How and Why to Have Difficult Conversations as a Leader

by Zach Montroy, SPHR

Just reading the title of this piece may have your stomach in knots. You’re not alone. Conflict is a highly misunderstood topic – especially when it comes to how and when it should be addressed by leadership. 

Too often, avoidance is the most commonly used strategy. It’s not a good one. Leaders have a responsibility to address conflict that arises within their team but, let’s face it – It’s not easy. Today, we’ll discuss why you can’t skip over difficult conversations to resolve conflict if you want a healthy organization. If handled well, conflict can be the doorway to agreement, and often lead to personal and relational growth.

Why Leaders Avoid Conflict

We’ve all been there. Maybe that “small” relational issue is suddenly snowballing into something much more serious. Maybe you’re sensing that nagging feeling that the situation with that colleague, boss, or teammate is only getting worse. Navigating conflict is hard, and somehow, it feels like we’re all hardwired to stick our heads in the proverbial sand and hope the problem just goes away. Pro tip: It doesn’t. If the issue isn’t dealt with, it compounds exponentially…and the relational carnage just gets worse. 

In leadership, we’ve often internalized the idea that conflict is a sign of a poor leader. We believe that if you’re a good leader, people will do exactly what you say without issue.  This is not true; conflict is unavoidable. It isn’t a sign of a dysfunctional relationship; on the contrary, when conflict is navigated in a healthy way, relationships flourish.

Recognize Signs That Conflict Is Present

As a general rule of thumb, if you have the inclination that conflict is present – it usually is.  As a leader, you’ve learned to be intuitive. Use that intuition to sniff out conflict and address it. Be especially aware of the following hallmarks of conflict:

  • Contempt
  • Criticism
  • Intentional silence
  • Defensiveness

Rewire Your Reaction

Before you begin to address conflict, recognize your own reaction. Our brains have been hard-wired to associate conflict with danger, triggering our amygdala (the section of our brain responsible for detecting fear and preparing for emergency response) to take over and thrust us into a fight-or-flight response. When the amygdala takes over, the prefrontal cortex (the region of the brain responsible for sophisticated interpersonal thinking skills and the competence for emotional well-being) is hijacked. 

What’s the solution? You’ve got to retrain your brain to recognize the benefits in actually dealing with the conflict rather than retreating (the flight response) or worse, blowing up (the fight response) and creating all kinds of relational conflict.

 Weigh the Risks and Benefits

Start with a needs analysis. If you have a solid “why,” it can be much more motivating to have a difficult conversation. Begin drafting the emotions that are telling you that you need to have the conversation. Are you hurt, disappointed, fearful, guilty or frustrated? 

Next, visualize the positive impacts of resolving the conflict. What are the relevant benefits in having this difficult conversation for this person? Is it greater emotional awareness, forgiveness, change, better performance, freedom?

Not only is it important to focus on the potential positives; it’s also important for you to identify the potential risks. If you have this conversation, what could happen? Could you potentially lose a friendship or coworker? Could you lose your job? We all think about the worst-case scenarios, so write them out. This exercise will help you see that oftentimes our biggest fears in having difficult conversations are irrational and unfounded. More times than not the benefits will outweigh the risks. 

Finally, list the costs and benefits of both having the difficult conversation and the costs and benefits of avoiding the difficult conversation. You’ll see that the reward is generally worth the risk.

Use a Guide

Remember, having a high-impact, crucial conversation might be new to you. When developing a new skill, it’s important to remember that we all need practice and that we need to remain incredibly thoughtful with our words. Remember the goal here is understanding. 

  1. Narrow the conversation. Decide the specific item you want to address – don’t pile on a bunch of stuff. Choose the behavior or issue that needs to be addressed and focus on that alone. Decide what you want to accomplish in the conversation. Reflect on what you want the individual to know, how you want them to feel, and what you will do as a result of this conversation. 
  2. Speak candidly, but kindly and with respect.  If you start off feeling defensive and self-protective, the other person will match that energy, and you’ll each leave the conversation frustrated. Don’t “spin” the message; be clear and direct but kind-hearted. Use “I” messages. For example, when you did _____(action or issuer you’re addressing), I felt _____ (insert your feeling here). It’s hard to argue with how someone feels. 
  3. Remain detached from the outcome. This is hard to face… but you’re not going to get your way 100% of the time. Be open to what the other person has to say. Your emotions are there to offer suggestions, not lead the charge. Let go of needing to control the conversation; rather, focus on speaking clearly. 
  4. Focus on actionable solutions. Most conversations have no action plan and nothing gets done. Ensure that you engage the conversation with a strong action plan. What are you taking away from the conversation? What steps will each person take, by when, and how will each of you know? 

Reap the Benefits of Successful Conflict Resolution

When properly structured, difficult conversations can still feel safe. When you work from a position of healthy leadership, the goal should be to create dialogue, in which both parties are engaged for the best possible outcome. Let’s lean into difficult conversations knowing they can be essential in creating high-quality relational connections that facilitate change and growth.

If you’re looking for a bit more support, our team at The Intention Collective works with entrepreneurial leaders to create a healthy team. We offer a variety of ways to coach companies and individuals toward growth, and we’d love to get in touch with you.

Related Posts

Download our Free Guide:

The 3 Stages of Building a High-Performance Team (With Your Current Constraints)

Knowing when and how to grow your team can be a challenge. This guide walks you through the process we use when helping our clients navigate how and when to hire.


Next Steps: Sync an Email Add-On

To get the most out of your form, we suggest that you sync this form with an email add-on. To learn more about your email add-on options, visit the following page ( Important: Delete this tip before you publish the form.