“The right word at the right time will unlock the door to treasures – the wrong one will close it forever” – Rasheed Ogunlaru

Think about a discussion you have been planning to have with your manager. For example, to ask for a raise. Perhaps as a manager, you may need to terminate an employee or resolve a conflict with a co-worker.

These are some of the many difficult conversations that we have to deal with quite often. However, it is important to realise what makes a conversation “difficult”. It is not the conversation itself that makes it difficult. It is our communication skills (or the lack of it) that make them appear difficult.

There are many situations in our daily lives when such conversations are necessary. Still, it can be a challenge for many of us, including managers and leaders.

Be it in our professional or personal lives, none of us enjoy having difficult conversations. We all love to hold on to our views and opinions, and don’t like being challenged. Our underlying fears prevent us from facing such conversations head-on.

But avoiding such a conversation does not resolve the issue either. While we tend to steer away from conflicts or disagreements, quite often, such discussions are unavoidable. The chances are, a delay in the discussion will make the situation even worse. 

In reality, making the most out of difficult conversations is extremely important for our personal and professional growth. Let’s see 9 steps explaining how to do that.

How to Go About a Difficult Conversation

How to Go About a Difficult Conversation?

You’re not learning anything unless you’re having the difficult conversations.” – Gwyneth Paltrow

Millions of years of evolution have taught our bodies to react in a certain manner to external threats. In moments of stress, our bodies react by releasing chemicals like cortisol that increase the heart rate. 

This is often termed “amygdala hijacking” by psychologists. As a result, we often overreact or behave irrationally. Basically, the neurochemical interactions in the brain make it even harder to think straight and behave rationally.

I believe being ready for tough conversations makes us better equipped to face challenges in life. When done in the right manner, difficult conversations have the potential to enhance a relationship and produce ever-expanding results over the long term.

While there are no defined rules for handling difficult conversations, I have found that these nine crucial steps can make a big difference.

1. Set the Right Context 

The right conversation in the wrong context is the wrong conversation. The first step is to set the right context for the discussion. The best leaders know how to set the tone of the conversation and guide it towards the desired outcome. Here is an example:

Imagine saying this to a client- “We need to talk about the project timelines being missed repeatedly from your end.”

Instead, try this- “ I wanted to divert some of our best talents to your team, but the project timelines keep shifting. Let us discuss the best ways to frame a workable schedule.”

Without context, we tend to react to what is being said rather than considering the bigger picture in mind. The right context helps keep the focus on what is really important. 

Before you enter a difficult conversation, take some time to prepare for it. While a casual approach does not help, rushing through a serious conversation is also the wrong approach. Also, give the other person enough time to prepare instead of catching them by surprise. Are you going into the conversation to prove your side of the story and to prove them wrong? Or, are you going to the conversation to solve a problem together?

The right context also helps to understand the social, psychological, cultural threads that are involved in the conversation. Have the discussion privately by creating a safe and congenial environment. It is important to enter the conversation as a “learner” willing to learn something new rather than as a “knower” who is there to prove something. You can also set up some mutually agreed ground rules to avoid misunderstandings and stick to the facts.

2. Be Willing to See Another’s Perspective

You cannot reason people out of a position that they did not reason themselves into.” ― Ben Goldacre

To clearly perceive an issue, you need to also understand the perspective of others. Many times, we use our perspective to understand others. However, this might be completely different from their perspective and can cause friction in the conversation

In the personal or professional world, there are hardly any situations when two people absolutely agree with each other. The fact is, disagreements are normal and they do not need to hamper a discussion. 

David Maxfield, the co-author of the book Change Anything: The new science of personal success, sums it up perfectly – “Ignoring the disagreements doesn’t work, and turning disagreements into fights doesn’t either. The key to a successful relationship is how you handle the inevitable disagreements.” 

Good leaders know that healthy arguments can be an integral part of creative problem-solving. The important thing is not to get stuck by the disagreement but to look deeper and understand what both parties really care about. Conflicts arise in a conversation when we fail to understand what is important to the other person. 

To avoid that, we need to listen attentively and go deeper than their positions to understand what they really want. Deep listening helps us understand the feelings and viewpoints of the other person. Leaders need to be open-minded about understanding different perspectives. 

How to Go About a Difficult Conversation

3. Separate Facts From Opinions

“Every man has a right to his opinion, but no man has a right to be wrong in his facts.” – Bernard Baruch

What is the difference between a fact and an opinion?

Basically, a fact is a statement that can be proven true or false by a reliable authority. But an opinion is a personal view that cannot be verified. Opinions can be based on individual feelings and emotions. 

Also, a fact is universal, but opinions can vary from one individual to another. Take this conversation for example:

“That movie has been a blockbuster according to New York Times and is number 1 on the box-office charts.”

“Is it? I found it boring.”

While the first statement is a fact, the second is an opinion. People often confuse the two, and that can be misleading during a conversation.

Asking the right questions is extremely important to get the facts underlying an opinion. Questions can help you to differentiate between facts and opinions. Once you have the facts and the data, use them to analyze the situation together. A statistical/logical approach also helps you to separate the objective reality from the subjective.

