Difficult Conversations Exercises

A difficult conversation is defined as a planned conversation that either covers an uncomfortable topic or a negative experience with the goal of sharing perspectives, gaining mutual understanding and developing respect.  Most often, navigating these conversations won’t come easily.  However, with practice comes confidence that will allow you to take on these challenging conversations and facilitate better communication in your relationships.

What are the three difficult conversations?

Coworkers at odds with each other.

There are three different types of difficult conversations you could possibly encounter in your personal or professional life.  While some are based on fact, others involve interpersonal issues.  Let’s learn a little more about them.

  • Factual: Factual conversations cover anything that is considered measurable such as facts, numbers or events.  This type of conversation might be easiest to tackle since it’s data driven and you should have written proof to support you in the discussion.
  • Emotional: The second type of difficult conversation might involve interpersonal issues on sensitive subjects that are hard to discuss. When the heart is involved you can be sure feelings will be as well so having a good understanding of your own feelings on the matter before diving in will be important.
  • Identity-based: Understandably the most challenging conversations to navigate are those that may challenge a person’s beliefs, self-concept or values.  Keep in mind that there are often other viewpoints that you may not have considered so it’s important to be open-minded and empathetic so you can learn more about the other person’s perspective.

What are some examples of difficult conversations?

Difficult conversations often revolve around sensitive topics, making them emotionally charged and often uncomfortable for both parties involved. These challenging dialogues encompass a variety of scenarios, including addressing hurt feelings that may have stemmed from a misunderstanding, a financial disagreement, or managing the care of a loved one. Examining these diverse difficult conversation scenarios can shed a little light on pivotal moments in both our personal and professional lives, highlighting the importance of mastering the art of navigating them effectively. These situations demand effective communication and problem-solving skills, showcasing the high stakes, differing opinions, and intense emotions at play. Other examples of crucial conversations involve scenarios that include making major life decisions such as relocating to a new city, marriage, or divorce.  Each must be handled with empathy, good listening skills, and respectful responses.

Female coworker arguing with male coworker

What is an example of a difficult conversation with an employee?

two business people working out conflict

A number of different factors can affect the dynamics of the workplace, but none like workplace conflicts.  When conflicts do arise, it’s important to handle them quickly and professionally, but as prepared as possible.  In the workplace, these conversations might involve conflicts of interest, a difference of opinions, constructive criticism, negative feedback, performance reviews or even delivering bad news such as layoffs or termination.  Navigating these conversations in the workplace will require honesty, empathy, an open mind and professionalism. Other examples might be discussing a coworker’s behavior, addressing performance issues, conflicts with the team or negotiating a pay increase.  Successful conversations will leave both parties feeling heard, problems addressed, and a beneficial outcome for both, often with measurable goals.  They will pave the way for future communication, build relationships, bring cohesiveness to your team and add a positive energy to the workplace.

What are scenarios of difficult conversations at work?

There are a variety of scenarios that will help you prepare for challenging situations.  Sharing constructive feedback is one of the most common in the workplace.  In this work scenario, a manager needs to have a difficult conversation regarding performance issues with an employee.  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 that the employee can use, set clear expectations on moving forward, offer support to help the employee make improvements, and come up with a solution that they’ll discuss at a later time, once the employee has had a chance to implement some of the discussion points.  The manager must stick to the facts and actively listen to any concerns of the employee to make sure he/she feels heard and valued.


Another workplace scenario involves addressing an employee’s punctuality issues.  The manager should begin preparing ahead of time by gathering instances of the employee’s tardiness and any necessary information. Then, he/she will need to schedule a meeting at a time and place that suits both parties, somewhere that offers both a professional and empathetic atmosphere.  Approaching this with a compassionate ear is important since the objective is to validate the employee’s feelings, even if disagreeing with their reasoning. He/she will need to clearly communicate the significance of punctuality, emphasizing how it affects not only their day but also impacts their colleagues and the overall functioning of the company. Ideally, throughout the conversation, the two will explore possible solutions and commit to follow-up to ensure progress is made.

Having a role play script between a manager and employee on scenarios like these to practice with a trusted friend or colleague will help you to gain confidence in how to handle scenarios such as the ones we mentioned in the crucial conversation’s examples.

How can I improve difficult conversations at work?

If giving constructive 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 cohesiveness to a team that will help them to honor each other and their time at work.  In a place where people feel valued, heard and able to share the hard stuff, performance tends to be higher.

