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

Are you talking yourself out of the conversation you need to have

We all know it’s important to be willing to tell clients what they need to hear, even when that may not be what they want to hear. I’ve written before about how to deliver difficult messages so that the communication is positive, productive, and trust-building. Today I want to talk about the ways we humans cleverly talk ourselves out of having these tough conversations in the first place.

In short, we do ourselves—and our clients—a big disservice by skewing our analysis. When we examine the pros and cons of raising a sensitive topic, we tend to:

  • Underestimate the value of forthrightness. This is especially in play when we fear what’s being said is especially unpleasant to hear. We forget that a willingness to face facts quickly is almost always perceived by others as a virtue, and almost always outweighs the uncomfortable message. Tip: Caveats can be a big help.
  • Overestimate the cost of disapproval. Those who face an uncomfortable reality—the one we’re in the position to bring up (hooray)—aren’t the ones caught up in all the worries, fears, and concerns that the entire relationship will be damaged in the process. They usually see it as something to be dealt with and to move beyond.
  • Overestimate the probability of a situation righting itself. It’s easy to rationalize that somehow you will be saved from ever having to address a difficulty or having to address it as boldly as you know a trusted advisor would. This reminds me of the TAMO phenomenon I learned about when I was a project manager (“Then, A Miracle Occurred”)—in desperation (and in humor), TAMO would sometimes appear on our Gantt charts. Too bad these kinds of miracles are rare in both projects and relationships.

Avoiding tough conversations makes a lot of sense if you overplay the downsides and underplay the benefits. Leaning in makes a lot of sense if you understand the relationship between risk-taking and trust-building (they’re inextricably linked) and adjust your assessment accordingly.

Make It Real

This week, revisit a past decision to not raise a tough topic (or to not raise it just yet). Consider the three tendencies above.

Learn More


Check into my July 23 no-strings-attached webinar on “7 Risks You Should Take to Build Trust,” or brush up on the three-question transparency test 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).