How to Handle Difficult Conversations with Your Boss

Working with a strict boss can be very demanding, but having difficult conversations with them can be an even bigger nightmare. Whether it’s having important conversations like a performance review, a salary increment proposal, or simply bringing up a concern, it’s very easy to feel intimidated and anxious when approaching your boss with a difficult conversation. 

This is an unavoidable nightmare virtually all employees face. Walking up to your superior to have a crunchy talk about your welfare or career progression might send chills down your spine, but it’s a must-do, because you likely won’t get what you want if you don’t specifically ask your boss for it. “Say it to see,” they say.

Whether you seek a promotion, salary increment, resources or other things, what’s standing between you and your desire is your boss, and you need to breach the gap by having the conversation in the best possible way.

In a bid to help you approach a difficult conversation with your boss henceforth, this article will outline a few carefully woven practical steps for your perusal 

8 Steps To Have The Best Difficult Conversation With Your Boss

Step 1: Choose The Appropriate Timing & Setting 

Timing is everything when it comes to having a difficult conversation with your boss. Don’t bring up sensitive topics when your boss is already stressed or preoccupied with other tasks. Choose a time when he’s most likely to be receptive to what you have to say, and make sure you’re both in a comfortable and private setting where you can have an open and honest discussion.

Step 2: Speak Concisely & Respectfully

When you do start the conversation, make sure you’re direct and clear about what you want to say. Don’t beat around the bush or sugarcoat the issue, as this can only lead to confusion and frustration. Be honest, concise, and assertive.

Also, endeavour to speak from a place of confidence and respect, regardless of what’s been talked about. Tough talk doesn’t necessarily mean having to talk tough.

Step 3: Be Objective

When having serious discussions with your superior, you have to remain objective in the face of  the anger being lashed out. Remember it’s not only about you, you have to consider your boss’ behavioural disposition at the moment.

In some cases, your boss’ mode may not have anything to do particularly with you, it could be a personal issue or mistake. Our bosses are humans too, after all. 

Be objective and considerate whenever you’re having tense conversations with your boss, doing that will ensure the direction is headed in the right direction.

Step 4: Be Humour Conscious

When having awkward conversations, humour can be a great way to break the ice and diffuse tension, although it’s important to strike a balance between being too funny and being too serious. 

Excessive humour can come across as unnecessary or flattering to deceive, while too little can make the conversation feel even more uncomfortable. Use humour sparingly and only when appropriate, and make sure to stay focused on the topic at hand.

Step 5: Keep Your Body Language In Check

Generally speaking, communication isn’t just about your audible contributions. In fact, according to multiple scientific reports, communication is 55% nonverbal, 38% vocal, and 7% words only. 

So, when having those important discussions with your boss, make sure your facial expressions, body posture, gestures, and eye movements are in line with what you’re passing across. Speak with your mind and body accordingly.

Step 6:  Active Listening

A conversation involves two parties, not just you. Listen carefully to your boss’s response and make sure you’re giving the same respect and attention that you expect.  Be open to feedback and be willing to compromise if necessary, but also stand your ground if you feel the conversation isn’t heading in your favour.

Step 7: Rehearse The Conversation Beforehand

If your boss’s presence intimidates you, or if you’re typically an anxious person, why not rehearse the intended discussion before you make your approach?

Of course, you can’t be so sure of how the conversation will turn out, but practising beforehand will help you to clarify your thoughts and can also help you to feel more confident when the time comes to have the conversation.

Step 8: Be Proactive In Managing Your Emotions

Before you even approach your boss, be mentally prepared ahead of the conversation. Truth is no matter how prepared you are, things could go south — and emotions could go flying.

However, as the professional that you are, you can’t fall victim to your emotions. Process your immediate frustration, anger or fear before, during and after crunchy discussions with your boss.

In conclusion, having difficult conversations with your boss can be a nerve-wracking experience, but it’s important to remember that addressing issues directly and respectfully can lead to better outcomes for both you and your employer. 

Before approaching your boss, take some time to prepare by clearly defining the problem, practising your approach, and considering any possible objections or concerns your boss may have. During the conversation, be concise, objective and less formal, but also remain professional and respectful. Listen actively and try to understand your boss’s perspective, and be willing to compromise and find common ground.

Remember that communication is key to any successful working relationship, and by approaching difficult conversations with a positive and solutions-oriented mindset, you can build trust, strengthen your professional connections, and ultimately achieve your goals.

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