How to Get Comfortable with Uncomfortable Conversations

“I love to have uncomfortable conversations at work”, said no one … ever. No question getting comfortable having a hard conversation with a colleague, a superior, or even a direct report (for some leaders) can be challenging. Yet, it’s an inevitable part of the workplace experience. For leaders or anyone aspiring to advance, it’s an essential skill to master with professionalism, clarity, and empathy. 

For some, the temptation is to avoid difficult discourse in hopes that it will simply go away or resolve itself. After all, people (including us) can get emotional and defensive. That’s not fun for anyone. But all too often, if left to smolder, exasperation and even resentment can set in, eroding trust. Plus, we may have missed a critical window to have a productive, mutual outcome. 

Avoidance has real consequences that can undermine the productivity and performance of a team. As a leader, isn’t that your responsibility? Alternatively, the benefits of addressing issues early and directly can propel a team forward, helping to build stronger relationships, improve communication, prevent unnecessary misunderstandings, fuel collaboration, and ultimately drive business performance.

So, how do we get comfortable with uncomfortable conversations? Here are some tips to help you get started:

1. Prepare yourself: Take some time to mentally prepare for the conversation. Think about the points you want to make and how you can express yourself clearly and respectfully. Also, try to anticipate possible reactions and how you might respond.
2. Choose the right time and place: Timing and timeliness is everything. Make sure to broach the conversation when both you and the other person are in the right mindset. Also, ensure you have chosen a place where you can have a private conversation without any interruptions or distractions. This can help create a comfortable and safe environment for both of you to express yourselves.
3. Be respectful and empathetic: When having an uncomfortable conversation, it’s important to be respectful and empathetic toward the other person. Try to understand their perspective and avoid being defensive or confrontational. Focus on finding common ground and working toward a solution together.
4. Practice active listening: Active listening is a key component of effective communication. Make sure to listen carefully and with an open mind to what the other person is saying. Ask questions and show that you are genuinely interested in understanding their point of view.
5. Check in and seek feedback: After the conversation, allow time for reflection and then check in to gauge how the other person is feeling. Is there a need for further dialogue? Ask for feedback on how the conversation went and how you could improve your communication with them in the future. Enlist them as a stakeholder to help you learn and grow from the experience. 

Remember, difficult conversations are an unescapable part of any workplace. For leaders, self-mastery is not optional. It’s imperative. Invest the time in yourself to get better at this. In turn, your people will get better. It may seem counterintuitive, but candor is kind and will fuel their growth, as well. By learning how to get comfortable with uncomfortable conversations, you can build stronger relationships, garner the respect of others, and create a more productive, successful work environment. All you have to do is take the first step.