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Top Tips for Holding Challenging Conversations

Throughout your working life, there will be times when you have to handle a difficult conversation. You may be required to approach a colleague to discuss a tricky subject, or it could be that you’re called upon to resolve an awkward situation yet you feel as though you’re tiptoeing through a minefield. 

No one enjoys these conversations, but they are often necessary. That said, situations often improve once you’ve had the initial discussion. It’s important to consider your behaviour and approach to ensure every difficult conversation you face is dealt with as swiftly and smoothly as possible.

  • Be Clear On The Reason For The Conversation

It’s essential to make sure the person you approach knows precisely what you’re looking to talk to them about and the reasons why. Otherwise, they may feel startled, more defensive and potentially more difficult to converse with.

  • Silence Isn’t a Bad Thing

There may be times when the conversation doesn’t flow as you would like, but don’t be tempted to butt in and restart the conversation. Periods of meaningful silence are sometimes misinterpreted as awkward silences. Get comfortable with these silences and see them as a time of reflection.

  • Be Curious

It is always best to approach challenging conversations with a curious tone rather than one that sounds like you’re accusing the person or have already made up your mind. Use the conversation as a fact-finding mission and approach it in a way that wants to find out more information. With an inquisitive approach, the individual may be more likely to open up.

  • Don’t Get Emotional

These conversations aren’t always easy, but it can help if you do your utmost to stay unattached to the topic as an outsider. If you get emotional, raise your voice or start to get upset, you may derail the conversation, and you’ll struggle to get things back on track.

  • Stick To The Topic At Hand

Although the topic might be sensitive and the conversation difficult, try to stay on topic as much as possible. It can be tempting to try and lighten the mood or change the subject to offer some relief, but it can be hard to pull back a conversation like this, so it is best avoided where possible.

  • Don’t Overreact

Even if your colleague “loses their cool”, it’s essential to take a deep breath and think about your response before you act. Any overreaction on your part may make matters worse.

  • Consider How You’re Going To Start

Make sure you think carefully about how you’re going to start the conversation. You may want to clarify what you hope to achieve from the discussion and then let them take the lead.

  • Don’t Put It Off

It can be tempting to put things off with any tough talk and leave the conversation for another day; however, if you do not move towards a resolution, you can make matters worse. If you need to have the conversation, do so as soon as possible. Don’t shy away!

  • End on Good Terms

When the conversation is finished, make sure you thank the person for their time and end on good terms. In doing so, you leave the door open (and remain in a solid position) to re-approach the conversation at any stage in the future, if required.

Having a challenging conversation may not be something you relish the thought of doing, but more often than not you’ll feel better when it is over. Always stick to facts rather than allowing too many emotions to surface, and you will enable the conversation to be ‘to the point’ and professional. You can explore our many leadership courses and training to improve your questioning and listening skills. As experts in organisation training and development, we’ve helped many leaders face tricky conversations head-on with confidence, building strong and productive relationships. You can find out more about how to hold difficult conversations in our digitally delivered course entitled Holding Difficult Conversations. Find out more here