8 Tips for Having Difficult but Productive Conversations at Work

What conversation are you avoiding right now because you know it will be difficult or uncomfortable? There’s a reason we call them “Difficult Conversations,” they’re NOT easy discussions to have with a friend, coworker, team member, or peer. A majority of people say they avoid tough conversations because they fear the other person will get defensive, argumentative or worse, might cry.

So, what’s the harm in avoiding the conversation, it will work itself out, right? Wrong. Avoidance is a sure-fire way to make a problem worse, it leads to dysfunction and in business it can impact morale, productivity, and turnover.

We want to challenge you to think differently about what this conversation is all about, let’s view it as an opportunity to help someone or to give them feedback, instead of a dreaded conversation. Here are a few steps to take to help you prepare:

1. Think through the conversation - How will you start the discussion, what’s your intent and the desired outcome? By the way, a great way to start a difficult conversation is to say, “Help me understand...”

2. Practice, Practice, Practice – The more you talk through the conversation out loud in front of a mirror or someone to help coach you, the more relaxed and comfortable you’ll be in the actual conversation.

3. Schedule the meeting – Assure you find a spot to meet that’s quiet, with no distractions.

4. Use empathy – Put yourself in the other person’s shoes, as you try to understand where they are coming from in the situation, it helps us better understand.

5. Don’t make assumptions – You are upset because Jim keeps missing deadlines, you assume he’s lazy, when in reality he may have important priorities, you know nothing about, that keep him from getting other work completed.

6. Forget the need to be right – This is key. The conversation should NOT be about you proving a point or teaching someone a lesson, it’s about resolving an issue and doing the right thing.

7. LISTEN – Listen to understand, don’t listen to respond.

8. Ask questions – Your goal is to better understand the situation.


No matter what the situation, being intentional about having a difficult conversation helps you be proactive, and it helps you build trust and respect with the other person. We can’t guarantee every conversation will go perfectly, but we can say if you keep your focus on having a simple, productive conversation, you can’t lose.