How to Have a Difficult Conversation

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Everyone knows it—no one likes it: a difficult conversation. The fact is that everyone who deals with people, whether professionally or privately, comes into situations every day in which they have to address things or have conversations that leave them feeling frustrated or anxious in advance. But why is this the case?

Why are we afraid of certain discussions or even frustrated right from the beginning?

Mostly, we are afraid of losing face or having to give up much of our own point of view. Our counterpart might confront us with facts that we haven’t considered before. Our entire position could be shaken, and the “balance of power” could permanently change. But it could also be that we suspect the conversation will not lead to a satisfactory outcome. Nevertheless, a difficult conversation is inevitable, and that frustrates us.

Managers are especially familiar with such situations. After all, the greater the responsibility, the more critical it is that a difficult conversation succeeds. You need to ensure co-workers and even superiors are productive. Above all, you need to approach them with confidence.

A difficult conversation is based on the same components over and over again. If you understand them, the solution to the problem will seem logical to you.

I’m excited to share that I have launched an on-demand course that walks you through an exercise to successfully have a difficult conversation. The course itself is only about an hour, but it will help you be prepared for all the difficult conversations you may have either at work or at home. It’s worth it.

See The Course

Different Perceptions

Our reality is actually made up of our own perceptions. This realization alone suggests that there are as many realities as there are people. Thus, there will never be one correct reality, the absolute truth. 

In a difficult conversation, one of the usual problems is that two or more people perceive the same situation differently. Each naturally thinks that he is the only person who has it right. The other person must logically be wrong. 

Naturally, a person does not see themself as part of the problem. The difficulty now is to understand that both points of view make sense in their own way. The different perceptions of a situation arise because:

  • Different information exists about a matter or decision and it it’s not always available to everybody at the same time.
  • And not only do the parties have always access to all information, there will be different interpretations about the matter or a decision, which in turn are caused by different life experiences. These life experiences shape the way we view and feel about things. 
  • Different levels of knowledge about a matter or decision: This is especially important for you as a leader when talking to co-workers who may not have the same knowledge as you because of their positions.

Preconceptions About an Intention

Especially in difficult situations, we like to assume that we know exactly what our counterpart’s intentions are. However, intentions exist only in people’s hearts and minds. Unless we talk about them, no other person can understand why we are really doing something.

It is only natural to make assumptions about our counterpart’s intentions. These assumptions, in turn, are based on what impact their actions have on us.

However, our thoughts run so automatically that we are unaware that our conclusions are ultimately just presuppositions.


Some situations make us so emotional that our feelings affect our ability to think, solve problems, and even communicate appropriately. In fact, if we are very upset and therefore have not communicated appropriately, we may not even be able to listen. 

In many conflicts, feelings are at the heart of the matter. They are the foundation, even if other symptoms overshadow them. Unexpressed feelings can exacerbate any situation. They can take the form of sarcasm, passive aggression, impatience, and other manifestations.

Blame and Reproach

It is typical for people to search for guilt in a conflict situation. The questions we ask ourselves or others may be:

Unfortunately, focusing on blame is ineffective because it inhibits our ability to understand what really caused the problem and contributes to its resolution. Blame and recrimination revolve around condemnation. On the other hand, effective conflict management is concerned with learning from mistakes, embracing different perceptions of a situation, and adjusting one’s own behavior to produce better results in the future.

Tools to Effectively Engage in a Difficult Conversation

Of course, there are tools you can use to conduct difficult conversations in a way that leaves not only your counterpart in good stead but also yourself.

1. Create a safe atmosphere for the conversation.

A safe conversational atmosphere is one in which both parties feel comfortable expressing their thoughts and feelings without fear of negative repercussions and without feeling threatened. You can create such a conversational atmosphere by:

  • Assuming mutual intent: You should care about the other person’s interests as much as your own.
  • Offering mutual respect: As soon as someone behaves disrespectfully in a conversation, it’s no longer about the point at hand—it’s about defending your own dignity. As soon as someone misinterprets your intentions, use a counter-statement. A counter-statement is characterized by first sending a message that clarifies what you don’t want or intend to do, then sending another message that explains what you intend to convey instead.

2. Listen.

The phrase “seek first to understand and then to be understood” should be set in stone. Knowing that we perceive things differently and make presuppositions ensures that we must first put ourselves in a situation where we can listen and really hear how the other person sees the problem and their real intentions. 

In a conflict situation, listening well requires open and honest curiosity about the other person’s arguments and the will and ability to keep our focus on the other person.

You should use these skills to become an exceptional listener:

  • Forget the words. Focus on authenticity. This means you listen because you care about what the other person is saying, not because you have to.
  • Listen to your own inner voice. If you really want to understand the other person, you should be able to express what is going on inside yourself. You might say something like, “I have to confess that as much as I’m trying to listen to you, I’m feeling a little defensive right now.”
  • Formulate open-ended questions.
  • Repeat yourself for clarity. Articulate to the other person in your own words what you understood from what they said. You may be surprised at what comes out.
  • Acknowledge the other person’s feelings. If the other person’s feelings are not adequately acknowledged, then feelings will always harm the conversation.

