Why You Keep Avoiding Difficult Conversations + 5 Tips to Help You Stop

Why is it that some conversations are just so hard to have?

  • You have to give your coworker some negative feedback but you keep procrastinating on it…
  • Every time you talk to your child about applying for college it turns into a huge argument…
  • You know you need to talk to your spouse about that money you lost in the market but you keep avoiding bringing it up…

Typically, we blame our avoidance on a few common culprits:

  • Communication skills. If only I had better tools for communicating more effectively…
  • Other people’s character. If only my son was more reasonable…
  • Other people’s emotions. If only she didn’t get so angry and defensive when we talked about money…

But the truth is these are mostly excuses…

  • Sure, conversations would be easier if your wife never got upset when you made mistakes. But is that really the problem?
  • Sure, conversations might be somewhat easier if you had more communication skills. But is learning to sandwich negative criticism in between two positives really the answer to your chronic avoidance of difficult conversations?

In my experience, there’s one huge elephant in the room that causes most of our trouble having difficult conversations. And nobody wants to acknowledge it.

Can you guess what it is?

We’re not very good at managing our own difficult emotions.

Think about it…

  • Are you avoiding giving your coworker negative feedback because you don’t know how or don’t have the right skills? Or are you avoiding it because you’re anxious about them thinking badly of you afterward?
  • Do your conversations with your son about college always end up in arguments because he’s just unreasonable? Or do they escalate because you mask your insecurity about him not having a good career with anger, which understandably makes him feel judged and attacked?
  • Are you avoiding that conversation with your wife about money because she can’t handle the bad news? Or are you avoiding it because you don’t want to experience the shame and guilt of admitting a huge mistake?

If you want to stop avoiding difficult conversations and become more confident having them—no matter how tough—you must learn to identify and manage your own emotions first.

Here are a few tips to get you started:

1. Identify all the difficult emotions at play

If the main obstacle to having difficult conversations is your own emotions, then you need to know what they are and how they show up.

This sounds simple and obvious. But our instinct with difficult emotions is denial and avoidance. We’re conditioned through years of experience not to see or acknowledge them. And instead, to pretend like they’re not there.

Of course, pretending like obstacles don’t exist is a good way to keep getting stuck on them.

And emotional obstacles are no different…

  • Your anxiety will keep holding you back if you keep pretending like you’re not anxious.
  • Your anger will keep holding you back if you keep pretending that you don’t get angry.
  • Your shame will keep holding you back if you keep pretending that you don’t feel ashamed.

So, step 1 is very simple:

Identify and acknowledge all the emotions you experience when you think about your difficult conversation.

List them out. On paper.

Now, keep in mind that this may take some time and a few different attempts.

Chances are you won’t notice all the subtitles of how you’re feeling about a particular conversation on your first go. You’ll have to ask the question several times and be willing to really listen in order to get an accurate picture of what your emotional landscape really looks like.

2. Validate those emotions

Okay, I’ve identified all these awful emotions. What am I supposed to do with them now?

First of all, I’d be careful about calling your emotions “awful.” There’s no such thing as a negative emotion.

Second, and more to your point, you’re not supposed to do anything about those emotions.

Emotions aren’t like lights in your kitchen you can switch on or off. They’re not bacteria you can blast away with a quick round of antibiotics. Emotions are a part of you. Like toenails or a belly button. And whether you like them or not, trying to get rid of them is a losing proposition and very likely to backfire in the long run.

Here’s another way to think about it: Emotions are like the weather. You might prefer sunny days to rainy days, but that doesn’t mean rain is bad and sun is good. Or that you should try and get rid of the rain and force the sun to come out.

You can put a raincoat on, but you can’t stop the rain.

Similarly, with difficult emotions that come along with difficult conversations, you’re not going to get rid of them. But you can learn to live with them more effectively. And the best way to do that is to get in the habit of validating them rather than avoiding or criticizing them.

Emotional validation is pretty simple: It means acknowledging that it’s okay (or valid) to feel whatever you’re feeling even if it’s painful or you don’t like it.

