A Guide to Uncomfortable Conversations

Life is full of awkward and uncomfortable moments. We’ve all been in situations that require a rewind button. These situations can be difficult to navigate for all parties involved and can escalate, causing additional problems. This can be especially hard when you run a small business and are in close quarters with your co-workers daily. While we can’t avoid them altogether, confrontation does not have to be unpleasant for either party. It’s impossible to know the exact outcome of each conversation, but reaching mutual ground is always possible.

If you find yourself falling victim to a painful chitchat, I recommend trying these tips for turning the conversation around.

The option I tend to explore first is using phrases that defuse tough situations.

A few of my personal favorites are:

  • “What do you think about this?”
  • “That’s a valid concern.”
  • “I hadn’t thought about it that way.”
  • “That’s a really good question.”
  • “Is there something I can’t see.”
  • “What I’m hearing you say is …”

All of these phrases acknowledge you are listening without discrediting anyone’s feelings or beliefs. Overall, entering a conversation with a collaborative mindset, versus an accusatory one, will show that you are willing to work together to problem-solve and will likely yield better outcomes.

Another option is to switch the topic of conversation. If the person talking is rambling about an uncomfortable topic with no end in sight, you can simply shift the conversation. Something like, “Wait—before I forget, how is your son doing? I saw on Facebook he recently accepted a new job, how is he liking XYZ company?” This also gives them a chance to brag about something they are passionate about without going into extreme detail. The idea behind this method is to give the conversation momentum, so you aren’t stuck. Don’t look uncomfortable, don’t hesitate, and don’t worry! If you start leading the conversation in another direction, most people will follow you into the next topic.

If you like avoiding conflict, then the last option may be a bit more difficult. However, sometimes it is best to just be direct—and maybe it’s the only option to shut the conversation down. Your co-workers very likely don’t want to make you feel unsafe or uneasy, so if that’s the case, don’t be afraid to speak up in the moment. Plus, they’ll feel a lot better knowing where you stand now than finding out from gossip (or worse, HR) later.


There are many ways to approach difficult conversations that can minimize potential tension and creative productive communication — these are just a few. Although not all problems or conflicts need to be addressed directly, certain conversations should not be avoided solely because they may feel uncomfortable.  Additionally, it is also highly likely that we are overestimating just how uncomfortable the discussion will be, you may quickly realize that the situation isn’t as uncomfortable as you thought.