Difficult Conversations at Work Case Studies

How Preparing, Learning Through Case Studies and Role Playing Can Help

Some situations you’ll experience both in your personal and professional life will require more careful attention than others.  When it comes to difficult conversations, most people would rather avoid them if they could but the chances of that relationship thriving into a new season may not be so promising.  Avoidance allows harsh feelings to occur, walls to be built, communication to become weak and anxiety to rise.  However, having a thoughtfully planned out discussion can have things back on the mend and add a new dimension to what may have ended in a turmoil.

A number of case studies have been done discussing how difficult conversations in the workplace just aren’t happening as often as they should be and, in some cases, aren’t happening at all.  In one study, it was concluded that close to ¾ of employees are failing to confront their peers, managers and direct reports.  They stated that they’re not only concerned about retribution but also perception thereafter.  These numbers haven’t changed in three decades, showing that this is an ongoing problem within the professional world.  While businesses focus on increasing the emphasis on communication and culture, they’re failing at building confidence within their team on conflict resolution.

In this article, we’ll help you learn how to prepare ahead of time for these situations so that you can build healthy relationships and develop a cohesive team.  By looking at various work scenarios, understanding the case study on difficult conversations above, and creating opportunities to role play with your team, we hope you’ll learn how having the right framework for difficult conversations can set you up for success.


What is a difficult conversation?


First, it’s important to understand just what a difficult conversation is.  A difficult conversation, regardless of personal or professional, is a discussion that involves topics that may be considered sensitive, can be emotionally charged or even lead to discomfort.  Some examples of difficult conversations in life hurt feelings over a misunderstanding, disagreement over finances or caring for a loved one.  In the workplace, they may involve conflicts of interest, a difference of opinions, constructive criticism, negative feedback, performance reviews or even delivering bad news such as layoffs or termination.  Regardless of the issue(s) up for discussion, handling these conversations professionally, with honesty, empathy and an open mind, will help find a resolution that works for everyone.

Why are difficult conversations important?

Difficult conversations are important for a number of reasons.  In the workplace, they can increase job satisfaction, help build stronger bonds with colleagues, and if you’re a manager, it can ensure your team members feel more valued, which will increase productivity, improve employee relations, performance and alignment with your company’s goals.  These situations require careful planning, effective communication skills, and emotional intelligence to navigate them successfully.  By promoting open communication, difficult conversations can also enhance team dynamics, foster both personal and professional growth for all parties involved and prevent issues from escalating that would involve even further problem-solving methods.


What are the scenarios of difficult conversations at work?

If feedback isn’t already a natural part of the culture at your business or organization, it may be a good idea to start implementing that now.  Open, honest communication will build good relationships and bring a cohesiveness to a team that it may lack otherwise.  In a place where people feel valued, heard and able to share the hard stuff, performance tends to be higher.  There are several different scenarios of difficult conversations at work including employee to supervisor, supervisor to employee and employee to employee.  Whether a supervisor needs to let someone go or an employee is looking for a raise, this wide range of situations can be uncomfortable, regardless of your position.  We’ll discuss a few examples of difficult conversations at work which might spark some role play scenarios you can have with your team.  Practicing these with one another will help when those awkward moments arrive and issues need to be addressed with professionalism and care.

What are some examples of difficult conversations at work?

A number of topics come to mind when it comes to the types of difficult conversations in the workplace.  Some examples include: giving constructive feedback, discussing a coworker’s behavior, addressing performance issues, conflicts with the team or negotiating a pay increase.

Often characterized by disagreement, tension and a potential misunderstanding, these conversations require careful handling, planning and follow-through.  If done successfully, these conversations should offer a solution to a problem and can establish or build upon existing relationships, open the lines of communication and support cohesiveness within a business or organization which will, in turn, increase productivity and introduce a positive energy to the workplace.


What is an example of a difficult conversation at work as a manager?

two ladies having a work conversation

In your role as manager, you’ll likely have a number of difficult conversations on a regular basis. Let’s say you need to discuss performance issues with an employee.  During this conversation, the manager needs to cover poor work quality, missed deadlines and lack of attention to detail.  It’s important for the manager to provide constructive feedback, set clear expectations on moving forward, offer support to help the employee improve, and collaborate on a solution to discuss once the employee has had a chance to implement feedback made during the discussion. The manager must stick to the facts, actively listen to any concerns of the employee and make sure he/she feels heard and valued.

Role-playing scenarios like this will help leadership feel more confident going into difficult situations, develop their communication and conflict-resolution skills, teaching them how to incorporate empathy into difficult conversations while maintaining professionalism.

You can use this example of a difficult conversation as a role play script in training other members of your leadership team on how to handle difficult conversations in the workplace.

How do you start a difficult conversation?

