How to have difficult conversations with anyone - Amber Hurdle | Globally Recognized Leadership & Personal Branding Expert

How to have difficult conversations with anyone

December 16, 2014

Many times difficult conversations are not had because proper thought and consideration have not been invested to make it respectful and comfortable for all parties. Or worse, they are had without preparation and it’s a train wreck that damages relationships.

I’m not going to lie—you have to get to a point where you simply have to (wo)man up and do the less desirable things. AND you owe it to yourself and the person you are having the “crucial conversation” with to provide the respect and dignity of a thoughtful conversation. Here’s how:


  • Organize your facts related to the issue and the impact it had in your business/family/friendship/etc…in one document or file
    • Document previous conversations
    • Gather emails that support your message
    • Note related feedback from others
    • Address previous commitments that were not met
  • Role play with a trusted advisor or peer if you lack certainty in delivering the message confidently and respectfully


  • Remove emotion from the conversation and focus on the desired end result
  • Build rapport first through casual conversation and a genuine interest in their current state of being.
  • Deliver the negative feedback in the middle of a praise sandwich.

Bread: Start with a compliment: “I appreciate your contribution to the team. Your creativity has elevated our game.”

Filling: Then deliver the criticism: “I have to bring to your attention that we just aren’t seeing the results that you committed to when taking on this project.”

Bread: Finish with a compliment: “I know once you refocus your efforts in the areas that will create an impact you will blow my expectations out of the water.”

  • Stick to the facts. (Never let your emotions or theirs cloud the agenda, nor allow for gossip to be introduced in a professional setting or “kitchen sinking” to ensue in a personal circumstance.)
  • Confirm understanding. (This may be verbally through allowing them to vocally shadow your feedback or through formal documentation.)
  • Ask what support (s)he needs to get the result you are requesting.
  • Confirm commitment to your plan.
  • End on a positive note: “I know you can do this.” “Thank you for your openness.” “I know we can accomplish this together.” “It is so nice being able to speak openly about our challenges. I’m glad we have this trust.”

So going through this process can help you have difficult conversations with employees, vendors, your kids, your spouse or really anyone that you need to address a less than positive issue with.

Does this give you a little more confidence? Can you see yourself having that challenging conversation that you’ve been putting off now that you know how to do with respect AND power? Let me know in the comments!


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