Difficult Conversations: Tips on How to Handle Tough Talks

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No matter how much we wish we were able to avoid them, having difficult conversations is a part of our universal experience. Even the strongest, most in-sync relationships will require a tough talk at some point down the line.

However, sometimes the toughest conversations, whether in our professional or personal relationships, are indications that you value the other person’s feelings enough to solve various minor or major clashes we see in everyday life.  

Having strong, meaningful relationships sometimes requires have these difficult but crucial conversations, because working through things in such a manner can enrich our lives, and make our time on this earth even more meaningful. 

But in order to keep these relationships strong, we need to understand not only the other person’s feelings, but also our own emotions if we are to come to a mutual understanding. When it comes to achieving positive interaction dynamics when dealing with tough subjects, there are actually quite a few practical skills that can be learned. 

In this article, we’ll explore the things that can make having difficult conversations easier, as well as look at certain scenarios where difficult conversations may need to be handled differently, or with an added layer of care than others. Here are some top tips and advice for navigating difficult conversations with the friends, family and professional members of your network.

What are difficult conversations?

Any conversation that you’re simply not looking forward to having counts as a difficult conversation. They aren’t always within our control, either. 

On the one hand, walking around knowing that you have to have a tough conversation with someone in your life can truly weigh on you until you finally have it. However, sometimes we’re hit with difficult conversations that we truly don’t anticipate. 

For example, having your boss call you into a meeting where he or she tells you that you’ve been let go, and today is your last day at the company. Or, having a romantic partner whom you’ve grown to love and trust tells you that they’re no longer interested in continuing the relationship. 

There are many factors that can make a conversation difficult. Here are a few common themes that are typically present when a conversation ends up being a difficult one. 

Having tough conversations

In the book “Difficult Conversations: How to Discuss What Matters Most,” the authors suggest that all difficult conversations can actually be broken down into three conversations: 

  1. What happened
  2. How both parties feel about what happened
  3. The right of each party to view and experience what they did as a result 

The “what happened” conversation

Oftentimes, difficult conversations need to happen as a result of an action of one or both parties involved. Perhaps a friend did not invite you to an outing that you typically would have been included in, and you want to speak to them regarding why. 

Or, you found out you were passed over for a promotion at work and need to speak with your boss to understand more about why that is. Maybe you’ve discovered something that suggests your romantic partner has been unfaithful, and you need to get more clarity on whether or not this has actually occurred. 

In the first of three conversations, both parties discuss what happened, each from their own viewpoint. The “what happened” conversation is a difficult one to navigate, because oftentimes one or both parties enter this difficult conversation feeling certain that their experience and viewpoint of what happened is the correct one. 

They may agree on the actions that were taken, but the meaning behind what those actions say or reflect, and what the intentions were of each party when the event happened may differ and cause conflict as a result.

Another point of contention within this first conversation arises when people assume they know what the other’s intentions were, and refuse to see it from the other perspective. This can make having a difficult conversation even more challenging –- especially if you’ve been ruminating over the event since it took place and have convinced yourself that this person acted out of malice or ill intentions. 

In order to avoid this, approaching them with an open mind and willingness to listen, without having already made your mind up about why this person acted in this manner is the best way to go into this. (Learn more about active listening here)

During the what happened conversation, it can be easy to want to assign blame. However, shifting the goal away from deciding who was wrong in these tough conversations and instead focusing on understanding one another better, especially the intent behind the action that was taken by either yourself or the other person can go a long way in turning this tough chat into a learning conversation.

The “feelings” conversation

The second conversation in the three conversations is the conversation about feelings. Feelings inherently make a conversation difficult. If something has occurred in one of your personal or professional relationships that warrants a tough talk, you usually feel compelled to have this conversation because of the way you are feeling. Likely, you hope that by having this difficult conversation you’ll feel better on the other side of it. 

However, sometimes it can feel intimidating to tell someone how something they said or did made you feel. The fear that the other will either dismiss your feelings or not care can be a heavy weight to bear during this kind of conversation. Telling someone how you feel also requires you to be vulnerable — something that can be hard for us to do. 

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But in order to strengthen your relationship and move forward, having the feelings conversation is crucial. Why? Because unresolved feelings can easily bleed into a relationship. You may notice yourself harboring resentment toward the other person and letting these feelings fester can sour your relationship overall. 

When having the feelings conversation, it’s important to note that even if your counterpart expresses feelings that you don’t understand or agree with, it’s integral that you listen, hear and acknowledge them. Before and during the feeling’s conversation, evaluate your own feelings and your beliefs about them. From there, pay attention to where you’re translating these feelings into assumptions about another person.

The “identity” conversation

The identity conversation occurs when a hard conversation at hand involves calling a person’s characteristics and personality into question. These conversations may bring up feelings in one or both parties of unworthiness of being loved or valued within the context of a relationship. 

tough talks
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Because of these beliefs, it may be hard for you or the other to admit to the wrong doings or mistakes you may have made regarding the situation at hand. If you’re entering the conversation feeling this way, work toward understanding that everyone makes mistakes, and that those actions don’t mean you’re not worthy of being in a healthy relationship with another person. 

