Story by CHRIS BURSLEM, with additional reporting by DEIRDRE CARROLL
Illustrations by MAR JEFFERSON GO

These days it’s hard to escape Donald Trump. Open a paper, turn on the TV and there the presidential hopeful is. But let’s not forget how he became a household name:
“You’re fired!”

THERE IS SOMETHING “succinct and very beautiful about the words ... they’re so definite and final,” he once told Newsweek of the signature line of his former reality TV show, The Apprentice.

He may find those words beautiful, but there are very few others who do. For most of us, those words are almost unutterable, no matter how badly they need to be said.

Much more likely is a rambling speech that starts off something like: “Listen John, I’m not quite sure how to put this to you, but I’m afraid we’re probably going to have to let you go. I hope you can understand. Sales are down, and it, um, doesn’t look good. And then there’s my wife. She said we need our employees to show up on time, be polite to customers, make sales, you know, that sort of thing. As for me, I’d love to give you another chance, but you understand, right? My hands are tied ...”

So how’d you do there? Well, you blame-shifted, told about three lies, all whoppers, and were barely coherent to boot. And this is probably after spending weeks or even months, dwelling on the issue and thinking of ways to approach it.

Let’s face it: As a species, most humans are not very good at managing difficult situations. No matter what the situation — dealing with an irate customer, a partner we don’t believe is fairly sharing the load, a longtime supplier who is no longer price-competitive, a repair man who always charges more than his quotation, or even an employee with a body-odor or chronic tardiness problem — most of us will do nearly anything to avoid these little conflicts.

But in business, such avoidance comes at great cost. It leads to what consultant and author Susan Scott calls a “culture of terminal niceness.” Everybody evades or works around difficult employees, problems don’t get tackled, and mediocrity is tolerated.

There are also personal and psychological costs for managers and staff when issues aren’t addressed effectively or honestly. Trust diminishes and misunderstandings multiply. Festering problems consume huge amounts of emotional energy and sap creativity.

In some cases, when the situation finally becomes unbearable, we do take action. But we invariably go about it the wrong way. We vent, point fingers and lay blame, leaving hurt feelings and the seeds of a new misunderstanding in our wake.

In contrast, when conflicts or difficult conversations are managed well, better decisions are made because goals are clear, teamwork and productivity increases and workplace morale surges. Conflict resolution, done effectively, also helps foster a climate of learning that allows people to learn from their mistakes and encourages managers to provide critical feedback.

But how to do it?

Dr. Tim Ursiny, author of The Coward’s Guide to Conflict, says there are seven ways of dealing with a difficult situation:

1. AVOID IT. (Bad, for the reasons stated above.)

2. GIVE IN. (Bad, because we don’t permit our- selves a chance to properly remedy the problem. We let someone else win the argument and then we feel bitter about it. Sometimes the other per- son knows we’ve surrendered, but most of the time they don’t have a clue and go about their business as always. Grrrr...)

4. BE PASSIVE-AGGRESSIVE. (Like when you huff and puff and scowl when someone uses a mobile phone in a movie theater. This is about as effective as giving in, even if we do make an effort to ensure the person knows our feelings.)

5. COMPROMISE. (Now we’re getting warmer! But still, compromise suggests that neither party got what they really wanted. After all, the focus of compromise negotiations is what you are pre- pared to give up.)

6. HONOR THE OTHER PERSON. (Sound sappy? You’re right, and this is a solution best saved for situations involving family and significant others. This is where you make a choice to give up something and enjoy the sacrifice — say, you decide to forego a disputed bit of parking space to help out a neighboring businessman.)

7. PROBLEM-SOLVE TOGETHER. (You’ve probably guessed; this is the best way to go.) Now, suggesting that you “solve the problem” might seem excruciatingly obvious — but what Ursiny, who is an executive coach and psychologist by training, is really advocating is the use of a technique that invites mutual analysis of an issue, takes into account the emotions on both sides, and results in a win-win situation. Easy to say, but surprisingly hard to achieve. And that’s because most of us are thoroughly inept at doing the basic things required to achieve such a goal, oh like listening properly, understanding the other person’s point of view, and refraining from making critical judgments.

