How to Have Difficult Conversations

Is there a conversation you need to have, and just the thought of it makes you uncomfortable and anxious? Hard conversations can be intimidating for even the most seasoned leaders. 

You will need to have more than one of those nerve-wracking, difficult conversations as a leader. So, how can you approach someone about a difficult issue productively? 

Effective leaders learn how to have difficult conversations because they know that conflict can lead to positive outcomes. Avoiding a discussion because it’s uncomfortable will only result in more conflict and missed opportunities. 

Tough conversations help you discover new ways to work better with others and areas that need to be improved. Structuring difficult conversations with the right goals in mind makes these conversations less intimidating and more effective.

As a leadership coach, I help leaders prepare for difficult conversations by using tips that create clear communication and shared understanding. If you’re ready to start a serious conversation, these suggestions are a great place to begin.

The Flow of Difficult Conversations

Clear communication is a skill of an effective leader who encourages collaboration, values different perspectives, and empowers others to make decisions. When we don't communicate clearly, passive-aggressive behavior, backchanneling, gossip, and overcommitting increase.

 Understanding the flow of difficult conversations can help you more clearly communicate in challenging situations. Steering the conversation to a productive outcome improves your ability to send and receive messages accurately and builds a culture of trust, engagement, and shared purpose. 

Having a clear, productive, and empathetic conversation means actively listening, staying curious and generous, leaning into vulnerability, owning our mistakes, and sticking with the messy work of problem-solving. 

The steps below serve as a guide for how to manage difficult conversations and use coaching skills to develop your team members. Each step is a skill for leaders to practice as well as ground rules to share with conversation partners:

1. Open with Curiosity & Willingness to Listen 

Try introducing your openness to both talking and listening. For example, "I'd like to talk with you about [XYZ topic] and hear your thoughts."

2. Next, Set intentions and Find Common Ground 

Reframe the conversation as a partnership by figuring out what you’re working towards and hoping to achieve together. For example, "We both want this outcome to be successful." 

3. Early and often, Check-in with Yourself 

What emotions are coming up? Name them in your mind or to your conversation partner. If you are getting defensive. How can you calm yourself in the moment? Remember to breathe and take breaks when needed.

4. Define the Context and Consequences

Figure out what’s happening in other areas that may impact the solution. What is out of scope? What if we get this wrong? What's at stake?

5. Get Curious about Assumptions and Differences 

Differences are hairy but stick with them to work through them. Listen, ask open-ended questions (who, what, when, how), and explore each other's stories. Reality check your assumptions about the other person's situation or intention. How something is impacting you does not necessarily equal intent, so ask for clarity.

6. Stay Focused  

Use "I" statements to own your parts (feelings & actions). Advocate for yourself and ask for what you need. Stay focused on behaviors that can change (instead of changing the person).

7. Identify the Problem 

After you've rumbled with your differences, get on the same page by exploring, "What is the problem we are trying to solve? What is the bigger picture?" Sometimes we haven't yet identified the specific issue. Sometimes we resolve the issue by talking through our differences.

8. Problem Solve 

Remember your common ground. What questions do we need to ask? What information do we need to solve this problem?  

Prepare for a Difficult Conversation Today

Facing a difficult conversation right now? Preparing ahead of time can help you better communicate and reach a better outcome.

Having hard conversations comes with being a leader, which is why learning these skills is a top leadership development goal. To be an effective leader, you need to be comfortable having these types of discussions with your team.

You can learn how to have difficult conversations as a leader through leadership development coaching, even before challenging conversations happen. I work to bring out the best in you so you can take on your role with a fresh new perspective.

Let’s talk. Contact us today to discuss what’s challenging you and how we can support you in navigating a path forward.

 
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