How do you start a difficult conversation?
Initiating these conversations is the first step in the process.  Once you’ve broken the ice, it may not be smooth sailing but you’ll have one thing checked off your list of difficult tasks!  Schedule a time that works for you both without having to feel rushed.  Be sure you reach out to the person with tact and clarity so they don’t feel blindsided, even though sometimes this is inevitable.  Set the tone when you begin so they know that you value their time and opinion, but most of all, them.  Stick to the facts and leave your feelings at the door.  It’s likely you’re in a leadership role which means you are representing the company/organization so their values are always something to bring your attention back to.

woman talking to her colleagues

Three techniques for approaching difficult conversations.

conversation at work between man and woman

To help build the framework for having difficult conversations, you’ll want to also understand the techniques that you can incorporate.  It will be beneficial to exercise your skills on difficult conversations with a trusted colleague or friend once you feel comfortable with your approach.  Try using these techniques in group exercises to practice difficult conversations with your team as well.

  • Active listening.  Most of us have the tendency of listening to respond.  Active listening shows that your full attention is on the other person, which helps them to feel more comfortable and confident in sharing their own feelings or concerns about the issue(s).  As they express their thoughts, avoid interrupting.  Be empathetic, putting yourself in the other person’s shoes to validate their perspective and build trust.
  • Asking open-ended questions.  These questions allow the person to elaborate on their response beyond a simple “yes” or “no”.  It will give both parties involved a better opportunity to understand the situation at hand, gain a clearer perspective of how each other feels and show your willingness to listen empathetically.
  • Use “I” statements.  While this conversation is more about the other person, you’ll want to be able to communicate your thoughts without placing blame.  This is your perspective based on the knowledge that you have.  Remember, you’ll want to have facts to support you in this discussion so it doesn’t feel like a personal attack.

How do you handle challenging situations and difficult conversations at work?

Up to this point, you’ve learned what a difficult conversation is, why it’s important to have them, examples for both your personal and professional life, scenarios within the workplace, difficult conversations managers may have to have, how to initiate one and some techniques to apply while you’re there.  Now it’s time to discuss how to handle these challenging situations.

Nothing has the potential to affect the dynamic within a company more than workplace conflicts.  It’s important to handle these challenging situations quickly and professionally, as soon as they arise so as to prevent any future issues that can occur such as further dissonance, poor morale and miscommunication due to increased stress and anxiety amongst team members.

Even though these situations need to be handled quickly, you’ll want to be prepared ahead of time because, as you might imagine, emotions will be running high which can naturally cause people to be on the defense.  When you come prepared with discussion points, facts about the issue at hand and ideas for a solution, you’ve already started on the right foot.

2 people looking at laptop

Here are nine key steps to ensure that you’re headed in the right direction when it comes to having difficult conversations:

1. Avoid avoiding.  It’s simple.  Don’t avoid these conversations just because they’re hard.

2. Prepare with a purpose.  What are your discussion points? What are your goals? What would you like to achieve? Come into the meeting prepared on what to discuss, how you’ll discuss it and with the goal of resolving the issue at hand.

3. Select a good time and place.  Be sure you have allowed for enough time to address the things you’ve prepared to discuss, give the other person a chance to talk, have a discussion and plan for a follow-up.  Privacy is important so that both parties can be confident in their vulnerability.

4. Be confident and direct.  Don’t beat around the bush.  Have facts to back up your reason behind the meeting in the first place. Sticking to the facts will remove the feeling of being personally attacked and encourage you both to stay on topic.

5. Listen.  Really listen. Remaining empathetic will validate the person’s feelings, build trust and give them comfort knowing that they are being heard and are valued.

6. Share your thoughts.  Just because the conversation is difficult and you may have specific points to cover doesn’t mean that you don’t have an opinion on the matter.  Share with the other person openly, honestly and respectfully.

7. Incorporate the three techniques.  As we mentioned earlier, it’s important to be sure you remain an active listener, use “I” statements and ask open-ended questions.

8. Come up with a solution.  Since you already have your goals in mind, how about working together to come up with a solution…a way to move forward that both of you agree on that still aligns with the goals you set ahead of time?

9. Follow-up.  This is almost as important as the initial meeting will be.  While you’ve come up with a solution together, you will have some measurable goals for this individual that you’ll need to follow-up on. They will appreciate that you care enough to take the time to meet with them again, especially if they felt heard and valued the first time, regardless of the nature of the conversation.

group of people talking at work

Don’t forget that difficult conversations can make people uncomfortable, causing anxiety and emotions to run high and thus leading people into defensive mode.  Careful and thoughtful preparation will help eliminate many of those potential challenges and will also help you to navigate them all the better when/if they do arise.  Practice difficult conversations through role playing, with various difficult conversations in the workplace, on your own or with a colleague or friend.  Understand that the ultimate goal is to encourage effective communication, build trust and strengthen relationships within your company.  We hope these tools will help you feel more confident and ready to effectively communicate with your team, even during uncomfortable conversations when they are necessary.