Tough Conversations: 3 Things NOT to Do

BY Jessica Helinski
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Tough conversations are inevitable. In addition to being uncomfortable, they also present opportunity to say something you may regret. But salespeople can navigate these conversations expertly and even guide them to a favorable outcome. Author James Detert has studied and researched communication, and in an article for Harvard. Business Review, he shares his insights. “I’ve found that people often forget a critical point: When navigating a difficult conversation, you need to craft your message while keeping the other person’s feelings and opinions in mind,” he writes.

When engaged in these conversations, don’t:

  1. assume your viewpoint is obvious
  2. exaggerate
  3. tell others how they should feel

Tough conversations aren’t all about you

It’s very easy to focus on yourself when conversing, especially when discussing difficult topics. But shifting the focus to the other person is key to ending things on good terms. Empathy and respect are so important in sales, and they can go a long way when handling sensitive subject matters. Below are only a couple of Detert’s suggestions of what not to do to when your sales discussions have shifted to tough topics.

Assume your viewpoint is obvious

By assuming that not only are you 100% right but your viewpoint is obvious, you risk insulting and alienating the other person. Your words can inadvertently do this without you even realizing it. “You may use words such as ‘clearly,’ ‘obviously,’ or ‘beyond doubt.’ If you do this, you’re falling prey to naive realism — the belief that you’re privy to some objective reality that others will clearly see and agree with,” Detert explains. Don’t let this attitude, or those insinuating words, make tough conversations tougher. Instead, rely on your persuasiveness and rational reasoning to get your point across.


Once again, word choice is so important. Phrases like, “you always” and “you never” are too generalized. Using words like that, most likely, are exaggerations. They will likely also shift the focus of your discussions. “Exaggeration will undermine your overall credibility and lead to a debate about frequency instead of substance,” he explains. “’That’s not true,’ the person is likely to retort, before proceeding to tell you about the specific date or occasion that runs counter to your claim.” These offshoot discussions will only keep those tough conversations going on longer and paint you as an exaggerator.

Tell others how they should feel

Part of what makes tough conversations is the fact those involved have differing opinions about something. Telling the other person how they should view things is implies value judgement. Likely, the other person isn’t going to like it. Instead, Detert suggests using phrases like, “You might consider…” or “Have you thought of…” to get the other person to consider your suggestion.

DO sweat the small stuff in tough conversations

When having tough conversations, whether they’re with prospects, clients or managers, salespeople should pay attention to small nuances of their speech. Doing so prevents any misunderstanding, hurt emotions or insults. As Detert writes, “getting the small stuff right is imminently doable, it just takes commitment to notice and minimize the use of these problematic words and phrases.”

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