How To Have That Difficult Conversation You Are Avoiding

Is there a conversation you have been avoiding? Maybe, you know, the one that just flashed through your mind as you read the title of this blog?

The truth is, many of us are sitting on an important and challenging conversation that we need to have.

The awkward, the complicated, the long-overdue- it all counts.

This topic is particularly relevant these days as we navigate personal and professional relationships in the context of a global pandemic and racial revolution.

We know from experience that avoiding or delaying a conversation can hurt our relationships and lead to complications etc., yada yada yada.

But what if it’s the LAST thing you want to do? What if you would literally rather do your own taxes? By HAND without a calculator.

Well, in this post, we go over how to do it anyways.

Here is what we will cover:

Why it’s so hard to have important conversations

How being conflict avoidant holds us back

How to finally have the important conversation you have been putting off

First, a disclaimer.

This post applies to those of us who are ready to have a tough conversation and are hesitating to carry it out.

In writing this, I am also assuming that you are safe with the person you are having this conversation with. Safety is always the most important thing to consider when having a difficult conversation, everything else is secondary. I will never advise putting yourself at risk of any kind!

What Is Holding Us Back?

Why is it so hard to just talk to someone?

Figuring this out is important because it helps you get to the bottom of what this conversation actually means to you.

Here are a few reasons why we find it so hard to have those necessary but difficult talks.

It’s Just So Awkward

To my fellow awko tacos…you know that sometimes we would do anything to make life even slightly less awkward than it already is, including avoiding tough talks.

Important conversations can be hard because they feel so unnatural. Maybe it’s an awkward topic because it has never come up until now. Or perhaps you are not used to talking about certain things with that particular person.

Awkward situations tend to increase anxiety, and anxiety is a feeling that people go to many lengths to avoid.

Being Vulnerable Is Hard

Vulnerability involves risk and emotional exposure. Having important and challenging conversations often requires vulnerability from both parties.

As Brene Brown says, vulnerability is a risk we have to take if we want to experience true connection. Vulnerability is the birthplace of so many wonderful things: love, belonging, empathy, joy, and authenticity to name a few.

It would be suspiciously easy if we could have all these things without launching out of our comfort zones, wouldn’t it?

And we can’t deny that being vulnerable can be really uncomfortable. To add to this, the narrative that vulnerability equals weakness has only been challenged recently.

On the surface, avoiding the conversation altogether does seem easier than being vulnerable.

The Potential Consequences Are Not Easy To Digest

Having an important conversation is hard when you are anticipating unpleasant consequences. Maybe you are afraid of hurting, disappointing, or angering the other party.

Or perhaps you have reason to believe that having the conversation means everything will change.

This can be very daunting and makes it difficult to enter that arena willingly.

You Have Already Had The Conversation…In Your Head

In my experience with clients, I’ve found that our minds become better storytellers the longer something goes unsaid. We’ll imagine explosive and dramatic scenes and somehow it always ends in us destroying the other party with our flawless arguments and killer comebacks.

Personally, I feel EXHAUSTED by how much mental real estate these imaginary conversations take up in my own head.

The characters of these conversations also tend to get ruder and more irritating the longer they are allowed to battle it out in my mind until….

Have you ever been angry at someone for something they haven’t done? Well, it’s not hard when you are mentally replaying a potential conversation or argument (that hasn't happened) again and again.

By ruminating constantly about the conversation and how it could go, we end up putting off the real thing. In a way, our brain tricks us into feeling we are doing something to resolve the issue, when in reality, we could be making it worse.

But Sarah, I Avoid Conflict At All Costs

One of the biggest reasons we struggle to have tough conversations is because they will cause some conflict between the parties. If you tend to avoid conflict or confrontation, you may be more likely to delay conversations.

How do you know if you are a conflict avoider?

Here are a few signs:

When approaching any conversation, you worry about your likeability

You spend a lot of time wording and then re-wording what you are going to say

When you sense a disagreement is about to happen, you will either soothe the other person or try and change the subject

Your response to conflict often sounds like “I don’t want to talk about this right now” or “It’s not worth it”

When you identify that a conversation needs to happen, you tend to think “I’ll bring it up next time it happens”

If this sounds like you, then you may benefit from re-framing what conflict is in the first place.

Why We Need Conflict

Most of us go about life knowing that we don’t like conflict or confrontation. By labelling conflict as a bad thing to be avoided, we lose the opportunity to think about it in a meaningful way.

A conflict is usually framed as a dispute where someone wins, and someone loses. This understanding of conflict is limiting because misses a key point:

We have conflicts to IMPROVE the relationship.

In fact, a good rule of thumb for getting into conflict situations is if you don’t care about improving the relationship, don’t have the conflict.

The challenge is to engage in the conflict, not to overpower the other person!

