Reprise: Aiming for trust-building mastery? Practice overcoming awkwardness and embarrassment.

by | Oct 21, 2025 | Monthly-ish tips

This post is part of our Monthly-ish Tips series.

Recent conversations with workshop participants about the personal mastery required to build deep levels of trust have me thinking about my old Victor story, and the embedded trust lessons about overcoming awkwardness and embarrassment.

I first met Victor in early 2017, then again 11 months later. He was my airport driver both times. He recognized me the second time but couldn’t figure out why. I didn’t recognize him at first … and then it all clicked. But I didn’t have the courage to remind him who I was.

You see, on our first encounter I had accidently slammed his rear passenger door into another car when disembarking at the airport (you can read about the whole drama here—timely if a lesson about being present resonates for you right now). I was back in the area and Victor was coincidentally assigned the (unlucky?) task of taking me to the airport again. He recognized my face but mistook me for someone he had picked up the day before. At first, I asserted (honestly) that he had mistaken me for someone else. But then the wheels started turning and within a few minutes I realized why we did in fact know each other.

Only I said nothing.

Harm done to him as a result? Absolutely none. (No harm done to his car door or anyone else’s this time, either, in case you were wondering.)

Opportunity cost for me? Big.

I say that because the reasons that stopped me from saying something were all completely self-oriented: embarrassment, shame, fear of his negative reaction.

And yet saying something would have given me an opportunity to practice being honest, courageous, self-deprecating. It could have gone like this: “Victor, I’m more than a little embarrassed to remind you that I’m the one who slammed your car door into someone’s rear view mirror at the airport earlier this year. That’s why I look familiar to you.” We might have had a good laugh about it. He might have said something nice that would have made me feel better. I’ll never know.

Instead I felt awkward and distracted the entire (thankfully short) car ride and for quite a while after. The awkwardness returns even as I reprise this many years later. Collateral damage.

Relationship mastery lies in a willingness to overcome all the baser human stuff and work your trust muscles all the time—whether it’s with a casual acquaintance, vendor, colleague, or client. Do this especially in the face of embarrassment, like when life re-presents you with someone from your past, or when you’ve forgotten someone’s name and really wish you hadn’t. Take the risk. Tell the truth. Reveal your humanity.

Then there’s also that important life lesson when it comes to relationship-building: it’s a small world and if you think you’ll never see someone again … think again.

Make It Real
This week, notice any tendencies to shy away from something embarrassing or awkward. See what happens if you lean in, instead.

Learn More
Brush up on the merits of personal risk-taking in Chapter 9 of The Trusted Advisor Fieldbook.

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Andrea Howe

As the founder of The Get Real Project, I am the steward of our vision and our service offerings, as well as a workshop leader and keynote speaker. Above all else, I am an entrepreneur on a mission: to kick conventional business wisdom to the curb and transform how people work together as a result. I am also the co-author, with Charles H. Green, of The Trusted Advisor Fieldbook (Wiley, 2012).

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