Tips for Having Difficult Conversations

Tips for Having Difficult Conversations

If you’re the type of person who avoids conflict like the latest flu outbreak, I’ve got good news and bad news for you.

The bad news: you can’t escape from it. Sooner or later you will need to have one of those difficult conversations – with your parents, with your partner, with your boss, with your best friend, with your grown child, with your employees.

Now for the good news: here are some tips to help you align deeply with the other party, so those difficult conversations go more smoothly.

Tips for Difficult Conversations

 1. The Care Factor.

 Remember the old saying “people don’t care what you know, til they know that you care”?

Your message will be better received if you have already taken the time and effort to develop a good relationship with the other party. Be considerate of their needs, show an interest in their thoughts and contributions.

2. Preparation.

As with so many things in life, preparation is key. Think about the conversation you need to have, and what you really need/want from it.

Jotting down some dot points, or rehearsing what you want to say in front of the mirror, will help you get the words out when the time comes.

Some people feel they express themselves better in writing, and an email or letter allows them to communicate AND keep unruly emotions in control. If choosing this method, make sure you let the other party know that it is coming – don’t spring it on them.

3. Timing is Everything.

Choose the timing for your difficult conversation carefully.

We might joke about being “hangry” (hungry/angry) but if you know your partner gets cranky or impatient when their blood sugar is low, make sure you time your conversation for after a meal – not before!

4. Listen. REALLY Listen.

When having the conversation, allow the other person to express their thoughts and feelings.

Show you are listening with eye contact, nodding, and making a conscious effort with your body language. Crossing your arms, tapping your foot, flaring your nostrils – all indicate hostility, so consciously open up your body and project warmth and friendliness when having difficult conversations.

Listen carefully to what the other party is saying. Use phrases like “what I heard was …“ or, “my understanding is that you want … “, and then reflect back what you heard. This gives them the opportunity to clarify if the message you’ve received is not the one they intended.

5. Focus on your WHY.

 A useful strategy is to focus on your core intention, the WHY, in difficult conversations.

Conflict usually occurs when the conversation moves to the HOW: the structure, the role/s, the strategy. When this happens, go back to that shared purpose, your WHY.

In this way, the parties in the difficult conversation are brought back into alignment.

Like colds and flu, difficult conversations are part of life and can’t be avoided. But you can minimise the disruption and keep your relationships – at work or at home – healthy!

Image Supplied under licence with Istock



Janet Camilleri
Janet Camilleri
After stints as a primary school teacher, check out chick, and debt collection officer, Janet Camilleri began freelance writing for magazines when her children were small. Since then, her work has appeared in hundreds of magazines, anthologies and websites, including the Huffington Post and Flying Solo. A multi-award winning business woman, in her “spare” time Janet enjoys blogging for fun at


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