In fact, those who are able to admit blame in a situation and move forward from it are often the people who have the most successful relationships in the long run. 

Before a tough talk, ask yourself these questions

Question #1: Should I even raise this issue?

Sometimes, it’s obvious when we need to have a conversation with a friend or family member. Other times, it may not be worth having – particularly if you know there’s no way forward or favorable end result that would come from having it. 

Sometimes this can be a hard reality to face, but the people we surround ourselves with may not always be reasonable or understanding in the face of an issue we’re having. At the end of the day, if something is truly bothering you and you need to get it off your chest, have the conversation. But being able to determine which issues in a relationship are worth letting go in order to move forward can help keep your relationships strong in the long run.

Question #2: What do I want to get out of this conversation?

Having a tough conversation with someone is never pleasant – so if you feel that a tough talk is necessary, it’s important to get clear on not only the reason for this talk, but what you’re hoping it will achieve. 

Sometimes, this process can reveal purposes that aren’t as honorable as we initially thought they were going into it. For example, you may want to have a conversation with a family member regarding your relationship in order to make it stronger – but the reason you feel you’re not as close as you could be may cast unnecessary blame on them. 

You may want to have a talk with your direct report about his or her work performance – but how constructive is the criticism you plan to offer? If the purpose for the difficult conversation is to truly help support someone in your personal or professional life, examining the way you plan to frame this tough talk will help set you up for success. 

Question # 3: Is your reaction to the situation an appropriate response?

Are you reacting to the problem at hand? Or have other things happened in your past and history that relate to this issue that have gone unresolved, and are making the problem seem bigger than it actually is? 

The relationship we have with ourselves sets the tone for the personal and professional relationships we have with others. For example, if you’re someone who has trouble being vulnerable and expressing when they’re having a hard time to others for fear of being a burden, having a friend come to you and “dump” the things they’re going through can make you feel resentful that they’re able to speak so openly. 

However, is the issue that they’re sharing too much with you? Or are they leaning on you an appropriate amount for a close friendship from their perspective? Sometimes having difficult conversations walks the line between standing up for yourself and supporting another person, and asking these kinds of tough questions in advance, and taking time for inner self-reflection can help steer the tough talk in the right direction when you do have it.

Question # 4: Are you making assumptions about the other person?

Just because you’ve perceived a person’s actions to have a certain meaning doesn’t necessarily mean that this was what the person intended you to feel when they acted in the manner that they did. Your feelings in the situation are valid, but the assumptions you make about the person who caused you to feel this way may not be. 

tough talks
(Nick Dolding / Getty)

For example, say that your boss gave you tough feedback in the middle of a big meeting. You may think he or she did so maliciously, or because they don’t necessarily like you as a person, or that they pointed out your flaws in that moment to make themselves look better. Though the way this feedback was delivered to you may have made you feel upset or belittled, this doesn’t mean they intended it that way. 

Question # 5: What role did you play in the problem at hand?

You don’t need to study at the Harvard Negotiation Project to know that emotions are intertwined in most decisions people make. As such, emotions and feelings can easily get the best of us when faced with a problem in a personal or professional relationship. 

While it’s easy to cast blame and see the issues that the other person contributed, it’s important to also own what we may have done in the situation that may have contributed to the problem. 

When you have a tough conversation, a successful outcome hinges on your ability to look at the situation objectively, identify your role in it and acknowledge this to the other person. Basically, being the bigger person about the things you could have done differently. 

This doesn’t mean you should shoulder all of the blame. But being able to own up to the role you played in this event will make it easier for the other person to do the same and be able to recognize what they could have also done differently as well. 

How to have difficult conversations

Now that we understand the general format and components of how difficult conversations typically flow, let’s take a look at the best methods for approaching them. 

Here are some other helpful tips for how to use communication skills to have those tough conversations with others and focus on problem solving so that you can have more success and more productive conversations. 

Don’t avoid them

The longer you wait to have those difficult conversations, the harder it will inevitably be. No one likes to give or receive bad news but holding on to the feelings you have about the problem you want to discuss can make the conversation even harder than it needs to be. 

Additionally, if the tough conversation centers around an event or action that took place, allowing more time to pass can blur the details of what actually occurred for both of the parties involved. Having the chat when the problem is fresh in the minds of both parties can help yield a more positive outcome. 

Adopt the “learning conversation” method

Learning conversations put emphasis on empathy and respectful listening. The ultimate goal of having a learning conversation with someone is to learn from the other person and allow the information you gather to inform how you both act and behave toward one another in the future. 

When having a tough conversation, your first instinct may be to relay the problem at hand from your own point of view. While this seems like an understandable place to start, the problem with this approach often makes the implication that what went wrong is the fault of the other person. This can actually make the conversation harder to have, as the other person is more likely to become defensive because of this.

Instead, approach the conversation by asking questions and listening to the other person’s perspective. Having an attitude of discovery and curiosity toward what the other person has to say will help make the difficult conversation feel less tense. 

