The inevitable downside of taking trust-building risks (and what to do about it)

by | Sep 30, 2024 | Monthly-ish tips

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

Something came up in a client conversation right after a Mastery workshop last week that was so meaty I promised to write a Monthly-ish Tip about it. It was a question about how to deal with the “ugh” that often arises when we’ve taken some kind of risk with a client and then don’t get the result we hoped for, which leaves us to stew in our own juices of rejection, failure, and/or loss. I’ve been thinking about it since then, and have drafted a few steps to help.

Playing it safe in our work relationships feels comfortable (upside) but diminishes/marginalizes our trust-building returns (downside). Choosing courage over fear strengthens our trust-building muscles (upside) but inevitably leaves us confronted by the above-referenced “ugh” at some point (downside).

What to do?

Spoiler alert: The answer isn’t, “take fewer risks;” the answer lies in how you manage yourself in the aftermath of risk-taking.

Back in 2019, I wrote about what you probably do (and shouldn’t) when you lose (meaning a proposal, or a project). I said then that the trust-based question is not, “How good are you at winning?” but, “Who do you prove yourself to be when you’ve lost?” Seems to me it’s much the same with the everyday situations that trigger a sense of loss or rejection or failure, like asking for a new client introduction or sharing a provocative point of view with an existing one. These are smaller in some ways than losing a seven-figure deal you’ve worked towards for years, yet no less ugh-inducing. The question remains: Who do you prove yourself to be in these moments of truth?

Here are my starter thoughts, organized into seven steps:

  1. Don’t step over/rush to “fix” the feeling. Being a trusted advisor requires that we intentionally listen for—and even encourage—not only others’ feelings, but also our own. Have a good vent with a colleague, pause to do a little journaling, ______ ß insert your own best practice here. Do something to name your emotions and express them.
  2. Put it in perspective. Is it a true loss? Or is it really a win in the bigger picture? Taking a new and different kind of risk is a big win in my trusted advisor book; it’s just hard for us to see the win sometimes. Ask yourself how a trusted colleague might view your situation. Even better, ask the trusted colleague for their take.One participant in the above-mentioned workshop wisely offered two thoughts after hearing his colleague characterize a recent effort to get a client meeting as “unsuccessful”: (1) If he’d been in his colleague’s shoes, he’d have felt exactly the same way and (2) From his own perspective-generating distance, he saw nothing but victory.
  1. Own whatever there is to learn. Maybe you weren’t quite perfect in how you handled something (true for us all when we’re stretching outside our comfort zone). Maybe you handled it perfectly but your reaction to the unfavorable outcome seems outsized. Learn from it all. Own it with grace and a little good humor mixed in. And then …
  2. Be a goldfish. This is a Ted Lasso reference, from Season 1, Episode 2 when football (soccer) player Sam Obisanya gets pummeled both physically and emotionally by a teammate during training (practice). Immediately after, Coach Ted asks Sam, “Do you know what the happiest animal on earth is?” He then shares it’s a goldfish, because of its 10-second memory. “Be a goldfish, Sam.”Be a goldfish, dear reader. Shake it off. Move on. It most certainly won’t matter a year from now, and doesn’t even have to matter tomorrow.
  1. Reorient to “true north.” Remember that humility isn’t thinking less of yourself but thinking of yourself less. Get your focus back on what matters: being of service, making a difference, helping your client make the best decision for them.
  2. Try, try again. In an unabashed shift from Apple TV wisdom to ancient Japanese wisdom, embody the proverb, “Fall down seven times, get up eight.” Look for the next way to engage with your client. Maybe your timing was off and it’s as simple as finding the right moment to try again. Maybe you see a way to be more effective on a second try. Just be sure you don’t … disappear.
  3. Look for ways to celebrate (yes, celebrate). Psychologists say that rewarding ourselves for our efforts makes our brains feel good and over time establishes a connection between the effort and the positive feeling. Look for ways to celebrate what you tried and what you learned. Even better, consider how to celebrate at the team/group/organization level. You’ll create a culture that rewards courage as much, and maybe even more, as it rewards a win in the more traditional sense.

It’s normal and natural to feel the “ugh.” It helps to have some concrete practices for recovering swiftly and powerfully so we can get back to doing what we love.

Until next time …

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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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