One of my least favorite tasks is having difficult conversations at work. I am generally non-confrontational, but there are challenging situations in the workplace that require tough conversations at the right time. This is one of those soft skills that both employees and managers need to develop and should be part of your training program.  

I’ve had a variety of these awkward and challenging conversations throughout my career and never had any training on this topic until ej4. Some of these situations occurred before Google was invented, so I had a harder time getting advice on how to handle them.  

It comes with the territory as a manager to provide constructive criticism or handle performance issues. Making mistakes at work is sometimes how you learn important lessons. My intention is never to make someone cry or feel beaten down after one of these coaching conversations. My goal is always to improve performance, fix mistakes, and help someone grow professionally. 

It’s even more difficult for employees to have concerned conversations without the authority of a managerial position. Employees need to be both empowered and trained to take the initiative when appropriate.


Examples of difficult workplace conversations as a manager: 

  • Angry customers. Dealing with rude or angry customers who demanded “I want to speak to your manager!” to our customer service representative. I managed a team of call center employees for the St. Louis Cardinals and I had these types of conversations daily. Our ticket policy was no exchanges and no refunds, and it was my job to enforce the policy to a slew of angry and rude fans.  
  • Sensitive issues. Addressing sensitive issues like workplace violence after an employee was involved in a physical altercation at a company event. The fight took place in the early morning hours after a night of drinking, and it was witnessed by employees and customers. This was a serious offense. I had another situation where I suspected an underperforming employee was having issues with opioid addiction.    
  • Dress Code. When I was in my late twenties, I had to have a difficult and awkward conversation with an employee who was my mother’s age about violating our dress code with her tank top and Bermuda shorts. The employee frequently pushed the limits on various company policies and had many interpersonal issues. I learned a lot about managing people from my experiences with her.


Examples of challenging conversations with peers, vendors, and difficult people in leadership positions as an employee: 

  • Vendor failure. I’ve managed several technology vendors over the years that had ongoing issues with extremely poor performance. In some cases, I was on the phone every day talking to them about bug fixes, broken applications, and downtime. These were hard conversations and I tried to provide constructive feedback without letting my frustration show. I was not always successful at hiding it because these were easy tasks that were getting messed up. If they were failing at the little things, how could I trust them with the big stuff?
  • Professional accountability. As a young marketing manager, I had to convince lawyers at HBO and Showtime to review my mail pieces and approve them according to my timeline. I was able to develop relationships with them ahead of time and communicate my timelines. My polite persistence paid off with successful conversations getting my approvals on time. 
  • Managing Up. In this same marketing manager role, I had to challenge both the Director and VP about their lack of action in securing co-op dollars from our partners. In the past, I was actively involved in the co-op project but was phased out. They did not choose to leverage my strong relationships with our partners. These conversations were extremely uncomfortable.

Training Topics to Improve Difficult Conversations at Work - ej4 blog graphic


Training Topics to Improve Difficult Conversations 

Different types of conversations need different training courses and skills development. Our off-the-shelf library includes all the topics I explore below. You could easily curate a curriculum for employees who are struggling with having hard conversations so they can think about the right approach for each situation. Or, as many of our clients do, open the library for employees to access at any time. 

Concerned Conversations. This course will give you an action plan so you have a better chance of a positive outcome from the conversation. Be clear and outline what you have observed. Be specific about what is wrong and discuss what needs to be done to fix the problem. Make sure the person knows how to fix the problem or change their behavior. 

Active Listening. One aspect of effective communication with these important conversations is active listening. This course will help you see how to pay better attention and not just formulate your response. The definition of conversation is “a talk, especially an informal one, between two or more people, in which news and ideas are exchanged.” This implies an open dialogue where both parties take turns speaking and listening. 

Giving Feedback. The goal of the feedback conversation is for the person on the receiving end to walk away with an understanding of their status. Some difficult conversations may have a disciplinary undertone, but it is possible for the person receiving feedback to feel positive and motivated to improve the situation or fix the issue. This course will share guidelines to follow when providing feedback. 

DISC training. Understanding the four different personalities will help you approach each conversation a little differently. Each profile approaches difficult situations a little differently. Once you and your team complete the personality assessment, you will be enlightened by the results. You may even identify the root cause of ongoing friction. The four styles are Dominance (D), Influence (I), Steadiness (S), and Conscientiousness (C). If you are a manager, you can go into more detail in our series on DISC leading skills.  

Emotional Intelligence. If we can better understand the emotions of ourselves and of the people around us, we can be much more productive. We can improve our interpersonal skills, effectively address workplace conflict, and have productive conversations. Our series will help you understand emotional intelligence, improve your self-awareness, and develop self-regulation.  

Empathy. Developing empathy is included in our series on emotional intelligence, but it is worth noting here. Consider the conversation from the other person’s point of view. Think about their skillset, workload, and specific needs. Try to understand the impact of their emotions in this conversation. It’s not about delivering bad news. The best result is to fix the problem or the cause of the difficult conversation.  

Confidentiality. Understanding professional boundaries, especially confidentiality, is important for employees and managers. Protecting confidentiality is necessary with day-to-day operations but it is critical when engaging in these constructive conversations. Both parties need to work to avoid a lack of trust. The topic of the conversation should never become fodder for office gossip.  

Nonverbal Communication. It’s important to be aware of your body language, eye contact, and facial expressions during these discussions. All of these can have a dramatic impact on the tone of your message and how it’s received. Our series also explores aligning your nonverbal communication with your intentions. If your goal is conflict resolution or to have a successful conversation, your body language can convey your positive intent. Crossing your arms, glaring your eyes, and having an aggressive posture may help you take control of a difficult conversation, but it may not achieve the best result.  

Managerial Courage. Managing people is not easy. Training managerial courage is a good topic to include in a leadership development plan. It will give your team leaders support when having difficult conversations, teach them how to build resilience, develop tact, and help them understand their own management style.  

Coaching Skills. As a manager, the act of having constructive conversations with your employee is part of the coaching process. Our training teaches you how to apply unique coaching skills for your rookies, contributors, key players, and your captains.

You can see that having successful conversations on difficult situations requires training on a variety of soft skills topics. Working with a company like ej4 who offers a full library of online training content makes this very easy. Many of our clients combine our videos with instructor-led sessions in live and virtual classroom settings for a blended-learning environment. In addition, they allow employees to explore the library on their and create a tailored learning experience for their unique needs and interests.  

If you would like to view any of the courses mentioned above, sign up for free trial of Thinkzoom, our LMS. You will have access to all courses in our Business Skills and Workplace Compliance Libraries. 


Additional Resources 

Chris Scherting

Written by Chris Scherting

Chris Scherting’s passion for marketing began in grade school where she served several terms as Commissioner of Publicity and Public Relations. She graduated from St. Louis University with her BSBA in Marketing and her MBA. She has worked for some of the most well-known brands in St. Louis including the St. Louis Cardinals, Charter Communications (now Spectrum), and Maritz. She joined ej4 in December of 2016 with the goal to bring her big brand experience to a growing company.

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