In conducting research for this book, I invited people to respond to the following question: “Imagine you have the opportunity to ask the world’s leading expert in interpersonal communication for advice on how to approach a difficult conversation. What would you ask?”
Here are some of what I view as the most critical questions and my answers to them:
1. How do I make sure the person does not feel attacked and become defensive?
Focus on using “I”—for example, “I am feeling out of the communication loop” versus “Why aren’t you keeping me informed?” Point your finger at yourself: “I’m sorry, but I am confused and would appreciate clarification,” as opposed to “You must be confused.” Use empathy and validate feelings: “I am sorry you are feeling that way, and I probably would be as well,” instead of “There is no reason to get upset over such a minor issue.” In general, use language that makes you and not the other person vulnerable.
2. How do I speak in a way that increases the chance of the other person really hearing me?
Begin by showing your commitment to understanding what the other person is saying. Use body language that depicts engagement, questions that show interest, and paraphrasing to demonstrate understanding. Your best chance of being heard happens after the other person feels heard. When you seek to present your views, use language and examples that will resonate with and make sense to your listener. For example, if you are a salesperson talking to a lawyer, do so from the perspective of wanting to protect the company and not just making sales numbers. Speak into the other person’s listening.
3. I keep having the same conversation over and over again. The other person says he is going to change, but he always goes back to his old ways. Is there anything I can do?
The key to this question lies in the words “goes back,” which implies that a change actually took place; you just didn’t do a very good job reinforcing it. Behaviors that change quickly tend to change back quickly if not reinforced. Although you have likely done so before, you should always check to make sure that the other person fully understood the request and why it was important. Also, make sure that the person has the resources needed to be successful and did not run into any stumbling blocks. If you have used the “confused and concerned” approach, yet the problem persists, be straight: “I feel that we have spoken about this issue several times and nothing seems to have changed. Am I wrong about that?” Assuming that you get at least half-hearted agreement, proceed with, “Is there anything you would like to share regarding why we are back to where we started?” You might also query his understanding of the importance of the task and the implications for not following through as discussed. I find that the primary reasons people do not follow through include: they do not understand what is being asked of them, do not understand why it is important, or do not have the resources and/or skills to be successful. If you are the person’s manager and there is still no sustained change after these conversations, then you should formally write him up and document what further actions will ensue if expectations are not met. Do not make empty threats. If you are dealing with a peer, you may have to escalate the issue to your boss. Last but not least, consider that it may be you who needs to do some changing!
4. How do I stop being nervous when approaching such a conversation?
Remember, being nervous primarily comes from a lack of confidence, the antidote to which is gaining skills and experience, and, thus, a sense of competence. Plan for the conversation, envision it, and practice it. Just like giving a talk, the more you practice, the less nervous you will be. Of course, a big contributor to your being nervous is that you say you are. You might also put the situation into perspective by comparing it to other conversations you have had throughout your life that were even more “difficult” but that you managed to work your way through. If it makes you feel better, the other person is probably equally or even more nervous than you!
5. How do I manage what I think will be an emotional or hurt response (the person will be hurt again by me bringing it up, but will also be hurt if I don’t acknowledge the past)?
Be honest and acknowledge that the other person might find what you say hurtful but that is not at all your intention. In fact, you feel strongly that if you do not discuss the issue, the situation may well become worse for him. You might say something like, “Toby, I want to share some feedback with you. I worry that it will come across as hurtful, and I apologize for that. However, if we ignore discussing this issue or beat around the bush, I fear that the situation will become more difficult to deal with later.” Whenever you are addressing a highly sensitive issue, remember that how you say something is just as important as what you say. If you always come from a place of authentically caring about the other person, whatever you say will sound more supportive than critical.
6. What is the best way to ask someone to resign?
Realize that giving someone the option to resign rather than be fired is often of considerable benefit to that person because it provides him with the opportunity to leave gracefully under what appears (at least on his résumé) to be his discretion. As always, be direct: “Trevor, it has come to the point where we need to part ways. I have spoken with human resources, and you are being given the option to resign. I will need your answer by the end of the week.” Do not engage in any conversation unrelated to this question, and do not be apologetic. The situation should be of absolutely no surprise to the individual because he has received ongoing performance feedback that has been well documented. If this is not the case, you have failed to do your job as a manager. I recommend not saying that you will do whatever you can to help him secure another job because it is largely an empty promise and makes no sense. If you are transitioning this person out of your organization, why would you be advocating for him?
