How to handle difficult conversations effectively

Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations and values.

Douglas stone

Difficult and uncomfortable conversations are something we all participate from time to time and are hard to avoid both in our personal or professional lives. A difficult conversation is any conversation in which there are strong differences of opinion and involves contentious and sensitive issues that may elicit strong, complex emotions that can be hard to predict or control.

Why are some conversations difficult?

Most of the times we enter into a conversation with certain expectations, opinions and positions which are often based on our relationship with the other and the circumstances surrounding the conversation. When our expectations/opinions/position are challenged, we often react with unpleasant emotions.

Whether it is a friend who may have left you feeling bad about yourself or a family member’s values or behaviour you may not agree with, it is natural to feel apprehensive, sometimes even embarrassed starting a difficult conversation and feeling nervous or fearful about how the other person may respond. If the person is someone you like and respect, you may feel awkward as you want spare their feelings or treat them more leniently because of your relationship with them. In the same way, if it is someone you find difficult to get on with, feelings of anger or frustration might get in the way of your conversation.

What makes us avoid difficult conversations

Difficult conversations is any situation where the needs/wants, opinions or perceptions of involved people involved are different and result in negative consequences and conflict. This is one of the reason, most of us tend to avoid. For instance, certain workplace conversations can be difficult to handle such as giving or receiving feedback, addressing an under or poor performance, seeking a clarification from a superior, or tackling instances of unacceptable behaviour of a difficult team member or dealing with a person who spreads rumours or negativity. Some of our own filters make us avoid such conversations to lessen the discomfort of hearing such as,

  • Dislike for disagreements and conflicts,
  • Making assumptions about the situation
  • Avoiding receiving or giving feedback
  • Letting your emotions cloud your judgment
  • Pushing your views onto others
  • Taking things personally
  • Focusing on tone rather than the content
  • Looking at the issue from only your perspective
  • Wrong interpretation of intent

Such filters make us miss the actual content leaving us with baggage of negative emotions like confusion and resentment. When we really need to confront the issue, we might try to soften the message or might never get to the real issue because of the fear of the outcome, complex emotions they lead to, and feelings of loss of control. As a result, we might simply try and avoid such conversations.

Why avoidance is bad for your personal growth

Avoiding difficult conversations is never an effective solution as it not only leads to negative consequences for everyone involved but also leads to poor working and personal relationships and workplace conflicts. When we are not well equipped to handle difficult conversations both personal or professional, we find ourselves in conflicting feelings, insecurity and vulnerability.

Also, the ability to manage and deal with uncomfortable or confrontational discussions is a prerequisite to effectively manage or lead and understand people with challenging behaviours and also to understand yourself better and to know how to draw upon your strengths to better manage your personal or professional relationships and to respond to different personality types.

How to handle difficult conversations effectively

Avoiding a difficult conversation will only lead to more problems and will make the situation bigger in your mind than it really is. We are usually reluctant to open a difficult conversation out of fear of the consequences as they usually involve disagreement over what happened. Key is to be aware of how you frame your thinking and what to avoid during such conversations. Here are some things that are important to handle difficult conversations effectively.

Your perspective.

It is not worth indulging in difficult conversations if you do not have a specific goal. Have a purpose as to what do you want to get out of difficult conversation. If you have clear purpose in your mind, you lessen the probability of conversation getting away from you. If you feel someone has mistreated you, the general temptation is to say, “I want to talk about how you treated me”, but that’s unlikely to go over well. Instead, own your opinion and start using ‘I’, not ‘you’. Say “I am annoyed the way you treated..” This will help the other person see your perspective and understand that you are not trying to blame the person.

Avoid name calling and finger-pointing. Don’t say things like, “I feel bad saying this..,” because it takes focus away from the problem and can make your counterpart feel obligated to focus on making you feel better. Instead of saying, “ but that’s not right!” when you disagree, add your perspective to engage in problem-solving to make it collaborative. Disagreeing with someone in a respectful and non-condescending way is tough. But if you feel strongly enough about your opinion, you should speak your mind.

Right approach

Handling contentious or sensitive issues often requires different approach from that is used in regular everyday conversations. Sometimes, despite your best intentions, things might veer off course. It may appear as though you enter into a conflict battling over who is right where each one is stuck to their position. This is because people normally assume that what they are looking at is factual matter and that their view of the matter is right and also each one differ in their interpretation of what facts mean and if what is important.

You can’t demand the other to hold the discussion exactly the way you want or force them to appreciate, understand or even hear your perspective. But you can use other approach and use phrases like, “you may be right, but I’d like to understand more.”, “I have a completely different perspective, if you think this is unfair, how can we fix this?”, “I’m not sure how this connects to what we’ve talking about” or “Is there anything I can say or do that might convince you to consider other options?”to get your point across. Make it your aim to reach a mutual understanding through a collaborative exchange of views and ideas for which you may have to move out of your comfort zone and be prepared to question your own assumptions.