We’re here to help you better navigate your way through difficult conversations, but first we need to address the 800-pound gorilla in the room. And its name is ... fear.

Our behavior in times of looming confrontation is invariably driven by fear. Fear of physical harm, fear of rejection, fear of losing a relationship, fear of anger, fear of being seen as selfish, fear of saying the wrong thing, fear of failing, fear of hurting someone, fear of getting what you want, fear of intimacy, fear that people will think less of us.

Sometimes these fears are rational or based on experience. You may have tried confronting someone before and it went badly. Or maybe you worry that talking will only make the situation worse.

And sometimes our fears are irrational. She’ll be crushed and kill herself if I tell her our clients hate her coffee. He will hire a Cessna and drag a 200-foot sky banner over my neighborhood telling everyone what a cheapskate I am if I don’t give him the pay rise.

Or maybe the anxiety wells up because of something that happened way back in your formative past — something at the very core of your identity. You’re afraid what the looming conflict will reveal about you as a person.

One of the things about the problems life throws at us on a daily basis is that we know deep down inside that the best way to deal with them is to put aside our worries and tackle the situation head-on. Don’t believe us? Think about your reaction the first time you saw Nike’s old “Just Do It!” ad campaign. You probably went out and did something ... didn’t you? With that campaign, Nike proved that they knew the shadows that lurk deep in our hearts. Everybody wants to act forcefully, without restraint. Few do.

And “just doing it” is still one of the best ways to summon the courage. No, that doesn’t mean that you should simply jump right into your difficult conversation without preparation. But you should commit to doing it as soon as possible, and then start taking the necessary steps to make it happen. Weigh up the pros and cons and focus on the long-term benefits. Recall a case where you confronted a problem and it worked out well. Except for those cases where there is the genuine possibility of a physical harm, tell yourself that the conversation won’t destroy you, that you can handle it, and most important, that it is the right thing to do. The relief you stand to gain will be permanent — as opposed to the temporary respite avoidance provides.

To give you that extra edge for your upcoming difficult conversation, we’ve compiled some expert advice from masters of the art of conflict resolution. Using it, you’ll find that disagreement is not only nothing to fear, it can be healthy. You’ll grow from it. Trust us.

But first, let’s examine the nuts and bolts of the conversation you are about to have.



The first thing to do when preparing for a difficult conversation is to pick the right time and place. It’s pointless to start such a conversation if you don’t have the time to do it properly or are going to be constantly interrupted.

Then, ask yourself some questions:

Why are you having the conversation? What do you hope to accomplish? If you think, “I just want to get something out in the open,” or “We just need to talk,” that’s not good enough. Your purpose is too vague, and vague goals almost always mean disappointing results. Your purpose needs to be forward-looking.

You also need to question your objective. You may think your motives are honorable, like educating an employee. But as soon as you start talking, you notice yourself lapsing into language that is highly critical or condescending. (And believe us, the employee does as well.) This is also a good time to think about how you contributed to the problem.

Work on yourself so that you approach the conversation with a constructive aim and see it as an opportunity to learn about the other person’s point of view. Think “I wonder why he keeps doing that?” instead of “That’s it. I’ve had it with the way he keeps doing that and I’m really going to let him know it!”

Second, investigate what assumptions you are making about this person’s intentions. You may feel intimidated, disrespected, or ignored. But you shouldn’t automatically assume that this was the other person’s intended aim.

Third, start thinking about the other person’s viewpoint. What might they be thinking about this situation? Are they even aware of the problem? If so, how do you think they perceive it? What fears and needs could they have? What solution do you think they would suggest? Stop looking at the other person as an adversary — instead, see them as your partner in solving the problem at hand.

Finally, ask yourself what reaction the other person might have that is most likely to throw you off balance. What if they accuse you of picking on them or acting unprofessionally? Identify which reactions would be the toughest for you to deal with and plan how you might respond if the other person breaks down in tears, gets angry, or withdraws. Don’t just “wing it.” If that’s your approach, you won’t be very effective.



