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Curated Questions

Celebrating The Power Of Questions

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#42 Ashley Kirsner: Want Connection? Skip The Small Talk

"It is much safer to be vulnerable than you might think." - Ashley Kirsner

"It is much safer to be vulnerable than you might think." - Ashley Kirsner

Ashley is the founder and director of Skip the Small Talk, and believes in the efficacy of high-quality person-to-person interaction for improving psychological health. She has conducted research with professors at prestigious organizations such as Cornell University, the Harvard Decision Science Lab, and the Harvard Business School, on social and clinical psychology topics ranging from decision-making and implicit biases to facial expressions in borderline personality disorder patients.

Ashley gained hands-on therapeutic experience as a suicide hotline phone responder and as a peer counselor at Cornell. Ashley received her B.A. in Psychology from Cornell University and turned down acceptances to doctorate programs in order to devote her time to Skip the Small Talk. She received a fellowship from the Harvard Divinity School for individuals who have demonstrated a social impact in the domain of creating meaningful communities. Skip The Small Talk events are regularly held internationally, as well as an online options.

In this engaging episode of 'Curated Questions,' host Ken Woodward sits down with Ashley Kirsner, the founder and director of 'Skip the Small Talk.' They explore the transformative power of meaningful conversations, the science behind vulnerability, and the surprising benefits of structured social interactions.

Ashley shares her experiences from the suicide hotline, her inspiration for starting 'Skip the Small Talk,' and how intentional question design can foster deeper human connections. The conversation also delves into the physiological benefits of social interactions, ethical considerations in community building, and the importance of creating safe spaces for vulnerability. Tune in to learn how these insights can help you build stronger, more authentic relationships in your own life.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

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Episode Notes

[00:00] The Power of Vulnerability

[01:57] Meet Ashley Kirsner

[03:55] The Impact of Active Listening

[05:02] A Transformative Call

[06:25] The Magic of Open-Ended Questions

[13:28] The Role of Basic Needs in Emotional Well-being

[17:10] The Birth of Skip the Small Talk

[25:18] The First Skip the Small Talk Event

[28:39] The Evolution of Skip the Small Talk

[32:56] Online Events During COVID-19

[34:58] Work At An Anxiety Lab

[38:08] The Importance of Positive Questions

[42:40] The Power of Repeated Questions

[45:33] Attending a Skip the Small Talk Event

[46:14] The Speed Dating Format

[47:21] Encouraging Anxious Participants

[48:45] The Power of Sharing Deeply

[49:32] Consistent Findings on Vulnerability

[50:13] Understanding Oversharing

[51:11] Structure and Time Management

[52:18] Facilitators and Norms

[53:12] Contact Information Norms

[55:06] Intentional Iteration and Safety

[56:37] The Role of Participants

[59:01] Financial Accessibility and Investment

[01:00:43] Balancing Accessibility and Compensation

[01:01:49] Compensating Facilitators

[01:04:39] Physiological Benefits of Deep Conversations

[01:07:00] Research on Loneliness and Connection

[01:09:02] The Impact of Loneliness on Health

[01:10:41] The Role of Sleep in Connection

[01:13:42] The Importance of Group Interactions

[01:15:10] The Power of Intentional Conversations

[01:20:26] Learning from Gathering Experts

[01:23:19] Right Now Question & Following Curiosity

[01:30:18] Where You Can Find Skip The Small Talk

[01:35:45] Takeaway Thoughts & Questions

Resources Mentioned

Skip The Small Talk

Chris Voss

Finding Good with Brian Fretwell

Dr. Nicholas Epley

DBT - Dialectical Behavioral Therapy

Brene Brown

How We Gather by Priya Parker

Power of Ritual by Casper ter Kuile

How We Gather by Dr. Angie Thurston - Harvard Divinity School

Death of Rasputin

Harvard Graduate School of Education

Harvard

Wharton Business School

MIT

GE Aviation

Act Blue

Beauty Pill

Producer Ben Ford

Questions Asked

When did you first understand the power of questions?

How would this possibly work?

What are we doing here?

How could this possibly be effective?

What is it that asking questions actually does for us?

In this deep end of the pool, for what you experience as a suicide hotline counselor, what does that look like?

How did that impact you?

Were there questions that you found most impactful on that end?

Are you feeling suicidal right now?

Do you have a weapon?

Do you have a plan?

Do you have any objects to complete that plan with you right now?

Are you comfortable being in a different room from it while we're having this conversation?

When's the last time you slept?

When's the last time you ate?

Can we get some food in you?

Can we take a walk?

Do they know anything you're experiencing right now?

If the roles were reversed and it were your partner or your cousin or your parent who were going through something like this, would you want them to tell you about it?

Do you think they wanna know if you're going through a tough time?

What if we had a space where we were all on the same page?

Can you take a moment to go home and be a little more vulnerable with your roommate, partner, family, or neighbors?

Can you take that skill with you into the rest of your life?

How are you doing right now?

How did you decide to do your first skip-the-small-talk event?

When's the next one gonna be?

Is this even possible?

How do you have people switch partners in a way that makes sense online?

How do we do this?

What do you got for us?

How do we do this for like hundreds of people?

Can you talk about that story of where you pulled the questions from, and why you chose the different questions that you did?

Where do you live?

What do you like about where you live?

What's the worst thing you've ever experienced?

When's the last time you cried?

When's the last time you experienced awe?

What's something you're proud of that you don't normally get to share with people or that might not be on a resume?

Specifically asking what are pieces of yourself that you don't normally get to share?

What is a favorite ice cream?

What was something that this organization has done right to help you?

What do you think it is about the structure that allows for that to happen?

What other elements are at play here?

Finances would be a barrier, can you help me out?

Do you wanna do it for free?

Due to your position in society, does it make you more or less likely to go to prison?

How can we do subtle things so that you don't have to necessarily out yourself as having an invisible disability, but still get your needs met?

How can we make people with marginalized identities feel comfortable opening up?

How do we make those spaces feel safer?

What is your right now question?

What makes an experience awesome?

What makes storytelling awesome?

Why was this moment so powerful?

Why do we dim the lights a little at dinner parties

What little things can you do to trick your physiology to be more immersed in an experience?

Does doing a new novel activity with someone, trick your brain into being more excited about hanging out with someone?

How can you make these memories more tactile?

What does the tablecloth feel like?

What do the napkins feel like?

Can you just do five more of these?

Can we do this throughout the year?

What assumptions are you making about how much others want to know about your inner world, and how might testing those assumptions change your relationships?

How might your community benefit from structured opportunities to practice deeper connection, and what role could you play in creating those spaces?

If you treated meaningful conversation as essential to your health, as sleep or exercise, how would that change your daily priorities and choices?

Are your questions designed to extract information or to create conditions where others can share the best parts of themselves?

tags: Ken Woodward, Curated Questions, Dallas Cowboys, NFL transition, sports representation, NIL deals, name image likeness, professional sports, athlete development, mentorship questions, life coaching, RXSports.net, CBD for athletes, college football, sports business, athlete representation, retirement planning, sports careers, coaching transitions, athlete advisory, sports entrepreneurship, professional development
categories: Listening, Community, Connection, Gratitude, Relationships, Belonging, Mental Wellness, Personal Growth, Social Impact
Wednesday 07.30.25
Posted by Kenneth Woodward
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