Last week, while in LA to give a keynote, I caught up with my friend and brilliant author Tara Schuster over dinner.
I opened up to her about a predicament, and in response she shared a similar experience of her own.
And then she did something that took me completely by surprise.
Tara leaned in and asked, “I’m curious: How did that land on you—me sharing a similar story in response to yours? Did it seem like I was trying to one-up you? Or did it feel like I was adding to the conversation in a meaningful way?”
It’s not often that someone pauses to directly ask about the impact of their words. I told her that I appreciated hearing her story—and above all, I absolutely loved the question she asked to check in with me.
That simple question—How did this land on you?—not only cleared the air of any potential misunderstanding, but also deepened our connection.
And if Tara’s response hadn’t landed well, that would have given us a chance to realign and to mend a potential rift before it widened.
I left dinner thinking about all those times I felt uncertain about how I came across in a conversation. Did I talk too much? Maybe my joke came off wrong. What if they misunderstood what I was saying? These doubts would spiral well after the conversation had ended, eroding my confidence and leaving a trail of unresolved, nagging thoughts. And the more I thought about how I was coming across, the less I could actually be present in conversation.
So much unnecessary worry that a simple question could have saved!
The same idea applies far beyond personal conversations. Think about the last meeting you had where someone seemed disengaged. Instead of stewing over it later, what if you asked, “I noticed you were really quiet. How did our discussion come across to you?”
Numerous times, I’ve stood on stage during a keynote, eyes scanning the crowd, only to fixate on a person sitting in the front row with a frown on their face. My mind would jump to dire conclusions (“They must hate what I’m saying.”). Yet, often, this same audience member would then approach me post-talk, with the same frown on their face, to tell me how much they loved my talk.
Our assumptions are often our worst enemies. They sneak into conversations and pollute them with all sorts of unspoken doubts and misinterpretations. A simple check-in question not only avoids misunderstanding, but it also shows others that you care about them. If Tara hadn’t checked in with me, I might have left feeling overshadowed by her story. Instead, her question made me feel valued.
Yes, it’s uncomfortable to voice that question. Most people would rather avoid putting the spotlight on these moments of doubt. But ignoring the obvious—pretending there isn’t an elephant in the room—doesn’t make the elephant disappear. It actually makes things worse, leading to strained relationships and unresolved tensions down the road.
So, the next time you feel uncertain about how you came across, don’t let your worst assumptions write out your script.
Instead, lean in and ask.
That act of bravery not only clears the fog, but also weaves stronger bonds.
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Bold
