Check out this article excerpt By Catherine B. Soehner and Ann Darling:

“What is a difficult conversation? For a conflict-avoidant person, it is any conversation that produces anxiety, that worries you, or that you have put off, and in which you are certain the other person will not like what you are saying. For a straight shooter who is not afraid of confrontation, a difficult conversation may become one in which, after “telling it like it is,” the other person becomes hostile, combative, or worse.

Different kinds of difficult conversations

A difficult conversation entered without reflection can become a difficult situation, and it may only go downhill from there. But what is difficult is in the eye of the beholder—or rather, the mouth of the speaker. However, some generalizations and common examples are:

Telling people they will not be retained or did not get a promotion. Hiring and promoting can be rewarding and even pleasurable conversations to have, and firing or denying promotions can be among the most difficult. Unfortunately, our jobs are filled with the give-and-take of this cycle, and thinking about how to manage the less pleasurable conversations that arise throughout the workday is important.

A leader might have to let someone go for many reasons, such as when grant funding for a position ends and there are no other funds to continue the position. Sometimes we have to let people go because they are not performing their job adequately. Often the decision happens after a long series of difficult conversations. If you have not been consistent about having frequent conversations and creating documentation, letting someone go can be a difficult process.

Similarly, telling people that they did not get a promotion or a position they applied for can also be difficult. Often people who have applied for a promotion have worked with you for some time. The employee may have become a friend and trusted colleague. In these instances, difficult conversations have an added layer of personal complication that must be considered.

Telling people they are not performing adequately. In many libraries and other academic units, we are expected to conduct performance reviews on an annual basis. We would like to report that their regularity makes them easier, but that would not be true. For most of us, these conversations are especially difficult precisely because of their regularity and because we conduct them with people we may know well.

Negative performance reviews are tricky because the task is to clearly identify behavior that needs to be changed while also motivating the employee to stay engaged and be willing to improve. Hiring new employees is almost always more expensive and time consuming than training and supporting current employees. Finding a way to conduct this conversation effectively is critical to success as a leader.

These conversations can be especially difficult if the other person believes he or she is doing an excellent job. However, avoiding telling people that they are not meeting expectations is unproductive. How can anyone improve his or her performance unless he or she knows that expectations are not being met? You can put off having the difficult conversation, wait until the yearly review, and then surprise the employee with a poor performance review, but that would be discouraged by any human resources department. It is unfair and unkind not to help the employee improve simply because you want to avoid a difficult conversation. Furthermore, ignoring poor performance can affect the morale of those performing well. It can be demoralizing to work hard every day only to see others making a minimal effort with no consequences.

Telling people you need them to do something they don’t want to do, or telling people you need them to stop doing something that they like to do or feel entitled to do. These types of conversations may be less formal in terms of institutional norms, but they are no less difficult. In academic settings like libraries, most of us have benefited from the opportunity to “own” our jobs. This privilege can make work rewarding, but sometimes we forget that the opportunity to create our own work is a privilege and not a right. All working situations change; new tasks get assigned and new technologies demand that old tasks be done in new ways. Redirecting people’s work is a common aspect of a leader’s job. This conversation is not likely to go well if not handled with some level of reflection and planning.

The good news and the bad news

No matter what you do to prepare, difficult conversations are never easy. There is a lot at stake in these types of conversations.

Telling people that grant funds have expired and they will not be rehired is tantamount to telling them that they will not be able to pay their rent or feed their children. Telling people that they are not performing tasks adequately is often interpreted as telling them they are inadequate human beings. You should go into each difficult conversation assuming that the stakes are even higher than evident on the surface.

Practical steps and learnable skills can be used to make difficult conversations go smoothly. Adequate preparation is important, and careful follow-up can ensure that such conversations result in desirable behavioral change and accountability for both the employee and yourself. Communication skills like listening, nonverbal immediacy, and clear messaging can go a long way toward making difficult conversations effective.

The good news is that these conversations can be productive and yield important change. People we supervise, armed with clear expectations and supported by compassionate messages, can transform into model employees. Through difficult conversations, we might learn what is keeping an employee from performing adequately and might be able to create supportive structures so that performance can meet expectations. There is much to be learned through a carefully navigated difficult conversation.

And the news gets even better. By having these conversations, you will gain confidence, strength, and integrity. A great irony of life as a manager is that avoiding difficult conversations makes work more difficult. Tasks don’t get completed on time and at the right level of quality. People can be confused and unhappy, which can make for low morale.

The difference between a minimally successful manager and a truly successful one is the capacity for having effective difficult conversations. You will be remembered and promoted not because you manage your budget well and meet deadlines, although these are very important, but because you help the people around you reach—and maybe exceed—their professional potential. Having these conversations may never be easy, but if you follow key steps and develop needed communication skills, you will become confident in your abilities and feel satisfied that there is integrity in the way that you interact with those under your supervision.”