10 Tips for Dealing with Difficult Conversations

Methods for better navigating those hard chats.

Difficult conversations. Annoying chats. Cringe-worthy interactions and intense meetings.

Whether in work or life, in relationship with loved ones or in dealing with strangers, these are moments we all must navigate.

I am not one to enjoy confrontation. I'll rarely pick an argument, and even if something has irked me, unless it's essential to flag it, I will try to let it go. I don't like to upset or annoy; but I do like to keep the peace and see everyone else with a smiling face.

Sometimes, this is a helpful way to approach things. Cooling rather than inflaming heated situations; being considered in my responses.

At other times, I am increasingly aware of doing myself a disservice, whether it be because I am left internally raging having not spoken my truth, or because I am walking away with less than I deserve.

And so, like many things we navigate in life, it’s about finding a balance.

That said, I do think there are some general approaches we can embrace and use to our advantage in times of hard talk, whether it's a question or conversation that's seemingly come from nowhere, or one for which we have time to prepare.

Here are 10 tips that I have picked up along the way, and try to put into practice. Quite possibly nothing here you haven't heard before, but sometimes it's good to see it all down in the written word, as a reinforcing reminder.

1. Find some empathy

Regardless of the conversation, who it's with and when it arises, consider where the other person is coming from and where are they trying to get to.

In moments (or whole terms!) of political disagreement, coming up against opposing thoughts and feelings can be challenging. It can leave you feeling helpless and dumbfounded, and wondering how you’ll speak to your friend/colleague/family member ever again.

But could you steer the conversation to better understand their motivations, and share yours, rather than focusing on the crux of the incompatible takes?

I think a lot of people for example, whether they have children or not, want to see a better future for the next generation. We may all just have different ideas about what that looks like.

But if you can start by, or even pause to dig into, some sort of common ground, the conversation is likely to be kinder and, I think, your points are all the more likely to land.

2. Take a breath

I don't buy into the ethos that if it's not an immediate yes, it’s a no, but I do buy into the notion of giving yourself time to pause, reflect, and then respond. Just because someone asks something of you in the moment, even in person, it doesn't mean you owe them an immediate response.

Needing to check the diary, check your work schedule, check about childcare, check in with your partner, check your bank balance, are all perfectly acceptable reasons (not excuses!) to offer someone there and then, before following up in due course with something more concrete.

Don't feel pressured to make a call on something you're not ready to, even if your boss/friend/relative is putting the pressure on. Take a breath, have a think, then respond in a more measured way.

3. Do your research and outline your evidence

Sometimes people will do something for you because they see it as the right thing to do.

Other times, they will do all they can to avoid it. In such times, you need to ask for what you want, and outline why you think it's right.

It might be a pay review. What are you asking for and why? What value have you delivered? What have you made happen? Spell it out, even if it feels entirely obvious, and send in advance of an IRL conversation if it feels appropriate.

It could be about asking for a refund. What's the company policy? When have they paid out before? Is the claim entirely within the terms? I'll tell you from experience that if you're dealing with RyanAir, this is likely a battle you will lose, and it gets to a point where the annoying chats (by phone, email, chatbox…) are no longer worth it. But at least you'll have tried.

On a more domestic note, it might be that you feel it's someone else's turn to do the dishes. They won't always clock this; perhaps they think you LOVE washing those plates. Ask them outright, tell them why you're asking (how many times did you do them last week? is there something else you need to do tonight?) and hope for an enlightened response.

4. Choose the moment

Where possible, try to use a bit of emotional intelligence, for yourself and the other person, to opt for the best time to raise or enter into a potentially difficult conversation.

If your boss has just walked out of a stressful meeting, they're much less likely to feel favourably towards your suggestion of a meeting to discuss a pay review, compared to catching them after a call celebrating a team win.

If your partner or flat mate is hungover, it ain't the time to ask about the dishes; wait until they're back from a gym session, high on endorphins.

If an overbearing relative has just popped in (again!) without a care for your plans or work schedule or little one’s nap time, your frustrations in that moment might lead to saying things you’ll regret and/or be unnecessarily hurtful to someone who thinks their presence is a welcome treat. Instead, take them out for coffee, at a time that suits you, and initiate a chat about boundaries in a neutral, calm environment.

