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Handle Difficult Conversations Like a Pro

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We all have plenty of scenarios where we have to have a difficult conversation with someone, be it in a work environment or our personal lives. As recruiters we love a good chat, but the more difficult ones can be less attractive and more likely to induce procrastination.

Recently, LinkedIn News Australia asked users to compile their best tips for having difficult chats at work. Answers included taking a deep breath before responding, utilising empathy and choosing the right environment. The general consensus is that it is far better to nip problems in the bud wherever possible, rather than waiting for them to become more entrenched or complicated. 

We’ve put together 5 simple steps to help you handle difficult conversations like a pro:

1. Begin With Your Endgame

This might sound like putting the cart before the horse, but if you don’t have a goal for having the difficult conversation, you’re not ready. Figure out why you are having this conversation, what you want to get out of it and a rough idea of how the issue can be resolved and write it down. You might need to refer to notes if things get emotional to keep you on track.

While you might think you’ll keep things on track when chatting, if you fail to plan the goal of the conversation you risk going around in circles talking sh*t and not resolving the issue. And who wants to end up revisiting an awkward conversation again in the future… no one!

2. Choose A Suitable Environment

This can be a difficult task in the workplace with hybrid and remote work, but wherever possible, get some face time. Be it in person or on a video call, there are too many subtle communication cues in body language and facial expressions to use a team chat or phone call. 

The environment you choose should depend on the issue, your relationship with the person and what would provide the setting for the most open discussion. Be mindful of what the setting you choose conveys, for example you wouldn’t choose a cafe to meet where the conversation may be deeply personal or emotive as it may seem like you don’t recognise the gravity of the issue for the other person.

3. Decide Who Should Have The Conversation

Before you jump in guns a-blazin’, stop and think about whether you are the right person to have this conversation. Is there someone else who could better handle the situation and get the outcome you need? Should you loop in someone else or handball it altogether?

Once you know that, put steps in place to make it happen even if that means bringing in someone more suitable than yourself to facilitate.

4. Be Respectful & Empathetic

Take a deep breath, step back and remember we’re all in this sh*t show together. Regardless of the issue that’s arisen, the person you’re about to have a difficult conversation with is a whole human with emotions, dreams, fears and a life outside of the current environment. 

Always approach an awkward chat in a respectful manner, from your language right through to body language. Be open to receive genuine feedback that may not please you, or a genuine reason why the person is having this issue. Try to put yourself in their shoes, even if they’re killer stilettos.

5. Use A Basic Structure 

There are no Jedi mind tricks to structuring a difficult conversation. The simpler the structure, the more you’ll be able to pivot and incorporate feedback. We like the observation method:

  • State what you’ve observed occurring that has initiated the need for a chat.

  • Explain how it’s impacting the team/budget/project/you/others.

  • Tell the person why you want to talk to them specifically about it.

  • Ask for their input or view of the situation, they may already be aware of the issue and need help.

  • Come to a conclusion, taking into account feedback and finish on a positive note of how to move forward.

Structuring a tricky chat might seem finicky, but this simple action can help you feel confident and stop you heading off on an irrelevant tangent about the last episode of The Mandalorian. 

Embrace Awkward Chats!

The mind is a powerful thing. You can make difficult conversations your friend by changing your mindset - approaching each instance head on, frequently and with structure. Using the tips above, you’ll soon find that the butterflies in your stomach disappear when the need for a ticky chat arises.

Difficult conversations are an inevitable part of life, but by being familiar with how to deliver them you’ll find yourself better prepared to handle them successfully and get the outcome you need. Nip issues in the bud, and you’ll create deeper and more meaningful connections with people both at work and in your personal life.


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Apr 21, 2022

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