How to have a difficult conversation

We’ve all had a personal interaction go rather badly wrong. Today we explore how to handle difficult issues like money, sex and even, yes… dog shit.

Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values.


Difficult conversations are easy to put off – but avoiding them only makes things more difficult downstream for you. They’re often about something that could improve your life, but the fact that it might be embarrassing or challenging for you or the other person can make you avoid it.

Remembering a few basics could make things a little bit easier for you.

First: this is a two-way street. It’s not just about you – the other person may also be defensive, nervous, uncertain, unhappy or scared.

Next, choose the right moment.

If it’s someone you know, think about their communication style.. If they don’t like being taken unawares, let them know you need a convo, and say what it’s about.

It’s always better to have a difficult conversation in person, but if you do have to use email or text, be careful about the wording; be as gentle 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 things to go a different way than you planned.

Finally, always leave the encounter having agreed on what will happen next. And don’t burn your bridges. Saying you’ll never speak to them again is guaranteed to make an already tough situation worse.


The basics:

  • Speak as calmly in a matter-of-fact tone as possible. This maximizes the chances that others will hear the content of your message, rather than fixate on your emotions.

  • If possible, stay at the same eye level. In other words, it’s best if everyone participating is either seated or standing. It’s generally not helpful for one person to be physically “above” or “below” others.

  • Avoid finger-pointing, whether blaming or literally pointing fingers. This makes the other person feel they are being lectured or put down.

  • Avoid name-calling, yelling, screaming, cursing, put-downs, insults, or threats (emotional or physical). No one in the history of the world ever calmed down by being shouted its to calm down:)

  • In describing your concerns and the things you’d like to happen differently, be as clear as possible and use specific examples. Avoid the words “always,” “never,” “everything,” and “nothing.” These may express your frustration, but they overgeneralize and are fundamentally inaccurate. As part of a communication process, they are unhelpful.

  • No interrupting. When the other person is speaking, consciously listen to what he or she has to say with the intent of hearing it. This is very different from waiting for the other person to finish speaking so you can respond. If you’re thinking about what you’re going to say in response, while he or she is still speaking, you’re not listening.

  • Make sure you understand what the other person has said before you respond. If you’re not sure what he or she said or meant, ask for clarification. “Could you please repeat that?” “I’m not sure what you mean. Can you please help me better understand?”

  • Approach the conversation with a kind heart and an interest in problem solving, rather than needing to be “right.” Anytime we see it as needing to be “right,” it means the other person has to be “wrong.” This kind of rigid either-or, win-lose, or right-wrong mindset makes conflict much more likely and mutual understanding much less likely.

  • Keep to the topic at hand. Focus on the topic of this conversation. Bringing up issues or complaints related to other topics or past events always interferes with healthy communication during the current conversation. Save those other issues for another time. If they continue to be important to you, you’ll remember them.

  • Do not walk away or leave the conversation without the other person’s agreement. Allow for the possibility of time-outs. It’s important to discuss and mutually agree on the concept of a “time-out” as needed. Time-outs are not just for young children or professional sports teams. If things start to become too heated, it’s important for people to be able to take a time-out. Time-outs give people the opportunity and the space to calm down and compose themselves, making it possible to continue.

  • Take responsibility for feeling the way you do, rather than blaming the other person. No one can make you feel a specific way. Use “I” statements — as in, “I feel...” Be clear and specific about what the other person did that contributed to your reaction. Rather than saying, “You make me so mad,” focus on the other person’s actual behaviours.

  • Drop your assumptions. Just because you have been living or working together for a period of time doesn’t mean you know what the other person is feeling or thinking. People grow and change. What you want, need, or expect from each other changes and may need to be renegotiated from time to time.


Asking for a pay increase

You want to do it, but you're scared.

Ask yourself why.

If you’re worried about talking to your boss, figure that out. 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 value you’re bringing to your organization? Have you taken on extra responsibility, or learned new skills? The crucial thing is to talk about the value you bring.

if you end up leaving, your employer will probably spend more on replacing you. So the extra $5000 you’re asking for is good value compared with the $8,000 they’ll spend on recruiting and training someone new.

If you’re told there’s no extra money, think about the longer term and get concessions somewhere else. 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 salary


Talking to your neighbours about a dispute

Don’t underestimate the value of friendly and cooperative neighbours. Good neighbours are like gold. Go a hundred miles before you have a row with them. So how do you deal with the overfilled recycling bins/uncut hedges/falling-down fences or excessive noise?

Make light of it – hint at the issue without criticizing. Why doesn’t the strata 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 with them while you’re doing it.

With tougher issues – noise late at night, a barking dog, inconsiderate parking - 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 gently say: Well, sometimes we do hear it – the walls are so thin in these houses.


Reminding someone they owe you money

Ideally, 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 may mean someone owes you 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.”

Do try to work out why you’ve not been paid: you don’t want to harass anyone or 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. There’s no point in having any 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 shit simply because you ask them nicely?

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 cleaned up your dog’s mess.


Saying no to an invitation

Don’t bother with a complex, convoluted story about why you can’t make it. Keep it simple and truthful. That said, this is one scenario where a white lie may not go amiss.

Better to say you have a prior engagement than you just don’t feel like it.

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 organize?”


I’m David. I am a coach and mindfulness teacher based in Vancouver, who works with clients throughout North America.

My clients are committed individuals who want a coaching partnership to create an impactful, thoughtful & productive life.

I invite you to find time to talk about what brought you.

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