The best way to improve difficult conversations at work would be to continue diving into a variety of scenarios rather than waiting until something comes up.  Then reach out to another leader, trust friend or co-worker to help you role play a few conversations from the scenarios mentioned above or others that you have found.  Study the techniques on how to manage difficult conversations and remember that you’re human.  We can get ourselves so hyped up about something that our own anxiousness causes the operation to fail when it doesn’t need to.  Be confident in your abilities, in what you need to share and hold yourself accountable at all times and you’ll soon navigate these conversations with ease.


How do you manage difficult conversations?

group of people talking at work

Managing difficult conversations with staff can be tricky.  However, with careful planning, preparation and implementation of some of the techniques we’ve discussed, you can not only improve communication within your company, but you’ll gain trust and confidence from your employees, foster growth in relationships and build morale within the team.

So far we’ve talked about 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 improve on them and now we’ll teach you some key factors in how to manage difficult conversations.

If these challenging situations are not handled quickly and professionally, lasting effects can occur including the creation of further dissonance, poor morale and further miscommunication caused by the increased stress and anxiety amongst team members.

However, handled quickly doesn’t mean without preparation.  Spend some time getting ready for a difficult conversation because, if you don’t, things could go south quickly.  As you can imagine, emotions will be high, people can become angry and defensive which, if you haven’t made sure your emotions are in check, might cause you to react poorly in return.


Come prepared with discussion points, facts about the issue at hand and ideas for a solution so you can start off on the right foot.  Here are eight key steps to ensure that you’re headed in the right direction when it comes to having difficult conversations:

  • Don’t avoid.  Avoidance is the worst thing you can do when it comes to these crucial conversations.  As we mentioned early, effects can be detrimental to your team and ultimately your business if you brush them under the rug or save them for discussion another time.
  • Be prepared.  Think about your discussion points and goals.  What would you like to achieve from this discussion? If you know ahead of time what you’re planning to discuss, knowing how you’ll discuss it and with the ultimate goal of resolving the issue at hand, then you’ll have little to throw you off course.
  • Select a good time and place.  When scheduling, make sure you allow enough for both of you to discuss the issue(s) at hand where you won’t feel rushed or distracted.  Privacy is also very important so that both parties can be confident in being vulnerable.
  • Be confident and direct.  Because you should have already come prepared with facts to back up your reason behind the meeting in the first place, the next thing you need to do is stick to the facts.  One thing people cannot argue with are the facts.
two ladies having a work conversation
  • Listen actively. Remaining empathetic will validate the person’s feelings, build trust and give them comfort knowing that they are being heard and are valued.  Engaging in a conversation is a two way street so if you want to be heard, extend the same respect to the other person involved.
  • Share your thoughts.  Of course sticking to the facts is best, but as a leader, this has had some effect on you and potentially your team. Share with the other person openly, honestly and respectfully about how this matter has made you feel.
  • Collaborate on a solution.  Find a way to move forward that both of you have had some input on.  This agreement is mutually beneficial yet still aligns with the goals you set when preparing for the meeting.
  • Schedule a follow-up.  This is almost as important as the initial meeting itself.  While you’ve come up with a solution together, you will likely have some measurable goals for this individual that you’ll need to follow-up on and there may have been some things that you promised to do to help them. 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.

How do you practice difficult conversations?

Now that you know how to navigate difficult conversations, how exactly do you put into practice what you’ve learned?  It’s simple – PRACTICE!  But how?  Role playing the various difficult conversations in the workplace on your own or with a colleague or friend is a great start.  Using role play scripts on difficult conversations in group exercises with your team helps develop their communication and conflict-resolution skills, teaching them how to be empathetic while also maintaining professionalism. You can use the examples of a difficult conversation as a role play script in training other team members on how to handle difficult conversations in the workplace.

Remember that difficult conversations can be emotionally charged, so it’s important to approach them with patience, empathy, and a willingness to listen. Practice can help you feel more prepared and confident, but it’s also essential to adapt to the specific dynamics of each conversation as it unfolds.

woman talking to her colleagues
Group Psychotherapy Concept. Mature Woman Expressing Gratitude For Psychological Help And Support During Group Therapy Indoors. Selective Focus

These challenging 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.  Understand that the ultimate goal is to encourage effective communication, build trust and strengthen relationships within your company.  The sign of a successful conversation will leave both parties feeling better about the situation than when they came in.  It’s hopeful that, even through any discomfort, they have been able to openly and honestly discuss a difficult issue.