What Would It Feel Like…?

What would it feel like to sit across the table from me as my spouse? My child? My coworker? My direct report? My friend?

In a recent keynote speech, I heard Ryan Leak pose a similar question that challenged me to think differently: “What would it feel like to be on the other side of me?” The question is one of twelve self-reflective prompts from his book Leveling Up (another one I need to add to my reading list).

At first, I misunderstood the question. I thought it was about my future self—what it would feel like to achieve the goals I’ve set. But the heart of the question digs much deeper. It’s about true self-awareness and reflection.

We’ve all looked in the mirror and thought both good and bad things about ourselves.

On a good day, we like what we see. We feel confident, and that confidence radiates to others.

On a bad day, we’re frustrated. Maybe it’s the outfit, the 20 pounds we still want to lose, or the anxiety about an upcoming interview, presentation, or tough conversation.

What we see in the mirror matters—but this question goes beyond that. It challenges us to sit across the table from others and see ourselves from their perspective. Are we self-aware enough to recognize how we come across to others?

We’ve all met someone who isn’t self-aware. They believe they’re the best boss, the best coach, the best speaker—and have no idea others might feel the opposite.

But what if that person is you?

I learned this lesson the hard way several years ago. I was sharing an idea with a leadership team that, unbeknownst to me, fell completely flat. Instead of noticing the cues and pausing, I kept going—nearly insisting that we move forward. Later, I was counseled that I had come across like a bull in a China shop and needed to do a better job of reading the room. It was a tough but invaluable lesson in self-awareness. I realized that my enthusiasm and conviction, which usually serve me well, could also overwhelm others when I wasn’t tuned in to their reactions.

There’s almost always a gap between how we think we come across and how others experience us.

Think about the last time you got into an argument with your spouse, child, or coworker.

You likely assumed you were right, and they were wrong. But is it possible to view the situation from their side of the table?

The argument doesn’t matter. Your tone does. How did your words make the other person feel? Even if they were wrong, could you have handled it differently?

This kind of soul-searching shouldn’t happen only after a single argument. It’s worth applying to every interaction, every conversation, every post on social media.

If your audience were to read or hear your message, how would they feel? Are you self-aware enough to know the answer? Have you ever asked?

When you’re ready to hear the real answer, ask the real question. Don’t ask, “I’m a nice person, right?”—that’s likely to earn a polite “sure.” Instead, ask, “How did I handle that conversation? If you wish I’d used a different tone or different words, what would they be?”

Tools like DiSC® and other behavior-based assessments can be great resources for building self-awareness. The first step in change is looking inward, and both paid and free assessments can help you get started.

Once you understand how you communicate, the next step is recognizing that not everyone communicates the same way. If you’re a dominant extrovert, you may need to adjust how you approach someone who’s a quiet, introverted people-pleaser.

The next time you find yourself judging someone for their lack of empathy or understanding, pause and ask yourself: How might they experience me?

That pause could be the start of a better connection—and maybe even a breakthrough.

To be sure you don't miss a single blog, subscribe on LinkedIn or sign up for my weekly newsletter. To learn more about my coaching, speaking, and training services, email me at doris@dunnwise.com, reach out via DM or visit my website at www.dunnwise.com. And be sure to listen to the Leaderish Podcast for great insights on Leadership.