How to Have Difficult—But Necessary—Conversations

how to have difficult conversations

We’ve all avoided difficult conversations, or worse, engaged in toxic communication patterns that made things worse. The cause for it was a disagreement with a friend, a loved one, or perhaps with someone at work. Wherever it was, you probably experienced some stress about dealing with it. Well, you can relax, because you’re not alone — and help and wisdom are abundant. Here’s how to have difficult conversations with people in your life when disagreement (inevitably) occurs. 

How to Have Difficult Conversations

Be Honest With Yourself

Most relationships have tensions from time to time. We’re more likely to resolve or ignore them at work because we have to get the job done. In our personal lives, however, we only have ourselves to answer to. That lack of accountability can let us off the hook, and so we rationalize the situation. It results in us putting up with it until it gets worse. So, when you acknowledge to yourself that something is amiss, you’re on your way to sorting it out. The next part is about recognizing the exact problem.

Trust Your Gut Feeling

You know you need to have that conversation, but you’re unsure what the real problem is. Did it start with an argument or upset, or was it a feeling that something’s not quite right. This Landmark Education model of an upset may help you ask the right questions to get started.

What happened? Was it related to one, two, or all three of these reasons?

  1. An unmet expectation?
    1. Did you expect something to happen that didn’t?
    2. What did you expect someone to do or say that they didn’t?
    3. Did something happen that you did not expect to happen?
  2. A thwarted intention?
    1. Did you try to make something happen that didn’t work out, fell flat, or turned into something else?
  3. Undelivered communication?
    1. Did you try or want to say something, but couldn’t?
    2. Or, you said some of what you wanted to say, but not all of it?

Once you pinpoint the issue, the next steps get more straightforward.

how to have difficult conversations

What’s Stopping You?

Many experts like Brené Brown, Simon Sinek, and Judy Ringer talk about the blocks that initially stop us. Again, once you acknowledge your part, your actions get simpler. Check out these example reactions. Do you recognize any of them?

Fear of

  • being judged;
  • getting it wrong;
  • making the situation worse;
  • losing relationships;
  • looking bad, silly, emotional;
  • admitting that we’re wrong; or
  • that unexplainable feeling in the pit of our stomach that stops us cold.

Regardless of these obstacles, it is still possible to reclaim your peace of mind. And as ironic as it may sound, difficult conversations can improve relationships.

Guiding Stars

Your purpose, values, and attitudes are essential in every aspect of life. In relating to others, they are crucial. But they’re like the north star guiding your way — especially when you’re feeling nervous or challenged. So be clear about your intentions and values first. Then set an attitude of curiosity and inquiry to lead your way.

What is your purpose of the conversation? Is there something you want to accomplish?

Do you want to restore your friendship or to criticize them? Are you more interested in being right or being in love again?

What do you value?

If it is integrity, then be honest. Compassion? Then be kind. And if it is understanding, then listen.

What are your assumptions about the person? Are you being curious about their intentions?

Have you decided things about them before you know their point of view or the facts? How do you know they don’t care anymore? Did they know you felt like that?

Getting Started

So far, you have:

  1. Figured out the source and reason for the conversation;
  2. Got past what’s been stopping you;
  3. Identified your purpose, values, and attitude.

Now, you’re not sure how to start. Below are some examples of conversation openers you can use — but choose your time wisely. If necessary, set it up for a later time. A well-rested and properly fed time of day is better than the tired and hungry hours.

how to have difficult conversations

Conversation Openers

  • I need your help with what just happened. Can we talk about it?
  • Hey, I’m stuck with something about _______________. I’d like to hear your thinking on this.
  • I’d like to talk about ____________ with you, but first, I’d like to get your point of view.
  • I need your help with something. Can we talk about it (soon)? Today, this afternoon?
  • When we’ve finished dinner tonight, I’d like to know what you’re thinking about _______. Okay?
  • I’d like to talk about ________________. I think we may have different ideas about how to ________________.

Getting Beyond the Opener

Once the conversation begins, our natural tendency is to be vague and hurried. It can be awkward and uncomfortable, so remembering curiosity and inquiry at this point is very useful — and so is breathing!

Be Specific

Getting to the specific point, as Simon Sinek suggests, creates clarity immediately. Using the Feelings, Behavior, and Impact (FBI) method makes the issue clear for both parties to respond to:

“When you raised your voice at me yesterday, I got nervous and couldn’t think straight. I’m worried that if you keep yelling at me that way, I’ll stop trusting you.”

Feelings — I got nervous and couldn’t think straight

Behavior — you raised your voice at me yesterday (specific action and specific day)

Impact — I will stop trusting you

Be Patient

After you have said your FBI statement, stop talking. Breathe and listen to their response.

As Sinek states, you may have to repeat your statement a couple of times for them to understand the impact of it. And that’s okay.

Be Clear

Staying the course with your intentions, values, and curiosity throughout the process will reveal the next steps. It may be that you have a request or ask of each other. It may take some problem solving by both of you. Whatever happens, you must pat yourself on the back for being courageous to lead the way in your relationship.


Before you end the conversation, check-in with your intentions. Did you complete what you set out to do, or is there more to say? If it went well, congratulations. If either of you needs more time, arrange it. But know that you have laid the best groundwork possible for your continued conversation and a better version of that relationship. And that’s very well done.

Having difficult conversations can be emotionally draining, but dealing with gaslighting tactics are on a whole other level. Here’s how to spot emotional gaslighting in relationships.


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