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How to have Difficult Conversations

Apr 7, 2022
How to have Difficult Conversations


At some point in your working life, you’re going to need to have a difficult conversation. Whether it’s delivering tricky feedback to someone in your team, or it’s reporting something serious that could affect your interpersonal relationships at work, mastering difficult conversations takes time, practice, and most importantly, learning how to be pragmatic.

There’s nothing wrong with feeling nervous about them, either.

Work is a big part of our day-to-day life. In fact, the majority of us spend more time with our colleagues than we do with our friends and family. Having a certain level of anxiety or nervousness is part and parcel of broaching a difficult conversation, no matter how experienced or senior you are!

Forbes produced a compelling article on this, highlighting that “When people are asked how they generally deal with conflict, they often say that they try to avoid it. In fact, one poll revealed that more than 80% of workers are running in fear from at least one scary conversation at work—a conversation they know they need to have but are dreading. 

This statistic isn’t surprising given that most individuals think of conflict in negative terms. Yet avoidance strategies don’t make things better. In fact, they usually make the situation worse. Issues escalate, resentment grows, and eventually, people become disengaged.”

This can be magnified if you have a strong bond with someone outside of work, too

It’s not uncommon to become close friends with the people you work with. Some people meet their lifelong friends at a role, and some even meet their future partners. This level of closeness, however, can wreak havoc on approaching work-based conversations pragmatically, as you have a deeper emotional connection to that person.

So, what can you start to do to be able to approach difficult scenarios better?
  • Take the emotion out of it

Let’s look at the scenario of your “best friend” at work doing something wrong. You know that from a moral and practical perspective you have to raise it with them and a manager, but from an emotional perspective, you’re scared that you’ll hurt them or lose them as a friend. 

The main thing you have to try and do is ignore your emotional attachment to that person and look at the facts, and then approach it in a balanced way. Naturally, you don’t want to jeopardise your friendship with someone, so think about how you can give them a “heads up” or speak to them privately before you then have to raise it with a manager. Sure, it may ruffle a few feathers, but you are still considering their needs and emotions personally, without letting them completely override the end goal.

  • Set boundaries

We are human, and it’s natural that boundaries can be blurred when we become really close with someone at work. Boundaries don’t mean that you will not be close with someone - but instead, sit down and have a conversation with them about what you both expect from each other in a professional setting when you’re at work, and not in “close friend” mode. 

Understanding their needs and wants and vice versa means that you will both know how to effectively communicate, a) without offending each other and b) still keeping it professional, in a professional setting. 

  • If you’re a manager, remember that you have a duty of care

Much like taking the emotions out of things when you’re working with a friend at a peer level, as a manager, you also need to be conscious of your seniority and also that you have a duty of care for people who report to you, as well as the wider business. 

If this duty of care will be breached because someone in your team dropped the ball (who is also a friend) you have to look at it through a pragmatic lens and nip it in the bud. Equally, you need to ensure that you create a safe space for those who report to you (especially) if you’re friends outside of work, to be able to speak with you on a professional level if you have dropped the ball. 

There can feel like there’s a power struggle when managers and their team members become too close, so again - remember that you have a duty of care, and put those boundaries and expectations in place. Also, if you aren’t a manager, think about how you would manage yourself

If you can start to think about this from this angle, you’ll start navigating situations from once more, a pragmatic lens.

  • If their reaction is emotional, give them space and remember you have done your best

You will offend someone at work at some point. You will rub someone up the wrong way. And, it’s not your job to manage other people’s emotions. Let’s look at the scenario of needing to confess something to your manager, let’s say a mistake that you have made or something that you’ve seen. 

If the reaction is completely emotional, create space and remember that you are simply doing your best. An emotional reaction is largely due to the other individual and how they process things, rather than a reflection of who you are as a person!

And finally, if someone is a true friend at work, they won’t let your professional life affect your personal life, and vice versa. It can be tough to have difficult conversations, and no one likes doing them, but practice makes perfect! Always remember to approach things pragmatically, set boundaries, and give space where possible. 

For more information on sustaining an inclusive culture for all of your employees, check out our free D&I in the workplace handbook, available to download now.

download our handbook for mental health at work


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