
Those conversations you keep putting off…you know the ones I’m talking about. The uncomfortable, even painful ones. But avoiding them is also uncomfortable, giving you a nagging feeling that makes it hard to focus on anything else. Addressing these issues will not only give you peace of mind but will lead to deeper, more fulfilling relationships. Navigating difficult conversations might seem like an elusive skill. Thankfully, it’s not as hard as you think.
What conversations are you avoiding?
“Miss Findley, do you have a minute?”
My student stood hesitantly in the door of the teacher’s lounge. She saw that I was shuffling through a stack of papers.
“Oh,” she said. “If you’re busy, we can talk tomorrow.”
I nodded, relieved she was giving me an out.
Then I frowned. “Well…” I began. Tomorrow I actually wouldn’t have time.
“You’re busy then, too?” Implicit in that statement was, You’re avoiding me, aren’t you?
“Let’s just talk now,” I replied, resigned.
You see, I knew what she wanted to discuss. She’d gotten a B on her essay, and in her mind, a B might as well be an F. But (anticipating that she’d be upset), I’d already written a lengthy explanation on her paper indicating why she did not get an A.
What more was there to say?
My unwillingness to talk to her boiled down to two factors:
- Assigning a fair grade on an English essay is tricky enough without having to explain why you decided on that particular grade. It’s slippery and abstract, unlike a math problem that’s either right or wrong.
- These types of conversations annoy me because?I was once that student. Obsessing over every B and A-. But where did this get me? Nowhere. Even if I still fixated over numbers, the “impressiveness” of your GPA shows very little congruence with that of your yearly income. This is demonstrated not just by my own story but countless others.
In retrospect, though, these were poor excuses for my avoiding the conversation. What matters is that my student feels heard. That she feels validated.
And that’s exactly what happened. It turned out to be a quick, painless conversation that ended on a bright note. She seemed satisfied with my explanation and my recommendations for getting an A on the next essay. I felt better for addressing her concerns and not avoiding her.
Why not just talk to them and get it over with?
We do this a lot in life. We put off conversations that we think will be uncomfortable.
Of course, this was a mild example. Sometimes, we fear that our relationship with our child, spouse, friend, or boss will be threatened if we attempt to communicate our true feelings.
Maybe we have something to say that the other person won’t like.
Or maybe we don’t know how to phrase what it is we want to say. We’re afraid that we won’t sound like the articulate beings we are in our heads. That the words will come out garbled. Maybe we’ll convey the opposite of what we meant. Maybe we’ll come across as an idiot or an insensitive jerk.
But as you’ve probably noticed, putting off these conversations doesn’t improve matters.
What resists persists.
Avoiding uncomfortable conversations creates tension within yourself because the longer you put it off, the larger your fear looms in your mind along with the guilt of putting it off. And it creates tension with the person who’s supposed to be on the receiving end of this conversation. They’ll wonder why you’re avoiding them.
Navigating Difficult Conversations: 4 Tips
1) Journal about it
What exactly is it that you’re afraid will happen as a result of this conversation?
Now, I’ve been a career avoider. But I wasn’t just avoiding particular conversations because I feared discomfort. It was because the emotions were buried so deep within me that I literally didn’t know how I felt about the situation.
By doing the journaling exercises in Debbie Ford’s The 21-Day Consciousness Cleanse, I found that the process of writing out all my concerns, anxieties, and unrealized fears worked to get them out of my head and give me clarity.
It also helped to minimize my worries. When I saw them on paper, they looked trivial, even silly.
2) Tune into what you’re feeling
Take the time to listen to and acknowledge these emotions for what they are. Sometimes uncomfortable emotions like sadness, guilt, or anger can be hidden even from ourselves.
Surprisingly, just identifying your emotions?can help quiet your head. As?Ronald J.?Frederick writes in Living Like You Mean It, “Once we recognize them and label them for what they are, they often stop vying for our attention; the agitation they generate decreases, and we feel calmer.”
Once you invite up any negative feelings you have, you can release them. This helps you to enter the conversation with a clear head.
3) Identify your goal
Imagine the conversation unfolding in your head. Plan out what you want to say.
Most importantly, though, keep your purpose in mind. What is your goal both for the conversation and for your larger purpose?
For instance, maybe you’ve noticed your teenager daughter has fallen in with a bad crowd (or if that teenager was anything like me, spends an unhealthy amount of time alone).
Obviously, her immediate reaction will be hostility and defensiveness. But your short term goal is to get her to listen to everything you have to say without storming out of the room and not talking to you for a week. Your larger purpose is to help her recognize that you have her best interests at heart (even if she won’t admit it) and to convince her to act in ways that are more aligned with who she truly is.
