5 Tips for Managing Difficult Conversations

How to Turn a Tense Situation into a Relationship-Building Opportunity


5 minute read

Dion Leadership-Blog Post-5 Tips for Managing Difficult Conversation

Challenging or difficult conversations are no strangers to the workplace.

They often show up when you need to give feedback, manage expectations, delegate responsibility, practice accountability, or lead a change initiative. Regardless of the reason, the story tends to play out the same way: When you begin to anticipate and plan for a challenging conversation, your anxiety spikes. It may come in the form of a slow churn in your stomach, or you may notice that your breathing grows shallow. You might find that you can’t stop the cycle of negative thoughts circling in your head. How do leaders overcome this commonplace issue? Is there an antidote? Here are five tips that have worked for leaders whom I’ve coached in the past.

1. Change the Record
Ever been to a wedding when the DJ plays a song that clears the dance floor? One minute, everyone is dancing and having a good time. The next minute, people are returning to their tables or grabbing their coats to leave. The whole positive vibe of the party is changed instantly because of one song. This is how our mindsets work as well. As soon as we spin a record that says the impending conversation is going to be difficult or awkward, we make the possibility of an open, genuine dialogue more unlikely. What do we do then? What’s our move? We play a different record. We pick a different song. We choose a healthier perspective. One that sounds more like, “Hey, this is an opportunity for me to clear the air” or “What a great chance for the two of us to become more aligned.” We choose an outlook that operates from a place of curiosity and possibility—one that cultivates positivity and optimism, or neutrality at the very least. This alone is the antidote to many potential conflicts.

2. Drop Anchor
We don’t have to be maritime experts to know that a ship drops anchor to prevent drifting. Similarly, we do the same by clearly stating our intentions at the beginning of a potentially difficult conversation. Such intentions commonly include our mutual desire to get aligned, optimize communication pathways, clarify expectations, or figure out a better means to support each other. Regardless, we drop anchor from the start and let the other person know that the goal of the dialogue is to better understand each other and improve the relationship.

Let’s actually repeat that last part: it’s about the relationship.

This is imperative. Orienting to the relationship helps us stay focused and present as to why we’re having the dialogue. It avoids letting the conversation fixate on stories from the past and prevents the dialogue from drifting astray into the waters of things we don’t control, can’t change, or don’t know much about. The latter are familiar pitfalls for when conversations turn into arguments and sound the death knells to productive discourse.

3. Acknowledge
Acknowledging may be a difficult step depending on circumstances and, as such, can be dismissed or overlooked, but there’s no question it also may be the most critical. Simply put, it is essential that we invite the other person’s perspective after setting anchor. If we recognize a misalignment in the relationship and genuinely hope for matters to improve, there lies a tremendous amount of value in giving the other person a fair opportunity to explain their intentions—and to listen actively without interrupting them while they do it. In short, we acknowledge their point of view—and not out of obligation, but earnestness. We make a deliberate effort to hold space for what they are thinking and feeling. Doing this, however, does come with a vital distinction.

The word is acknowledge—not agree.

They are not the same. We can accept a point of view without condoning it. We can recognize a viewpoint without sharing it. This matters for two reasons. First, recognizing the distinction helps us manage our emotions more effectively when dealing with a colleague who holds a different point of view from our own. And second, recognizing this provides an opportunity for them to feel seen and heard, which is fundamental to civil discourse. Without it, we risk falling victim to one of the most common provocations that escalates a conversation—when one party no longer feels visible or heard by the other. Thus, by acknowledging the other party, we let them know that we see them and hear them. This can certainly be difficult when emotions are involved, but this alone is an incredibly disarming, deescalating step. It allows room for the other person to feel safe, which is necessary for trust to grow, and once these two elements begin to emerge, we set foot on a pathway toward genuine conversation rather than misunderstanding and conflict.

4. Own Your Half
As much allowance as we give to holding space for others to share their intentions, so, too, must we create the opportunity to discuss our own thoughts and feelings. We can’t assume this will automatically be built into the dialogue. It’s a delicate balance in that we can’t make the dialogue solely about our experience, but we also can’t overlook the fact that our experience has merit. We can, however, control both what we share in our insights, observations, and questions and the length to which we share them, as well as how we share them. The latter demands that we don’t only prepare for the authentic, meaningful message we plan to communicate, but we equally consider the tone and non-verbals we demonstrate when delivering it. These elements work well together to create impact and understanding. We are 100 percent responsible for 50 percent of any relationship we’re in, and these elements galvanize an opportunity for us to genuinely, tactfully communicate our intentions and expectations in service to our half.

5. Set Course
Sticking with our previous maritime example, a ship will likely not raise anchor until it has set course for its next destination. The same goes for charting the end of a conversation that was originally perceived as difficult. Without a map, our relationship risks drifting again toward recursive, problematic patterns. Same behaviors, same outcomes. Instead, we can take time with the other person to envision an optimal version of the relationship, what matters to each of us, and the specific, actionable steps we’re committed to taking to achieve it. The more specific we can be about why our aligned course matters and how we chart our points on our map together, the more likely we are to successfully reach our destination—a healthy, vital, and prosperous relationship.

Dion Leadership-Team-Joe

Joe LaDuke

Vice President, Coaching and Consulting Services

Joe is passionate about helping organizations grow their people. Inspire them. Motivate them. Develop them. He partners with Dion Leadership clients to craft solutions that address their leadership and organizational development needs. He then engages our full team of resources to ensure outstanding results.

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