Individual Leadership

How to have difficult conversations

Written by Dylan Gerstley

4 Min Read

Difficult conversations, those talks we don’t really want to have, aren’t fun. From asking your parents for that one gift that was just out of reach, to breaking off a relationship, to navigating the manager/employee dynamic, tough discussions are just that — tough. But with a little preparation and connection to your empathetic side, you can make difficult conversations a little easier.

Up in the Air, a 2009 comedy drama starring George Clooney as Ryan Bingham, masterfully puts the human side of communication into focus. Bingham, a cold and calculating man who travels the country firing people. Bingham’s methodically efficient lifestyle is threatened by a young Natalie Keener, played by the wonderful Anna Kendrick, who introduces a different way of doing business: firing people over video chat.

Bingham is, understandably, reluctant to adopt this strategy. He prefers to fire people in person as it protects what he believes to be the sanctity of the circumstance, something Keener fails to grasp.

It’s all put together in little quips by the cerebral Bingham, like when the hysterical Keener says, “Brian broke up with me by text!” to which Bingham replies “That’s almost like firing someone from a computer.” Though Keener is well-intended, her lack of human understanding is palpable, and serves as a lesson for real-world conversations.

Difficult conversations are just that; difficult, and it’s worth knowing a few things before you hurt someone’s feelings or find yourself in an unexpected position.

Before your next difficult conversation, try one (or all) of these strategies!

Prepare your words

It’s important to give any conversation the preparation it deserves. Running through what you want to say is a good idea, but an even better one is to put it down on paper. Write out your goals and try to find the best and simplest way to communicate your intentions.

Whether it’s a discussion between you and a team member, or you and a significant other, you should consider what might change after you’ve said your piece. Ideally, any negativity would preferably be avoided, so choose your words appropriately. Only you know what you’d like to accomplish from the conversation, and if you’re particularly upset it’s best to consider how the person on the other end may interpret what’s happening.

Being direct and specific will get you farther than implying or hinting at your message. Take the time to choose your words and manage your emotions so the conversation can be truly productive and not combative or upsetting.

Consider the other’s response

So you know your goals and you’ve chosen your words. The other person in the conversation is equally important, maybe even more so. Consider their response to what you’re trying to say and accomplish. Receiving critical feedback may not be their strong suit. Can you start the conversation off with some things the other does well? Starting off positive before giving critical feedback or pointing out a weakness in another may help dull the blow.

Positive reinforcement of another’s strengths is an excellent strategy, but if the conversation revolves largely around bad news, it is necessary to consider how the other could respond. How do they act when they hear difficult news?

If it’s a professional conversation, nobody welcomes a dip in work performance. If it’s a discussion to work through relationship issues, then it’s probably best to say your piece while maintaining a largely positive outlook. By considering how the other will respond, you can better prepare yourself to react to another being upset, or avoid it altogether.

No matter the conversation, offering a solution or some type of support is much better than offering a critique with no clear improvement opportunity. Put yourself in their shoes so you can understand more closely how they feel and then offer options to help them work through the issue.

Sleep on it

Difficult conversations can plague your mind and make it hard to focus on your other daily responsibilities. If you find this to be the case, take a step back and breathe. Assess your options before saving the issue for another day. A good night’s sleep may give you the clarity you desire.

Giving yourself time to think it through lets you see the issue in its truest and clearest form. Any reactive response you may have had initially will subside and let you tackle the issue in a fair, professional, and positive way.

Ultimately, approaching a difficult conversation requires some introspection on your own feelings and how you’d like to be perceived and treated. Though Bingham makes a point to include some humanity in his firing of people with lives and families in Up in the Air, he misses out on a truly special romantic relationship in his personal life in the end because he neglects that same humanity he pushed for. “You know that moment when you look into somebody’s eyes and you can feel them staring into your soul and the whole world goes quiet just for a second?” To which a breathless Kenner says “Yes!” only to hear Bingham dryly respond “Right, well I don’t.”

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