An Easy Read on Having Difficult Conversations

Sky Capriolo

We’ve all been on the receiving end of heart-plummeting conversation starters like:

“We need to talk…”

“Please come into my office for a few minutes…”

“There’s something I need to tell you…”

“Close the door behind you…”

Did your tummy get a little queasy reading any of those? While the recipient legitimately can feel instant apprehension upon hearing someone say those words, the speaker has probably been reeling from internal turmoil leading up to the conversation for quite some time. If you’re in need of having a difficult conversation, what are the best tactics to employ so everyone walks away feeling, at the very least, less sick to their stomachs?

Just Do It

First of all, if you’re uncomfortable about something, says to recognize it as a signal that a good, albeit hard, conversation needs to happen. The author says these talks are about learning, not winning. 

Harvard Business Review published tips on tackling challenging situations, especially for conflict-averse individuals. They include:

  • Don’t push it off
  • Don’t worry about being liked
  • Be direct and respectful

Using active listening skills and conflict resolution strategies can be critical to the outcome too. Goals for a positive result, according to, is to find: 

  • a solution,
  • a plan, or
  • an understanding

Even though you’re wading into murky waters, keeping a proactive outlook will help steer the conversation to a safer harbor. 

Think of the Positives

Mindset has a key role in how a critical talk plays out. The University of Delaware suggests looking at the positives from the moment you decide to engage someone in a potentially uncomfortable confab. One way to do that is to forecast the outcomes you hope to see, such as:

  • Resolving a problem
  • Embracing constructive change
  • Gaining a better understanding of a person/situation
  • Repairing valued relationships

If a relationship, job or project is worth having, it’s worth the few moments of uncomfortable uncertainty that come at the onset of a dreaded discussion. If you focus on the hopeful result, you’ll set yourself up with “good vibes momentum” that your conversation partner will feel. In addition, it could acknowledge the “elephant in the room” you were both feeling, giving you credit for getting it out in the open. 

That Sense of Relief

Some people put off going to the doctor or dentist only to realize after it’s over, that it “wasn’t that bad.” (How often do we say that to our kids about a shot?) It’s natural to build up worst-case scenarios in your mind when it comes to things we just don’t enjoy doing. And for many people, putting your own emotions on display while knowing you’re likely to be the reason someone else’s emotions erupt can be daunting at best. 

Reality is often much easier and more resilient than you anticipate. Have faith that you are putting in effort, coming from the right place and looking for a better future when you embark on your next difficult but critical conversation. Hopefully, this blog has given you the motivation and tools to calm your gut and lead with your heart. Good luck!

Related Posts