Keeping It Cool: A Successful Supervisor’s Guide To Handling Difficult Conversations

Posted on August 14, 2015

Across every industry and workplace, an unavoidable part of every job is dealing with people. And, while standard employees can get away with limiting the intensity of their workplace interactions to the superficial talk at the water cooler, supervisors must often be the hosts of many kinds of difficult conversations.

This can be tricky – mediating employee conflicts, handling complaints, evaluating behaviors, and even letting people go when necessary. However, becoming comfortable and competent with these types of conversations is a necessity for any person serving in a supervisor capacity. Accordingly, here are three key tips for how to fine-tune your conversation style and best prepare and handle difficult conversations with employees.

Go In As Your Best Self

When growing up, people give you a lot of advice about what to do prior to taking a test, or performing in a show, or competing in a match – have a good breakfast, take a deep breath, clear you mind, etc. The thing about these constant reminders though, is that the reasoning behind them holds weight.

One should never go into serious dealings when you don’t have the basic essentials sorted out. Being tired or hungry or stressed can and will affect how you converse with somebody. Ergo, before having an important conversation, make sure you have taken care of all of your base human needs so that when you are in that meeting your best self is fully present. 

Keep Your Emotions In Check, But Keep Them Nonetheless

A lot of people will tell you that when having difficult conversations it is best to check your emotions at the door entirely. This is understandable, as you should not allow personal feelings (positive or negative) to influence your employee-supervisor dealings because fact should be at the core of these difficult conversations.

However, never forget that empathy (even tempered or internalized empathy) is an asset too. Resolving issues, or helping people overcome whatever struggle you are currently addressing is much easier when you understand them. So blocking out empathy completely is as unhelpful to the person you are confronting as it is to you.

A successful supervisor is neither made of stone nor made of pudding. A balance is required – objective, logical proceedings mixed with understandings. For, if not for the first you might end up being a pushover, and if not for the second you might end up alienating your employees.

Talk With Your Employees, Not At Your Employees

When preparing for a difficult conversation or confrontation, it can be easy to follow into the trap of preparing a whole speech in your mind of what to say. The problem with this, though, is that it is unrealistic. A supervisor-employee conversation is not like a presentation or a dramatized monologue; it is not just you in that room. Moreover, it is not all about you.

The point of a conversation is to converse so, while there is nothing wrong with preparing for hypotheticals and giving thought to what key points you want to cover in the meeting ahead of time, over prepping is a bad idea. Speak from the heart, not a script. Ask questions. Involve the other person. You are there to talk about them, after all.

Into The Gray

Every difficult conversation you will face as a supervisor in the workplace is different because every employee is different. As such, there is no exact map to navigate you through each occurrence.

However, that is okay. You were made a supervisor because the people above you believed you could supervise. So, trust yourself, trust your instincts, and keep these three tips in mind. If you do, you will be poised to handle difficult conversations with the empathetic grace and shrewd demeanor of a pro.

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