What Are Difficult Conversations?

Want to become more effective in the difficult conversations in your life? Sometimes our conversations don’t play out that well, run off the rails, and people leave feeling demoralized or belittled. We know what it’s like to walk away from a conversation that we are still carrying hours, days, or even years later. That is why we’ve created this FREE resource entitled 15 Ways to Turn Hard Conversations into Win-Win Dialogue  It will help you start to navigate even the most challenging discussions. Click here to download the guide now!

What Are Difficult Conversations?

“Our partnership is over.”

“This business is finished.”

“This relationship can’t be fixed. There’s no point in even trying.”


These are just a few of the common phrases I’ve heard over 25 years of consulting leading businesses throughout the country on how to navigate through difficult conversations.

I’m usually asked to come in to solve the unsolvable and fix the unfixable, often arriving to see eyes rolling at the very attempt to bring resolve and health to what’s upset within the critical relationships there.

I’ve seen millionaire partners at each other’s throats (literally), and decades old partnerships at the brink of disaster.

Yet time and time again—with great resolve and courage—I see them using time-tested tools to emerge with forgiveness, consensus on a legitimate path moving forward, and a plan to be accountable to others in the organization to stick with it.

How does it happen? It’s really not about me. I’m simply using the tools that many people don’t realize are there to use in the first place.

And why is that? Because most of the people I meet, most of the people reading this article right now, don’t realize what Difficult Conversations really are…

In order to break down what Difficult Conversations are, we need to first take a closer look at how we define “relationships” in our life.

Everyone has relationships. In fact, you likely have many relationships in your life—even with people you don’t particularly like.

Don’t limit the concept of relationships to marriage, family, and close friends—we are including the critical connections with coworkers, your boss, and the people who report to you.

Some relationships are deeper than others, some are more important than others. Several relationships are especially key to keeping things on track at work.

Communication is critical to how we work out those relationships. We are talking all the time with the people around us—no matter what our business or relational connection. The career you are in is made of people, by people, and for people.

What happens when all of the sudden the conversation in one of those relationships takes on a disagreeable tone?

People start feeling at risk—they are afraid of being hurt, looking bad, or even losing their job. A natural reaction to this risk is shutting down, getting defensive, or worse…losing tact completely!

What’s the root of this downward spike in the conversation? Something has just been put at risk, and the tension begins to rise.

Often, when people don’t know where the conversation is going, walls come up, and even body language starts shouting “I’m uncomfortable, get me outta here!”

This is a difficult conversation.

It is a conversation in which one or both parties feel at risk and often begin to respond in unhealthy ways.

Destructive things can be said that hurt. People are ‘triggered’ inside by fear, loss, or a reminder of previous pain.

Difficult conversations are inevitable when we are insecure about what’s going on and attempt to avoid the conflict entirely.

In the midst of those conversations that don’t feel good, we must learn to lean in and take the road less traveled.

I run into people all the time who say, “Please…help me take the ‘difficult’ out of difficult conversations.” I always tell them the same thing—that’s not possible!

The tools don’t exist to remove difficulty altogether, but rather to help us navigate and be effective to get past the difficulty to actually strengthen the relationship.

Difficult conversations are always going to feel difficult, even overwhelming at times.

Where does the difficulty come from? There are many reasons why—but usually it’s the combination of negative emotions and risk.

It’s overwhelming to think about losing your job. It’s overwhelming to think that something you might say may permanently damage a relationship.

However, the power of becoming effective at difficult conversations is that you are emboldened to face even the most awkward, tense dialogue with courage and skill.

Learning how to be vulnerable, empathic, listen responsively, practice candor… these are all powerful insights that will immediately boost your confidence and ability in turning difficult conversations into win-win dialogues.

Don’t wrestle over an issue too early in a conversation or you are not going to hear each other at all. You’ll simply continue to bang away ideas with no fruitful end or result.

The problem is not trying to get to resolution—it’s trying to get there too quickly. If you take the right approach, you’ll strengthen the relationship. Even though you may disagree, you want to hear the other party out.

Resist wrestling. Gather puzzle pieces of perspective. Push away the urge to find agreement too quickly and trust that agreement will arise if and when the right pieces are on the table.

Realize that if you can become effective at creating an environment for people to share their thoughts and feelings, not only are you going to grow relationships—you are going to help solve more and more conflicts.

Why? Because you are able to see all the angles of perspective, challenge assumptions, and actually get down to the root of the issues.

This sets up success in the conversation. Unresolved conflict is often the result of not collecting informational puzzle pieces.

Remember, the heart posture of empathic listening asks:

What are you thinking?

I noticed you got emotional when you said that, what are you feeling?

What’s most important to you in all of this?

After collecting those pieces of information, you can share what you are thinking, feeling, and what’s important to you. Give the other party a chance to listen empathically.

You are the authority on you, they are the authority on themselves.

Say back to them what they are saying as effectively as possible.

Remember, we were all born with two ears and one mouth for a reason! Listen twice as much (or more) than you speak.

In all of this you want to remain ‘agenda-free’ as much as possible. Declaring up front your intention to gather perspectives without knowing exactly where the conversation is going will help the other party open up.

If you act like you know the solution before the conversation has even begun—people will shut down and it will be difficult to work towards agreement and consensus effectively.

Here are more insights that will help you navigate handling difficult conversations effectively in your life and career.

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