Difficult Conversations Handbook

This Handbook is intended as a quick reference guide for you in your role as staff, faculty and/or student. It is meant to be a guide when you come across a conversational situation that is uncomfortable or likely will become uncomfortable. These occurrences are frequent and show up in a variety of environments—from your home/residence hall, to your work/classroom, and also including social situations.

Having some tools in your pocket that you can readily access will serve you well. This is only an abbreviated reference guide and you are encouraged to seek out other resources on and off campus who can help you navigate the complex waters of challenging conversations. Here in the Ombuds Office, you can learn about all of those resources and more.

If you have specific challenges in communicating with someone, consult with the Ombuds Office for help with resources, role-playing, and feedback. Email is ombuds@wellesley.edu and phone is 781-283-3385.

Based on recurring themes brought to the Ombuds Office, here are some ideas to help you through these 4 situations:

Someone says something hurtful (Responding)

For all of these examples, I believe that two of the most important capabilities are Emotional Intelligence and Assertiveness.

Emotional Intelligence (EI) consists of both: 

  • Personal Competence (self-awareness, self-regulation and appropriate motivation), and
  • Social Competence (empathy for others and social adeptness to induce others’ good responses

EI facilitates our capacity for resilience, motivation, reasoning, stress management, and effective communication. It is responsible for over half of your performance on the job and in the classroom. Those who ignore or fail to nurture their EI can end up engaging in bullying, harassment, and aggression. By paying attention to and increasing your EI, you are more likely to positively, effectively and assertively respond to someone who says something insensitive, derogatory, or damaging.

Assertiveness is the ability to analyze a situation between people, decide on a reasonable solution, and then use language that is objective, confident and respectful. It allows to you get at the problem rather than getting at the person. It is neither passive nor aggressive and seeks resolution of interpersonal conflicts. Having this communication style will reduce stress and allow you to cope with problems.

Example: Person A trying to get Person B to commit to a meeting time to work on a shared project.

Passive –

A: Uh, I was wondering if you would be willing to take the time to meet with me about our project?

B: (Listening to music) Not now, I’m busy.

A: Ok.

Aggressive –

A: Listen, I’ve had it with you not even talking about planning a simple meeting. Are you going to do it?

B: (Listening to music) Not now, I’m busy.

A: You only care about yourself and your stupid music. You never do your part in any project and you won’t even take 5 minutes to talk about it. I have to do all the work all the time! I’m sick of it!

B: Oh shut up, nagger. Leave me alone and go tell someone else how righteous you are. You think you are always right. Get lost.

Assertive –

A: I know scheduling a time for a meeting to discuss the shared project isn’t the most exciting activity, but it needs to be done. Let’s plan when we will do it.

B: (Listening to music) Not now, I’m busy.

A: This won’t take long. I feel that if we just put it on our calendars, it will happen and we won’t have to worry about it.

B: I’m not worrying about it.

A: I’ve already found a couple of times that work for our schedules and have a skeleton plan for our project. Will you look at the suggested times and let me know which one you like – say, after dinner?

B: Oh, I don’t know.

A: I’ll come see you after dinner and we can finalize the meeting time. Ok?

B: I guess so.

A: Good, it won’t take long and I’ll be relieved when we have it firmly on our calendars.

The passive person begins with asking permission, suffers silently, and becomes a silent martyr; the problem doesn’t get solved. The aggressive person begins with an attack, replays angers, slings insults, tries to dominate and storms away feeling miserable; the problem doesn’t get solved.

The assertive person begins with a small request (merely deciding between two dates) that shows that they’ve done homework and prepared something fair; they stick to the point and ask for a commitment to a definite time when a decision can be made, and then rewards the other person by noting satisfaction when the other person agrees to choose a date for the calendar; the problem gets solved.

In general, a successful outcome will depend on how emotionally intelligent you are and how assertively you say it. It’s important to acknowledge (your and their) emotional energy and direct it towards a useful purpose. If the other person makes verbal attacks, do not take them personally and instead help them come back to center.

