How to Have Hard Conversations (and Keep Strong Relationships)

‘When we avoid difficult conversations, we trade short-term discomfort for long-term dysfunction’.

In our personal and professional lives, hard conversations are inevitable. Whether we’re talking to a colleague, a client, our loved ones or even strangers, chances are we will come across a situation where a difficult and even painful conversation is necessary.

You know the kind. It happens in business all the time. A client who insists on unreasonable deadlines – and you’ve had enough. A colleague who keeps crossing boundaries of what’s acceptable – and you need to tell them to stop. An employee who you need to discipline.

As an entrepreneur, relationships with clients, suppliers, employees and partners are absolutely critical to a successful company. So what can you possibly do when you need to have that hard conversation? We’ll outline how you can navigate this tricky state of affairs.

1. Remember the purpose of the conversation

Before you open your mouth and start the conversation, stop and think for a minute. Why exactly do you need to speak the words you are about to speak?

The purpose is generally twofold: to fix an issue and to maintain a relationship.

The purpose of having a dialogue is to ‘nip in the bud’ an underlying issue that’s bothering you and making it more difficult for you to run your business. It is not to disparage, insult or humiliate somebody. It is certainly not to hurt somebody’s feelings (although this may be unavoidable in some circumstances).

2. Ask yourself some questions

The following three questions are absolutely critical for any manager of a company.

• Are you being consistent? In other words, are you treating all your employees or clients or colleagues the same way?

• Are you doing this out of spite or because you don’t like being wrong? A colleague may have called you out on something or corrected you where it was necessary. Just because you disagree with somebody, it doesn’t mean they did anything wrong.

• Do you need a witness? You may need a witness or a file note to keep up your sleeve in case you need evidence later down the track.

3. Be ready to articulate the issue

Do not fluff around. Do not skirt around the issue. Do not sugarcoat the message. Do not go off topic.

Be ready to clearly articulate the problem, how it is impacting you and others and what needs to change. Use facts, statistics and examples to back up what you’re saying.

For example, if you need to have a difficult conversation with an employee, you can break it down (in your head) as follows:

Problem: The employee is consistently late to work.

How it is impacting you and others: It is negatively impacting your company’s operations and making it difficult for colleagues to complete their work.

What needs to change: Attend work on time.

This is what you can say to yourself before the meeting.

4. Schedule the conversation

Depending on how formal you want to make it, you can schedule the conversation on a neutral premises. It could be in the board room, a common area or perhaps even a coffee shop.

If it’s a colleague, you could even just stop by their office. If it’s a client, invite them to a Zoom or Teams call. If it’s a friend or a family member, maybe a coffee shop is the best idea.

You could send an email like so:

Chris, I’d like to schedule some time to discuss what happened in meeting this morning. Are you free to chat this afternoon at 4.00pm in the boardroom?

If appropriate, you could also send a text message like:

Hi mate. We should talk about really the Harrison issue. Can we grab coffee at Rocky’s Café tomorrow at say 10am?

By scheduling a meeting on neutral grounds, you can also give the other person some time to muster up energy and gather their thoughts about what they want to say.

5. Be civil

When the time comes to have the actual conversation, always be polite and civil. Never let emotions get the better of you. The last thing you want is a screaming match – because that is no way to keep a relationship strong.

This may be harder than you initially think. Difficult conversations are difficult because you’ll be dealing with some serious topics. It could be performance, finances, hygiene, conflict, attitude or anything else. Always treat the person with respect and dignity.

Even make sure you clarify that the relationship with this person means something to you:

Look Jack, I really value our working relationship here. We’ve done some really great work together. This conversation is just a moment in time. I want to walk away with a strong relationship – just how it always is.

6. Work with the person (not against them)

Although you may be in a ‘higher’ position than the person you are speaking with, it is critical to collaborate with them (and not just dictate to them).

When you ask the other person a question, give them time to gather thoughts and articulate what they want to say. Don’t just ask a question, and then continue speaking just to fill an awkward silence gap.

7. Actively listen

Don’t constantly think about what you’re going to say next when the other person is talking. Actually listen to what the other person is saying, try and understand their point of view and never talk over them.

Ask questions when the other person has stopped talking to show them that you are actively listening:

            You mentioned X. Tell me more about that.

            You just said Y. How does that make you feel?

If you don’t actively listen, the chances are you won’t really tackle the underlying problem. You’ll end up frustrating the other person to the point where there may be no point in continuing the conversation.

8. Look at the situation from their perspective

It’s very easy to focus on how you’re feeling. That’s often the case if you’re feeling hurt. But before you draw any conclusions, empathise a little.

• Where is the other person coming from?
• Why did they do whatever it was they did?
• Is what they did out of character?
• What’s going on in their life?
• Did you do something to anger them?

Remember that nothing everything is about you. By discovering answers to these questions, you may be surprised at the information you’ll learn.

9. If things aren’t looking good, take a break

Sometimes the difficult conversation won’t go to plan. Perhaps the other person is getting upset, frustrated or emotional. It may very well be that things are going nowhere.

If that’s the case, there are a few things you can do.

• Ask the person to vocalise how they’re feeling. Emotions are always better let out than bottled in.

• Ask someone else to join you. It’s best if that third party isn’t closely involved in whatever it is you’re talking about.

• If things are getting too heated, walk away and try again later. Give the other person some time to let emotions simmer.

10. Be kind to yourself

No matter how the hard conversation progresses, things can get heated. People can get hurt. Your own wellbeing is your priority.

It is perfectly fine if you need to take some time to let people cool down and come back to the conversation. Switch off, listen to music, meditate or go and do something that make your you feel good.

Do some reflection and be proud that you actual mustered up the courage to start this conversation in the first place. It takes guts to do something like that. Most people will just choose to ignore the problem and let it fester.

11. Pick your battles

Sometimes, the conversation truly will go nowhere. There won’t be a fairytale ending all the time. And that’s fine.

Sometimes you’ll need to do just agree to disagree, accept each other’s differences and even part ways if you must.

If you need any help when it comes to navigating tricky conversations, get in touch with us. We can help you figure out the key issues, and help you tackle them head on in a productive dialogue.