7. What is the best way to tell someone that she is being let go due to an organization restructuring?
With great compassion and candor. “There is no easy way to say this, Tania, but as a result of the reorganization, we will be eliminating your position. I am truly sorry.” Have human resources ready to offer whatever support they can. Be ready to handle any reaction from crying to yelling with calmness and kindness. Assuming she is a good employee, it would be considerate of you to have already reached out to your personal contacts who may be interested in interviewing her. And during the period she is still employed, be flexible with her schedule to allow her time for interviews. Also, if possible, allow her to have a say in how the announcement of her departure is made. She might, for example, want to tell her closest colleagues first.
8. How do you determine if additional people (human resources, boss, etc.) should be present for a critical conversation?
It depends. Having said that, here are some situations in which having another person present may be prudent. If the goal of the conversation is to provide highly critical feedback or reprimand the individual, I would ask a human resources representative to attend and take notes on the meeting. If you are dealing with an individual that you believe will make false claims or allegations regarding the conversation, you will want someone else present and you need to make sure to fully document the interaction. If you are faced with a he-said-she-said situation, bring both people together after speaking with each individually.
9. My boss is always being critical of my work, and I’m tired of it. How do I just tell him to lay off?
Try something such as the following: “Luis, I am committed to doing my job to the best of my ability. It seems that recently you have been extremely critical of my work and unhappy with my performance. Am I wrong?” Whatever flavor of yes or no you get, you will want to continue the conversation. Ask him to confirm his specific expectations and the criteria by which your performance will be evaluated. Make sure you are on the same page regarding how tasks are prioritized. Request that you regularly have one-on-one meetings to review your performance and that he immediately bring it to your attention when you are not meeting expectations. I would also ask that he let you know when you are exceeding them.
10. How do I create the sense of an open and safe environment so people feel as though they can come to me and have difficult conversations?
Creating an environment in which people feel they can share openly without fear of being criticized or otherwise adversely impacted is critical. This requires a trusting relationship that comes from showing you have the other person’s best interests at heart, always keeping your word, and having a history of authentic and straightforward conversations. In terms of starting the conversation, you might try, “I think we should discuss what happened. I know that it is a very sensitive issue, and I want to assure you that what we discuss will remain between us.” Of course, if you have not kept your word in the past, this option is off the table. Under certain circumstances, the other person may feel a greater sense of security and comfort if someone else is in the room. Another tactic that can be helpful is to agree that notes either are or aren’t taken; if notes are taken, the other person may find it comforting that there is a record of the conversation, and if they are not taken, you can agree that the conversation is “off the record.” I would ask for her preference. Also, make such conversations collaborative in nature and demonstrate a level of vulnerability and humility: “I really appreciate your willingness to share your concerns with me. I honestly don’t know how to best address this situation and would appreciate trying to figure it out together.”
11. I was fortunate to get an internal promotion, and now I am the boss of someone with whom I had a good peer relationship. I feel that he is angry about not getting the promotion, and I think he believes he should have gotten it. It is really awkward, and I don’t feel that I can ask him to do anything. Help!
This is unquestionably one of the most challenging situations. Just be candid. “Elias, I know that you were hoping to get the job, and I can imagine that you are very disappointed, maybe even angry. It is my hope that we will continue to have a good collaborative relationship. If you are still interested in advancing, let’s work together to sharpen your skills so you are in the best position possible when another opportunity presents itself.” Never take on the I’m-your-boss mindset. Instead, consider giving this person a great deal of autonomy. Since you have an established relationship, you may be in an informed position to give the person some additional responsibilities or opportunities that you know he would find desirable. For example, you might know that he really wanted to receive specific training, and you can make that available. If it becomes clear that the person has a difficult time getting over his disappointment, you might have a sincere conversation about helping him find another role in the organization. Have empathy for him, and imagine if the decision had gone the other way.
12. I tend to sugarcoat or try to protect people’s feelings, and then the person doesn’t get the weight of what I’m saying. How can I get comfortable just saying the thing that needs to be said without feeling bad myself?
This is a common challenge for most people. Begin by asking yourself, “Would I want someone to sugarcoat the feedback to me?” Probably not. Say what you have to say, but have it come from a place of genuinely caring about the other person. It is a disservice to give someone a watered-down message, and she may well end up upset with you in the long run for not being more direct. Personally, I avoid the “sandwich” approach—positive feedback, criticism, positive feedback—for the very reason that the core message becomes diluted. I prefer to stay focused on getting the primary point across. Of course, one thing that will make you more comfortable going into such conversations is the mindset that you are offering constructive feedback that is important to that individual’s growth and development.
