Speaking your truth during tough conversations at work

When it comes to difficult conversations, it can be easy to avoid them and put them off. No one likes to feel uncomfortable. However, in order to grow — whether in a professional, cultural awareness, or personal sense — getting uncomfortable is the true marker of growth and elevating your current understanding.


The key to tackling challenging conversations is the ability to shift from "I need to explain myself" to "I need to listen and learn more about what's going on."


In this guide, we'll cover the different types of difficult conversations and techniques for handling these conversations.


Types of difficult conversations at work

There are many types of difficult conversations that take place at work and in life. Challenging conversations may centre around the following topics:

  • Culture and ethnicity: Dealing with different cultures and ethnicities in the workplace can create tension between employees. That's because different cultures have varying perspectives, values, and behaviours.

  • Inappropriate behaviour in the workplace: From sexual harassment to using offensive language, there are various inappropriate behaviours employees engage in. This can lead to uncomfortable and awkward conversations.

  • Feedback on poor performance: It's never easy to hear that you're not performing up to par with company standards. This can make for a tough conversation as well.

  • Letting someone go from a job: No employee wants to hear that they're fired from a job. It can be difficult for both parties. On the one hand, the employer doesn't really want to let an employee go, especially if they admired the employee's work ethic. On the other hand, it can be hard on the employee because they enjoyed the job and liked the pay.


Here are a few difficult conversation examples:

  • Harassment: Imagine that an employee is uncomfortable with the way someone is treating them at work, but they aren't sure if it's blatant harassment. Even though they find the behaviour offensive, it's so subtle or sporadic that they fear their boss or HR will think they're overreacting. To get the issue addressed, the employee must stop avoiding the problem and face their boss.

  • Insubordination: Imagine that an employee is refusing to work towards the agreed upon goals of a project within the framework set out. As a result, the employee is disrespecting his/her supervisor and teammates with offensive language and gestures. Management is caught off-guard and buys time to figure out how to handle the situation. But this is allowing the insubordinate employee to get away with their behaviour. A supervisor must pull the employee aside and tell them that their behaviour is unacceptable.


When it comes to difficult conversations at work scenarios, remember that you're dealing with individuals with different emotional intelligence levels, who may need different communication styles to get through. But avoiding confronting the issue will always make it more complicated.


Although it may be uncomfortable to address issues at first, it can help alleviate conflict in the long run.


Examples of difficult conversations in life

Whether it's with family, close friends, or a romantic partner, difficult conversations happen outside of work, too. Here are some examples:

  • The racist friend: Shawna's best friend Romeo is always making offensive comments about Indigenous People. This makes Shawna very uncomfortable. Although Shawna was hesitant, she finally brought up to Romeo that his remarks were offensive and ignorant because he actually doesn't understand his own bias nor the history of that group of people.

  • The unsupportive husband: Whenever Mary brings up starting a career in cosmetology, her husband always has a negative response. For example, he would say, "You'll just quit like you always do." For a while, Mary shrugged it off and ignored these comments. But eventually, she told her husband how they made her feel.


Techniques for managing challenging conversations

To deal with managing challenging conversations, follow these tips:

  • Don't avoid it. The longer you wait to have a conversation, the more difficult it will be. Try your best to address issues as soon as they arise.

  • Be open to the other person's perspective. Good communication isn't just about being able to say how you feel. It's also about listening to how someone else feels. So, don't be quick to respond when someone is expressing their feelings. Sit back and listen.

  • Use "I' statements. Start your sentence with "I" instead of "you." This avoids put-downs and promotes positive communication.

  • Come to a common ground. You may need to prime a difficult conversation with a topic you both agree on that is less serious or uncomfortable in order to open the person up to receiving this kind of communication from you and being willing to address the uncomfortable issue.

The key to tackling difficult conversations is being able to find your voice and feeling safe to share different perspectives. At Tough Convos, that's exactly what we help companies achieve. With a focus on brand values, anti-Black racism, and cultural intelligence, we help cultivate a diverse and inclusive workplace. For more info, book a call with us today.