QuestionAble Strategy – Details, episodes & analysis

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QuestionAble Strategy

Antonia Hellman

Education

Business

Frequency: 1 episode/30d. Total Eps: 10

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.

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Data updated on 04/07/2026

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Score global : 73%

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A Young Adult Author Asks... with Christina Li

Season 1 · Episode 10

Tuesday, February 4, 2025 • Duration 01:00:20

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.

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A Communications Expert Asks... with Matt Abrahams

Season 1 · Episode 9

Tuesday, December 24, 2024 • Duration 49:01

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.

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A Mentalist Asks... with Jason Suran

Season 1 · Episode 8

Tuesday, November 5, 2024 • Duration 48:49

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.

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A U.S. Congressman Asks... with Rep. Gabe Amo

Season 1 · Episode 7

Tuesday, October 22, 2024 • Duration 29:04

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.

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

Season 1 · Episode 6

Monday, July 15, 2024 • Duration 57:10

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

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A Kindergarten Admissions Director Asks... with Babby Krents

Season 1 · Episode 5

Tuesday, July 2, 2024 • Duration 01:02:18

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.

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A Customer Success Director Asks... with Marco Carrubba

Season 1 · Episode 4

Tuesday, June 18, 2024 • Duration 54:58

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.

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

Season 1 · Episode 3

Tuesday, June 4, 2024 • Duration 45:17

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.

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

Season 1 · Episode 2

Thursday, May 23, 2024 • Duration 46:55

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.

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An Aspiring Podcaster Gets Asked...

Season 1 · Episode 1

Tuesday, May 14, 2024 • Duration 25:37

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.

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QuestionAble Strategy – Details, episodes & analysis

Podcast details

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QuestionAble Strategy – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities