Author: Kim Zastrow

Many of us look forward to pursuing goals and being more successful in our careers. As we achieve the positions of supervisor, team leader, or even business owner, there comes the added responsibility of handling difficult conversations and conflicts in the workplace. In today’s world, conflict is everywhere and cannot be avoided. The way in which you as a leader conduct yourself when difficult situations arise will say much about your leadership abilities. Delivering bad news comes in all forms, from giving a negative performance review to relaying budget cuts or maybe even laying off people. You must therefore be prepared to master these difficult conversations rather than shy away from them.  What can help you be better prepared to handle these inevitable situations?


This characteristic may seem counterintuitive. However, as a leader, you can’t view yourself as too important to handle conflicts that may arise in your company. Also, as the boss you have to humbly accept that sometimes it is your job to be the bearer of bad news. Supervisors or team leaders who opt to delegate unpleasant communication tasks, rather than manage the crisis personally, could be communicating to the staff that they are “above the rest” and that this is not their problem to deal with. Regardless of potential unpopularity, a great leader will assume the responsibility in order to show that he or she cares about the organization and their values.


Do not be afraid to acknowledge that a problem exists. If you choose to ignore the issue, it could impact your employees or business in a negative way. We know this principle to be true in another area of life. If you hear a noise in your car, it may be easier for you to ignore it and put off taking it to the repair shop to get it looked at. Eventually, one day your car will break down, and the reality of the situation is upon you. Similarly, in the workplace, by addressing problems when you initially realize they exist saves you from an even larger problem down the road. As a leader, don’t sidestep around trouble; have the courage to take action and find a solution before it becomes a larger issue.

“If we really drill down on what holds us back from having these conversations it usually comes down to fear.”

Bill Boulding, Harvard Business Review

Perhaps, you may fear having an awkward conversation with an employee or, even worse, upsetting the individual! Although this fear is valid, remember that you are the boss and you have to take the entire team and work environment into consideration. An unresolved issue may be causing the whole work atmosphere to suffer. Those in leadership positions must be willing to embrace uncomfortable and sensitive topics in order to develop the environment of having open, honest conversations with all employees.

Preparation for You and Them

How can you prepare yourself?  Work to streamline your feelings and thoughts.  The time not to have the conversation is when you’re angry about the situation that has developed.  Get calm and organize your comments. Figure out the real issues. Often difficult conversations are not just about the dialogue being said, but the emotions behind the words that need to be said. Although your reasons may be strong, always display respect and dignity to those who are on the receiving end of the conversation. When you mentally “put yourself in their shoes,” you can engender more respect and potential for a favorable outcome, both in the employee himself and in the other employees who are observing the ramifications.

Before having any formidable conversation, take into account all the facts. Also know that you will have to justify whatever bad news you are delivering, so be prepared to have concrete reasons to support your decision. After delivering the negative, say something positive and help your employee look towards a solution. One longtime business leader said, “When you take on the responsibility of leading a team, you’re not just a boss, but you’re also a coach. You have to provide your employees everything they need to succeed.” So always try to leave the challenging conversation on a positive note. This will help your employee feel not as a failure for some mistake or disagreement, but hopeful that they can progress and improve. Lastly, be prepared to follow up. Bad news may involve some “cleanup,” but a good leader will keep updated on the progress made.

Overall, don’t allow difficult conversations to wreck all the efforts you’ve made to attract and retain good employees. Although conflict will arise from time to time, it is your opportunity as a business leader to show your ability to manage a crisis without losing control. Don’t fear the awkwardness, but instead, with humility, embrace the chance to have an open conversation and point towards a positive outcome. You will find that your workplace environment will flourish when you display good leadership abilities even under the most difficult of circumstances.

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