And if you know you're entering into a conversation that could feel draining / antagonising / demoralising, plan something that can fill your cup, before and after.

Could a pre-work yoga session help calm your agitation ahead of a performance review where you're the one delivering feedback to a prickly line report?

Perhaps pick out your favourite book to climb into bed with after raising that unspoken disagreement with your partner that's been niggling away for months?

Crafting the moment can be as important as choosing it.

5. Remember it’s never too late

Sometimes there is something to be said that is unlikely to be shared unless you initiate a conversation about it. It might be regarding something you have done, something that has been done to you, or a topic you want to dig into someone's views about.

These sorts of chats can be tricky, and so we might put them off, until there's a "good time". But time is precious, so get it said. Even if you've waited for what feels like too long, it's better late than never.

Last year, I spoke to a friend about something between us that I'd been pondering over for months; I wasn't quite sure where either of us stood on it, but felt that I needed to say my piece to feel more settled in myself. Turned out she had been pondering over it too, and was grateful I had shared my reflections, as she had felt unable to without perhaps upsetting me. We hugged it out, and ordered more coffee, glad that things had not been left unsaid for several months more.

6. Practice makes perfect

Before diving into a difficult conversation, act it out with someone you trust. Test out ways to bring up the matter. Role play how you'd respond to different routes the conversation could take. Get someone else's take on how to make the best of it (or steal their quippy one liners).

Not got someone you'd feel comfortable doing this with? Well, there's always AI... But if that's a step too far, get out your journal and write through it.

Write before you bite.

7. Be prepared to make compromises

Even if you've prepped and laid out all your key points in a fantastically thoughtful and eloquent way, you might still get a no, a why, or a I still want to do it my way.

At this point you could suggest possible compromises.

Can you meet them half way on the proposed payrise?

Can you accept you'll do more of the chores because the cleanliness of your home matters more to you than who you share it with - but maybe they’ll do more of the batch cooking?

Can you agree not to discuss politics anymore with that certain someone, or at least for a set amount of time, lest you risk too much challenge to maintain good relations?

Remember you don’t have to make a counter offer or suggested compromise in the moment. You might still ask for the time to go away and ponder, sit with those annoying feelings and lean into what feels right.

8. Embrace the discomfort

These are tips to try and help you better navigate hard chats, but I'm not saying that taking these snippets of advice is going to make it easy. Such conversations might still be awkward or sad or frustrating, regardless of how much you prepare, pick the right moment, and plan a treat for afterwards.

Sometimes you might blurt out exactly how you feel in an inflammatory way which in hindsight feels entirely unhelpful. But that's life. You're human, and it's normal.

Conversations aren’t always happy or smoothing or satisfying. Don't add more upset to the situation by expecting yourself to feel unnaturally calm and contented about something that might just be hard to deal with.

Challenge is a valid feeling too.

9. Bring it back up

Tackled the conversation once but didn't feel like it went your way? Well God (whoever she/he/they might be to you!) loves a trier, so get back at it.

Don't feel disheartened if the response isn't as you'd hoped, or you didn't have enough time to get across all the points you felt were important. Reset, find another opportunity, and go again.

Think about what will help your case.

At work, can a friendly senior stakeholder help back more funding for your project?

At home, can you ask your partner for advice on a disagreement with a friend?

At a family dinner, can you calmly restate your concerns around policy implications as a way of opening perspectives, rather than focusing on a hatred of the figures making those policy decisions?

Fight your corner, and reinforce your points, before you decide it's time to walk away.

10. Seal the deal in writing

Whether it’s your bestie, your colleague or your boss, reiterate through the written word what you want them to have taken away from that difficult conversation.

Get on email a record of the date they agreed your next pay review and the actions you will take in the meantime.

Whatsapp your pal to remind them again they are the best and thank them for their understanding on what you had to say.

Sometimes one big red heart will suffice, if you're of the emoji persuasion.

This step, I think, makes it all feel more considered and personable, as well as acting as a door closed, or a bow tied, on that hard chat you were brave enough to dive into.

I do hope this list will be helpful for you the next time you see a challenging chat on the horizon.

If it feels overwhelming, just pick one or two of the approaches to try. Maybe you're using some already!

What works well for you? What has been your top takeaway? Any additional pointers to share?

Meet me in the comments with any thoughts…

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