How to Stop Avoiding Your Difficult Conversations

Claire knew she should approach her colleague, Pat, about a serious issue she’d noticed. Pat didn’t seem to notice that some of her direct reports were struggling. Often they came to Claire with questions, taking up her time instead of turning to Pat. Claire felt that Pat needed to be more approachable and reach out to people to ask about their needs. But whenever she thought about broaching the subject, she let the anxiety in the pit of her stomach talk her out of it.

Whether a conflict has been acknowledged by both parties—or whether it’s brewing under the surface, as with Claire and Pat—resolving it is crucial. It’s hard to bring all of your passion and creativity to your work when you’re caught up in the frustration of conflict that remains unresolved.

There’s a lot at stake here. We can predict which projects will succeed or fail with 90% accuracy by assessing whether teams can have difficult conversations, assert the authors of Crucial Conversations: Tools for Talking When Stakes Are High. Yet more than 80% of people delay having tough but essential conversations.

Why We Avoid Conflict

Too often, leaders avoid having hard conversations due to fears of what could happen. In reality, delaying the conversation harms relationships and prevents personal growth. When you’re a leader, challenging people is a crucial way of showing you care, as Kim Scott explains in Radical Candor.

Here’s a quick breakdown of some of the most common issues we tend to avoid. Have you faced any of these issues in your work?

A desire to provide critical feedback
A breakdown of trust
A controversial insight that clashes with what others believe
Differences in personality, work style or communication preferences

Regardless of the topic, you can address all types of conflict using the strategies I’ll share here through clear and productive communication.

Strategies for Resolving Conflict—and Emerging Stronger

I’m going to share the strategies that have worked well for me and for my clients. Use them whenever you’re faced with a challenging conversation. By strengthening your approach to conflict, you will also improve your daily interactions.

Preparing for the Conversation

Let’s break down a few vital steps to organize your thoughts and start from a place of calm.

Name what you are navigating.

Tough conversations actually have three layers:

1. What happened

2. How we feel about it

3. How what happened intersects with or threatens each person’s identity

In Difficult Conversations: How To Discuss What Matters Most, Douglas Stone outlines these three layers. In the first layer, you’re establishing the “facts” of the matter. Remember that the other person has a valid perspective, even if it seems to conflict with your own.

In the second layer, acknowledge your feelings without attributing them to the other person. Ask about their feelings in turn.

In the third layer, establish psychological safety by affirming the nuanced identity of the other person. Maybe you’re sharing constructive criticism about one aspect of their work, but at the same time, you appreciate their positive contributions. By acknowledging their nuanced identity, you create a safe space for criticism.

Before the discussion, consider each of these layers. With a fuller awareness of everything that is at stake for the other person (and yourself), you can approach the conversation with more empathy.

Consider the assmptions you’re making.

What assumptions might you be making—and perhaps perceiving as ultimate truth? Consider this before beginning the conversation. For example, don’t presume your direct report ignored your instructions because he believes you don’t know what you’re talking about. Maybe he misunderstood or forgot! There’s still a challenge to address, but it might not center on your assumption.

Remember your intentions.

Think about your real intentions for the conversation. Do you want to hurt the other person’s feelings? Probably not—your real purpose is probably to catalyze improvement within that individual or your relationship. Connecting to your motives will help you tap into your empathy and lower stress.

In turn, think of the discussion as a constructive conversation or a learning conversation rather than a tough conversation.

Don’t write a full script.

Think of different possible responses—depending on how the conversation goes—but don’t write a whole script. That will feel too stilted and artificial, and you don’t know how the conversation will go. Instead, stay flexible.

Now, let’s discuss how to have a genuine dialogue that leads to resolution of the issue.

During the Conversation

During the conversation, take steps to make yourself heard without allowing it to descend into a heated argument.

Lower defensiveness.

How can you best open the conversation, mitigate defensiveness, and have a productive dialogue? Here are three of my favorite tips:

As Kim Scott says in Radical Candor, expressing a desire to be helpful at the onset of the conversation will frame your intentions in a positive way. Most people will then want to listen.
Asking for permission to share an observation can help lower defensiveness as well. This gives the other person a sense of agency and makes them feel respected.
Good body language brings positive energy to a discussion. Simply nodding as the other person speaks can validate their perspective and show you’re truly listening.

