How To: Breakthrough Conversations

I was going to call this “difficult conversations,” but I firmly believe that confrontation and feedback don’t have to be difficult. Oftentimes the most difficult part happens in our own heads; we’re afraid to speak up, don’t want to start a fight, aren’t sure if we deserve what we want to ask for.

This is a guide to having open and honest conversations - especially when it seems difficult. I’ve used this process with romantic partners, friends, family members, and almost constantly at work, where many of us are thrown in with people who have different values and communication styles.

Use this approach when you want to reset the way you relate with another person, when they’ve been doing something that bothers you for a while, when there’s something not quite right, when you’ve been afraid to bring something up, when you get suddenly angry or upset, or in a variety of other circumstances.

Note: Throughout this guide I will refer to “the other person.” Most conversations around “difficult” or emotional subjects should happen 1:1. There are exceptions to every rule, and if you feel your particular breakthrough conversation needs to happen with a group of people, everything else still applies.

0: The only thing you really need …

The core of all successful communication is respect. Respect means that you do not expect to control or manipulate another person into doing something you want them to do. You will present them with your feelings, with your concerns, and with options that seem reasonable to you. They will choose whether to receive them. And then in turn, you are free to choose how to respond to that. Respect also means that you understand that your reality is not everyone’s reality. You will listen to the other person’s feelings and concerns, decide how you’d like to respond, and respect their decisions.

Respect is at the core of this process. You can’t anyone do something they don’t want to do. But these tools will help you approach a conversation in a way that gives both participants the best chance at real communication and a useful conclusion.

1: Self-soothe

If emotions are running high, comfort and calm yourself before having a conversation. A quick meditation or just a few deep breaths can help. Other times, you may need to take some more time before confronting the issue.

Remember that we are all responsible for our own emotions. No one can “make” you feel anything. It’s easy to feel like we need something from someone else when we’re in the middle of reacting. Ask yourself, what can you do to make yourself feel better first? Then do it.

This isn’t about letting the other person off the hook for their actions. It’s about making yourself feel better rather than setting out to make someone else feel bad. When you approach a “difficult” conversation or confrontation from a place of inner peace, where you are truly trying to create deeper understanding rather than blame or inflict pain, then you open the door to true communication. And, when you take full responsibility for your own well-being, you create a closer relationship with yourself.

2: Investigate

Investigate what you’re feeling. Ask yourself:

What action triggered this reaction in me?
What core beliefs are contributing to this reaction?
What fears are running through my mind?
What do I need from the other person to feel better?
Is this a reasonable expectation?

The goal of this is to strip away the parallel minutiae that we may confuse for an actual cause of our distress or anger, and to determine what is the real issue at hand that we need to discuss. Usually, someone says a certain word or phrase, or tells us about a plan, or asks a question in a certain tone, and it triggers a story inside of us. Get in touch with both the triggering event and the story, and resolve to be completely honest.

3: Set a Timeline

Sooner is always better than later, but privacy and bandwidth are important factors. If possible, take a few minutes to calm down and review your needs and then share your feelings. If you or the other person are busy or you’re in a public setting, wait for the right moment or even schedule a time to talk. If this is something you’ve already been sitting on for a while, it might be worth it to take a bit longer to make sure you have the right words.

Regardless, make a commitment to yourself right now to discuss at a specific time. Your feelings, and any communication issues, will only get worse if they aren’t confronted.

4: Choose Your Words

Now that you’ve found your inner peace, it would be a shame if the first few words out of your mouth threw your conversation partner into the same triggered and reactive space you were in. First, find a way to indicate that the conversation is important but not intimidating. For a personal relationship, I usually go with “Can we talk about something?” In a professional setting, I’ll say that I’d like to offer some feedback or discuss our working relationship.

Then, identify the key points you want to communicate and find a way to broach the subject that isn’t accusatory or demanding. The four-part nonviolent communication process by Marshall Rosenberg, PhD., is a great place to start for your opening sentences (see below).

5: Have the Talk

State your observations, feelings, needs, and requests, and then let the other person respond. Be open to what they have to say. As the conversation progresses, be honest, but focus on “I” statements, not “you” statements. Come back to your feelings and needs, and encourage them to share theirs.

Every conversation will go differently. Try to remain calm, and ask for a break if you need one. Remember that you are here for communication and understanding, not control.

6: Move Forward

Ideally, you will have reached some sort of conclusion by the end of your conversation, but not always. Sometimes, we have to be satisfied with sharing our feelings, and our requests aren’t agreed to. Sometimes, the request will just be listening in the first place. Whatever happens, you’ve communicated your truth. The rest is up to you.

Congratulate yourself for being so brave! We are conditioned to be dishonest about our emotions and hold back from everyone around us. Vulnerability is the ultimate strength.

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Cover photo by Sergey Turkin on Unsplash