Tips For Difficult Conversations At Work

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Nobody likes conflict and nobody likes to be uncomfortable. So yeah, having difficult conversations at work is no picnic. Whether it’s with a co-worker, employee or boss.

Today, I’ll share some ways in which I prepare for those difficult work conversations, and I hope you find it super helpful and useful.

Tips for Difficult Conversations Work How to Prepare

Tips For Difficult Conversations At Work

Tip 1: Get it scheduled ASAP.

Don’t let it fester. As soon as you know the conversation needs to happen, or this matter needs to be addressed, set a date.

Tip 2: Write your plan.

This should start with you asking yourself,

“Okay, ultimately, what do I want to come out of this?” 

And you really need to be very specific about that.


Am I trying to…

  • win an argument?
  • change somebody’s beliefs?
  • get an apology? 
  • have someone forgive me?
  • clearly outline expectations and see if they can meet them? 
  • break things off? 
  • make them step up? 
  • get them to understand where they’re missing the mark? 
  • show them how to do a better job?
  • terminate them? 
Regardless, you’ve got to ask yourself whether or not you’re hoping the conversation brings up possible solutions or exit strategies. 
Tips for Difficult Conversations at Work Exit Strategies

Tip 3: Construct a timeline.

The way I prepare for a difficult conversation is I do a timeline. Basically, it’s just a fact-finding session. 

I take out a big piece of paper, start writing down dates and facts, and — most importantly — I take all the emotion out of it.

Remember, the more emotional you are, the less productive a conversation can be. 

While business may feel personal, you can’t make it personal. Hence, the less involved you feel emotionally, the more likely you are to be very reasonable. And that just boils down to developing your interpersonal skills. 

Because so much of this conversation isn’t just what you say, it’s also your:

  • body language
  • delivery
  • tone
  • pace
  • inflection 

All the bullets above are so much easier to manage when you can manage your emotions.

Tips for Difficult Conversations Work Take Emotion Out

Tip 4: Imagine their side of the story.

What’s the old adage? Something to the effect of,

There’s three sides to the story. Your side, my side, and then the truth. 

Hence, I’d like you to just really try and imagine the other person’s side of the story — as if they’re telling it to their spouse. You must consider their lifestyle, their personality, their interests, etc.

This will not only help with having empathy, but, also, better prepare you for the impending talk.

For so much more related to this topic, like:

  • How difficult conversations were role-modeled for you (growing up)
  • The main key to a difficult convo
  • My tip for those who feel they may be the recipient of a tough conversation

Then, you must check out this episode of Build Your Tribe:

And don’t forget to subscribe to BYT for weekly shows dedicated your business and social media growth!


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