Skip to main content
Close this search box.
Close this search box.


Conflict Resolution Through Difficult Conversations

One of the most challenging things about being a new manager are the moments we have to have conversations we wish would…have themselves. Going from boss to coach means difficult conversations are an opportunity for growth; for you AND the team member. You will learn more about conflict resolution from the tough conversations than from the easy ones.

How do you learn to have difficult conversations? You have to have them. You have to be willing to be uncomfortable, make mistakes, and learn from them.

Why Do We Hate Difficult Conversations?

We all arrive in our roles bringing our entire lives up until this moment. The environments we grew up in shape our view of how to communicate, how to interact with conflict (or how to avoid it) and how to empathize. 

We don’t teach kids in school all of these crucial conflict management skills. No offense to your favorite math teacher, but perhaps some communication skills could have gotten as much air time as the isosceles triangle?

The adults we become then show up in the workforce with varied viewpoints and have to magically know how to navigate these difficult situations. We hate difficult conversations because we:

  • Don’t have the skills to navigate them.
  • Don’t want to hurt someone’s feelings.
  • Have grown accustomed to avoiding conflict. 

There’s actually a huge fallout to avoiding these conversations. According to Bravely, 70% of employees are avoiding difficult conversations with their boss, colleagues, or direct reports. This actually costs companies money, time, and employee engagement

Types of difficult conversations

Maybe you’ve not come across a difficult situation just yet, but let’s go dive into the deep end and make sure you are ready for these types of conversations:

Addressing differing perspectives and workstyles

  • These can be minor and based on interpersonal reasons or even work-specific perspectives that need to be ironed out.
  • An ongoing discomfort in your relationship with a team member (i.e. increased misunderstandings, tension, etc).

Identifying a workplace behavior that has a negative impact

  • You’ve got a super start on your team, but they tend to roll in Monday morning sharing about their weekend and are TMI gold medalists. Some team members feel a little uncomfortable and before it gets worse, you’ve got to address it. 
  • You have a team member who has attendance or lateness issues.
  • A team member hasn’t been pulling their weight.

Managing conflict between two team members

  • Two team members regularly disagree during team meetings causing discomfort for the team and delaying team action. 
  • There’s been an actual incident in the workplace of conflict that must be addressed ASAP.
  • A project is stalled because of conflict between co-workers.

Having to fire someone

  • Negative performance has been a pattern and after all appropriate action has been taken according to HR. You have to let the person go. 
  • Budget cuts or layoffs are impacting the company and a person’s position is being eliminated. 

Starting Difficult Conversations

The reality is these types of conversations usually cannot wait. The impact of waiting can make the impact even worse for the individual, your team and yes…you. Similarly with giving feedback, how you START the conversation can really set the tone for a productive face-to-face interaction. Here’s some conversation starters that help to level the playing field as you approach a conflict situation:

  • “There’s something I think we should discuss that will help improve our working relationship.”
  • “I’d like to talk about ____________ with you, but first I’d like to get your point of view.”
  • “I think we have different perspectives about ____________. I’d like to understand how you are thinking about it. 
  • “I’d like to see if we can come to a mutual understanding regarding___________. I really want to understand where you are coming from and also share my perspective.”

These difficult conversation starters help to interrupt fear and make it clear that this will be an exchange. Notice there is no judgment about the differences that may be present. This is part of becoming a good leader. Embracing that there are people who have valid perspectives that you may not agree with and understand is critical to being able to create mutual respect as you collaborate and lead others.

Difficult Conversation Planning Strategies

For all you color coded planners out there, YES you can plan for a difficult conversation. However you don’t want to OVERPLAN. Let some of it be organic. It’s tough to trust yourself but remember you can always criticize yourself with some self-deprecating humor later with a friend. Here’s a helpful guide to preparing for these conversations:

  1. Determine the desired outcomes from the conversation, for YOU and the team member. 
  2. Pick your conversation opener. Don’t overscript it, but have a general idea.
  3. Remember to use your active listening skills to better understand the person’s point of view, even if you don’t agree.
  4. What are the MOST important things you need to get across?
  5. What information do you need (if any) to support the conversation?
  6. Anticipate some possible responses and consider how you will handle each one. This is not supposed to freak you out, it’s just to give you some batting practice for the big game.
  7. What is the BEST case scenario? (Yes, let’s get positive going into this. We often go to a place of gloom and doom, making crucial conversations like this more difficult than they have to be.)
  8. What are the next steps you need to communicate in conversation (i.e. does this conversation require any follow up?

Remember our FEAR about these challenging conversations is usually bigger than the actual conversation. You will often let out a huge sigh of relief after you have one, so remind yourself of the COST of waiting. Go all Nike on this one and just DO IT!

Talent Development in the Age of AI


Picture of Stephanie Licata M.A. A.C.C.

Stephanie Licata M.A. A.C.C.

Stephanie is a learning and leadership strategist and coach who thrives on helping organizations create workplaces that work for everyone. She has trained thousands of Cloverleaf users at all levels to maximize the platform's potential. In addition, she has trained thousands of leaders across several industries in the art and science of coaching for developing individuals and teams. Stephanie has a Masters in Organizational Psychology from Columbia University and is an ICF and NYU certified coach.