We need conflict in our closest relationships because it helps us figure out when our needs are not being met and gives us an opportunity to do something about this.


When done right, people should feel closer and more in sync after a conflict.

I know I know; this understanding of conflict is less fun than the dramatic, explosive, mic-drop version you've been mulling over.

Think about this though: if we subscribe to conflict as a means to be closer to the people that matter, we will be more willing to engage in that conversation. Suddenly, a potential conflict isn't as daunting.

Window Of Opportunity

Avoiding conflict in relationships we care about can cause us to miss a window of opportunity.

I like to think of this as the time when both parties are in the best position to respond to the conversation in an effective way.

Here is an example of a very important conversation that misses its window of opportunity.

Let’s say you are starting to re-think the idea of having children. You understand how important it is to discuss this with your partner, especially because you both went into the relationship assuming that you would have kids one day.

This conversation will likely cause an upheaval in your relationship and you are absolutely dreading this. You tell yourself that you will talk to your partner when it’s more convenient to deal with the consequences.

However, there is never a convenient time. The conversation is delayed until it reaches a point where the unspoken information is causing other issues in the relationship. Now the conversation demands to be had.

The fall-out and consequences occur anyways, and both parties are in less control of the outcome. It's less a conversation and more an ultimatum now.

This example is an extreme one! It’s not meant to scare you. My point is to illustrate how missing the window when a conversation will be best received can create further issues.

Let's talk about how to avoid these types of outcomes by having the conversation.

How To Have That Conversation You Are Avoiding

I'm going to walk you through how you can prepare for and carry out a conversation you have been sitting on for some time.

Remember - challenging conversations are a part of life! They are unpleasant in the anticipation and perhaps even in moment. In hindsight though, many people find that these conversations help them grow, learn, and have better relationships.

In short, it's worth it.

Preparing For The Conversation

Before you talk to anyone, here are some questions to ask yourself.

What is your purpose in having this conversation? Pay attention to hidden goals- you may think you have a noble purpose but maybe you are also intending to stick it to that person. Spend some time thinking about what you really want to accomplish

What are the needs you are hoping this conversation will address?

Have you made any assumptions about the other party’s intentions or position? If you have been sitting on this conversation for a while, it’s likely that you have a quite a few assumptions to unpack!

What is your attitude going into the conversation? If you are going into it expecting it to be a disaster, it’s more likely to turn into one.

Are there any long-term gains this conversation will create for the relationship? Focusing on this will help guide your inner dialogue into a more calm place.

We Need To Talk

Now that you have done some thinking about your purpose, attitude, and assumptions, let's discuss some tips on having the conversation itself.

Approach The Conversation

Bring it up! You may find it easier to brainstorm certain opening line such as:

"I have something I've been meaning to talk to you about for a while. Can you set aside some time this week?"

Pick a time when no one is in a rush and a place that is comfortable. It's also okay to admit you are feeling nervous, worried, or apprehensive. Have something nearby that brings you comfort or reminds you both why this relationship is important.

Set Up Ground Rules

Ground rules keep things respectful or professional (depending on the context), and remind us to stay on track. Some possible ground rules include: avoiding insults, no interrupting, focusing on the topic at hand, and allowing for 'time outs' as needed.

Be Curious

In the beginning of the conversation, the goal is to learn everything you can about the other party's point of view.

This looks like listening without interrupting, being curious without judging them or taking what they are saying personally, and watching for what may be going unspoken as well. For example, is there something that is implied, and not being said? What could be the reason behind that?

Learning about WHY certain issues are so important to the other party can go a long way.

Validate And Acknowledge

Here you want to spend some time communicating that you understand and acknowledge their point of view.

Try summarizing or repeating it back to ensure you're both on the same page.

Acknowledge and communicate that you are feeling defensive, hurt, surprised, etc. Keep in mind that acknowledging someone's perspective does not mean you agree with them! You are not losing anything from recognizing that you hear and understand the other person.

Advocate For Yourself

This is your opportunity to share your perspective and feelings. If you feel that your position has been misrepresented, clarify it (without undermining the other person's).

Work Together On A Solution

Now that both parties have put everything you have on the table, you can brainstorm solutions. This stage might not happen right away, especially if there are strong and complicated feelings to deal with.

Closing Time

Tough conversations can be daunting. But the anticipation is often so much worse than the conversation itself!

I hope that this post convinced you to shed the burden of carrying around unspoken truths and provided some inspiration on how to approach THAT conversation.

Remember, even if the conversation ends in an less than ideal outcome, most of the time it leads us down a path we can be grateful for in the future. Personal growth, opportunities for connection, and lifelong lessons are usually born out of the courage it takes to have a tough conversation.

Something to think about - what is holding you back from having that conversation?

As always, if you need support with this, flip me an email, or book an appointment with anyone from my awesome team!

Until next time,