How to Deal with Difficult Conversations

Sometimes, it’s impossible to sort things without talking them out. This gives rise to dreading difficult conversations. 

However normal and unavoidable, things can get out of hand if not handled properly. 

Difficult Conversations: How to Discuss What Matters Most equips you with the skills and steps to handle conversations.

Written by Douglas Stone, Bruce Patton, and Sheila Heen, it can help you navigate conversations in a way that fosters understanding and effective problem-solving. 

And now, let’s talk about what makes a conversation difficult. A difficult conversation is one that you find challenging to talk about. 

It can be anything. From:

  • Ending a relationship
  • Asking for a pay raise
  • Addressing a hurtful behavior

Your personal and professional lives may encounter any situation at any time. 

Every conversation follows a certain structure. 

There are three types of difficult conversations that present different issues and complications:

Types of Difficult Conversations

  • The What Happened Conversation
  • The Feelings Conversation
  • The Identity Conversation

Often, you may strike up a conversation to prove a point or get others to do what you want. 

The problems arise because each party focuses on their agenda and viewpoint. 

You can effectively manage difficult conversations by:

  • Shifting your goal from persuasion to learning.
  • Learning how to manage the three types of conversations.

Let’s start by zooming in on the three types of difficult conversations. 

After that, we’ll explain how to create a learning conversation. 

The What Happened Conversation

The What Happened Conversation revolves around different views. 

  • What happened or should happen
  • Who is right
  • Who is to blame

While conversing, each party feels their point of view is correct. 

But they assume this based on three fronts:

Truth: this is often about ‘I’m right, and you’re wrong.’ 

But most difficult conversations are about conflicts in subjective values or perceptions. 

For example, telling someone, ‘You’re too inexperienced’ or ‘you’re driving too fast’ doesn’t make them facts; these are only opinions.

Intention: You may think you know the intention behind the other party’s action or non-action, except that you might often be wrong. 

For example, you think your colleague is shouting to humiliate you when he’s just trying to make himself heard above the noise. 

Blame: We’re quick to blame others.

This blocks us from examining other factors that may have contributed to the situation (like ourselves).

So how can you address these issues separately?

Uncover the Truth

Don’t argue about who’s right. 

Instead, explore each other’s stories. 

Remember that arguing is counter-productive. 

And even though no one disagrees that a story has two sides, deep down, we believe our story is the right one.  This gives rise to the thinking that the problem lies with the other one. 

When you assume someone is naïve, you try to teach them the truth. The other person assumes you’re an arrogant know-it-all. 

The argument leads nowhere, ending up in a damaged relationship. 

Understand that everyone has different stories and perceptions about the world because:


We filter information differently. For example, an artist may look for different things from an analyst. 

An observer sees a situation differently from the person in charge. 

No one knows your complex inner state better than you do. 

We interpret the same info differently due to our past expectations and different implicit rules about how the world works. 

For example, boys are told that they must not cry.

Or some people tell you to squeeze the toothpaste from the bottom of the tube. 

We’re biased toward our self-interests, paying more attention to data and conclusions that fit our interests and beliefs. 

One way to deal with this is to shift from certainty to curiosity. 

Start by acknowledging that you don’t have all the facts.  So, be curious about the other person’s story as well as your own (including the assumptions underlying your story and responses). 

It’s not your job to decide who’s right or wrong.  Instead, you’re supposed to understand where you’re coming from so you can jointly move forward. 

And it’s not about your story or theirs. 

Learn to embrace your story and theirs. 

For instance, Jane made a mistake, and you made things worst. You hurt Tim, and he embarrassed you publicly. 

Understand their story instead of accepting or rejecting it. 

Clarify Intentions

It’s not necessary that the other person intended bad outcomes. So, separate the intent of their actions from the impact. 

Often, we make wrong assumptions. We attribute intentions based on the impact. 

For instance, if we feel hurt, we assume the other person meant to hurt us. 

We also assume the worst of others but the best of ourselves. So, if a staff member forgets to submit a report, she’s careless. But if you forgot the report, you’re just overworked. 

Such assumptions hurt relations because we relate bad outcomes with bad intentions and that bad intentions are due to a bad character.  And when we accuse others, they get defensive. 

This leads to our assumptions becoming self-fulfilling. 

You think your boss doesn’t trust you with responsibilities, and you may get demotivated. Your lackluster performance leads to your boss giving you fewer responsibilities. 

Sometimes, we think our good intentions don’t have a bad impact. But this often backfires because we miss what they’re actually saying. 

When someone says, ‘why did you do this to hurt me?’ He’s saying that you intended to hurt and that he’s hurt. 

And yet, when you clarify your intentions, you only address the 1st message and neglect the 2nd one.  To us, our motivations are over-simplistic. 

But in reality, our intentions are never purely good or bad. 

And we may not even be aware of our complex motivations. 

Understand that your intentions don’t matter; how the other person feels does.

To avoid these mistakes:

  • Separate impact from intent.
  • Acknowledge the other person’s feelings. 