When you lower defensiveness, the sky's the limit. You’ll both fully hear each other and have a genuine discussion rather than each pursuing your own agenda.

Pay attention to your emotions.

Attend to your own emotions during the conversation, staying alert to signs that you’re approaching your tipping point. Are you clenching your jaw, having trouble listening, or feeling your hands shake? If so, the conversation might be at risk of devolving into a spiral of defensiveness.

But that doesn’t need to happen.

Have a grounding tool ready to use in the moment. Simply naming your emotions to yourself, and evoking a one-word quality you want to embody, can keep you centered. Your groundedness can help anchor the conversation in a place of calm.

Use language that gives the benefit of the doubt.

You might fear that phrases like “You may not be aware of this” sound weak, but they can soften criticism just enough to make it more palatable. Likewise, it’s often best to share facts without leaping to conclusions. We usually don’t really know what the other person was thinking when they engaged in behavior we’re trying to correct. Again, don’t assume they had the intent to cause harm.

Listen actively.

Listen to their perspective with genuine curiosity. Ask how the other person actually feels about the issue at hand. Listen to understand, showing you’re absorbing what they’re saying. Being humble by listening closely is a big part of radical candor, showing a high level of respect that makes the other person want to hear your ideas in turn.

Practice tough compassion.

Exercising tough compassion essentially means showing you value someone as a person while firmly pointing out what needs to change. This approach views honesty as compassionate and uses empathetic persuasion to spark real change in the other person. As you may note, it dovetails with radical candor and enhances psychological safety.

Storytelling aligns well with this approach, getting a concept across in a non-accusatory way. “With storytelling, you can take a tough stance and show the other person the results of their actions without launching a direct attack,” writes Elizabeth Svobody in TED’s “How to Be a Better Human” series. If someone has made an offhand comment, you can respond by telling a story about how such language makes a friend of yours feel, for instance. This helps the other person understand the impact of their speech on an emotional level.

You can even tell a story about how you’ve made a similar mistake. This will strengthen your bond with the other person in the moment, creating a shared sense of identity.

Slow your pacing.

Talking quickly amplifies the urgency of the situation. Meanwhile, slowing down can help alleviate tension and advance the conversation. Slow the pacing of your speech to bring in a sense of calm.

Finally, shape a solution and make sure you’re both feeling good about it.

Finding Real Resolution

The goal of every tough conversation is lasting resolution. Here’s how to get there.

Arrive at a solution together.

If you already have ideas for potential solutions, bring them. But don’t approach them as being set in stone. Instead, design a plan together, one that allows the other person to have agency in creating a solution. When voicing ideas, ask what the other person thinks about them.

Acknowledge what went well.

At the end of the conversation, acknowledge positive outcomes and share gratitude. If all is not resolved, note any progress made or other positives, like effective communication.

Follow up.

Check in with the other person later on to make sure they’re feeling good about the solution. Give feedback on what is going well or pointers on how to keep improving. They’ll appreciate your attentiveness, even if all is going according to plan.

Growing from the Conversation

Every conflict you encounter is an opportunity to grow personally. Make sure you’re making the most of this opportunity after it happens. Debrief the discussion on your own, reflecting on what went well and what you can do differently.

Did you achieve your goal or make substantial progress?
What might have brought you closer to your goal?
How did you communicate? What worked, and what could improve?

This reflection will help you deepen your self awareness and continue to strengthen your approach.

Claire finally approached Pat and explained the challenge she saw Pat’s direct reports experiencing. She calmly shared some ways of becoming more approachable that she felt Pat could use. Pat seemed a bit caught off guard at first, but with Claire’s compassionate approach, she relaxed and engaged in a good conversation about the issue. At the end, she shared genuine appreciation, and Claire noticed her talking with team members more regularly. Everyone benefited, and now Claire didn’t have the weight of the conversation hanging over her head!

Are you struggling with difficult conversations at work? Let’s chat! Book a call with Amanda to talk about how coaching can make the difference.