In addition, you can also summarize each other’s understandings or note them down. This will ensure that you are on the same page. As a result, proceeding with a difficult conversation can get much easier. 

4. Mutual Respect

“I speak to everyone in the same way, whether he is the garbage man or the president of the university.”– Albert Einstein

Mutual respect is to a conversation what oxygen is to humans. Take it out and the conversation dies. Being respectful goes much beyond the use of “please” and “thank you” in a conversation. True respect lies in understanding, courtesy, and kindness for another’s opinions.

For this, there are two important steps. Firstly, you should listen to the other person without criticizing or indulging in any form of personal attack. Secondly, you need to be aware of how you are treating the other person. No two people are the same, so understanding their individual perspectives is very important.

Even if you feel frustrated during a conversation, avoid negativity. Insulting or ridiculing the other person will lead to a loss of respect. Good leaders do not allow their emotions to hijack their responses at any moment.

Emotions can be a big asset in a difficult conversation (as they can reveal what each party cares about) but they should not be allowed to overpower our reasoning. It is the faculty of reason that allows us to choose the best path in a challenging situation. We can then use our emotions to guide us along that path.

Also, understand that we all make mistakes. In case mutual respect has been violated in some way, it is important to apologize. That helps in removing any ill feelings from a relationship. At the same time, it allows the conversation to move forward.

How To Resolve Conflicts?

5. Keep the Focus on the Shared Goal

A few years ago, there was a situation when the strained relation between two engineers led to multiple confrontations and delays in a project. All it needed was a timely intervention from the manager to bring them together as members of the same team, and help them see the common goal of their discussion. As it turned out, they both cared for the project and were arguing for different ways to complete it. Once they could see that they both wanted the same end result, they themselves managed to come to a resolution.

When people realize they want the same things, it is easier for them to work together and not against each other. Sometimes emotions can take the better of us, but it is very important to attack the problem, not each other. If you can focus on the common objectives of both parties, you can argue like comrades rather than competitors.

6. Brainstorm Together, Not Against Each Other 

Speak when you are angry and you will make the best speech you will ever regret.”- Ambrose Bierce

A difficult conversation need not be a victory for one and a loss for the other. A conversation is about finding solutions and not about seeking victory for the ego. Rather, it can be an effective brainstorming session for the generation of ideas and finding solutions. 

At the same time, it should not be a temporary compromise to keep the ball rolling. An open conversation that can explore the root cause of any issue is required to get over an impasse. In reality, when individuals work against each other, the business is the real loser.

By brainstorming and allowing the creative juices to flow, you can look for a 2+2=5 outcome. This simply means the sum is much greater than the individual parts, or the final solution works better for both the parties involved.

Conflict and Disagreements Are Natural

7. Express Gratitude

Appreciate everything your associates do for the business. Nothing else can quite substitute for a few well-chosen, well-timed sincere words of praise. They’re absolutely free and worth a fortune.” – Sam Walton

Always be thankful to the other person for participating in the conversation. This important step can create a positive mood for driving the discussion forward. However, it is often overlooked during a conversation.

Offering thanks shows appreciation for the other side’s efforts in the conversation and helps to strengthen the relationship. Thankfulness allows individuals to focus on the positive aspects instead of being trapped by negativities. Genuine gratitude is also a great motivator. It expresses confidence in the future.

As a leader, you can also assure the person of your help and support. It is also important to display a positive outlook during the conversation and express confidence in the abilities of the other person. This can result in positive interactions during a conversation.

8. Make Sure to Follow Up

It is wrong to assume that the task is complete once the conversation is over. No conversation is fruitful unless it leads to the desired changes and outcomes. You need to follow up and make sure that what was discussed and promised is being done.

Note, following up is not about finding faults, but about keeping track. Both parties are mutually accountable for the outcome of the conversation. But we all know, agreeing to change our behaviour is a long way from actually changing it.

For a leader, follow up is also an opportunity to collect and share feedback. Feedback is vital for making any changes to the decided plan of action.

 9. Reflect to Become Better

Once a conversation is over, we can reflect and learn lessons from it for our next conversations. We all make mistakes in the heat of the moment, so it is important to reflect and learn any lessons for future conversations.

Here are a few important aspects that can be improved in most cases.

  • Expressing our emotions aligned with our values rather than suppressing them or exploding
  • Enhancing self-awareness and recognizing the signs of “fight or flight”.
  • Using the right words and body language
  • Directing our emotional energy towards the common objective

As with all other skills, the art of dealing with difficult conversations will get better as you reflect and practice. As you practice, the conversations remain the same. However, they stop being “difficult”.

6 Steps To Deal With Difficult Conversations


We all deal with difficult conversations from time to time.  When we act in a “my way or the highway” manner without considering the views of the other side as legitimate, it becomes very difficult to make progress in conversations.

But it is best to handle them proactively by overcoming our fears and hesitations. At the end of the day, it is important to keep your eyes on the shared objectives of both parties. A good leader is one who is ready to address difficult topics and look for win-win results, also strengthening the relationship in the process.