Once you reframe the conversation so that you’re seeking to help the person or at least come to some sort of mutual agreement, rather than trying your hardest not to upset or enrage the person, you’ll feel much calmer about what lies ahead.
4) Prepare a conversation “toolbox”

While having the actual conversation, there are pointers you can keep in mind that will help it run more smoothly. This article mentions some helpful guidelines for navigating difficult conversations such as avoiding over-generalizations like “always” and “never,” sticking to the topic at hand (i.e. not dredging up past issues), dropping your assumptions, and using “I feel” statements rather than “you.”
This last point is a particularly good one. In middle school, we had a substitute teacher who taught us the importance of avoiding “you” statements. Of course, as middle-schoolers we were a bit baffled and there were certainly some sarcastic comments.
But guess what? I still remember his advice. And it makes sense. When I hear “you,” I immediately get defensive. But I can’t argue with someone else’s feelings.
Now, you might not remember all these pointers in the heat of emotion. Trust me, I’ve done most of the things that the list said NOT to do and then spent hours rehashing how the conversation should have gone.
But the more you practice having these types of conversations — and bringing up issues when they bother you, rather than letting the emotions build up (or avoiding the person who’s trying to have this conversation with you) — the more adept you’ll become at navigating them.
How do you prepare for challenging conversations? Or conversely, have you had any conversations that did not go so smoothly, and what did you learn from the experience?
Navigating these situations can be very difficult. Thanks for the great tools!
Thanks, Sheereen! Yes, I think the difficulty comes from the fact that we don’t always feel we have the right tools and don’t know where to start, so I’m glad you found the tools helpful.
The point you made about having the difficult conversations leading to more fulfilling relationships is so important. So many people avoid addressing conflict thinking they’re protecting the relationship/person, but the opposite happens over time. Assertive ‘I’ statements, over ‘you’ statements is also an invaluable tool, and learning to stick to the goal of the conversation. You’re right, difficult conversations are hard for all of us, but we can definitely keep developing those skills. I try to do a lot of the steps you’ve suggested in preparation for a difficult conversation and find them very helpful. ‘Perspective taking’ makes all of those steps a lot more effective, but that in itself is a complex skill to master. Thanks for this!
Thank you, Sunday, for reading and for your thoughtful comment! Yes, I’ve certainly made the mistake of not bringing up tough conversations because I think it will hurt the relationship. But as you said, it’s actually the opposite because it leads to resentment and tension. Also, having these sorts of conversations actually enriches your relationship and makes it stronger.
This is a great article! I avoid conversation like the plague. I will definitely be trying some of these. Tuning into your feelings about it is so important!
Thanks, Megan! Yes, for years, I’ve avoided those types of conversations too and it’s still something I battle with. Tuning into your feelings is definitely important because sometimes when I go into the conversation without a clear idea of what I feel or what I want, I say the opposite of what I mean and make the situation worse!
Really helpful post. I love the journaling idea. Putting it all down on paper can often really help us think things through. It really does bring clarity and sometimes we come up with a different perspective altogether.
Love your posts.
Thanks so much, Liz! Yes, journaling really does help to bring clarity to a situation and to your feelings in general. It can help bring up unconscious doubts and fears that you’ve been hiding as well as help you to formulate a more clear idea of your goals.
”What resists persists.” is so true. Journaling is also what helps me in this kind of situations. Instead of resisting, I try to understand it and accept it.
Yes, Ivana, acceptance is such a key concept!
This post is great! So true and relatable and great tips too. I often procrastinate conversations. But sometimes I do, just to make sure it’s not just a misunderstanding or it’s actually worth the hassle. It can go both ways sometimes. Thank you for sharing this with me!
Yes, Teresa, you’re right that sometimes it is just a misunderstanding. Either way, it’s better to talk about it and to clear the air than to have the tension linger. Thanks for reading!
So many times we put agonize over a conversation, building it up to a huge conflict in our heads, instead of just having it. The truth is, most times if we just took the bold step and go it over with, it wouldn’t be as big of a deal as we thought it could become.
Absolutely, Blythe! It’s the anticipating that makes it so much worse, almost like it’s collecting all these heavy emotions that weren’t initially there.
Oh yes! Very useful points.
Thanks, David!
Great article. Most of us really do run from uncomfortable conversations instead of just facing them. I love number 3 on your list identifying your goal and re framing the situation. The best kind of information – useful and practical!
Glad you found it helpful, Crystal! Yes, for years I’ve been the type that runs from these types of conversations, which only made the pressure worse. But when I face them as soon as the issue arises, they actually go pretty smoothly.
My problem has always been that I?m overly diplomatic and avoid the difficulti conversations. Really useful post.
Thanks, Phill. Overly diplomatic — that describes me as well. I have a difficult time talking about things that bother me, to the point where it practically has to be pried out of me! But once it’s out, it feels much better.