The best way to start is much the same way you would for a meeting: Set out an agenda. This outlines the problem to be discussed, establishes that you want to hear the other person’s perspective, that you want them to hear yours and that you would like to do some joint problem-solving. Use the opening part of a conversation to be upfront about why you’d like to talk and what your main point is. You’ll engage the interest of the other person and help them understand what follows. When describing the issue at hand, state it neutrally, the way a mediator might. For example, instead of saying, “I want to know why you insist on making the staff wear these silly Santa hats,” you can begin with, “It’s obvious we both care about the business. And we both want to do what we think is best. But you and I have different approaches to marketing. Let’s see if we can talk about that and find some middle ground.” This approach includes bits and pieces from both sides and seeks to close the gaps between your two perspectives. No one will feel attacked and you’ll be off to a smooth start.

Then, invite the other person to share their side of the story first. Don’t feel compelled to dive in with your perspective. You’ll actually be more persuasive if you let your counterpart get their side out first.

This way, you get to learn what they care about, how they see the problem, and you can respond accordingly. Also, until the other person feels heard, they don’t have the mind-space to hear you. It’s infinitely harder to persuade someone who hasn’t felt heard than someone who has.

Remember too, as Stephen Covey, author of The Seven Habits of Highly Effective People, says, “to listen to understand and not to reply.”

Often one of the things blocking our pursuit of the truth is that we think we not only understand our own point of view, but we also believe we know for sure what the other person did, said, and thought on the subject. He always does that because he knows it irritates me. She intentionally came in late to make me mad. She knows exactly what is expected of her, but doesn’t want to do it.

The problem is, such tough discussions are not about things that can be shown to be right or wrong, say Douglas Stone, Bruce Patton and Sheila Heen, authors of Difficult Conversations: How to Discuss What Matters Most. They involve facts, but they are not at heart about facts. They are about conflicting perceptions, feelings and values. They’re not about what a contract says, they’re about what a contract means. They’re not about which sales technique is most popular; they’re about which sales technique the store should employ. Finally, they’re not about what’s true, they’re about what is important.

If you automatically think you’re right, the conversation becomes one of trying to get the other person to admit he’s wrong. As strategies go, this is a poor one — the other person immediately becomes defensive and closes down.

The mistake of assuming we’re right leads to a second common error: We don’t ask enough questions. Studies have shown that about 90 percent of what is said during a failed conversation is advocacy, and only 10 percent inquiry. That means, the two parties find a lot of different ways to state their own views over and over again. Understanding is never reached. And too often, poor decisions result.

One of the first things you’ve got to do to get through a tough talk is to understand how the two of you see things differently. And doing that requires questions, questions and more questions.



When you sense that the other person has been able to unlock some of their energy and express the essence of what they want to say on the topic, it’s your turn.

From what they’ve told you it should be clear what they don’t understand about your position. Start by trying to clarify your view without minimizing theirs.

Be quick to identify the problem areas that remain. Be authentic too. There is something in us that responds to people who level with us, who speak from the heart.

Regularly summing up what you’ve said can boost the quality and accuracy of the dialogue — and eliminate many of the problems caused by misunderstandings.

Use words that reflect the other person’s meaning as well — “What you’re saying is that you feel that when I’m busy, I’m prone to treating people like they don’t exist. Am I understanding you right?” This way you demonstrate empathy and also get the chance to confirm that you’ve got it right.

If the conversation becomes heated or adversarial, go back to asking questions. Asking for the other person’s point of view usually neutralizes emotions. The challenge is to reframe the conversation from “whose fault is this” to “where did the misunderstandings occur, and how can we correct them so we can move forward?”

If the other person keeps saying everything is your fault, you can say, “I know I’ve contributed to this problem. Let’s talk about that, and we should also make sure to discuss ways that you’ve contributed to the problem as well.”

Be persistent in your efforts to keep the talk constructive.



Once you know what the other person wants and they know clearly what you want, then it’s time to find a solution. There is no guarantee this will be easy but at least both sides now are aware of all the factors in play.

Remember to keep asking questions. Ask your colleague what they think would work. Whatever they say, find something that you agree with and build on that.

Often such discussions get caught on the question of what’s fair. But, remember, fair is a subjective matter. What is a fair salary when the economy is doing badly? What is a reasonable vacation policy when the company is under-staffed? Your opinion and that of your counterpart are almost certain to differ. Of course, this scenario is specific to employee conflict, but the underlying principles remain the same.

