Handling Difficult Conversations in the Workplace

Embrace the challenge of difficult conversations with confidence! Our team course will give your team the skills and tools they need to tackle any tough conversation, empowering them to navigate any topic gracefully and effectively.
Write your awesome label here.
This is a preview of the course's introduction. Click the big red button below to enter the full course.
Your Next Steps
Add to Next Meeting
Incorporate this session into your upcoming team meeting's agenda.
Review Manager Guide
Find out what is in the course by reviewing the manager guide.
Start Session
Once you have started your team meeting click the red button.
Ready to Start with Your Team?
Empty space, drag to resize

Enter the course by clicking this button, but please note that courses are not optimized for use on a smartphone.

Membership includes access to all team courses, starting at $36 per month.*

Course Details
45 mins - 1 hour  |  In-Person or Virtual  |  Beginner to Intermediate
Digital Coach: Ben Kill, MCIPD
Items needed for the session: Pen and Paper or use the activity template. 
Course Resources
Manager Guide
Activity Template
Summary Guide
Models & Tips
  1. Three factors that can influence difficult conversations
  2. Check, Prepare & Act model
Course Agenda

1. Theory: Factors That Influence Difficult Conversations and How They Impact the Workplace

Ben will begin by discussing the various factors that make difficult conversations so difficult. Specifically, he'll talk about how high stakes, high emotions, and differences in opinion can hinder dialogue regardless of our communication skills.
Duration: 5 minutes

2. Discussion: How Well Does Our Team Handle Difficult Conversations?

Once the team understands which elements make for a difficult conversation, Ben will ask the group to consider how well each member communicates when these factors are in play.
Duration: 15 minutes

3. Theory: How to Prepare for Difficult Conversations Using the Check, Prepare, Act Model

Next, Ben will demonstrate a model specifically designed to help make approaching difficult conversations easier. Remember, conflict can be toxic in the workplace. That’s why ensuring every team member can effectively approach tough discussions is important.
Duration: 3 minutes

4. Discussion: Trying the Check & Prepare Stages

Here, the group will get a chance to practice with the Check and Prepare stages of the model. This way, you’ll be able to incorporate more easily the next time you need to approach a difficult conversation in the workplace. 
Duration: 10 minutes

5. Theory: How to Facilitate Difficult Conversations with the Check, Prepare, Act Model

In this section, Ben will focus on the Act stage of the Check, Prepare, Act Model. He’ll then cover how to execute the conversation without causing conflict by informing, listening to feedback, and proposing solutions.
Duration: 4 minutes

6. Discussion: Trying the Act Stage of the Model

In the final discussion, two team members will apply the Act section of the model to one of the previously-identified conversations. Afterward, the group will get a chance to evaluate the conversation and provide constructive feedback.
Duration: 15 minutes

7. Theory: Wrapping up the Session

Finally, Ben will cap the session by going over what the team has learned and how it can be used going forward to facilitate a better work environment.
Duration: 1 minute
Write your awesome label here.

Course Trailer

Completed this team course?
Why not share your feedback with us, allowing us to further enhance your team's development.
Team members often come to me asking what the right way is to approach tough conversations with their colleagues. This session helped demonstrate that there is no ‘right way.’ It all comes down to proper preparation and listening skills. I’m extremely happy that my team is equipped with this knowledge."
Roberto De Melo
Operations Director

Empower Your Managers to Make a Difference

Discover why top-tier organizations trust Teamioed as their go-to solution for learning and development.

Sign Up for News From Teamioed.

Be the first to hear about our latest team courses.

Your questions, answered


How do you handle a difficult conversation?

  • Stay attentive to the other person's words without planning your own response during their speaking time.
  • Truly listen to what they are expressing.
  • Seek to understand their viewpoint.
  • Utilize questions like "Tell me more about that" or "How does that make you feel?" to delve deeper into their thoughts and emotions.
  • Refrain from talking over them or interrupting their communication.

What are the five steps to having difficult conversations at work?

  • Begin with empathy, acknowledging emotions.
  • Use visuals for clarity.
  • Ask three questions to engage.
  • Tell stories to communicate.
  • Prompt with "What If" scenarios for reflection.

What is a difficult conversation at work?

Difficult workplace conversations can happen when giving developmental feedback to a team member. They can also arise when needing to tell employees about job cuts, requesting a raise or promotion, dealing with the ramifications of lackluster work, or investigating misconduct complaints.

How do you handle difficult interactions?

  • Address Difficult Conversations Promptly.
  • Prepare Key Points, Avoid Scripting.
  • Stick to the Facts.
  • Empathize with Their Perspective.
  • Foster a Relaxed Atmosphere.
  • Exude Confidence with Compassion.
  • Practice Active Listening.

What are the 4 D's of difficult conversation leadership?

The "4 D's" of difficult conversation leadership—Discover, Define, Discuss, and Decide—offer a structured approach to navigating challenging discussions, especially in a leadership context. This framework helps leaders manage conflicts, address issues, and make decisions in a way that is constructive and leads to positive outcomes. Here’s a breakdown of each step:
  • Discover - The first step involves gathering all relevant information about the issue at hand. This means actively listening to all parties involved, seeking to understand their perspectives, feelings, and the facts surrounding the situation.
  • Define - Once you clearly understand the situation, the next step is to define the problem clearly and concisely. This involves identifying the core issues that need to be addressed and distinguishing between symptoms and root causes.
  • Discuss - With a clear definition of the problem, you move into the discussion phase. This is where the actual conversation takes place, involving an open and honest exchange of ideas, feelings, and perspectives.
  • Decide - The final step involves making a decision on how to move forward. This decision should be based on the insights gained during the Discover, Define, and Discuss stages.

Collaborative Team Courses

What is included with each Teamioed team course?

Each Teamioed soft skills training session consists of a 45-minute to 1-hour guided learning experience. Leaders, managers or individual contributors are provided with a course and summary guide to help them direct each team learning and development exercise. However, our knowledgeable Teamioed virtual coaches will handle most of the work, so there’s minimal preparation involved. Simply gather the team together and get ready to learn!

Does Teamioed provide coaching tips or resources for managers? 

We do! Leaders, managers or team leaders are provided with an in-depth guide covering each team eLearning course. This lets them better understand what we’ll cover in the soft skills training experiences. It also gives them valuable information on how to contribute to the Learning experience and development activities. 

Where do I run a team course?

Teamioed’s team eLearning courses have been built to complement your team meetings or to be run as standalone team sessions. You can conduct the experience as an in-person or virtual meeting, as team-based soft skill learning is perfectly suited to any environment. Simply log in, access the session of your choice, and hit “begin.” It’s as easy as that. If you do plan to host your course remotely, just know that you will need to use virtual meeting software (e.g., Zoom, MS Teams, Slack, etc.) as Teamioed does not provide its own.   

How do I access new Teamioed courses?

New soft skills online courses will be added to your subscription automatically. You can access them through your Teamioed account as soon as they are launched. 

What skill level is required for team courses?

All of Teamioed’s eLearning courses and training activities are designed for beginners and intermediates. However, everyone can benefit from ongoing soft skills training, enhanced problem-solving skills, and teamwork education. No matter your industry or business model, our courses are a great way to bring your team together while learning critical skills. 
*Minimum terms and notice periods may apply. For full details, please refer to our Terms and Conditions.