This is going to hurt: how to have awkward conversations

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Tricky conversations are easy to put off – but dodging them only makes things harder. They’re often about something that could make life easier or better but the fact that the exchange may be embarrassing or difficult for one party or both, forms a big barrier.

Remembering a few ground rules could make things easier. First: this is a two-way thing. It’s not just about you – the other person may also be nervous, uncertain, defensive, scared or unhappy.

Next, choose your moment. If it’s someone you know, think about their style of communication. If they don’t like being taken unawares, let them know you need a chat, and say what it’s about. It’s always better to have a tricky conversation in person, but if you do resort to email or text to set the conversation up, or to clarify issues afterwards, be very careful about the wording; be as even-handed as possible. Before you press send, read the email, imagining how it would make you feel if you were receiving it.

For the conversation itself, make sure you’re in the right mood. And be prepared for a curve ball. If the other person brings unexpected factors into the mix, park the chat for a while.

Finally, always leave the encounter having agreed what will happen next. And however unsatisfactory it has been, resist throwing your toys out of the pram. Saying you’ll hand in your notice, or never speak to them again, or trading insults, is guaranteed to make an already tough situation toxic.

As a rule of thumb, the trickier the conversation, the more you need to practiseDr Tracy Towner

Asking for a pay rise

You want to do it, but you’re terrified. Ask yourself why, says executive career and leadership coach Denise Chilton. If you’re worried about talking to your boss, unpack that. “Many people think the stakes are higher when they’re talking to someone more senior, but why should that be the case?”

The key element is to work out how much you want, and go into the conversation believing you’re worth it. “What’s the added value you’re bringing to your organisation? Have you taken on extra responsibility, or learned new skills?” The crucial thing, she says, is to talk about the value you bring.

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Women, in particular, often need a confidence boost, so think about it like this: if you end up leaving, your employer will probably spend more on replacing you. So the extra £3,000 you’re asking for is good value compared with the £5,000 they’ll spend on recruiting and training someone new.

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If you’re told there’s no extra money in the coffers, think about the whole package. Try: “OK, but I’d like to carry on working two days a week at home and have some more professional training.” And set a date for when your company can review your pay.

Complaining in a restaurant

Any restaurant worth eating in will be keen to know if you’re unhappy, says Mandy Yin, chef/owner at London’s Sambal Shiok. But make your point straight away – don’t eat the dish and then complain about it. “Be conciliatory, never aggressive,” advises Yin. “Remember that servers are people, and sugar is always better than vinegar. Don’t just plunge in by going on about how bad it is; give staff the chance to explain why something is as it is. If something doesn’t taste right, it may be just too salty or whatever for your taste. But the restaurant should be sympathetic to that, take it away and bring you an alternative.” It’s the same with wine: if you order a glass of something and realise straight away that you don’t like it, any good restaurant will replace it.

View image in fullscreen Photograph: Richard Drury/Getty Images

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Talking to neighbours about a problem

Don’t underestimate the value of friendly and cooperative neighbours, says mediator Dr Tracy Towner of Normanton Chambers, who says some of her hardest mediations involve neighbour disputes. Good neightbours are the holy grail: go a hundred miles before you have a row with them. “Once, I said to this person: how did it start? Walk me through the story – and they couldn’t even remember.” But these are people’s homes, so emotions run high. So how do you deal with the overfilled recycling bins/uncut hedge/falling-down fence?

“Make light of it – hint at the issue without criticising,” says Towner. So for example: “I can’t believe it’s that time of the year again: the hedges are on a growth spurt.” Or: “Why doesn’t the council give us more bins: I can’t squash any more into them.” Another ploy is to role model the behaviour you want from your neighbours. Cut your own hedge, repair your own fence, and chat to them while you’re doing it.

With tougher issues – noise late at night, a barking dog, inconsiderate parking – Towner advises that you practise before you go round: “The trickier the conversation, the more you need to practise.” But a good ploy is, again, to turn it back to yourself – don’t be accusatory, be contrite. “Can I check we weren’t disturbing you with our music the other night?” often leads to the response: “Oh not at all – I hope you don’t hear ours either.” And then you can very gently say: “Well, sometimes we do hear it – the walls are so thin in these houses.”

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Talking to your partner about sex

The best way forward, says Relate senior sex and relationship therapist Ammanda Major, is to approach this as half of a team – and never to be accusatory. So instead of “You never make me come any more”, try: “I’ve always loved having orgasms with you, and I think our sex life would be better if I found a way to enjoy more of them.”

The last thing you want to do here is inflict blame or shame. And pick your moment. “Don’t have this conversation when you’re in bed or when you’re angry or upset,” says Major. “Be curious. What would your partner like? How are they feeling?” This is the chat above all others that you should have in person.

Dealing with someone being disruptive on public transport

This is very tricky: there’s already at least one emotional person here, and things could easily get out of hand. Should you say anything? Or might it better to call the driver/guard/police? If you do weigh in, says Towner, stay neutral and flat-as-a-millpond calm. “The last thing you should do is go in saying something like ‘This is ridiculous’ or ‘Back off now’,” says Towner. “Try: ‘Hey, is something going on here?’ Ask for information – ‘what’s happened?’; ‘has something upset you?’ – because then the person has to stop what they’re doing and answer you.

Reminding someone they owe you money

Ideally, says Marc Hekster, consultant clinical psychologist at the Summit Clinic and fellow of the British Psychological Society, don’t lend money in the first place – or if you do, lend it knowing you may not get it back. But we live in the real world, and splitting the bill for an Uber or a shop may mean you owe someone cash.

The easier thing, he says, is to set up a PayPal account and check they have one; then all they need is your phone number, and they can pay from their phone. Email or text can be good for this conversation – that way you can remind them of the information they need. Try something like: “Just wanted to check you’ve got my bank details/mobile number so you can send me that money.”

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Do try to work out why you’ve not been paid: you don’t want to harass anyone or to make them feel guilty. Perhaps they’re in difficulties or they’ve just forgotten, in which case they won’t mind a prompt.

Asking someone to clean up after their dog

This is a really tricky one, say our experts. There’s no point in having any tricky conversation unless you believe you can get the outcome you want: and really, why would anyone who’s already ignored widespread social convention AND all the signs in the park pick up their dog poo simply because you ask them nicely?

But there are ways. If you’re walking your own dog, “you could exaggerate the fact that you’re cleaning up after your dog,” says consultant psychologist Emma Citron, “but it’s very hard to change someone’s behaviour on this.” If you do say something, make it as emotion-free as possible. Try asking if they’ve run out of bags – if you’re walking your own dog, you could offer one of yours. If you do confront, be apologetic, try: “I’m sorry to have to say this, and I know it’s incredibly embarrassing, but kids use this park, and I can’t help noticing you’ve not cleared up your dog’s mess.”

Declining an invitation

Don’t lay on a complex, convoluted story about why you can’t make it, is Hekster’s advice; keep it simple and generally truthful. That said, this is one scenario where a little white lie may not go amiss. Better to say you’ve a prior engagement than you just don’t fancy the do. “We all have busy lives, and people understand you can’t do everything,” says Hekster.

Covid is seeming a bit tired as a get-out (unless it’s true, of course). And if it’s something you just couldn’t bring yourself to do, honesty may be best. Something like: “It’s a lovely idea, but I’ve never enjoyed camping and don’t think I want to do it again. Is there something else we could organise?”

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