For example:

  • If you’re feeling anxious about an upcoming conversation, you might say to yourself: I feel pretty anxious about what Tom might think of me after I give him the bad news. But it’s normal to feel anxious ahead of giving someone negative feedback. I don’t like feeling this way, but that doesn’t mean it’s bad or I have to stop feeling anxious in order to have the conversation.
  • If you’re feeling ashamed about a topic you need to have a conversation about, you could say something like this: I’m feeling guilty about what I did and I know I’m going to feel ashamed when she knows what I’ve done. I hate feeling ashamed, especially in front of Sandy. But the feeling of shame is normal. It feels gross but everybody feels ashamed when they’ve done something wrong or made a mistake and other people find out. What I did was wrong, but how I feel is not.

Validating your emotions won’t make them go away. But it usually helps take the edge off your overall level of emotional resistance.

And sometimes that can be the difference between continuing to avoid a difficult conversation and finally having the courage to face up to it.

3. Write out your difficult conversation before it happens

Think about this:

  • Musicians rehearse before a concert.
  • Athletes practice before a game.
  • Soldiers drill before combat.
  • Doctors train before surgery.

And yet, when we have to perform during a difficult conversation, what do we do…? We wing it!

This is crazy.

Difficult conversations will always be difficult. But they’re usually far more difficult than they need to be because we rarely prepare for them. Instead, we cross our fingers, hope for the best, and then dive in.

This is nuts. And deep down, your brain knows it. Which is part of why you feel so much emotional resistance to your difficult conversation.

Fear of having a difficult conversation is often your brain’s way of telling you that you need to prepare first.

So what does this look like exactly—preparing for a difficult conversation?

It’s hard to say without knowing the specifics of the people and issues involved. However, there’s a way to prepare that’s helpful in just about any situation involving a difficult conversation…

Write it down before it happens.

Imagine you’re a screenwriter and it’s your job to write down the dialogue for the conversation. What would that look like?

  • I’d probably open the conversation by saying…
  • He’d likely respond by saying…
  • My response to that would probably be something along the lines of…

Now, keep in mind, you don’t have to get it right. The point of this exercise isn’t so much that you understand ahead of time exactly what will and won’t be said.

By writing out how the conversation might go, you’re preparing yourself emotionally for what might happen and how you might feel.

By imagining what might be said—and how you might feel as a result—you’re taking away some of the surprise factor. And as a result, a good chunk of the anxiety around the conversation.

And while this won’t eliminate your avoidance, it might lessen your fear enough that you feel just confident enough to actually have the conversation.

So, if you’ve been chronically avoiding a difficult conversation, take 20 minutes and sit down with pen and paper and write down how you imagine the conversation might go.

If nothing else, you’ll have broken the cycle of avoidance and procrastination and started to approach—even if just in your imagination—the conversation instead of running from it.

4. Clarify your conversation goals

In addition to thinking through what might happen in a difficult conversation, it’s also important to clarify what you want to happen. In other words, what are your goals for the conversation?

Now, this probably sounds simplistic and obvious—know what you want out of a conversation. But if you think carefully about it, I think you’ll realize that, especially with difficult conversations, we’re surprisingly vague about what our goals really are. And this vagueness is part of the reason we feel like avoiding the conversation.

For example:

  • Say you’re avoiding giving a coworker difficult feedback. Well, what exactly is the goal? Is it simply to deliver the feedback? That might be part of it. But chances are, you have other less obvious goals…
  • Perhaps you want to deliver the negative feedback but to do it in a constructive way—one in which the person feels empowered to learn and grow rather than become defensive and unresponsive.
  • Of course, you can’t control how they respond entirely. But you can influence it by considering carefully how you word things, when you have the conversation, how you react to their difficult emotions, etc.
  • So really you have at least two goals: 1) communicate the required information; 2) do it in a way that’s most likely to be productive.
  • The first one is fairly straightforward, but the second is quite complex. So, if you haven’t thought about it carefully and made plans for it specifically, it’s not surprising that your brain is a little nervous about getting into that conversation.