Shift Away from the Blame Game

Blame is about judging if someone caused a problem in the past and if they should be punished. 

Pinning the blame on one person barely solves the problem since there are always multiple contributors. 

Imagine an employee who takes bribes from a supplier.  While the employee is clearly at fault, firing him won’t address the contributing factors. 

You must keep the hiring process, lack of internal checks and balances, and cultural norms in check. Besides that, you must also diagnose how various parties and factors contribute to an outcome. 

It helps uncover what happened and how to improve the situation. Your goal should be to seek understanding, not assign blame. 

Most importantly, instead of playing the blame game, map out how you may have contributed to the problem. 

  • Did you avoid the problem till now?
  • Were you unapproachable?
  • Did you shut down a discussion when things got heated up?
  • Did you impose your implicit role assumptions on others?

Identify your contribution by using the following approaches:

  • Reverse the role: put yourself in the other person’s shoes.
  • Become a neutral third party: observe things in the third person.


The Feelings Conversation

According to the authors, feelings are at the heart of difficult conversations. 

Feelings influence our thoughts and actions. 

So, avoiding them will only lead to more hurt and misunderstanding. 

During a difficult conversation, you may try to hide your feelings and stay rational. 

For example, you may pretend to have a professional discussion with your boss about the new team structure even though you’re silently upset that he promoted your colleague over you. 

Bottling up your feelings will only backfire. 

You may be unable to control your tone of voice or body language. 

And so, your feelings can leak out or explode in destructive or embarrassing ways. 

This leads to distractions from fully listening or expressing ourselves. 

In the long run, it leads to a loss of confidence.

Here’s how you can handle feelings in difficult conversations. 

  • Sort out what you really feel. 
  • Negotiate with your emotions.
  • Reexamine your story and theirs. 
  • Acknowledge the other person’s feelings.
  • Share your feelings.

Remember to share your feelings without being emotional. 


The Identity Conversation

It’s human nature to protect our sense of self. 

And that’s why you might find yourself in an inner battle of questions like ‘what does this say about me.’

For instance, a pay-raise discussion isn’t just about the money. It’s about your self-worth and image. 

When someone says something that questions your identity, it may throw you off-balance. Ultimately, it makes it hard to think clearly or communicate effectively. 

In a nutshell, you can struggle with these three key identity issues: 

  • Am I competent?
  • Am I a good person?
  • Am I worthy of love?

Unfortunately, humans are wired to think of things as black or white. So, you may believe you’re good or bad, generous or greedy, competent or useless. 

This leads to responding in 2 extremes:

  1. We deny feedback to protect our sense of self. 
  2. We exaggerate the feedback and change our self-image. 

In reality, professional and personal lives hold gray areas, too.

That’s why it’s inevitable to hear unpleasant things about yourself during a difficult conversation. 


How to Navigate a Difficult Conversation

Now that you understand the challenges with each of the three conversations, here’s how you can prepare and navigate each. 

Consider the 3 Conversations

Start by:

  • Unraveling what happened. 
  • Understanding your feelings.
  • Anchoring your identity. 

Know Your Purpose  

  • Get clear on your purpose and what you hope to achieve from it. 
  • Understand their story.
  • Express your emotions and viewpoints
  • Find ways to solve the problem together or move forward.

Remember not to start a conversation if:

× The real conflict lies within you than between you and the other person

× There are better ways to resolve the issue

× Your purpose isn’t a good one

Understand that sometimes, it’s best to simply let go.  

Start from the Third Story

Instead of starting from your own story, observe in the third person. 

And even if the other party initiates the conversation, you can still gear towards the third story. 

As a third person, your views can differ, but they cannot be better or worse. 

So, listen to both sides but don’t give up on your views. 

Even if you disagree, you’ll have a better mutual understanding and a higher chance of finding a way forward. 

Explore Their Story & Yours

Explore the three conversations by taking turns from a different point of view.

  • Explore the source of your story
  • Share its impact on you
  • Take responsibility for your contribution
  • Describe your feelings
  • Examine identity issues
  • Listen out for their feelings and acknowledge them
  • Ask them if they think differently about the problem
  • Express yourself, loud and clear


Take the Lead in Problem-Solving 

Once you have reached a mutual understanding, you’re ready for the next phase:

To solve the problem from its root. 

Remember that you can find a mutually-acceptable solution even when you don’t completely agree with each other.

As they say, you must agree to disagree.

Do this by:

  • Explaining the parts of their story that don’t make sense to you instead of presenting the gap using your story. 
  • Share how they can persuade you and ask if there’s anything that can convince them. 

Lastly, brainstorm creative solutions together and invent options. 

Instead of squabbling over whose approach to take, consider if there are specific standards or principles you can apply.

And if you still can’t agree, decide if it’s best to accept less than what you want or the consequences of a disagreement. 

And there you have it – the A-Z of difficult conversations and how to navigate them like a pro.

Do read the book Difficult Conversations: How to Discuss What Matters Most for case studies and sample conversations.

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