Approach the conversation with confidence

The energy you bring to difficult conversations sets the tone for how it will go, and can impact the other person’s mood and perception as well. No matter the topic at hand, coming into the conversation in a confident manner shows that the problem you’re looking to discuss is one that you’ve been thoughtful about, that you feel comfortable speaking about and that holds value to you. 

Don’t underestimate the power you have over the mood and tone of difficult conversations. 

Let the other person speak first

Instead of starting the conversation by talking to or at the other person, ask to hear the person’s take on the problem at hand — then listen to what he or she has to say. 

tough conversations
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They may give a short answer, in which case you can ask to follow up questions to help move the conversation going. Open-ended questions such as, “How did you feel our last meeting went?” or “I’d like to talk about what happened last weekend, and I’d like to hear your perspective first because it’s important to me” can help set the stage for the tough talk at hand.   

Try to understand the other person’s point of view

In order for the difficult conversation to be an effective one, both parties need to be willing to see what happened from the other person’s point of view. You don’t have to agree with everything that comes out of a difficult conversation. But the most effective difficult conversations are ones where both parties make a solid attempt to put themselves in the other person’s shoes for a moment and try to believe that this person had the best of intentions in mind when the problem occurred. 

Even if you disagree with them, their views or feelings are still valid, and it’s important to act that way out of respect during these tough talks.

Focus on “I” statements vs “You statements”

One way to ensure that you’re not casting blame during difficult conversations is to pay attention to how often you’re using statements that begin with “I” versus how many statements start with “You.” 

In an ideal scenario, tough conversations should include “I” statements that express how you’re feeling, how you interpret it, what your view of what happened was and how you see the problem being resolved in order to move the relationship forward. 

“You” statements tend to cast blame on the other person or allow us to make assumptions about the other person that may not be true, which can make the other person defensive. 


Pay attention to how the conversation affects your conversation partner. You may want to shoulder on through the conversation to get it over with but doing so at the expense of the other person won’t be helpful to your relationship. 

If you notice that the other person is becoming emotional, or that their body language indicates that they’re feeling uncomfortable, pause what you’re saying and check in with them on where they’re at. This shows that their feelings are valid and important to you and may make it easier for them to be vulnerable with you as the conversation progresses. 

Follow up after the conversation has concluded

Even if the conversation seems to have ended favorably, new thoughts, feelings and perspectives might arise after the conversation ends. The other may need a few days to truly process the conversation, especially if bad news was delivered or if they weren’t anticipating the conversation you both ended up having. It’s important to be aware that this may occur. 

A few days after your conversation concludes, set some time aside to check in to see how they’re feeling. If possible, try to have this meeting in person rather than virtually. Following up face to face can feel more personal and help foster the connection between the two of you. 

What to do if your tough talk goes south

Unfortunately, despite your best intentions and preparation for your tough conversation, there’s always the possibility that it won’t go as well as you’d hoped for. There are a few tactics you can try during the conversation to help steer it back on the right track. 


When listening to what the other is saying, it can be beneficial to try and reframe the blame that’s being cast into a more understandable context. For example, say that they are blaming you for making them feel a certain way. Using the three conversations as a framework, you can validate the way the person is feeling, then reframe the conversation to focus on the original intent of the action. In order for the conversation to move forward, the person casting blame needs to feel understood. 

Naming the dynamic

Sometimes when emotions are running high, we’re unaware of the actions or behaviors we’re exhibiting in the moment.

difficult conversations at work
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If your tough talk is not going well and the person continues to keep the conversation on a track of blame, sometimes naming the behavior can help them better recognize what they’re actually doing. 

For example, if the other person continues to deny the emotions you’re feeling, saying that you shouldn’t feel that way or that your feelings are not valid, talking about the act of minimizing — what it is, what it involves and how it’s impacting the current conversation may help shift things toward a more productive conversation. Learn more about the Wheel of Emotions – it could be a helpful tool to add to your toolbelt. 

Problem solving

Once the conversation has been had and both parties have said what they feel they need to, the final step is deciding how to move forward. Sometimes, this is as simple as offering an apology over a misunderstanding. But more often, both parties need to enter into an agreement on what can be done to solve the problem currently, as well as in the future. 

For example, if the problem at hand is that your boss offers criticism publicly and you don’t respond well to being criticized publicly, the compromise may be that you and your boss meet before an important meeting to review what you’re presenting so that you’re both aligned. If one person in a friendship feels that they’re putting more effort into maintaining the relationship than the other, the solution may be agreeing on a monthly cadence of spending time with one another in which turns are taken to set the plans moving forward. 

In the event that one or both parties decide that the problem at hand is unsolvable, they may decide to walk away from the relationship altogether. This may seem extreme, but if this is the case, the person who has made that decision should take the time to explain why that is in order to provide closure.


No one likes to have tough conversations or hear bad news. But having them is often a necessary part of any successful relationship. We can only control our own words and actions during difficult conversations, and it’s important to understand that the other person’s reactions and responses are not something we can change or influence. 

All we can do is enter the conversation with the best of intentions, attempt to understand the other person’s perspective, honor and validate their feelings. If at the end of this potentially volatile conversation the other person decides to walk away, know that you’ve done everything within your control.

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