventional questions has guided his whole career. They discuss how architecture reflects culture, honors history while shaping the future, and transforms communities through deep listening and honest dialogue.
Episode 10: A Young Adult Author Asks… with Christina Li
What drives a story forward? Is it the characters, the setting, or the questions that reveal their deepest desires and conflicts? In this episode, Antonia sits down with award-winning novelist Christina Li to explore how curiosity and conflict bring stories (and characters) to life. Christina, author of beloved children’s books like Clues to the Universe and Ruby Lost and Found, shares how her own experiences and imagination shape her writing. They discuss crafting narratives that resonate, balancing research with creativity, and the parallels between storytelling and entrepreneurship.
Episode 7: A U.S. Congressman Asks… with Rep. Gabe Amo
How do members of Congress learn enough about a subject to pass legislation? What role do questions play in bridging the divide between party lines? How do you ask AND answer the correct questions to get voters to trust you on the campaign trail? Rep. Gabe Amo (RI-01) shares his experience as a freshman congressman and all the steps that have gotten him to where he is today. He and Antonia discuss the challenges that come with being the youngest person in a professional setting, the importance of preparation, the role that silence plays in effective participation, and how to ask questions to find common ground.
Episode 6: A Tech Accelerator Managing Director Asks… with Eamonn Carey
How do you spot the next unicorn in a sea of startups? Where do you even begin when evaluating a founders’ potential? And here’s the kicker: how do you reflect on your own entrepreneurial successes & failures and use that perspective to help others? For answers, we turn to Eamonn Carey, former Managing Director at Techstars London. He has seen it all - from major successes to spectacular flameouts. His stories will either make you rethink the glamor of being a founder OR get you itching to start that next project that’s been on your mind. You’ll just have to listen to find out which one applies to you…
Episode 5: A Kindergarten Admissions Director Asks… with Babby Krents
What questions do you ask a four-year-old to determine if they’ll be a good student at your school for the next thirteen years? Wait, back up. What questions do you ask a four-year-old, period? And even scarier - what questions do you ask parents at their most nervous, to get an accurate sense of who they are? No one knows the answers to these questions better than Babby Krents, Head of Admissions at The Dalton School in New York City. After 30 years in the role, Babby shares the wisdom she’s learned and her wildest stories exclusively on QuestionAble Strategy.
Episode 4: A Customer Success Director Asks… with Marco Carrubba
How does a customer success director bridge tech buyers and sellers? What questions can you ask job applicants to screen for key characteristics? How can young professionals present themselves most effectively on LinkedIn and connect with mentors? Marco Carrubba has mastered the art of maintaining strong, trusting relationships, which is vital for his career in customer success, building teams, and mentoring startups. Antonia and Marco discuss what customer success is, his greatest interview secrets, and advice for young professionals.
Episode 3: A Couples & Sex Therapist Asks… with Eva Dillon
How can questions heal and enhance our most intimate relationships? How do they help couples have more fulfilling sexual experiences? Antonia speaks with Eva Dillon (LCSW, CST) about how she uses questions to help people work through extremely private, personal challenges. The conversation covers topics ranging from different types of listening to habits that are guaranteed to boost your sex life.
Episode 2: A Tech Venture Capital Investor Asks… with Roy Bahat
Antonia sits down with Roy Bahat, Head of Bloomberg Beta, to talk about the questions he asks when evaluating startups and their founders. This conversation covers how his experiences working for NYC Mayor Mike Bloomberg, as a Rhodes Scholar, and starting his own company helped shape his approach to asking questions in his day-to-day life - backing founders that are building the next big thing.
Episode 1: An Aspiring Podcaster Gets Asked…
Host of the QuestionAble Strategy Podcast, Antonia Hellman, gets a bunch of your questions out of the way: Why is she doing this? Who is she? Who are her dream guests? Why should you care about any of this at all?