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How to handle difficult conversations like a pro

As a business owner you will inevitably have difficult conversations. Even if you’re a solo entrepreneur you need to deal with suppliers, shipping companies and customers. When things turn sour, here’s what to do.

Many would argue that one of the greatest aspects of small business is that you know everyone you work with. You’re a web, a family of sorts, and you know all about each other. Even if you have no employees, chances are you work with the same people multiple times. Maybe the same man has been delivering you packages for years.

It’s a support system which can make you feel comfortable and validated. But, when things go wrong, it can be hard to address the problems.

Addressing issues quickly can help stop them from becoming more severe. I’m going to help you with some easy guidelines to follow when it comes to having those difficult conversations.

Figure out exactly what’s wrong.

We’re all prone to a gut feeling every now and again, but a ‘gut feeling’ won’t give the person you’re talking to any answers. Try to identify exactly what the issue is.

In some cases, a problem can be obvious. If you use a local service to print products, they might have messed up your past few orders. But other problems can be a lot more nuanced. If you share an office with another person, for example, even small things like their smoking habits can become an issue.

Often, people become defensive and anxious during difficult conversations. Having clear examples and reasons for your discomfort is important for that reason. The print shop owner might deny any mistakes unless you can clearly point them out. Just saying, ‘oh you were wrong’ leaves too much open. You must  be able to use examples.

Second guess yourself.

Often our grievances snowball. We start off annoyed at a little thing, and end up finding everything terrible. Before you make plans to sit someone down and ask for change, you need to be sure that you’re not part of the problem. It’s important to ask yourself some questions.

- Is this the kind of thing which would annoy other people?

- Has anything changed?

- Why is this irritating you now, and not before?

- Are you making any assumptions about the person you need to speak to?

- Are you more riled up than you need to be? Are you emotional?

- Have you contributed to the problem? Could something you said have gotten misinterpreted?

- Is this issue setting you off because of something in the past?

I’m not trying to say that you’re in the wrong. Or that this problem must be your fault somehow. But it’s always worth trying to see any issue in a broader context. It makes you more empathetic, open to feedback and more aware of your own actions.

Having these things in mind can completely change the direction of a conversation. You can turn something accusatory and uncomfortable into a positive step forward together.

Create your ideal scenario.

Before moving forward picture exactly what you’d like to happen. Maybe your smoking colleague could light her cigarettes outside, instead of as she’s walking out the door. Perhaps your print company could give you a refund on the damaged goods, or a discount moving forward. Maybe someone who’s not pulling their weight simply needs to be let go.

There’s no use holding a meeting unless you have a proposal in mind. And it’s no use asking the person you’re talking to what they think should happen. If they’re stressed, angry or upset they’re not likely to provide you with your dream solution.

Instead, write down some solutions which would suit you. Then, you can ask which one suits them.

It’s also a good idea to keep in mind which scenarios you wouldn’t like. Imagine all the things that could happen during your conversation. Then, you can come up with ways to minimize those you’d like to avoid.

If you’d like someone to change a behaviour but want to keep them on board, for example, you need to make sure you don’t come across as angry. It’s never a good idea to burn bridges, so try to keep your relationships intact.

Pick the right place.

Having a tough conversation isn’t just about what’s said; it’s about where. Having a chat with someone in front of others could be embarrassing for them. If you’ve got an office, dragging them into it could upset the power balance too much.

Ideally, you want to find a neutral space. This could be a quiet coffee shop, or a separate meeting room.

Of course, lots of business is run online. If you need to have a chat with someone online make sure you schedule a face to face meeting using a program like Skype. Phone calls aren’t as effective, and text and email shouldn't get used at all.

It’s also best to schedule meetings early in the day. Otherwise, you’ll both end up stressed by the time it comes to talk.

Before you make plans to sit someone down and ask for change, you need to be sure that you’re not part of the problem. It’s important to ask yourself some questions.

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Get to the point.

The best way to have an effective conversation is by getting to the point straight away. Five minutes of small talk beforehand will only prolong the inevitable, and it won’t break any ice.

Don’t spring anything on the person you’re meeting with, either. Telling someone you’d like to meet for a friendly coffee when it's not the case is unprofessional and unkind.

Another thing you ought to avoid is questioning them. Statements like ‘why do you think I’ve asked you to meet’ are unlikely to get useful answers. They will only cause panic or annoy and can even cause anger. Exactly the opposite of what is needed to resolve a conflict.

Give them a heads up that you’d like to talk to them, along with where and when. Let them know why straight away. For example, you might say, ‘Hey, could you meet me at Café Loma tomorrow at 10? I wanted to have a chat about the work you’ve been doing'. Or, you might say ‘Hey, could you give me a buzz on skype around one tomorrow? I’d like to discuss my latest order’.

That way, they have an idea of what’s coming and can prepare themselves. It might also give them some time to reflect and realize that they’ve made a mistake before meeting with you.

Once you’re talking, lay out your thoughts clearly and concisely. Don’t drag in unrelated or unnecessary things, and keep what you need to say straightforward.

That said, allow for silences. Chances are the person you’re talking to will need a few moments to think. Let them. If they get sarcastic or start swearing, call them out on it and don’t copy them. Stay calm and say something like ‘I can’t understand what you’re trying to say right now’.

Be consistent.

The worst thing to do after a difficult chat is to pretend it never happened. Or to ignore the person you spoke to.

This is especially the case if you’ve had to let someone go but they’ve still have work to do before they leave. Starting to ignore them could make them feel uncomfortable. Instead, acknowledge the situation and stay professional.

If you lay out plans during a chat, follow up on them. Meet with the person you spoke to again to check how things are coming along.

And, importantly, make sure you have the same rules for everyone. Don’t ask only one person to change if two are exhibiting the same behaviour. Be consistent in your approach to the people you work and network with, and they’ll respect you for it.

Make sure you have the same rules for everyone. Don’t ask only one person to change if two are exhibiting the same behaviour. Be consistent in your approach to the people you work and network with, and they’ll respect you for it.

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Don’t stick your head in the sand

Sometimes conversations are hard to have. But the cost of not fixing problems isn’t only financial; it’s stress, anxiety and unnecessary work. Be clear, open, fair and firm and try to keep things short.

Not having a conversation could end up being more stressful than the conversation. So go schedule that meeting, and good luck.

Lena Klein

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