Corporate Wellness

5 Strategies To Navigate Tough Conversations With Your Boss

How does one manage to have unpleasant conversations and yet maintain a healthy relationship with their manager? Here are 5 strategies to navigate tough conversations at the workplace.

By Snehal
12 Dec 2022

Having tough conversations at the workplace can be tricky if they involve your boss. Irrespective of your equation with them, pressure and anxiety usually builds up because of various reasons. Most people worry that it may hamper their relationship with their seniors, whereas others might hope for the problem to resolve itself rather than confronting their boss. In such scenarios, how does one navigate through the stress and have a difficult conversation with their boss? Well, the answer lies in the question itself.

Firstly, you need to stop categorising the conversation as ‘difficult’. Have an open mind so that you can approach the issue objectively. This will also help you present your concerns clearly, without bias. Understanding that such discussions are crucial to your well-being and success at the workplace.

These conversations with your boss can, in fact, help strengthen your professional relationship. If done, in the right way. A survey conducted by Fractl, an organic search growth agency, showed that about a whopping 81% of working professionals are likely to acknowledge the uncomfortable situation and ensure their employees are made to feel comfortable during such conversations. This proves that transparency at work is one of the key factors to a healthy work environment. And having tough, yet honest conversations at work is the glue that can bind the team together.

Dr. C Manjula Rao, Clinical Psychologist at Apollo Hospitals, Hyderabad, lists down 6 essential points to consider when having a tough conversation at the workplace. These include: 

1. Be aware of you body language.
2. Keeping the tone of your voice even while making an assertive point. Be sure to not raise your voice.
3. Keep your physical stance open - Uncross legs and hands while sitting.
4. Use 'I' statements to address issues and focus on your needs.
5. Be specific and direct.
6. Summarize all that you've spoken in the meeting before concluding.

Related story: How To Survive Your New Boss


What Can Be The Reasons For Having These Tough Conversations At Your Workplace?

While there can be various reasons for an individual to have tough or awkward conversations at the workplace, some of the most common ones may include:

Negative Subordinate Feedback: Sharing negative feedback of a colleague or a subordinate can be challenging as you don’t want to make it sound personal, but at the same time highlight the issues persisting in their performance.


Salary Negotiations: There can be instances where you may feel that the salary you are drawing could be higher with reference to the effort and hard work you’ve been putting in. The same Fractl report also suggested that about 56% of employees feel uncomfortable negotiating for a raise.

Sometimes the pressures of work can be unbearable when there are fewer resources or your boss doesn’t have a lot of efficient employees to rely on. In that case, you might easily find yourself loaded with work to the extent that you’re doing the job for two people at the salary for one.


Striking A Healthy Work-life Balance: Having a healthy work-life balance has become a non-negotiable for many. How can you convince your boss that you need to be equally attentive at home and give your family and yourself all your time post-work?


Related story: How To Professionally Ask For A Raise 


5 Strategies To Keep In Mind While Navigating Tough Conversations With Your Boss

1. Keep Calm: The first step to bringing up difficult conversations with your boss is to be level-headed. Keep calm, and present your concerns objectively. There may be changes or opinions that you may want to assert but do so by keeping your cool.

2. Be Respectful But Honest: Always be mindful of the hierarchy when raising an issue. But, at the same time also be honest while sharing opinions. These conversations can make or break your bond with your manager.

3. Have Everything Documented: Documenting everything is extremely crucial. Depending on how serious the conversation is, it is in your best interest to back everything with solid proof. This is because your manager is going to need references or instances to understand and respond to the situation. Documentation is especially useful when the conversation involves feedback on the performance of colleagues or subordinates.

4. Listen To Your Boss’ Perspective: Keep some time aside to have your boss share their take on things. The changes or suggestions you make may need different levels of approval or involve various procedures to be implemented. Give your boss the time to process the information, share their take on it, and then find a common solution that works best for you both.

5. Have A Solution-oriented Approach:. While you and your manager may have different opinions, it is important that you work toward a solution together. For instance, if the purpose of your discussion was to have a healthy work-life balance, ensure that by the end of the conversation, you have planned your workload in a way that helps you achieve the goal with the support of your boss.

Gather your thoughts, jot down the key points discussed in the meeting, and prioritise the issues you’d like your boss to focus on depending on how the conversation goes. In a couple of months, circle back to discuss the progress and also shed light on the less-prioritised tasks from the list.


Related story: Hybrid, WFH, Or Full-Time Office: Which Is Better For Your Health


In conclusion, having difficult conversations at work can have you trapped under anxiety but, at the end of the day, these talks can help improve your relationship with your boss, and make you an even more confident, reliable employee. Tell us in the comments below, how you have tackled similar, challenging conversations at work. 


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