QuestionAble Strategy

QuestionAble Strategy

What's the one skill that will supercharge your professional AND personal lives? Asking better questions. Join startup founder Antonia Hellman as she sits down with people who "ask questions for a living," ranging from venture capital investors to kindergarten admissions officers, from couples therapists to U.S. congresspeople, from talk show hosts to folks who just go on a ton of dates. It's about time we start asking questions about asking questions, but questioning looks very different depending on your goals. Let's break down the strategy together. Let's get QuestionAble.

Episodes

July 29, 2026 57 mins

What if faith is less about having answers and more about asking the right questions?

In this episode of QuestionAble Strategy, Antonia speaks with Rabbi Angela Buchdahl, Senior Rabbi of Central Synagogue and author of Heart of a Stranger, about curiosity, identity, grief, and belonging. Angela shares how growing up Korean, Jewish, and Buddhist shaped her leadership, and how having the “heart of a stranger” became her s...

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How does an education technology founder channel curiosity to spark change in a system often criticized for disengagement and rigid expectations? What kinds of questions does it take to challenge how students learn and how mentors teach? Is nurturing curiosity the missing link between passion and academic success? In this episode, Antonia goes deep with Audrey Wisch, founder and CEO of Curious Cardina...

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April 29, 2025 55 mins
What shapes the spaces we inhabit-and how do the questions we ask reveal what truly matters in a community?
In this episode of QuestionAble Strategy, Antonia welcomes her uncle, acclaimed architect Mark Harris, for an intimate conversation about curiosity, design, and the human stories behind every building. Mark, a featured artist at the Venice Biennale, shares how his lifelong habit of asking unconventional quest...
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    What drives a story forward? Is it the characters, the setting, or the questions we ask about what they want—and what’s standing in their way? 

    In this episode of QuestionAble Strategy, Antonia sits down with award-winning novelist Christina Li to explore the art of storytelling through curiosity and conflict. Christina is the author of “Cl...

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    What impact can the right questions have on your communication style?What if the key to captivating conversations lies not in what you say, but in how you ask? Could mastering your listening skills be the key to overcoming social anxiety?
    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 questionin...
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    November 5, 2024 48 mins

    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 invites Jason Suran, a renowned mentalist from New York City, to explore these intriguing topics. Join us as we delve into the fascinating intersection of psychology and magic, rev...

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    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 ...

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    How does a managing director of a tech accelerator evaluate thousands of startups at different stages - including their own? What kinds of questions do they ask to support and set companies up for success? Is the art of questioning more valuable than having all the answers in the startup world? In this episode, Antonia speaks with Eamonn Carey, former managing director of Techstars London and experien...

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    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? 

    There’s one person who knows the an...

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    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?

    In this episode, Antonia speaks with Marco Carrubba, Senior Director of Customer Success at UiPath. Throughout his de...

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    How can questions heal and enhance our most intimate relationships? How do they help couples have more fulfilling sexual experiences? Our most intimate relationships are often ones that we keep the most secret, yet they can be some of the most important to talk about and continuously work on. 

    In this conversation, Antonia speaks with Eva Dillon (LCSW, CST) ...

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    Antonia sits down with Roy Bahat, Head of Bloomberg Beta, to unpack the questions a tech venture capital (VC) investor asks. Bloomberg Beta is Bloomberg LP’s investment arm, and Roy specializes in supporting startups in the “future of work” space. Previously, he worked for former Mayor Michael Bloomberg and even launched a company himself. All of his career experiences and mentors, a...

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    What is QuestionAble Strategy? Why did you decide to start the podcast? Who in the public domain asks terrible questions? 

    These are all questions that Antonia has been asked leading up to the launch of QuestionAble Strategy, so she thought that she may as well cut to the chase and address each of them head-on. In this first episode, Antonia explains what li...

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