The best, most straightforward way to approach any issue is to put on the table what both sides want and then brainstorm to see what is doable. In this instance, maybe a higher rate of commission based on achieving a new sales target would better reflect the economic conditions and the employee’s performance.


Start by knowing why your brain acts the way it does.

They often don’t seem it, but almost all conversations are incredibly complex.

“Lovely day outside,” the cashier says as she rings up your toothpaste.

Was that sarcasm, you wonder. Why was she smiling at the cereal I was holding? Maybe she was flirting?

And that’s an easy conver- sation. difficult ones are so much more complex.

In their book Difficult Conversations: How to Discuss What Matters Most, Douglas Stone, Bruce Patton and Sheila Heen theorize that each difficult conversation is really three simultaneous communica- tions.

There’s the standard “what happened” conversation, with the two sides’ competing ver-sions of the “facts” and their significance.

Second, there’s the “feelings” conversation, with unacknowledged emotions running amok.

And there’s the “identity” conversation, which affects our sense of self in the world.

The question of how to deal with feelings in the workplace is complicated. Some conversations are at heart about feelings, and the only way to communicate efficiently is to acknowledge them. If you don’t raise feelings of fair treatment, for example, morale drops, and more “positive” feelings, like passion and respect, fade away. This is significant. Studies suggest that almost 50 percent of people who leave jobs quit because they feel underappreciated.

The other thing about feelings is that no matter how hard you try to suppress them they will be heard, either in your tone or body language or some other way.

Obviously, you can’t spend time processing everyone’s feelings. But be aware the “check your feelings at the door” ethos can be harmful.

“Identity” conversations are hard because they pose a threat to how we see ourselves. One mistake many make when they feel their identity is being impugned is to take the criticism as absolute. But criticism is not all or nothing. A manager who makes a mistake is not a bad manager. The store owner who says “no” to a day off is not an evil slave driver. Becoming familiar with the identity issues that are important to you allows you to look out for defensive reactions.

The psychology of tough talks is that they tend to expose us for what we are: complex beings riddled with competing emotions and conflicting needs.

It is because we lead our lives according to “Big Assumptions,” say Robert Kegan and Lisa Lahey, psychologists and the authors of How the Way We Talk Can Change the Way We Work: Seven Languages for Transformation.

“Big Assumptions” are ideas we accept as truths. They once may have been true, but now it is no longer necessarily the case. Nevertheless, these assumptions are difficult to change because they’ve been reinforced so many times.

The authors suggest the answer lies in reflection and experimentation. Once you become aware of these patterns, try to transform using a three-step approach.

First, be on the lookout for when a Big Assumption is guiding your actions. Secondly, explore its validity, and finally, test it. Refuse a small request and see what happens. Then try a bigger one.



A successful outcome will depend on two things: how you act — centered, curious, persistent — and what you say. Don’t expect to handle every difficult conversation with ease and poise. At the beginning, you may be tongue-tied, scared and inarticulate. That’s OK. Your goal is not eloquence. It is openness and honesty. As with any other skill, you will get better with practice. Keep in mind that failure is the best teacher.

It is also worth noting that there are times you should walk away from a difficult conversation. There isn’t enough time to confront your partner, boss, staff or clients every time they annoy you.

But if walking away ends up being your response most of the time, you’re on the wrong track. Your feelings will fester. And in the long run, if you don’t raise important issues and have those difficult conversations, you will damage the relationship you were hoping to protect.



Here are some more tips and a few conversation starters to help you:

Don’t aim for perfection. Difficult conversations are tough for a reason. Aim for gradual improvement each time.

You don’t win a difficult conversation. Your goal is not to get the other person to capitu- late and admit that you were right all along. It’s to express your feelings, allow the other person to express theirs and hopefully reach an understanding you both can live with.

Need to deliver bad news or fire someone? There are no magic words that will somehow make it less upsetting. The best you can do is be honest, to the point, and sympathetic. You can’t take responsibility for the other person’s feelings. If your accountant is inept and messed up your books, you need to let him go. His feelings are immaterial to the outcome. It is only the facts relating to his poor performance that matter. The success of a conversation should not be judged by whether someone gets upset or not. (And don’t try to trick the person into accepting blame first.)

