5 Tips for Tackling Difficult Conversations

If conducting a difficult conversation fills you with dread then you’re not alone. You may be fearful that you will cause a conflict or upset your colleague and because of this, it is only natural to approach these conversations with trepidation.

The temptation to put your head in the sand and wait for things to just blow over is understandably strong, but if you leave a problem to resolve itself there's a real possibility that it might fester and become even more difficult to tackle when you inevitably have to. Not to mention, ignoring an issue that you are experiencing routinely is only likely to ratchet up the anxiety about facing it.

Clear and direct communication is a key skill in both life and business, so here are five tips for tackling difficult conversations.

Have a plan

Before diving into a difficult conversation, it’s important to understand just what it is you are hoping to achieve. Being clear about the end goal will help you figure out the key points that need to be communicated in order to get you there. Think of the conversation as a journey that you need to plan, and write each step down so that you help to lodge each of the points you need to cover in your memory.

Don’t be a robot

Preparation is important but your conversation isn't going to be a tightly adhered-to script. You can keep in mind your final destination and the points that you want to cover but it is OK to take the odd pit stop or diversion if that's where the conversation takes you; if you feel you have wandered too far off course you can gently steer things back on track. Also, remember that a conversation is a two-way street, actively listening and trying to really hear and empathise with the other person is vital to reaching a point of resolution. 

Leave out insults

You are in a workplace, not a playground and there is no place for insults. Gaslighting, sarcasm or backhanded compliments are also not productive. You want to persuade the person to see things from your perspective, and guiding them to do this will be more effective than instructing them. Have models of expected conduct to hand but try to inspire rather than degrade.

Be wary of distractions

A difficult conversation will hopefully lead to the turning of a new leaf — a change in behaviour or increased diligence. Keep the endgame in mind, remember all of the points you want to cover and try to keep the focus on that.

You can be in control of a conversation without being domineering. When people feel backed into a corner they might resort to defensive behaviours or might attempt some whataboutery, trying to distract you with someone else's issues. Just keep your plan in mind and be firm about tackling the current agenda. Be mindful of your tone, temperament and goal, take your time and don't be deterred by any obstructions laid in your path. 

Nip problems in the bud

Difficult conversations will often get harder to conduct the longer problems are left to ferment.

Not only might a problem grow if left unchecked but correcting something that you have been happy to ignore for a while might come across as hypocritical.

Asking for help, breaking bad news or setting rules and boundaries might feel uncomfortable but they are not going to resolve on their own accord.

Try to get in the habit of identifying and discussing problems as they arise. Make it a cultural change, not just something that is dictated from above. Reiterate to your team that any failure isn't an opportunity to admonish but rather a chance to learn and improve. Be clear that addressing problems doesn’t mean you are trying to micro-manage or criticise but that you are trying to optimise; recognise situations in which you can offer guidance, or help someone at risk of dangerous or upsetting practices. A happy workplace is one that is open to learning and evolving, one where difficult conversations can motivate rather than demoralise.

Communication is key

In all communication, it is important to stay calm when addressing the other person, maintain good eye contact, open body language and not be manipulative. Directly addressing problems is far preferable to passive aggression. And, when handled correctly, difficult conversations will lead to better productivity, stronger relationships and a happier workplace.

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