Emotional awareness.

By their very nature, difficult conversations are stressful because they often elicit complex emotions. Most of us ignore the emotional content, but unexpressed feelings can cloud your judgment, blaming and can make it difficult to keep an objective view of the situation. But in an emotionally charged up situation, being calm and assertive can help to temper the emotions. The solution is to identify and understand the emotions involved and share them clearly. Acknowledge that feelings are an important part of the situation, whether they are rational or not.

Reevaluate the thoughts, perceptions and beliefs that trigger the emotions. In a difficult conversation, your goal should be to keep things on track. So, instead of saying, “I didn’t say this”, you can say, “I think there has been a misunderstanding” or what “I meant by that statement was…”and you can restate your point. This way, you can clarify as opposed to argue. Another go to phrase in such conversations is, “I’m sorry, you feel that way”, which makes the other dismissive of their emotions. Instead, when things get uncomfortable, try acknowledging their feelings instead of apologising, be more empathetic like by saying,“ it sounds like this is really upsetting you..”

Reframe if the other person indulges in blaming or arguing about who is right. Take the essence of what the other person says and translate it into concepts that are more helpful. For instance, blame statements can be reframed in terms of contributions. You can move the conversation in positive direction until the other person feels heard and understood. When the other perpetually puts the conversation off track by interrupting or denying emotions, name the behaviour and raise the issue for discussion. This makes the other more aware of the behaviour and it brings out more unexpressed thoughts and feelings.


Listening is also a crucially important part of handling an uncomfortable conversation. It helps us to understand the other person and the feeing of heard makes the other more able to express themselves. The key to being a good listener is to be curious and not to spend thinking about what you want to say next when the other person is talking. Avoid questions that are statements, do not cross-examine, instead paraphrase to clarify your own understanding.

When you want to convey your feelings and views, use the stance and avoid exaggeration’s such as, ”you always” or “you never” and do not use hints or leading questions. Share information, reasoning and experience behind your views. Help the other person to understand you by having them paraphrase, or ask how they see it differently. Be prepared to listen even if you disagree with points that have been made. It lowers defences and enables greater understanding.

Other perspective

It can be easy to get caught up in your own perspective and how you feel, especially if you’ve been hurt or feeling awkward about something. Most conversations fail when people try to describe the problem from their own perspective and lead to identity crisis. This implies a judgment about the other person and so provokes a defensive response. Not being open to other perspective makes conversations difficult because they threaten and challenge a person’s identity, question their competency or their goodness.

All-or-nothing thinking can make you more vulnerable. The more easily you admit to your own mistakes, intentions and your contribution to the problem, the more balanced you will feel during the conversation. Remind yourself of others’ limitations, and do not try to control other’s reactions. Understand that not every conversation is going to go your way and not everyone is going to agree with your point of view, but you can try to understand other’s point of view and let the other know you are acknowledging their feelings.

Positive intent

We often tend to assume that if we are hurt, the other person meant to hurt us. However, it is most unlikely and our beliefs about another’s intentions are often based on our interpretation of what the other’s intentions are. We tend to think worst of others and the best of ourselves. To avoid this, ask the other what their intent was and remain open to theirs and your own interpretation of what it really is.

Some more phrases that can help you take the conversation forward are “Here is what I am thinking..” “I come to the conclusion because..” “Do you see any flaws in my reasoning…” “I would like to hear your perspective on things…” Acknowledge other’s feelings and consider the possibility of your own complex motives. Avoid focusing on blame. Accusations cause defensiveness and obstruct our ability to learn what’s really causing the problem and to do anything to correct. Avoid accusations and if you feel accused of having bad intent, discuss what your intention truly was.

Questions for self-reflection

How do you deal with challenging and uncomfortable conversations?

What is your purpose during a difficult conversation – Is it to express your point of view or to problem-solve or to understand the other perspective?

How do you respond to conflicts or disagreements in a conversation – do you tend to avoid or be open to participate?

Did you ever resolve any disagreements with your friends or family members and was there any relational damage afterwards?

What role do you play when you are a part of uncomfortable workplace conversations- do you tend to blow things out of proportion, blame or do you try to reach an amicable solution?

How do you rate your current ability to handle difficult conversations?

Do you try to see from other or a neutral perspective in a conversation?

To conclude,

Becoming confident in having difficult conversation is a skill that takes a great deal of time and effort to develop. When you have a strong sense of your own personal set of skills, your emotions no longer hold sway over your resolve to tackle problems instead you view them as opportunities for learning, growth and development. By adopting the right approach, developing right mindset and behaviour, you will be able to maximise your ability to handle the most uncomfortable conversations effectively and steer them in right direction towards an amicable solution that is suitable to all involved.

The art of conversation is the art of hearing as well as of being heard.

William Hazitt

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