6 Practical Tips for Having Difficult Conversations

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This was originally published as a Mind of Steel Newsletter. It’s one email a week that helps you build mental strength. Sign up here (it’s free).


No matter who you are, you’ve had at least one difficult conversation in your life.

You know the type. It’s uncomfortable to bring up, even worse to go through. You stress about it for days, weeks, or months beforehand, and usually after as well. It usually involves talking about something very uncomfortable with somebody you’re either very close with, or not close enough.

From STD talks with your partner or breaking up with someone to asking for a raise or coming out to your parents, it’s stressful to say the least. How do you bring it up? How will the other person respond? Will your relationship change?

You’re unsure of everything but one thing — this is important and needs to be talked about.

Last week, I’ve had to have a number of tough conversations, both at work and in my private life. Like everybody else, I dread tough conversations because… well, they suck. There’s nothing good about them. No matter what you think, you have 0% knowledge of how the other person will respond. Their reaction may be much better, or much worse, than whatever you expect.

But I’ve had enough such conversations in my life to learn a few things from them. These pointers help me go through with them with much less stress than I used to.

1. Be completely sure about your “why”

The most important absolute of difficult conversations is that you need to know, with a fiery dedication, that this conversation is important. Even if the other person doesn’t agree and doesn’t want to talk about it, you must.

No matter what, you must never back down from having such conversations because they are too hard or uncomfortable. As the Jerzy Gregorek quote goes: “Hard choices, easy life. Easy choices, hard life.”

The alternative is that the dreadful, gut-wrenching feeling you feel right now will keep growing. Once it grows too much, it can transform into hate, regret, or any number of things. By avoiding these conversations, you’re not solving the underlying problem, just postponing the inevitable.

The longer you wait, the worse it will be once it finally happens. Don’t wait for the “perfect time” or the “perfect settings.” The perfect time is now. As for the setting, well…

2. Prepare the scene

Important discussions require a time and a place. Don’t try to bring them up casually, while driving with your spouse or passing your boss in the office hallway. Inform the other person you’d like them to put aside some time for an important discussion, but DO NOT make a big deal out of it. Telling someone “I have something serious to talk about”, they’ll think the worst and will enter the discussion anxious and flustered.

Instead, say something like: “Hey, can you set aside some time for me? I’d like to talk to you about something and I don’t want us to get disturbed.”

If possible, never have the conversation on your home turf. Either visit the other person in their home or pick a neutral place, like a secluded coffee shop. You will later see why this is important.

3. Have the conversation in person

I know you want to avoid this because it’s harder, but suck it up! Telling someone in person shows them not only that you respect them, but that you’re not afraid of facing whatever they throw at you (even if you’re shitting yourself from the inside).

This also allows you to pick up subtle clues from their body language. That way, you can adjust your message based on their reactions. If meeting in person is not possible, schedule a video call, so you can at least see their face. No texts or phone calls!

You might think you’re taking the easy route, but by avoiding a face-to-face conversation, you are disrespecting the other person, which is a surefire recipe for an unpleasant reaction.

4. Don’t beat around the bush

I used to do this a lot. I’d sit someone down and knew exactly what I wanted to talk about, but to “prepare” them, I’d give long intros and disclaimers (which would only make them more anxious). Don’t make the same mistake. Your first sentence should be: “I want to talk about X” or “I want to tell you that I am X”.

No introductions or “before we start”. Just get to it. It’s harder at the moment, but trust me, it’s always the better option, no matter how unpleasant.

Also, don’t give out monologues and try not to justify your actions too much. Keep it as short as possible and then let the other person respond.

5. Keep the conversation civil

The other person may engage you in a calm, rational discussion. What’s more likely is that they will get angry, feel attacked or insulted, yell at you, get defensive… the works.

You can hope for the best, but in the end, you can’t determine someone else’s actions. No matter how the other person responds, do your best to avoid stooping to their level and try to steer the conversation back to civility.

If they keep following in the destructive path, be direct: “I am not interested in having a screaming match with you. We don’t have to agree, but let’s talk in a civilized manner. Preserving our relationship is more important than X.

6. Give the other person time

In most cases, the conversation will never be completely finished on the spot. You just shocked the other person with unexpected news and, while you’ve had time to prepare and know what you’re going to say, they haven’t. They’ll feel overly emotional and might say the wrong things in the heat of the moment. Continuing such conversation is a waste of time and energy, and makes everybody involved feel shittier.

When you realize things have gotten out of control, say something like: “I know this is a shock to you and that you weren’t prepared for this. Let’s take a few days or weeks to calm down. We can meet again and continue this discussion with cooler heads.”

Then, even if the other person doesn’t agree and wants to keep fighting, get up and leave. This is why it’s important to be anywhere besides your own place, as you can’t leave your own home.

Then wait. Wait for the other person to reach out, they usually will. If weeks pass and you still haven’t heard from them, send them a message asking if they’re okay and try to see if they’ve calmed down or if they’re still furious. Once the passions have subsided, meet again and have a more productive talk.

This outline should work for all difficult conversations. It won’t be literally applicable to all situations (e.g. you can’t walk away from your boss), but the underlying lessons hold true regardless of the situation, person, or the topic of the conversation.

No matter how bad things get, remember to stand your ground: this is important and it must be discussed. Even if the other person tries to attack you or dismiss you, stand up for yourself. Don’t let them treat you like shit, but don’t get sucked into pointless arguments. Always aim to be the calmer, rational side.

If you want more lessons like this on how to build and keep a strong mindset, grab a copy of my book Mind of Steel Handbook: The Essential Rules of Mental Strength.

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