Master Difficult Conversations

By Tatiana Chalkidou

One of the ironies of our technologically connected world is that people have great difficulty communicating with each other face-to-face. Managers who have to approach situations with political correctness or deal with thin-skinned coworkers or subordinates sometimes find it difficult to be candid without crossing the line.


It takes effort to be direct while being tactful, to be crisp without being rude. However, it is a key management skill and a critical success factor that will serve you well throughout your career.

Part of the skill is knowing when and how to have conversations on sensitive subjects.

Although sometimes heart-to-heart conversations require you to be honest, one should know that these are delicate and difficult conversations. Within the workplace, topics may range from how an employee’s personal life is affecting performance to how an employee is alienating other people with an aggressive attitude, etc.

Most of the time, these conversations are initiated by you--the manager--and are designed to effect some change on the part of the other party--your employee. In doing so, you need to show a level of conversational maturity that accomplishes the objectives while minimizing conflict.

And make no mistake--the potential for conflict is very high in these situations. The personal nature of the topics discussed can generate a range of negative emotions in employees that can escalate to resentment, formal litigation, or even workplace violence.

The reality is that few managers are properly trained to handle the emotional and psychological aspects of these conversations. Unfortunately, management-training programs provide minimal instruction on controlling the emotional facets of performance improvement, behavior change, or disciplinary meetings.

Timing is the key. You begin these stressful conversations with an employee at a point when you can no longer tolerate the behavior. In some cases, you want the person to change an attitude overnight, or leave!

Instead of addressing an issue when it is first identified, some managers may choose to ignore it in the hope that it is a one-time event, or to avoid the discomfort of addressing it. In waiting until the situation must be addressed, you may be so frustrated with the behavior that you merely want the issue to stop and the employee to go away.

If you do not want things to escalate to that point, here are some tips on how to have a delicate conversation and reap the benefits:

1.) Before being frank with an employee, try to be frank with yourself! Approaching a difficult conversation will require you--the manager--to truly want the employee to change the behavior and continue employment. You also must have the courage (heart) to admit to errors, fearlessly confront the employee’s behavior or performance shortcomings, as well as your contribution or lack of it, to the situation. And remember: The sincerity of your motives will play a major role in the employee’s commitment to change. Lack of sincerity on your part will result in a fight/flight/freeze reaction. When this is activated, an employee will find it very difficult to think rationally.

2.) Think carefully about where and when to have a conversation. Some managers prefer to host these conversations away from the office because it creates some anonymity. However, this tactic may not be beneficial if you suspect that the employee may start crying, or become upset in the middle of a restaurant. In such instances, a private space may be more appropriate. When it comes to the best time for discussion, start the dialogue towards the end of the day. Think how an employee might feel if you pose a possible career-changing question at 10:00 a.m., and then expect him or her to work efficiently for the rest of the day. In the event you have that conversation over dinner in a restaurant, remember that you're still having a workplace conversation. Thus, you are still a manager talking to an employee, and not two friends having a chat.

3.) Don’t make assumptions that the employee knows what you are talking about. Sometimes, an individual is not aware of a specific behavior and how it affects others. Therefore, approach the situation assuming that he or she is not aware, and you are there to present “the big picture.” Opening up a dialogue may even reveal that your own behavior has played some role in the problem.

4.) Explore ideas instead of offering suggestions. Let’s assume you are having a conversation with an employee who has already been passed over for a promotion and is complaining to you about it. At this point, remember to do more listening than talking, and try to help the individual brainstorm, rather than make recommendations. And don’t forget that although you are trying to have a heart-to-heart conversation, you are still the manager. Whenever you're not sure what to do or say, don’t forget you are not alone. Talk to the human-relations people. They can help you avoid the sandbank, and if necessary, try to pull you out!

5.) Regardless of the topic, recognize there are some typical triggers for conflict. Two of the most common are lack of respect (i.e., self-respect and/or respect from others) and the fear that the person is not in control (defined as freedom to exercise free will). Now, add to these triggers the fact that the employee is interpreting information about your emotions and intentions from your words and body language. The potential for conflict increases. There is a high probability that the employee will misread these emotions and intentions. In contrast, a heart-to-heart conversation aims to interact with an individual in a manner that protects his or her dignity, self-esteem, and independence in order to resolve an issue. In most lawsuits, it is the perceived insult of inappropriate treatment that motivates an employee to seek “justice” via the courts, rather than the employer's specific disciplinary actions. So, treat an employee with respect, especially when delivering “bad news.”

The bottom line is that having a sensitive conversation is a skill managers should have, as it helps enrich relationships and reduces the possibility of an employee misreading emotions and intentions. Furthermore, it helps establish respect and control as the driving forces behind words and actions.

Dr. Tatiana Chalkidou is a post-doctoral fellow at Oklahoma State University, working in different park-management projects. She holds a Ph.D. from Oklahoma State University in Health, Leisure, and Human Performance, a M.BA. and a M.Sc. in Human Resources Management and Development from University of Leicester in the UK, and a B.S. in Physical Education and Sport Science from University of Athens, Greece. She can be reached via email at