Overcoming The Fear of Having Difficult Workplace Conversations

February 27, 2019

A few weeks ago, I was speaking to a group of young professionals. As it usually happens, the most interesting part of my talk was fielding questions from the audience. One of the questions in particular resonated with me.

The young man said, “I am not sure if the company I am working for can offer me the opportunities for growth and advancement that I want.  I need to have this conversation with my boss, but I am afraid it will offend him”.

This young man was not asking about whether he should change companies or look for other opportunities.  His question was not about seeking ways to pursue growth and advancement. The advice he sought was how to approach his boss and have what he believed would be a difficult conversation. His dilemma was how to have the conversation without being offensive or, even worse, damaging their working relationship.

This is not an uncommon problem. Quite often, someone announces a major career decision that takes their supervisor by surprise. When asked why they didn’t talk about this beforehand, the most popular response is “I didn’t really know how to approach the conversation”.

Fear is one of the primary reasons people avoid discussing a situation, problem, or looming decision with their boss—particularly fear of reprisal. We fear the discussion could hurt our potential, damage our reputation, or cause us to be seen in an unfavorable light. There is also a fear of the unknown and uncertainty when it comes to our supervisor’s response. If the topic is a touchy subject, there can be an overall fear of engaging in a difficult situation. When close relationships exist, we may be fearful of offending the person on the receiving end.

Fear is undeniably a powerful emotion, but we shouldn’t allow it to interfere, especially if the outcome involves a major career decision. While fear may be difficult to overcome, there are a few steps to help manage the feeling in difficult conversations.

Here are the three pieces of advice I gave the young man to apply when an uncomfortable discussion becomes necessary:

Be prepared. 

When beginning any conversation that involves uncertainty or difficult topics, it’s highly important to prepare beforehand. However, don’t go in hoping to remember all your talking points; invariably something will be forgotten. Have your thoughts and points in writing. Go into the discussion with the specific concerns, goals, and desires outlined in an orderly fashion.  More importantly, be prepared to offer solutions and ideas. No one wants to hear about problems without hearing about potential solutions.

Be open and honest.

This is not the time to attempt to hide or conceal. Don’t try to talk around issues. Be ready to address all items and honestly share your concerns, expectations, and ideas. Most astute business leaders can quickly spot when someone is hiding an agenda or purposely leaving out key elements. If this becomes apparent, the discussion will likely head down a path that is neither productive nor meaningful.

Control emotions and be professional.

In these discussions, it’s important to remember that you are speaking with a leader who may have some influence over your work. Becoming overly emotional hinders your ability to have a productive conversation. Assuming a demanding or condescending tone will never produce a positive outcome. Keep your emotions in check, while maintaining a professional demeanor. If the response is unexpected, continue to maintain control over your emotions to prevent creating further issues.

The meaningful discussions that transform your career are rarely brought upon by others. They come from you taking the initiative to begin and manage impactful conversations. Allowing fear to take control in these moments can cause an overwhelming amount of worry; this concern can affect both work and attitudes, possibly resulting in regrettable actions. 

Work towards having candid, thoughtful, and respectful conversations. You’ll find the outcome to be much more successful, as you’re able to expand perspectives, advance your career, and grow valuable companies.


Brian T. King is the founder/owner of multiple businesses encompassing design, construction, real estate and manufacturing. A well-respected construction industry CEO, Brian enjoys offering guidance to young professionals, rising managers and entrepreneurs on a variety of topics – from personal and professional growth, to work/life balance – through his bi-weekly blog, national podcasts, and speaking engagements around the country.

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