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Struggling with Difficult Conversations? Here’s how to Ease the Discomfort

HR consultant Amanda Hudson shares her advice.

Difficult Conversation

By Amanda Hudson

Having worked with many women business leaders while running A Modern Way to Work these past eight years, one thing is abundantly clear: we don’t love having difficult conversations. Not only would most of us do anything to avoid them, those who claim to do them well generally take an “I just tell it like it is” approach that doesn’t always get them the outcomes they’re after.

It’s tough to feel in control of your business when struggling to carry out difficult conversations while keeping them productive. So, if your aim is to become a more effective business leader, it’s worth taking a closer look at why some discussions are so difficult and what you can do to ease the discomfort they cause.

Why do we find certain conversations so difficult? 

Most difficult conversations are the result of one person wanting another person to change. Not only can it be tricky to handle such a proposition diplomatically, it almost always involves a breakdown in trust. This can make the stakes for getting the conversation right—and not breaking the relationship down even further—feel exceptionally high. 

Many of the women I work with also identify as ‘people pleasers’ who don’t like the idea of upsetting others. Mix all these factors together and it’s easy to see why a simple ask that someone improve their performance can turn into a difficult conversation pretty quickly.  

Is there a legitimate way to avoid having difficult conversations?

It’s not uncommon to avoid addressing an issue we have with another person the first time it happens. In fact, many of us secretly hope that by ignoring a certain situation, it will end up resolving itself. What happens in most cases, however, is that the issue persists while the conversation required to address it becomes increasingly difficult.

There is one legitimate ‘hack’ business owners and leaders can use to avoid having a difficult conversation that doesn’t involve ignoring the issue. The next time you’re faced with an uncomfortable discussion, try assuming the behaviour you want the other person to change is completely your fault. 

As leaders, it’s easy to blame others for outcomes we don’t like or want. By accepting 100% responsibility for those outcomes instead, you’ll likely discover that shifting some of your own behaviours will get you closer to the results you’re looking for. 

3 Tips for tackling difficult conversations you can’t avoid.

If you’ve determined that a particular difficult conversation is unavoidable, here are a few strategies for making your discussion more rewarding.

  1. Know your purpose. Many people initiate a difficult conversation because they’re unhappy or annoyed with someone and want an opportunity to air their grievances. It’s important that you only enter into a difficult conversation when you’re clear on its purpose and what you want to achieve.

You’ll know you’ve identified your purpose when you can articulate what you want the other person to change in a single sentence. If your ask is unclear, they’ll never be able to meet it, and your conversation will likely only increase any tension or frustration. 

  1. Focus on gathering—not giving—information. When we initiate a difficult conversation, it’s usually because we have a lot on our minds that we want to share. But what if you entered the conversation from a different place? 

You could, for example, assume the other person wants to do a good job—rather than telling them how they aren’t living up to your expectations— and acknowledge that it’s your role to find out what’s getting in their way. Then you could make it a point to gather great information by asking open-ended questions, listening—and then listening some more. 

The truth is that the better you can understand the other person’s situation and perspective, the more likely you are to craft your message in a way that will resonate with them.   

  1. Drop your assumptions. Most of us are very good at telling ourselves stories about why someone is acting a certain way—particularly when it’s not the way we want them to be acting! One of the many things we assume about other people’s distressing behaviour, in fact, is that it’s meant to be a personal attack. 

Taking the time to identify, label, and then drop your assumptions before entering into a difficult conversation will give you an unfiltered view of what’s really going on. This open-mindedness will serve you better in turn by making it easier to see potential pathways to achieving the outcome you want.

There will always be situations where having a difficult conversation can’t be avoided. If, however, you find yourself having the same discussion with someone over and over, there’s a good chance you’re not having the real conversation that will help get the issue resolved. 

In any difficult conversation, the key to communicating well is ensuring your message is clearly understood while remaining empathetic to the receiver. To help steer ritualistic exchanges in a more productive direction, make sure you go into every difficult conversation prepared to listen and armed with open-ended questions that will help the other person feel heard and acknowledged.

Amanda Hudson

Amanda Hudson

Amanda Hudson is the founder of A Modern Way to Work, an HR consultancy and antidote to outdated HR that delivers forward-thinking recruitment services, manager training and fractional HR. She and her team are also the creators of the Difficult Conversations Card Deck, a leadership tool for navigating tough conversations with ease.