Tip #100: How To Have A Difficult Conversation

Tip #100: Know that it’s going to be okay.

The why: Have you ever had to have a difficult conversation? A conversation that makes you want to run away and begin a new life in Outer Mongolia? A conversation where the very thought of having to have it sends your heart thumping at the speed of light?

I’m sure we all have.

Whether that’s with a friend, a teacher, a colleague, a waiter who brought you the wrong order, difficult conversations are a part of our day to day existence.

But, for someone who has anxiety, they can be as scary as giving a speech to an audience of 100,000 people.

I used to think that I was the kind of person who didn’t shy away from the hard things, who took ownership of mistakes and who didn’t back down from standing my ground.

However, after recently evaluating how I have reacted to certain events in my life, I realise that I am not always so good at practising what I preach.

Because, truth be told, it’s terrifying. If a friend has done something to hurt you, or you feel you’re letting your boss down, or if you feel like you’ve done something to hurt someone else, the idea of having to have that chat, to hear something you may not want to, to own up to making an error, can be too much.

So instead, silence, and in that silence, the problem often grows far, far worse.

For instance, if someone is consistently acting in a way that upsets you, it may be that you wish to avoid confrontation at all costs. You let them continue. But what happens then?

They may not realise that what they’re doing is impacting you in such a way, so they carry on, and slowly but surely that friendship fades.

Difficult conversations are, by nature, difficult. But so worthwhile to improve your life, and help you take ownership of your life.

Standing up for yourself, accepting and making right your wrongs and sorting out your problems are the keys to a happy life, and for experiencing true personal growth.

So, here are my top tips on how to deal with them:

Number One – Don’t Be Confrontational

Having difficult conversations is hard enough, and often people assume that you have to prepare for them as you would prepare for entering a war zone.

Absolutely not.

You should never go into a conversation in a confrontational manner, no matter how angry or upset you are. If you come in hot and outraged, the other person will immediately go on the defence. No one likes to be told what an awful person they are

If you come in hot and outraged, the other person will immediately go on the defence. No one likes to be told what an awful person they are, and if you offend them or their ego, you’ll never get through to them.

Instead of arguing, try effective communication instead. You may not win a fiery debate, but you can win someone over by remaining calm and courteous.

See the difference in these two approaches:

“You’ve been doing this thing all wrong, you’re so incompetent and you bring the entire team down!”

If you say this, the person is likely to become angry and dejected, and possibly even retaliate, escalating the situation.

“You do a lot of really amazing work, and are a really strong asset to the team. However, there is one slight area with room for improvement. May we try it this way instead?”

If you say this, the person is likely to feel good about themselves, and be more receptive to your point of view.

Number Two – Be Understanding

It is very easy to see things from one perspective. Your perspective.

Even if we see ourselves as being selfless individuals, we often still believe that we are at the centre of the universe.

So, when you feel the need to have a hard conversation with someone, try to first think about the situation from their perspective. What have they got going on in their lives that might be affecting the way they act? What are they like as a person? Is it truly solely their fault?

If you try to understand them, it will be easier to know how to deal with them. Each person is very much unique, and it’s important to bear their idiosyncrasies in mind when thinking about how best to approach them.

Understanding also sets a precedent for the tone of the conversation. If you are receptive to them, they will (most likely) be receptive to you, and appreciate you taking the time to work them out.

For instance, try saying:

“I know that you’ve been having a rough time at work recently, and I appreciate you’re under a lot of pressure and am grateful for all you do, but I would still really like it if you could help out at home a little when you have the time. Can we talk about a chore schedule?”

Number Three – Rehearse

Pretend like you are a famous actor, about to perform a Shakespeare play at the Globe Theatre in London.

Rehearse what you’re going to say.

Of course conversations don’t always go to plan, but for the anxious mind, having an idea of what you’re going to say and how you’re going to say it can reduce the stress of the situation.

This is because you feel more clear and in control, and are less likely to say things you later regret and worry about.

It’s really helpful to have ideas about the things you really need to get off your chest before you let them out into the world, because you can’t take back words, as much as you may want to.

It also means that you won’t later remember something important you wanted to add, but forgot to say.

Number Four – Realise It’s For The Greater Good

You have to remember why you’re doing this hard thing.

If your friendship or relationship is worth it, it is always worth trying to fix it. It’s for the greater good.

If your work environment or job is worth it, it is always worth trying to fix it. It’s for the greater good.

If you got the wrong order and are going to miss out on your favourite good, it is always worth trying to fix it. It’s for the greater good.

You can’t live your life afraid to speak up and speak out for yourself, or else you will never really have a chance to grow and change, or sort out the issues in your life.

Take back control of your world.

These conversations may be hard in the short term, but you know what’s harder? Accepting negativity that could be changed into positivity.

Number Five – Accept That Things May Not Change

Sometimes you have to prepare for the worst, and people with anxiety are really, really good at planning for worst-case scenarios.

In truth, sometimes you will have a conversation with someone, and it won’t go well. They’ll continue to be mean, be defensive and rude or try to gaslight you into thinking you’re the bad guy.

What you have to remember is that if someone doesn’t respond to your reasonable request, if someone doesn’t want to accept their mistake, if someone doesn’t wish to work on your relationship, then you know what?

Skrew ’em.

You don’t want or need people like that in your life. As hard as it may be to accept, everything is a matter of give and take and compromise, and if someone can’t meet you halfway, then they are not worth it.

Number Six – Make Sure It’s Really A Conversation

When confronting someone, or admitting you’ve made a mistake, it can be very easy to make commands of someone, to recite an entire soul-destroying speech or a self-damning account of events, to feel righteous or subservient.

These factors can often mean that we’re not actually having a productive conversation, we’re simply saying what we have to say, and being too afraid of the response to properly listen.

Make sure that to truly solve the problem, you are really communicating, really engaging with them.

You can do this by asking them questions such as:

“I apologise for this behaviour, what can I do in future to ensure this doesn’t happen again?”

“How do you feel we can work around this issue if it occurs again?”

This makes them an active and vested stakeholder in the conversation going well, and makes them more likely to want to come to a resolution. It also makes the other person feel as though they have some control and agency, making them more receptive and less likely to shut down.

Number Seven – Keep In Mind The End Goal

Whenever you’re about to enter into a difficult conversation, make sure you know what you want from the conversation.

Before you speak with them, think about what you want from the conversation, whether that be their forgiveness, them to stop leaving their muddy shoes on the carpet, or them to stop disrupting your work with hilarious videos of cats knocking things off tables.

Having a goal in mind will ensure that your conversation has a direction, and ensures that you stay on track. A hard chat without an end goal

A hard chat without an end goal is essentially a confrontational rant, a way for you to feel better about yourself in the short term, with no actual change.

It’s a lose-lose.

So, go out there, and politely yet firmly start taking back control.

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