Tough Conversation Incoming? Think About Your Language

By Libby Wagner

Innovators & Entrepreneurs, February 2025

The skill of navigating a tough conversation is essential for all of your life. That’s a pretty heady sentence to begin with here, but the truth is that misunderstandings, miscommunication, and missed opportunities are almost assuredly rooted in a common denominator: Language.

I’ll refrain from a smug sense of I-told-you-so from years ago conversations with teenagers in my English language classes. “When will I ever use this?” they’d bemoan after a lesson on grammar, or commas, or writing a clearly articulated thesis statement. Language is so important, so essential, and we’re getting worse, not better, at using it!

Have you ROFL-ed or LOL-ed or FWIW-ed lately? These acronyms aren’t bad per se for a short digital text response, but this shortening of sentiment contributes to our losing our abilities to use the nuances of language to convey things that matter.

As a dynamic entrepreneur, the question is not if you’ll need to prepare for high-stakes, emotionally charged conversations, but when you will have them. If you’re looking toward a business conversation where you want the outcome to be positive-oriented and forward-looking, there is some risk involved. It is worth your time to prepare and differentiate yourself before any words are spoken. Risk, in this situation, means that it could negatively or positively impact one or more of the following: Relationships, business outcomes, timing/efficiency, quality metrics, performance, or more. There is a literal cost to this kind of conversation going wrong!

What sorts of things can help?

Translate what’s undesirable to what you want instead. The human brain is wired to be negative and to find out (and often point out!) what’s wrong or not working. It’s a long-ago survival skill where we needed to scan the horizon for dangers and threats. It’s not that we don’t need this skill anymore, but that when we are relying on human interaction and interdependence to collaborate inside our working relationships, beginning with what’s wrong, negative, or not working can create a tone or atmosphere that puts the other person on the defensive. And, beyond that, when we create a long list of negative things we don’t like or want to change, we actually create a picture of what we don’t want. Instead, translate that thing you don’t want into what you want instead. Frustrated with missed deadlines or late arrivals? What would you like instead?—met deadlines and on-time arrivals. Concerned about a team member’s constant interruptions and talking down to other team members? What would you like instead?—open sharing and listening, allowing each person to have a voice, and respectful consideration of other ideas. Be clear about what you want, and what you want to ask, before you enter the conversation.

Framing is your friend: Offer context and acknowledge your own intentions up-front.Sometimes, based on history, personalities involved, or the sensitivity of the topic, you might anticipate a volatile or upsetting conversation. You might feel like the other person is primed to be defensive before anyone says anything! Framing the conversation means that right up front, you share why you’re having the conversation, what you are hoping will happen, and what your intention is. This tactic is even more powerful if you do so with sincerity, authenticity, and vulnerability.

For example, beginning with a statement like this: “You know, John, I’ve been thinking a lot about our most recent meeting, and I wanted to talk to you about something that’s important for both of us . . .” or “John, I want to begin by saying the last time we met, I know it was pretty stressful for both of us. Today, I really want us to be able to hear each other, share what’s important, and agree on what will happen next . . .” Or, “John, I realize you might be wondering why we are meeting today, and I want to let you know my intentions before we begin . . .” Even this small preamble can help the other person see where you are, and what you are hoping for, which can encourage equal participation and mutual respect.

Listen and deliver empathy to de-escalate a potential emotional response.People are messy and unpredictable. That’s why, even if we are really prepared for a tough conversation, we cannot know how it will go, and we cannot completely anticipate someone else’s response. Being clear, translating to the positive, and framing your conversation can all help to proactively de-escalate and invite a calm, rational discussion. But, maybe not. If someone is surprised or hurt by your initiating a conversation about something that matters or is sensitive to them, it helps to be ready for the unexpected, too.

I usually recommend the Three P’s for remaining calm and confident: Preparation, Practice, and “Plexi-glass.” That third, odd idea is about preparing yourself emotionally by understanding what your own triggers might be, but also to set your mindset in the space of openness and listening. Sometimes, we must be honest with ourselves about our own story or attitude about the person or the topic at hand. We don’t want someone else’s emotional response to trigger us, so we plan for listening and delivering understanding to move the conversation along in a respectful way. Delivering empathy means that we demonstrate understanding what someone is likely feeling and why they feel that way. We can use language such as, “you sound really frustrated because you feel like we made the decision without consulting you?” We don’t agree, disagree, or pass judgment. We are just confirming what we think the feeling plus the content is.

Get clear about what’s next for both of you.Often, we are so relieved by finally having the courageous conversation, and we walk away from that encounter thinking, “thank goodness that’s over!” Then, we are surprised that the change we were hoping to influence isn’t taking hold immediately as we wished. Before ending the conversation, we need to confirm what’s next, and especially how to close the gap between a verbal “yes” and a behavioral “yes.” Depending on the nature of the relationship, whether it is peer-to-peer, supervisory, or more complex, gaining commitment to follow-up is part of an effective conversation. Make agreements, and confirm the first, next step. Agree upon a timeframe, or follow-up action. Use specificity to clarify so each of you understands what comes next. And then, make sure you follow through on your part.

For many people, it seems like the easy way out to avoid challenging or tough conversations. Or, they’ll have them, but they aren’t very skilled and create wreckage or make things worse. Paying attention to language, being prepared, and practicing what you are going to say will help you be more present in the conversation, and that allows you to notice what’s happening. It allows you to be able to listen more deeply, to recognize non-verbal signals and tone. To show up fully and sincerely to a conversation, even acknowledging that indeed this is challenging for you has the potential to create an even more trusting relationship, and that is what makes having conversations easier and more fruitful in the long run.

Libby Wagner is a poet, speaker, and trusted advisor who works with organizations large and small to create high-trust cultures fulfilling their purpose and mission. Libby is the author of two Amazon best sellers, The Influencing Option: The Art of Creating a Profit Culture in Business and What Will You Do With Your 90,000 Hours? The Boardroom Poet’s Thoughts on Work, and can be contacted at https://www.libbywagner.com.