3. Adopt an attitude of “Yes, and…”.

This is precisely the attitude that ensures both points of view are raised to an equal level.  “Yes, and…” causes the points of view of both you and the other person to be heard. They exist on the same level and have equal value. When you listen to your counterpart, you should not see your own point of view dwindle.

The “Yes, and…” attitude ensures that you recognize that both points of view mean something. It makes clear once again that the world is a very complex place. As soon as you express exactly that, your counterpart understands that you are not only repeating your own view but also his. 

The critical point is that you simply need to be able to clarify your stance on the one hand and listen to the other person’s point of view on the other. But once you reach that point, you can move on.

4. Recognize that effect and intention are different things.

Now that we really understand each other – what is a good way to solve the problem? Learn to acknowledge both stories and separate effect from intention. We form stories in our minds when we add meaning to another’s behavior or words without checking to see if our conclusions are correct. Very often, we repeat these stories over and over again in our heads.

To keep both of you from falling into this trap, you can ask yourself three questions:

  • What did the other person really say or do?
  • What impact does that have on me?
  • Based on the impact, what assumption am I making about what the other person was trying to accomplish?

Once you have honestly answered these questions, the next step is to acknowledge that even the answers to these questions are merely conjecture.

Your guess may be correct. It could just as easily be wrong. What the other person said or did affected your feelings, but those feelings may be based on false conclusions.

In a conversation, you might share what you observed, how it felt to you, and what your assumptions were about the other person’s intentions. It is important to make it clear that you are only guessing. After all, a guess can always be corrected.

5. Use “I” messages.

Messages that begin with a “you” often lead into the trap of blame. They ultimately create an atmosphere in which the other person must defend themselves. Sentences that begin with an “I” are less inflammatory, and they also imply that you are taking responsibility for what you are about to say.

6. Focus on involvement, not blame.

Contribution asks how you both helped bring about the situation. This question aims to understand what part you each had in the conflict and how you can avoid such situations in the future. It says, “Let’s not get bogged down in blame, and let’s find a way to avoid those exact parts in the future. Let’s learn about each other and how to work together to be healthier and more productive the next time we meet.”

It makes no sense at all, even in difficult situations, especially as a leader, to look for fault.  Blame is for kindergarteners, not leaders, because they never lead to a solution.

As a leader, your job is to provide solutions. You lead your team, and it shouldn’t be difficult for you to have difficult conversations every day. If you constantly have to worry about standard tasks like a difficult conversation, you’ll have a hard time getting things done. Unfortunately, that’s exactly what puts your success at risk.

Difficult conversations may not be particularly comfortable for you. Still, if you have possible solutions for how you can both walk out feeling good at the end, your success is assured.

No success was ever based on a path sprinkled with rose petals. It’s always about removing difficulties and obstacles.

Be sure to create a situation in your team where people are happy to talk to you. Otherwise, you run the risk of never addressing contentious issues. As a result, an explosion will occur at some point, often for the most trivial reasons. Under certain circumstances, an entire project may be in danger because all parties involved will break into dispute. You should avoid that at all costs.

If we are honest, we all want to work in an environment where all communication is eye-to-eye. This is not to be confused with different levels of hierarchy. It simply means that you should always be concerned that your co-workers are happy to talk to you because they know you’re interested in finding a solution.

In life— professional or private— there will always be different points of view because perceptions are as varied as the people on Earth. We cannot assume that everyone sees the world the way we see it. 

Use this realization as an opportunity to understand better how your team works. When you do, you can distribute tasks wisely because you know each individual’s different perspectives and focuses. That’s what makes a good leader. 

Good leaders can communicate their own concerns clearly without having to speak over others. They create an atmosphere of good communication in which people enjoy working and exchange ideas honestly.


The next time you go into a difficult conversation, keep this in mind:

  • Take your time.
  • Create a safe, conversational atmosphere where you can both really talk.
  • Be a good listener.
  • Frame both concerns by connecting them with a “Yes, and…”.
  • Effect and intent are different things.
  • Start sentences with “I” instead of “you” to avoid blame.
  • Direct your focus to involvement rather than blame.

Photo by Warren Wong on Unsplash

About the coach​

Kai Boyd has been a leader, trainer and facilitator since 1989. He supports leaders and their teams to work together effectively, trustfully and with ease. This involves each and everyone – in their respective roles and as people. Tailor-made formats and genuine attention enable potential to unfold and synergies to emerge.

The graduate industrial engineer, managing director and former management consultant knows the requirements of his clients from many perspectives. He works systemically, strength- and solution-oriented. Leading international teams as well as work and academic programs in the USA and the UK enable him to always contribute the international perspective.

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