Don’t waste time and energy defending the weak parts of your argument. In any tough conversation, no one is 100 percent right or wrong. Each side has weaknesses, and it is wise to acknowledge the problems. Take responsibility for your share and focus on a solution.

Controlling your emotions is crucial to avoiding a destructive argument. You need to look forward — not try to defend a position or win an argument. If a conversation is getting heated, use silence to slow it down, says Scott.

Stay with the issue; straying will always sabotage your mission. You’ve had a great year and you would like to discuss bonus levels with your sales manager. But he notes how two years ago, he didn’t get a bonus when (he believes) one was promised and doesn’t feel he can trust you in this discussion. Suddenly you find yourself debating your role in the conversation. In such situations, refocus on the future.

Use “I” statements rather than “you” statements when discussing your thoughts and feelings. “I” clarifies for the other person what you think and feel while “you” can make them feel criticized. “I” reduces defensiveness and fosters communication. Good “I” statement: “I feel uncomfortable when you interrupt me during meetings. I feel it shows a lack of respect.” Bad “you” statement: “You always interrupt me during meetings. You have no respect for me!”

Say “and,” not “but.” The word “but” has the power to erase everything good said before it. For example, “Joe, I really liked the way you closed that sale, but next time don’t spend so much time talking about how bad insurance reimbursements are.” Far better to say, “Joe, I really liked the way you closed that sale and I think it would be better if you didn’t mention our issues with the patient’s insurance provider.” This is something improvisational actors are taught. The basic premise is not to reject what is proposed and focus instead on elaboration, to create new ideas and move forward.

Similarly, avoid negatives and absolutes as they shut down communication. Example: Negative: “Why can’t you ...” Positive: “What if we ...” Absolute: “We must do it this way.” Non-absolute: “Here’s a good idea to consider...”

Avoid judgmental words like “bad,” “ugly,” “wrong,” and any that imply fault like “unprofessional” and “inappropriate,” Ursiny recommends.

The same goes for you. Many misunderstandings arise from faulty assumptions. So when in doubt, say what you mean. Hinting isn’t good enough. Don’t rely on subtext.

Remember that acknowledging the other person’s feelings is not the same thing as agreeing with them. Saying “I can understand this is really important to you” indicates an effort to support the other person, but doesn’t mean you’re going to go along with the decision.

In cases where you find yourself poles apart, use the “100+1 approach.” Find the one percent of the other person’s position you can agree on and endorse it 100 percent. That suggests that you are committed to finding middle ground.

Research shows that we spend a lot less time talking to people close to us than we imagine. These same studies also show that many of our more challenging dialogues could be avoided by staying in more regular contact.

Blaming the other person for not understanding you — or for you not understanding them — is pointless. Be willing to recognize when you don’t understand or need to know more. If you don’t have a clear understanding of what the other person is saying, keep trying until you do. It could be that their thoughts are unclear. Encourage them to be specific.

What if it’s someone you’re going to have to work with again — for instance, a high-performing sales associate who is suddenly suffering a five-alarm case of body odor? Same deal. Take him aside and let him know his new antiperspirant isn’t quite up to the task. Of course, he’ll be embarrassed but eventually he will thank you. Knowing that you can’t control the reaction of the other person in a conversation can be liberating, say Stone, Patton and Heen.

The best decisions are the ones that people reach themselves. So be lean on the advice, but generous with help and support.

Don’t just listen to the words, listen to the “music” as well, including body language and voice quality. Also, look for clues in what is not being said. Ask yourself and the other person, “What is it they really want, really mean?”

Being genuine is at the heart of all worthwhile communication. Don’t be afraid to share your feelings. Author Scott recalls a conversation with a friend who said: “I notice I’m becoming defensive, and I think it’s because your voice got louder and sounded angry. I just want to talk about this. I’m not trying to persuade you in either direction.” The acknowledgment helped the two to re-center, she says.

