What if that Courageous Conversation Goes All Wrong?

“Courageous conversations aren’t ordinary exchanges of information:

…they are conversations about things that matter; there’s risk involved, emotional content, and complicated context. They’re not the easy ones.”

Having an engaged, high-performing work culture means people talk to each other! And it doesn’t mean that people always get along, that there’s no conflict or strife, or that no issues ever arise. In fact, the biggest difference between a highly functioning team and one that struggles with dysfunction is that when change or crisis occurs, the highly functioning team quickly gets back on track.

That means that we need to be having courageous conversations with regularity. We need to talk about things that matter and not let things fester or get worse. Sweeping things under the rug, ignoring them, or proceeding in grand denial isn’t a long-term solution. Having these conversational skills is essential and impacts both the quality of the working relationships and the quality of one’s life. Courageous conversations aren’t ordinary exchanges of information: they are conversations about things that matter; there’s risk involved, emotional content, and complicated context. They’re not the easy ones.

I’ve written extensively, and my coaching and consulting helps people prepare for these conversations by doing the following:

  1. Assess the relationship. What’s your level of trust? Do you need to repair or build it? Are you committed to the same goal or outcome? Are you on the same page? You might need to get clear with each other first.

  2. What do you want? This is a simple yet profound question. Many people know what they do not want and go into the conversation armed with their grievances. This rarely produces the results we want: a resolution and positive change. So, preparing to ask for what you actually want is a step many people skip, at their own demise.

  3. Consider the impact and the positive consequences for everyone involved. The more specificity we share, the better the other person will understand. How will respectfully resolving the issue create a possible win-win-win situation?

Participants in the Influencing Options courses think through, practice, and prepare for these conversations. They go in ready!

But, what if it goes . . . terribly wrong? What if the person misunderstands you, gets defensive or angry, shuts down, or says nothing at all?

It’s probably no surprise that the above questions are why people avoid these courageous conversations or confrontations. Everyone has been the giver or the receiver of a terrible confrontation. Emotions are high, things go awry, and we’ve taken three steps back instead of the two steps forward we wanted. What can you do, especially since you cannot predict how someone will respond?

Try the following to recover and redirect a conversation that’s gone off course:

  1. Listen deeply and actively. What’s going on with this person, and what’s the content and context of their response? Are they surprised or shocked? Are they afraid of change? Do they feel hurt or angered by your message?

  2. Demonstrate Empathy. What’s the feeling you see demonstrated and the reason behind it? Don’t judge; just understand. Even if it’s hard to see where they are coming from, what if you did? If you were them, how might you receive the shared message or request? Delivering empathy is a huge deposit in someone’s trust bank account and one of the biggest de-escalators of emotion.

  3. Ask Clarifying Questions to understand. If you don’t get it, ask. If you do get it, but it’s obvious they don’t think you get it, ask anyway. Watch your tone of voice and speak more quietly and slowly than usual. Be focused.

  4. Restate Your Intentions. One thing to do before a courageous conversation is to frame it: share why you want to talk, what you hope will happen, and how it can benefit both of you. This often helps someone hear you better and prevents defensiveness, but if you forgot to do this or need to recalibrate by restating, that’s an excellent way to help someone de-escalate.

  5. Use a Facilitative Question, such as “where do we go from here?” or “how can we resolve this?” to engage the other person in moving forward and problem-solving.

Remember, you can make things better or worse in each interaction and conversation—there are no neutral interactions! There are no solid, long-term relationships (at work or home!) that do not require courageous conversations, do-overs, forgiveness, or amends. Having a great work culture with positive, productive working relationships isn’t about everyone being perfect and happy all the time, but it is about how we navigate and evolve our relationships and conversations over time.

Want to learn more about this topic?

Check out the following recommended Influencing Option Leadership programs:

  • Fearless & Fair Communication

  • Performance Coaching and Influencing program

Libby Wagner

Poet, Auther, Speaker & Business Consultant

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