13. What is the single most important element in making a difficult conversation effective?
Maintaining a collaborative mindset. I say this because doing so will lead you to engage in all kinds of key behaviors, such as actively listening to the other person and trying to understand her point of view, seeking compromise, not making the other person wrong, and respecting the other person as a colleague. Any conversation that you enter with the mindset of it being confrontational will lead to counterproductive thoughts and behaviors.
14. How do you approach a difficult conversation so that it doesn’t come across as a personal attack, but rather an attempt to fix a problem and reach the same goal?
Start by getting full agreement on the goal. For example, “I want to make sure that we are on the same page. The purpose of our conversation is to resolve the billing error with the client.” You might then say, “As I see it, there was some miscommunication around expectations, and we both probably should have been more careful in checking things over. I am not interested in finger-pointing or placing blame. That doesn’t matter to our client. We just need to concern ourselves with fixing the problem.” If appropriate, you might also say, “I realize that I have been trying to place the blame for this on you, and that isn’t fair. I can imagine that it may have made you feel like I was attacking you, and I apologize for that.” In the vast majority of cases you will get some version of, “Thank you. I appreciate you saying so,” at which point, you both can focus your energy on the task at hand.
15. What’s the biggest mistake people make when starting a conversation that’s likely to be uncomfortable or perceived as confrontational?
Using language that is accusatory or denigrating and puts the other person on the defensive—for example, “I can’t believe you did this,” “What were you thinking,” or “You got this all wrong.” And, of course, starting with the mindset that it will be uncomfortable and confrontational will lead to verbal exchanges that increase the likelihood of each person becoming defensive and/or aggressive in order to prove themselves right and the other person wrong. Or it may be the case that one or both people may be so conflict-averse that the conversation never really gets off the ground and the core issue is never fully addressed out of fear of escalation. Keep your focus on creating and maintaining a healthy conversation that results in a positive outcome for both you and the other person.
16. I delivered critical feedback to an employee, and now he is totally demotivated. What do I do?
Sounds like you screwed up by being “critical” rather than “constructive.” As always, be straight. “Ludwig, I have noticed that you have been less engaged since our conversation, and I apologize if my feedback came across as harsh. I shared what I did because I want you to be successful. Was there anything in particular that I said that you found upsetting?” If sincere, apologize. For example, “I am sorry that my comments came across as overly critical. It was not my intention. I respect you and believe that I owe it to you to be honest.” Keep coming back to the theme that your goal in giving the feedback was to be constructive and was in no way meant to demoralize him. You may want to ask if there is anything that you can do to help the other person get fully back in the game. Also, make sure to set the person up for success with the next assignment and offer authentic praise for a job well done.
17. Whenever I try to deliver critical feedback, the other person criticizes me for things not going well.
Beyond remaining extremely open to the other person’s feedback and perspective, I would actually invite it, “Ibby, I want to discuss what is going on in terms of getting the reports back later than we’d agreed. Let me start by asking your view of the situation.” Expect the person to blame you. Remain calm and avoid acting defensively; ask questions and paraphrase to show you are committed to understanding her perspective. Assume responsibility for your part: “You are right. I should have made sure that you had gotten those numbers sooner. I believe we both had a role to play. My goal in discussing the situation is to make sure we are clear regarding responsibilities and expectations going forward.” Do not let the other person’s criticism dissuade you from holding her accountable.
18. How do you deal with a colleague who lies, cheats, and steals? People who are just fundamentally bad?
To the extent it is possible, don’t. Have as little interaction as possible, and document any inappropriate behavior. Report more egregious acts to your manager and human resources. Communicate as much as possible over email so that you have a record of conversations. As much as you may be tempted, avoid bad-mouthing or gossiping about the person. You do not want to give him any fodder to use against you. At the same time, protect yourself by building alliances with other team members who can have your back.
19. How do you approach conversations with people who don’t think they are part of the problem when the fact is they are at the center of it?
