5 Easy Ways to Ace Through a Difficult Conversation

It all comes down to preparation

Kunal Walia
Be Unique
6 min readSep 4, 2020

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Whether you’re about to break up with someone, resign from your current role, or tell your loved one about your plans to relocate to a different continent, the build-up will always be excruciatingly painful.

You know the conversation isn’t going to be easy. You worry about the tears, the unpleasant reactions, maybe even the anger that might come your way. And sure, while you wish you could fast-forward to the next scene, you know that’s not an option.

Perhaps you think you’ve just got to roll your sleeves up and get on with it. But you and I both know that a hurried approach potentially risks an even less favorable outcome. So how do you best approach these situations?

Well, having faced some of these instances not too long ago, here are a few tricks I’ve managed to learn along the way.

1. Press Pause for a Second — Do You Really Need to Say What You’re About to Say?

Sometimes it’s easier to let things slide rather than vent your frustrations. Many a time, you’ll be too caught up in your emotions — so much so that you’ll struggle to see the bigger picture. And if you act on your emotions there and then, there’s a high chance you’ll make a rash decision which you then go on to regret.

Don’t resign from your job because your boss told you that you could’ve done a better job at the last presentation. Don’t break-up with someone because they forget to buy you flowers at the beginning of every date — like they once did during the “honeymoon” phase.

It’s critical you don’t head into a battle that can easily be avoided. And the best way to do so is to actively request a second opinion from an outsider.

Seek the advice of a close friend or family member. Ask them if you’re being irrational. Find out what they’d do if they were in your shoes.

Your first step should always be to sense-check whether or not it’s worth going down the path of having a difficult conversation. Of course, in some instances this little sense-check doesn’t make much sense, in which case, let’s see what else you can do.

2. Go Out of Your Way to Purposely Distract Yourself

The only way the conversation will go well is if you’re able to convey what’s on your mind in a clear and logical manner. Doing so requires shifting your thoughts and emotions away from their current state of frenzy, and towards a place of tranquillity.

As such, it’s vital you give yourself a break prior to gathering your thoughts. Go for a walk, surround yourself in nature, listen to a podcast.

The aim is to take your mind off the situation such that you’re able to pinpoint what it is that you want to get off your chest. And why it’s so important that you do so.

3. Write Down Your Thoughts in Advance

Once you’ve taken a moment to gather your thoughts, it’s time to organize and edit them.

At this point in the preparation process, you want to be able to answer the following type of questions:

  • How are you going to begin?
  • What are your 3 key points?
  • What details are you going to skip over?
  • Do you need/have a back-up plan in case things go badly?

Personally, I find writing everything down extremely helpful. After I’ve separated myself from the situation and de-cluttered my mind with a long walk, I’d then open up my laptop, and begin typing.

And once I’ve laid everything out on the table, I’d look to organize the countless bullet points into a handful of key items. Sometimes, I’d even rewrite these 3–4 important factors to ensure I commit them to memory.

But whatever you do, never convince yourself that you’re better off “free-styling it” on the day. Walking into a tough conversation with the faintest idea around what you’re going to say, and how you plan on saying it, is simply a disaster waiting to happen.

4. Practice, Practice, Practice

Next, it’s time for a rehearsal. You want to come across as confident, but not arrogant. You’d like to show some concern for the other person (especially if you’re about to break up with them), but you also want them to know that your decision can’t be swayed.

In other words, you want to portray yourself as cool, calm, and collected — but you also want to feel cool, calm, and collected. And the best way to do so is by practicing and observing what you need to do differently.

Stand in front of a mirror and begin speaking. Record how you sound using your selfie camera. Or if you find that too awkward, close your eyes for a few minutes and imagine how you’d like the conversation to go. Embrace the power of visualization.

Spend a few moments re-creating the scenario in advance. It will help ease your nerves when the situation does eventually arise.

5. Before You Start Speaking, Do This

So you’ve done all of the above. You feel somewhat prepared. Everything’s laid out clearly in your mind. Well, now it comes down to how you perform on the day.

And so, when it’s eventually time to sit your partner, colleague, or friend down, and get everything off your chest, it’s crucial that all the preparation you’ve gone through beforehand doesn’t get hurled out the window.

In the heat of the moment, there’s a high chance you’ll rush your opening sentence, get flustered, or worse, go off-script and say something you shouldn’t.

As such, before you start speaking, always remember to take a long, deep breath. Sure it might look odd, but looking odd is way better than panicking and ending the conversation badly.

And besides, if the other person sees you physically calming your nerves, they’ll instantly know you’re about to say something serious. You’re sending a subtle signal to the recipient that the build-up to this moment hasn’t been straightforward for you. Often, that can prompt the conversation to start on a lighter, more comforting note.

A Quick Recap

Here’s a reminder of the 5 tricks to implement prior to entering into a tough conversation.

  1. Ask yourself, do you really need to say what you’re about to say? Sense-check with a close friend or family member whether you’re being irrational and whether you might be better off letting things slide.
  2. Go for a long walk in nature to de-clutter your mind. Give yourself time to gather your thoughts by stepping away from the situation.
  3. Write down what you’d like to say in advance. Structure your points. Use this as an opportunity to remember that if it isn’t worth saying, don’t say it.
  4. Practice what you’re about to say in front of a mirror. Get comfortable with imagining how the conversation might go.
  5. And most importantly, remember to take a deep breath. Don’t let the hard work you’ve put in through steps 1 to 4 go to waste. Give yourself the best possible chance of success by taking the time to prepare in advance.

The right preparation will always serve you well when it’s your time to shine.

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Kunal Walia
Be Unique

27. Finance nerd by day. Writer by night. Dreamer at all times. Finding new ways to learn. Sharing more ways to grow.