Behind Our Masks: 10 Questions to Create Connection

Today, while walking the dogs and trying to ignore the fact that central Texas is actively trying to cook us alive, I listened to an NPR podcast featuring Brett Goldstein (a.k.a. THE Roy Kent from Ted Lasso).

Mid-interview, he said something that made me stop – like, literal pause-in-the-middle-of-the-sidewalk stop.

"I think if you look hard enough at anyone, you can love them."

What a thought. What a beautiful, slightly uncomfortable, wonderfully challenging thought.

And then came the caveat: "You just have to ask the right questions [to find the key]."

Because we don’t usually hand over our full humanity on a silver platter.

Instead, we protect it. We mask it.

We armor up like we are going to battle.

Why We Wear Masks (No, Not N95s)

In her research on shame, Dr. Brené Brown coined the term "shame armor" to describe the masks we wear to protect ourselves from vulnerability.

These are the polished (err...usually) personas we present to the world – the overachiever, the people-pleaser, the jokester, the unbothered, the stone-faced skeptic – all covering the same fundamental fear: If people saw the real me, they wouldn’t accept me.

And let’s be honest, we all do it.

Whether it’s clamming up at work, pretending to love small talk (we don’t), being intentionally dismissive to that one manager, or offering the ever-convincing "I’m fine" when literally everyone in our vicinity is fully aware of the fact we are very much not fine.

Research from social scientists like Dr. Kristin Neff and Dr. Adam Grant shows that vulnerability and authentic engagement are crucial for trust and psychological safety (the same psychological safety that research has shown is the most crucial factor for long-term employee success, by the way).

And as it turns out, one of the most effective ways to get past someone’s armor isn’t with a crowbar or shame or even clever manipulation.

It’s with open curiosity.

10 Powerful Questions to Build Connection

If you want to start seeing the humanity behind someone’s masks and start experiencing more meaningful connection, then you have to start by asking better questions.

Open-ended, nonjudgmental questions that are rooted in curiosity. Sorry to be a stickler here, but you have to actually listen to the answer, too. I know – life is full of demands.

So what's one more? Stop with the "why" questions. They often trigger defensiveness, especially when someone is already experiencing stress or burnout, leading to a quick and often ugly end to the intended conversation.

Borrowing from motivational interviewing, social psychology, and a few personal favorites from my own coaching practice, here are ten questions to either keep in your back pocket OR to start practicing in the week ahead:

1. What’s something you’re proud of that most people don’t know about?

   1. This one gently sidesteps surface-level small talk and invites authenticity. It also gives people permission to share a piece of their identity that doesn’t usually get airtime in their regular day-to-day.

2. What are some of your favorite places to visit?

   1. This question invites storytelling rooted in joy and experience. It often uncovers values like connection, curiosity, or comfort, while allowing people to relive and reconnect with positive memories. Travel can be a window into what someone cherishes, how they recharge, and what brings them alive.

3. What's been one of your biggest lessons from the past year?

   1. Perfect for reflecting on growth and overcoming struggles or obstacles. It encourages people to share a meaningful moment of learning, often revealing for both of you some of their prominent strengths, resolve, resilience, and insights gained from the experience.

4. When do you feel most like yourself?

   1. This uncovers the environments, activities, and relationships that bring out someone’s truest self – a powerful way to understand what lights them up. In a world that rarely encourages this type of reflection, this can often bring an energy to the surface that we do not regularly allow ourselves to experience. Be prepared: the answer to this can often surprise you!

5. Who’s someone that shaped you in a meaningful way?

   1. One of my favorite coaching questions, this helps surface stories of mentorship, love, and influence – often rich with personal connection and emotional depth. It also highlights what values and/or character traits are most important to this person.

6. What’s a past risk that you’re now glad you took?

   1. Great for drawing out and reflecting on courage. This question invites a success story that was born from uncertainty, and permits the individual to reconnect with their resilience and sense of pride in taking a risk or trying something new.

7. What's one food that – even if you learned you were allergic – you'd still find a way to enjoy?

   1. A favorite for breaking the ice and inviting a little fun. The added (hypothetical) danger brings the answer to life and encourages people to tap into their imagination. It also tends to reveal a lot about someone’s passion, personality, and maybe even their risk tolerance – all without getting too serious.

8. What are some of your core motivators (or main drivers)?

   1. Understanding what motivates someone taps into their values, goals, and sense of purpose. It also reveals whether they’re fueled more by external achievement or internal fulfillment, which can offer a richer sense of who they are and how they operate when challenges arise.

9. What’s something you wish more people understood about you?

   1. This question gently opens the door to deeper connection and empathy, allowing people to articulate how they want to be seen. This can often provide important insights into the parts of a person that are most often masked or protected (and sometimes even the reasons behind it).

10. What’s a challenge that changed you, and how did you grow from it?

    1. This question invites storytelling with a purpose. People share not just their pain but how they came through it – fostering vulnerability, strength, and resilience, while providing meaningful insight into someone's past and how it has shaped them.

Please keep in mind that these aren’t interrogation tools. They’re invitations that should be treated with respect.

And when used with thoughtful intentionality (and some practice), they can often build bridges where walls once stood.

Final Thoughts (Not Everyone Loves 20 Questions)

A few months ago, in an attempt to practice more open-ended questions and sharpen my coaching skills, I turned my curiosity toward my husband.

He tolerated it for approximately six and a half questions before blurting out, "Why are you asking me so many damn questions?!"

Fair.

Not everyone enjoys feeling like they’re being interviewed by a sentimental FBI agent, and I was – intentionally – trying to ask a lot of questions.

But when you lead with genuine curiosity, an open heart, and just the right amount of self-awareness, these questions have the power to transform everyday conversations into meaningful moments of connection.

Because here’s the kicker: community and connection are two of the biggest predictors of long-term happiness, according to research from Shawn Achor and many other positive psychology experts.

Not wealth. Not job titles. Relationships.

So yes, some people might be prickly at first, they might make you work a little harder to find the key, and it may be tempting to just talk about the stupid weather.

But as Brett Goldstein said – if you look hard enough, you can learn to love them.

You just have to ask the right question.

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If you'd like support in creating more meaningful connection in your life, I'd love to connect and support you along the journey. Schedule your first coaching session today!