This isn’t rocket science. It just requires a little bit of time and careful thought.

So the next time you find yourself procrastinating on or otherwise avoiding a difficult conversation, take 10 minutes, sit down with a nice cup of coffee or tea, and ask yourself: What are my goals for this conversation, really?

A little specificity goes a long way toward alleviating anxiety about difficult conversations.

5. Reflect on your core values

Remember that difficult emotions like fear or shame aren’t something you can avoid entirely. Which means making the choice to have a difficult conversation will always involve some difficulty and discomfort.

Thankfully, there are ways to lessen that discomfort using strategies we’ve talked about like acknowledging and validating your emotions, or thinking clearly about what your goals for the conversation really are.

But you can also get over the hurdle of difficult emotions by strengthening your motivation to have the conversation despite those difficult emotions.

More motivation? Sounds good… but how?

One of the most powerful ways to boost your motivation is also one that almost never gets talked about: values.

Specifically, by reminding yourself of your personal values and why they matter for your difficult conversation, you can increase your motivation, and along with it, your odds of actually having that conversation instead of continuing to avoid it.

For example:

  • Let’s say you’ve been avoiding a conversation with your spouse about whether to travel or not for the holidays because you know she really wants to and you really don’t.
  • You’re dreading the argument that you’re almost positive will result. And that dread—that fear—is what’s really keeping you from the conversation.
  • Well, one way to boost your motivation to have the conversation despite your fear is to tap into the motivating power of your values.
  • You might reflect, for example, on what your values around travel and the holidays are.
  • On the one hand, you value peace, which is part of the reason why you’re hesitant to travel for the holidays—it just adds so much stress and complexity to a time that, in your opinion, should be calm and peaceful.
  • But as you reflect on other values you have around the holidays, you realize that another value you hold is loyalty—specifically, loyalty to family, both your immediate family and extended family.
  • The more you reflect on this value, the more you start to remember how important it is to you that your kids spend quality time with their grandparents and other extended family who live out of state.
  • As a result, your resistance to traveling for the holidays isn’t quite as strong as before. In fact, while you’re by no means sold on the idea of traveling, you feel more confident in your ability to talk about it with your spouse in a calmer, more open way.
  • Now, as a direct result of reflecting on your values, your resistance to at least having that difficult conversation is much lower than it was even 10 minutes ago.

Values are a powerful source of motivation. If you need a little more motivation to have a difficult conversation, consider what values you hold might be related to the topic of the conversation and spend some time reflecting on them.

You might find that you don’t have to push quite so hard to have that difficult conversation because your values are pulling you toward it.

All You Need to Know

At the end of the day, the real reason we avoid difficult conversations is because we’re not very good at managing our own difficult emotions.

Whether it’s anxiety, shame, anger, or grief, whatever emotions are holding you back, the key is to get curious and work with them rather than avoiding them.

Here are 5 tips to get you started that we talked about:

  1. Identify all the emotions at play
  2. Validate those emotions
  3. Write out your difficult conversation before it happens
  4. Clarify your conversation goals
  5. Reflect on your core values


Add Yours

I honestly appreciate guidelines of emotional intelligence and the methods to apply in real-life situations.
Please continue to educate and uplift me while rebuilding my mindset.

Are personality tests accurate? Does your personality drive your thoughts and thus your emotions?

Thank you Very strongly for this article…very well-worded with precise ideas for bringing out tough subjects. Thank you ????

Thanks for the article, Nick! Honestly, I learned a lot from your articles. They really saved and awaking me. Please continue to educate us.

Bonus points: Having to have one of those difficult discussions… But you ALSO have Borderline Personality Disorder.


I always fear LOCKING UP (going mute) or dissolving into tears. Either way, nothing good comes of it

I think that you’re way over simplifying this. I agree on the why but those things in no way shape or form are going to lessen the blow or make it easier. Especially with a high fear of rejection.

I have been avoiding two difficult conversations with my husband for 10 years! I think not having them is disrupting my sleep! This article has given me a shred of confidence that I can finally do this. Thank you!

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