You need to talk with someone about a touchy subject (Initiating)

If you need to initiate a conversation, perhaps because someone earlier had disagreed with you in a very disrespectful manner, it is a good idea to respond with an intelligent and respectful reply. Begin with making eye contact and say something like “I heard your argument yesterday that X is the problem and that Y is the solution and there may be some merit to it; what I’d like to suggest is that Z is the problem and that A is the solution and here’s why …”

This method of conversation is effective and allows for both sides to really listen to each other, acknowledge what they’ve heard, explain the reasons for their disagreement and either keep the conversation going or simply move on. It is a far cry from harmful labelling and selfish lecturing. Especially when there is a sensitive undercurrent of differences, we should try very hard to aim for the greater purpose—what is good in what you value and what is good in what they value. This is not about persuasion or compromise; rather, it is about understanding and learning.

When you come up against resistance, use curiosity to learn more about what the other person considers to be important and what that person fears might happen if things changed. When the other person is heard, they open up. When you truly hear them, it gives you a new perspective. Consciously manage the tension, recognize that multiple viewpoints exist and are essential, and identify the best overlapping areas of your beliefs. You will end up with more options as well as a peaceful co-existence.

Tap into empathy and respect, rather than being judgmental or argumentative.

You witness someone saying something objectionable to another person (Bystander)

Many times we are not directly involved in an objectionable dialogue, but we witness one. What do we do? Ignore it, jump in boldly, or tiptoe into it carefully?

The way in which we respond may partially depend upon how those who are affected want the tensions to be handled. There are three ways to handle such problems. On one extreme, we may want to merely expose the problems and hope the tensions take care of themselves. On the other, we may want to make the tensions explode to a point where we expose the other parties and call them out with accusations and/or one-sided demands. The third route can be to raise the tension-heavy issues directly in a dialogue which is both respectful and substantive and end up with some tangible, meaningful and effective change.

It may not seem to be the easiest, this third route of dialogue, but it is the most positively effective one. It is a face-to-face exchange of ideas and/or opinions on issues, with a view of possibly reaching an amicable resolution. It allows the people to explore the matter together. If both people approach this dialogue with ground rules of respectful language and the purpose of finding a solution rather than merely venting or ripping someone apart, then the chances of a successful encounter will be multiplied.

These types of talks cannot only benefit specific relationships, but they can change your life. Many people fear having a difficult conversation because they may believe that they will lose the friendship, be the object of anger, cause someone else to be hurt, and/or be perceived as a bad person. However, when you have a truly good conversation—where you both show compassion and understanding—you and the other person end up helping each other grow.

You want to avoid either receiving or doling out either Retaliation or retaliation (Avoiding negative consequences)

Speaking up to a supervisor, professor, colleague, etc., may land you in very hot water—from “capital R” (firing, getting a failing grade on a paper, being ostracized from a committee)—to “small r” retaliation (being subtly ignored, not being called on in class, being removed from projects that could help your career). Being able to improve communication in such a way so that neither type of retaliation is as likely to ensue will be an important skill.

Here are some suggested steps for improving communication:

  1. Establish trust. Respect appropriate confidences. Let people know that you are a team player.
  2. Check for unfinished business. If you have an issue that has been a problem in the past, you should address it head-on. If you need an apology or explanation, ask for it. If you need to offer constructive feedback (not criticism), do so in the framework of the situation and explain that what was said/done was hurtful, why it was hurtful, and how you would like for things to go forward from now on.
  3. Communicate your intent to learn. As the other person responds to your intent to learn (and not just defend your point of view), they will be more willing to learn about your position. Ask clarifying questions, summarize, and let the other person know that healthy disagreement is ok.
  4. Listen carefully. Really listen and pay attention to what the other person is saying.
  5. Watch your language. Be aware of your words and use “I” statements rather than “you” statements. Try not to say “should” and “don’t.”
  6. Deal with emotions. In having high emotional intelligence, you recognize and regulate emotions in yourself and even in others. When negative emotions come up, take a break and decide calmly how best to respond to what happened.

After an important conversation, it’s helpful to summarize what was said and steps that will be taken.

If you are dealing with a group, all perspectives need to be honored and any discussion that follows should go in the stages of objective, reflective, interpretative and decisional in order to meet your goals.

One other very important point … all persons at any meeting should put away all electronic devices except for emergencies and in that case, to take the device outside of the room to handle them. We cannot be fully present and mindful if we have more than one thing going on at the same time; also, it is rude to be distracted while someone else is trying to talk.