How to Prepare When You Have a Difficult Conversation Ahead

How to Prepare When You Have a Difficult Conversation Ahead

Facing the Awkward Conversation Head-On

We’ve all been there in some context or another – the awkward, difficult conversation that we’d rather avoid. Maybe with a client, a colleague, or a friend. You messed up big time, or maybe someone else messed up, but lucky you – you get to deliver the bad news.

We know it’s not gonna be pretty. Nobody wants that job. Yet we can’t skulk away trying to dodge the bullet, hoping in vain that the problem will just disappear. Because we all know how well that goes.

When I was a virtual project manager for a real estate company, I often had to deliver bad news to a client, property manager, or co-worker. Houses got broken into, projects cost more than expected, or water pipes burst and flooded a newly completed rehab. Those difficult conversations helped me learn to stay low-key, gather all the information, and think through possible alternatives before starting the conversation.

When it comes to the awkward conversation, I’ve learned:

  1. It’s best to just stay calm and face it head on.
  2. Usually (usually!) talking to them is not as bad as I imagined.
  3. It helps if I can soften the blow with some possible alternatives, solutions, or encouragement.
  4. I handle it better if I jot down a few notes or talking points ahead of time. I can stay calmer and focus on the points I need to make rather than getting emotional.
  5. Slow, deep breaths.
  6. Listen to them. Really listen and convey that I understand their point of view rather than coming up with a defense.
  7. Own any mistake I’ve made and offer to help somehow.
  8. Keep it low key, low drama, and look for ways to frame it in a positive light.
  9. I try to put it into perspective. Yes, this is important and needs to be handled, but how much does it really matter in the bigger picture? The drama will pass, so don’t let the stress spill over into every area of my life.
  10. Be classy. They’ll remember how I handled it just as much as the problem itself.


The other issue to consider is delivery. Consider your relationship with the other person, how they typically prefer to communicate, and the degree of difficulty of the information you’re giving.

Is the news best delivered:

  • written out in an email? This can give you both time to process your thoughts and cool down. However, choose your words carefully since tone is difficult to convey and often misinterpreted in emails.
  • over the phone? You can hear each other’s tone of voice and explain, answer questions, talk through ideas, and hopefully diffuse any concerns as they arise.
  • in person to read each other’s faces and try to keep it friendly? Sometimes it’s harder for them to get upset when they’re face to face with someone who is truly remorseful or sympathetic. You can also discuss more in person and brainstorm possible solutions. This tends to generate a lot more ideas and camaraderie than emails.


No one enjoys being on either end of bad news, but sometimes it can’t be avoided. We have to suck it up and forge ahead. I’ve learned it’s better to do so calm and prepared.

How about you, do you try to avoid the difficult conversations or have you learned some other techniques that help? I’d love to hear more ideas – share in the comments below!

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