You need to start by getting buy-in from the person that there is, in fact, a problem. However, I would replace the word “problem” with “issue,” “concern,” or “challenge,” as people are more likely to admit to playing a role in such situations rather than being responsible for a problem. Using this alternate language also makes addressing the situation less daunting. Recognize that underlying this question is the assumption that the person must be aware of and understand her role in the “problem” in order to make changes in behavior to alleviate it. I would challenge this hypothesis. It is not necessary to convince people that they are part of the problem for them to be part of the solution. In fact, people may be more willing to offer assistance if they do not feel blamed. Your goal should be to make the other person feel empowered to take actions that will make a real difference in improving the situation. With all this in mind, start with a very open-ended question, such as, “What is your take on the client’s concerns?” Then probe a little further: “What are your thoughts on how to get things back on track?” You might then ask a question such as, “At this point, what do you suggest we should each be doing?” In general, just focus on getting agreement that something needs to be done differently and then have a problem-solving conversation around it.
20. What do I do if in the middle of the conversation the other person starts to get very emotional, for example, cries or yells or even walks out?
If the person walks away, that is fine. Let her. Wait for her to follow up within the next 24 hours, and if she does not, reach out to her. Regarding crying, if you get the impression that the person will be able to compose herself quickly, just remain present and calm. If there is a tissue box nearby, offer it. If the person is extremely emotional, suggest that she take whatever time she needs to compose herself. In terms of yelling, request that the other person lower her voice. If she does not, say that she can reach out once she has calmed down, and then walk away or end the video call. Obviously, all these responses are tempered by your relationship history with this individual. For example, if it is a good friend who starts becoming emotional, you would likely offer comfort.
21. I just found out that a new hire with less experience is making more than I am. I am extremely angry and want to approach my boss, but if I say what I really want to, I don’t think it is going to go well. How should I approach the conversation so that it is constructive and not destructive?
This is a lousy and difficult situation to address. I would probably not say anything that acknowledges that you are aware of the other person’s compensation. I suggest approaching the situation by researching what someone in the position with your credentials and experience is paid. In other words, find out your market value. If your salary is low, ask to meet with your manager to discuss the issue and ask for a raise. As my friend Jeannie says, “You don’t get what you don’t ask for.” Obviously, such a conversation is more natural within the context of a performance review, so if you have one coming up, hold off until then. If you do not get an increase, try to negotiate a bonus or raise based on reaching certain performance goals. Another classic way to go is simply to get yourself another job offer, and if you really want to stay with your current company, ask that they at least match it.
22. I have an employee who is very enthusiastic and is always coming up with ideas and suggestions that, unfortunately, really aren’t very helpful. I am afraid that if I keep shooting down his ideas he will become demotivated.
Before you start focusing on why your employee’s ideas won’t work, make absolutely certain that you are not being closed-minded. Personally, I am a very in-the-box thinker and have found myself dismissing ideas that I view as “out there” and impractical. Without question, there have been times in my life when being more receptive to others’ creative ideas would have served me well. Once you’ve checked in and been straight with yourself, try being candid with your employee: “Tip, I love your enthusiasm and admire your out-of-the-box thinking. I sincerely wish that I was able to come up with such novel solutions. I realize that you have come to me with lots of suggestions, and it seems that I keep shooting them down. I worry that I am going to demotivate you, and that is the last thing I want to do. I respect your creativity and want to make sure that the team benefits from it. At the same time, we need to make sure that we can realistically implement your suggestions. Would you agree with me?” Most likely, he would, and you have opened the door to what will be a very fruitful dialogue.
23. I am used to holding meetings in person, and now they are all taking place over video. Especially when it is going to be a difficult conversation, how should I be doing things differently?
Fundamentally, your approach should be the same. Go into the discussion with clear goals and a positive mindset, and use the strategies and tools you’ve learned to foster a healthy conversation. Begin the meeting with an introductory statement such as, “I would prefer to be speaking in person and look forward to doing so again, hopefully, in the not-too-distant future.” Make sure to attend to any nonverbal cues that may suggest the other person’s desire to speak. Obviously, how you end the conversation will be different. In person you would likely shake hands (or bump elbows) and walk out of the conference room together; your separation would be slower and include small talk, as compared to the curt ending of the click of a mouse. Be prepared with a simple, thoughtful, and clear closing, such as, “Yin, I appreciate having this conversation and look forward to following up. I hope you have a good rest of the day.” Depending on your relationship and how the conversation went, you might choose to end on a more personal note, “Please give my best to John, and I hope Lina’s college applications are going well.”
Perhaps most importantly, recognize that people may be experiencing many stressors while working at home. So, if the conversation you plan on having concerns a performance issue, consider giving that person some latitude and have empathy for her circumstances. An initial conversation to fully understand the challenges the person may be facing and discuss how you might support her would be appropriate.