Not sure how to open the conversation? Consider some of these lines:

  • “I need your help with something. Can we talk about it?”
  • “I think we have different views about [insert topic]. I’d like to hear your thinking on this.” “I have something I’d like to discuss with you that I think will help us work together more effectively.”
  • “I’d like to talk about the recent changes to our compensation structure with you, but first I’d like to get your point of view.”
  • “I’d like to see if we might reach a better understanding about our store’s dress code. I really want to hear your feelings about this and share my perspective as well.”

Final tip. Realize difficult conversations are part of life. They aren’t going away, but they can become easier, less anxiety-causing and more constructive if you work on it.


One of the tough discussions we had with an employee was about getting involved with our patients in personal matters — selling/buying cars, planning play dates, making social plans, etc. She did not understand why it was inappropriate and was indignant at first, but we explained that if anything “went wrong” in her personal relationship/dealings with the patient, then it might negatively affect the doctor/patient relationship and possibly our bottom line. She eventually understood, and we now have a “WWDD” (What Would Doctor Do) policy.

Our tough talks are most often with a ven- dor. We took on a lot when we opened, including frame lines, labs, etc. Sometimes you nd a line or company simply doesn’t t your vision and you have to say goodbye. The toughest part of all is that you truly build great personal relationships with people. So business decisions are made but in the end you can feel like you hurt someone’s feel- ings. Nonetheless... we must do what is right for our shop.

I called a doctor out on his chronic tardiness starting the day. He asked if I always saw my doctor on time. I told him this wasn’t my doctor’s of ce, it is our patient’s doctor’s of ce, and we see our patients on time. He was never late again. People are unreasonable only because no one has ever told them they are being unreasonable.

When I was the manager of a large retail chain store, a married-with-children associate and a lab tech had an affair. None of our business until it started to affect work. It was interrupting our customer flow as well as causing other associates to complain. The lab tech was an exemplary, invaluable associate. We carefully explained the facts that were affecting his performance, careful not to mention the relationship, although he had to know that was part of his problem. I didn’t think it went very well. I honestly thought we would lose him. We were lucky. The retail associate had been making the rounds and the problem corrected itself.

I fired an employee. I sugarcoated why and said that she would be a better off elsewhere. I needed to be more honest that she couldn’t do the job and show her all the times that we tried to train her to, because she sued me for age discrimination. Being honest and direct could have avoided this. I now follow this guideline, “To be kind is to be clear, and to be clear is to be kind.

Telling a potential vendor you aren’t interested in their product is always tough. I recently had someone come in and while showing me trays asked me if I wanted to start writing up my order. I was so shocked that I said what I always want and never do: that I was allowing them to show me their product but I never said I would be taking it on.

Had several talks with a new optician. She was sloppy and kept dropping the ball. She was a hard worker, but made mistakes that added up. We decided that she would work closer with me. We worked like that for five weeks. Now, she is a great optician with a huge following!

I had a frame rep that was very disrespectful to my optician. I called and spoke to her personally. She was not remorseful, so I dropped the line. I was professional and gave her the opportunity to make things right. Since I felt that I handled myself well, I did not regret phasing out the line.

We had a patient that was very rude to the staff every time he came in and no one wanted to assist him. I addressed his attitude, asking if we had done anything to anger him or if there was a way we could serve him better because we wanted his experience to be great with us. He apologized to all of the staff, has remained a patient, and has developed a great relationship with all of them.

I’ve had so many difficult conversations with our team over the years. I’ve not always been good at it. I came to the realization after listening to an episode of the Dave Ramsey Entreleadership podcast, that by not confronting the issue there would still be tension. By acknowledging the issue (and the tension) at least everyone knows where everyone stands. So, I have been embracing the 800-pound gorilla. The main issue is communication. I know that gets a lot of lip service, but if you are committed to truly communicating it means having those difficult conversations.

I once kept a lab tech around for a long time thinking I had to have him due to our high volume. My instincts kept telling me he was a problem. He was very confrontational. One day in my absence, an associate asked him how long a single vision job would be, and it set him off. He threw trays and yelled while customers and staff watched. I had to terminate him. My lesson was to follow my instincts and document any issues with staff no matter how uncomfortable you feel.