Stuck Before You Start: 5 Reasons Hard Conversations Stall

Amanda* typed out the same message and then deleted it. It was 11pm and this was the third night in a row she’d thought about sending this message. Her roommate had left dishes in the sink again, and she’d promised herself this time she’d actually say something instead of doing the dishes herself and seething about it. She tried rewording the sentence but eventually closed the app, put her phone face down on the counter, and went to bed with the message unsent. 

If you’ve rehearsed starting a hard conversation, you already know this isn’t about the dishes.

This pattern is more common than you’d think. I recently sent readers a poll asking if they’ve struggled to start a hard conversation, and 93% said yes, more than once. The rest said they’re in the middle of this struggle right now. Nobody was stuck on whether to have the conversation. The decision was already made. What they couldn’t do was start it. 

That gap between making the decision and starting the conversation is where most of us get stuck. And as a recovering people-pleaser myself, I know it well. It’s rarely just about not knowing how to start. It’s hard on many levels at once. I’ve narrowed it down to 5 ways it gets hard. If you notice other ways, let me know. I’d love to hear them.

1. You don’t feel ready 

But let’s get honest, you won’t feel ready, ever. When are we ever “ready” to start something not knowing how it will go or how it will end?

This reason is relying too heavily on readiness as a pre-condition to starting. Unfortunately, the “ready, set, go” approach only works when you know how it’s going to go. When other people are involved and the topic feels like it might start something big, the uncertainty of which directions the conversation is going to take is way too high.

Instead of relying on a feeling as the trigger to start the conversation, decide on a trigger condition to start the conversation, something like “Sunday afternoon” or “Next time [X] happens.”

2. You are trying to manage their reaction 

This reason becomes a problem when you are trying to game out how they are going to react. For each possibility, you’re looking for a way to say what you need to say without upsetting them or hurting their feelings.

This backfires because you don’t necessarily know how they are going to react. You might have an idea, but their reaction is going to depend on a lot more than just what you say. Things like how they are feeling when you bring it up and their thoughts on the subject will play a role you have no control over.

The trick to addressing this reason is to focus on what you’ll say, not how they’ll feel. You need to be true to your experience and feelings and at the same time express yourself in a tactful, respectful way. That’s it. Their reaction is their reaction.

3. You haven’t yet built an airtight case for your position 

I’ve talked a lot about over-explaining (see Why You Over-Explain). If you find yourself over-explaining a lot, it’s because you’re struggling with wanting the other person to agree with you or understand your position. But your experience is not up for debate, so quit trying to win it. Own it. It’s your experience, your preference, your opinion, and that is airtight enough in its own right.

Instead of finding reasons why you are right, make a decision instead. Talk about your decision, not the reason it is the right one. Focus on the decision you’ve made and how that decision works for you, not the reasons you made it or why the other person should agree.

I remember when I decided I was no longer willing to mow the lawn. It was in response to my husband’s unwillingness to cook dinner, ever. But, I didn’t give a reason for no longer being willing to mow the lawn. I just said no. If I said I was too busy, he would have said I could mow it when I was no longer busy. If I said it was too hot out, he would have said I could wait until it cooled off. And if I’d said, ‘not until you cook dinner,’ he might have cooked dinner once and then used that to justify why I should mow the lawn. See what I mean? I just stated my position and didn’t explain.

Often other people push us for reasons because they want to change our minds. This is another way our desire to be agreeable gets us in trouble. Don’t give examples or reasons, just state your decision.

4. You don’t have an opening line 

This is the most mechanical reason for not starting the conversation. How exactly should you even bring up the topic? Until you know that bit, the whole conversation is just an abstraction. An abstraction will remain an abstraction until you have a concrete way of starting it.

Here’s a short template for what to say:

• One sentence about the other person’s situation.
• One sentence about how it affects you.
• One request.

Here’s an example:

• Hey, I know you’ve been annoyed with me for several reasons recently.
• I feel your annoyance and it upsets me because it wasn’t my intention.
• Could we talk about what’s going on between us?

The nice thing about this template is the other person doesn’t feel like they haven’t been considered because you started with them. It makes it a bit easier for them to listen to you. By asking if they’d be willing to talk about it, you are (hopefully) getting their agreement right away. If they want to but can’t right now, I’d suggest setting up a time to talk later.

5. You assume it will end catastrophically 

The fear that I see getting in the way most often is that the conversation will start an argument that will end the relationship. This is usually fed by the fear that you may not be lovable or deserving of the relationship in the first place. Because you fear these things are true, anything that feels in alignment with these fears feels true, making the whole scenario feel likely.

This catastrophic thinking backfires, though, because it treats an unlikely outcome as almost inevitable. Depending on the conversation, that outcome may be at least feasible, but it is far from the only one and rarely likely. Remember, people (including you) are incredibly poor at predicting the future. 

The best approach to this problem is to consider other outcomes, not just the worst one. Also, consider how you might handle each one. For example, maybe the other person gets so mad they can’t continue the conversation constructively. In that case, suggest talking more later. Or, maybe the other person provides information you didn’t know before. It may shift your perspective. Be open to that possibility and suggest talking more later after you’ve had time to consider the new information.

If you hadn’t considered these as possibilities, if you only focused on the relationship ending, then of course it felt too hard to start. But, now you’re better prepared and no longer catastrophizing.

Summary

With all these reasons, I’m sure you can see why you might feel stuck trying to get a hard conversation started. The poll numbers bear this out. It’s genuinely hard. It’s not a character flaw or personal failing.

Amanda finally decided to take her roommate out for lunch and in the middle of their discussion matter-of-factly asked her to do her dishes before going to bed. Her roommate didn't get mad. She just said 'sure, no problem,' and they moved onto another topic.

Each of the ways it can be hard to start also comes with ways to address the problem. This should make starting hard conversations a bit easier, even if having the conversation is still hard. Remember, it’s better to talk about what’s bothering you rather than bottling it up or avoiding the issue. You never know. The other person may also have been thinking about the same issue and will be glad to talk it through.

If you’d like help figuring out your opening line, get my Effective Communication Workbook for People-Pleasers.

*Amanda is a composite of many clients with variations on this same issue.