Having Difficult Conversations

boundaries communication entrepreneur tips Jan 13, 2023

What do you do when you have an important client who continually changes things at the last minute? What about the employee who is a life savior and great at their job but lashes out when stressed? How about business partners who are friendly but are always struggling to meet deadlines or underperforming? There are so many examples that we can face in our day-to-day when dealing with difficult people or difficult situations with clients, customers, employees, supervisors, contractors, etc.

You can't escape these tough talks. The best thing you can do is make sure you are as prepared as possible.

Preparing For Difficult Conversations

  • Confront your fears. Many people want to avoid these difficult conversations because of a fear of confrontation or because it is just a really uncomfortable topic. Regardless of the reasons, however, these conversations still need to happen.
  • Take time to investigate the matter. Some conversations might be a simple "Hey, I saw this issue. Just so you know, you should do XY instead." But for more significant conversations, it is important to put in the research to see if this is a recurring issue or to better understand the problem.
  • Write down the main points of the conversation. This can help you get your thoughts and talking points in order. This will also help you stick to the facts and avoid any emotional response.
  • Make sure to focus on the facts. If this was an issue that personally affected you, you will want to make sure that you don't allow them to get a reactive response from you. Sometimes, even if this isn't something that happened to us, having these tough talks can be emotional; we can feel sad, angry, embarrassed, etc. It is important to remember that when we are in that discussion, we need to remain focused on the end goal. When we start to focus more on the emotional aspect or become reactive to what they are saying, the conversation can quickly derail and devolve.
  • Find the appropriate place and time to have the conversation. There are some discussions that are better to be had one on one or in a group setting. Some conversations are important immediately or after some more time and investigation into the matter.

During The Conversation

  • Be direct, open, and honest in this discussion. Stick to the facts you have written down and try to remain as neutral as possible.
  • Give them time to share their side and listen to what it is they are saying. Remember, this is a conversation, so we need to give the person room to say their piece or clarify some of the points we brought up. Put effort into truly understanding what it is they are saying and try to see this through their perspective.


Typically, when we go into these conversations, we have specific goals in mind for what needs to happen. When you are having this conversation, you want to make sure that you remain adaptable. After talking with the person, you may have a better understanding of their perspective and realize that there is a better alternative that is fairer for the situation at hand.

When we are in a position where we have these tough conversations, it is important that we exercise discretion. Keep confidential matters, confidential. Now that may not be 100% possible, depending on what the conversation is and if you need to take actionable steps or have a discussion with multiple people. But it would be best if you did not involve people who don't need to be in this conversation or situation. The goal is to honor their privacy and not start or feed into local gossip or inner-office shaming.

You will also need to be consistent with your treatment. If you are pulling one employee into the office for a discussion on their behavior, then you need to address that same behavior in other employees too. It can be hard when we have a work “bestie” or a favorite, but it is important that you show all your employees a clear and consistent message on what behavior is and is not appropriate.

Having these difficult conversations is always tough at first. Even for people who don't have a fear of confrontation, no one likes to be on either side of these talks. It's an uncomfortable situation, which is okay. When you are sitting on either side of these conversations, the biggest thing to remember is to be empathetic or, at the very least professional because no one wants to be in those situations unless they are necessary.