QuestionAble Strategy

About 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.

Publisher

Antonia Hellman

Category

business · education

Language

en

Explicit

Yes

First episode

14 May 2024

Latest episode

29 Jul 2026

Latest episodes

13 episodes in the feed.

1. 

   29 Jul 2026

   A Rabbi Asks... with Rabbi Angela Buchdahl

   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 superpower. You do not need to be Jewish or know anything about Judaism to connect with this conversation. It is for anyone who has wrestled with big questions, felt like an outsider, experienced loss, or tried to understand someone with a different point of view. You’ll learn: Why questioning and wrestling with uncertainty are central to Jewish faith and tradition How to find the deeper need hidden beneath questions that have no easy answers What Jewish mourning practices teach us about supporting people through grief How sacred traditions can evolve through interpretation while staying connected to their roots How to begin to understand people whose beliefs differ from our own Join us for a thoughtful conversation about faith, doubt, identity, and seeing the humanity in one another.

2. 

   14 Oct 2025

   An Education Technology Founder Asks... with Audrey Wisch

   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 Cardinals, a transformative ed-tech company pairing high school students with college mentors to bring learning to life. Audiences will get a first-hand look at how thoughtful questioning shapes career pivots, drives product innovation, and instills a culture of lifelong learning. From this episode, you can expect to learn about: How diverse interests and non-traditional backgrounds give founders a unique edge in education and tech The art of asking the right questions to identify and pursue impactful startup ideas What it means to learn from failure and how self-reflection (driven by honest questioning) propels growth How effective questioning empowers both students and mentors What it takes to build an environment that sparks curiosity in students who feel disconnected from classroom learning The behavioral science behind effective mentor matching and the key traits to look for (Spoiler Alert: contagious passion and humility) How feedback from students and mentors leads directly to product improvements and better learning experiences Why continuous learning and intentionally embracing a “thinker and doer” mindset matter as education, technology, and kids’ needs evolve

3. 

   29 Apr 2025

   An Architect Asks... with Mark Harris

   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 questions led him to a career at the intersection of art, functionality, and social impact. Together, Antonia and Mark delve into the ways architecture reflects and shapes culture, the importance of honoring both the history and future of a place, and the transformative power of listening deeply to clients. Mark recounts how asking the right, sometimes difficult, questions can turn programming sessions into moments of real connection and even catharsis, especially in communities that have long felt unheard. In this episode, you’ll discover: How formative childhood experiences and environments can spark a lifelong curiosity. Why architecture is more than just buildings; it’s a social science rooted in empathy and context. The role of conflict, vulnerability, and honest dialogue in uncovering what people truly need from their spaces. How design decisions, from glass classroom walls to communal music labs, can break down barriers and foster belonging. The art of merging logic and creativity to create environments that change lives. Tune in for a candid, inspiring exploration of architecture as a practice of asking, listening, and building for the heart of a community.

4. 

   4 Feb 2025

   A Young Adult Author Asks... with Christina Li

   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 “Clues to the Universe,” “Ruby Lost and Found,” and “True Love and Other Impossible Odds.” She’s also making her adult literary debut this May with her upcoming novel, The Manor of Dreams. From childhood snacks to intergenerational family dynamics, Christina shares how her own life inspires her writing and how she crafts stories that resonate deeply with readers of all ages. Together, Antonia and Christina reflect on their Stanford days, the challenges of drafting and editing, and the parallels between writing novels and building startups. In this episode, you’ll learn: How to ask meaningful questions that shape character development. The balance between research and imagination in historical fiction. Why miscommunication can be both frustrating and narratively rich. The emotional core of storytelling: ambition, longing, and connection. How small cultural details can create big moments of resonance for readers. Join us for an inspiring conversation about curiosity, creativity, and the questions that bring stories—and characters—to life.

5. 

   24 Dec 2024

   A Communications Expert Asks... with Matt Abrahams

   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 questioning. They dig deep into fundamental patterns and practices that enhance communication. Join us as we explore how curiosity and connection can elevate your interactions, whether in casual conversations or high-stakes situations. From this episode, you can expect to learn about: 1.Strategies for managing anxiety when speaking and asking questions. 2.The importance of active listening in improving communication. 3.Techniques to make small talk feel more natural and engaging. 4.How improvisation can enhance your questioning skills. 5.The role of emotional intelligence in fostering meaningful connections.

6. 

   5 Nov 2024

   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 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, revealing the secrets behind his captivating craft. From this episode, you can expect to learn about: The art of asking questions to uncover hidden thoughts. Techniques mentalists use to create engaging performances. How emotional awareness enhances mind-reading. The importance of audience interaction in mentalism. Strategies for dealing with challenging audience members. The role of curiosity and observation in mentalism. Insights into performing for diverse audiences and venues.

7. 

   22 Oct 2024

   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.

8. 

   15 Jul 2024

   A Tech Accelerator Managing Director Asks... with Eamonn Carey

   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 experienced founder and investor. They explore the art of asking better questions in entrepreneurship, how questioning strategies shape career decisions, and the role of curiosity in building successful startups. From this episode, you can expect to learn about: How diverse interests contribute to a founder’s skillset Asking the right questions when starting a company Learning from failure through self-reflection and the key questions to ask after unsuccessful ventures The role of questioning in mentorship Insights from managing a startup accelerator and creating an environment for founders to discover the right questions and answers The power of leveraging dense networks in startup ecosystems How to evaluate potential startup ideas The importance of continuous learning, especially as markets and technologies evolve

9. 

   2 Jul 2024

   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? There’s one person who knows the answers to these questions better than anyone, and that’s Babby Krents. Babby has been the Head of Admissions at The Dalton School, a private K-12 school, for the past 30 years. Once named “the most powerful person in New York City” by a former editor of the New York Times, Babby has interviewed thousands of children and parents. In fact, Antonia was one of them! Listen to their illuminating and hilarious conversation to get a glimpse into the crazy world of kindergarten admissions in NYC.

10. 

    18 Jun 2024

    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? In this episode, Antonia speaks with Marco Carrubba, Senior Director of Customer Success at UiPath. Throughout his decades-long career in customer success at companies like Microsoft, Vodafone, and VMware, he has mastered the art of bridging buyers and sellers - maintaining strong, trusting relationships. His interpersonal skills and care for others also make him a highly effective team-builder and startup mentor. Antonia and Marco discuss what customer success is, his greatest interview secrets, and advice for young professionals.

11. 

    4 Jun 2024

    A Couples & Sex Therapist Asks... with Eva Dillon (LCSW, CST)

    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) about the questions she asks in her work as a couples and sex therapist. Eva is a psychotherapist based in New York City, with a degree from The University of Michigan and certification from The American Association of Sexuality Educators, Counselors, and Therapists. She shares how she supports individuals and couples through challenging times and tips for how we can all work on our relationships - both with our partners and ourselves.

12. 

    23 May 2024

    A Tech Venture Capital Investor Asks... with Roy Bahat

    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, as well as growing up in NYC and being a Rhodes Scholar, helped shape Roy’s approach to asking questions in his day-to-day life, backing founders that are building the next big thing.

13. 

    14 May 2024

    An Aspiring Podcaster Gets Asked...

    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 listeners can expect from this podcast and how it will help you live a more fulfilling life. Whether you’re looking to make a major career change or your dates a bit more interesting, QuestionAble Strategy has you covered.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

5 ratings

Spotify

5.0 / 5

14 ratings

Podcast Authority Score: 24 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

27

Social presence

0

YouTube

0

Engagement

51

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Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.