How to Make Difficult Conversations Easier

Difficult conversations are typically those that we know we should have yet keep putting off. They range from having to remind your best friend about the money they owe you, or telling your other half that you don’t want to have dinner with their family every weekend or trying to tell your colleague that they have bad breath.

Why do we put these conversations off? We dread the reaction, we don’t want to rock the boat, we are afraid people may think we are being unreasonable and petty or just don’t want confrontation. Whatever the reason, there are many subjects that we may find difficult to talk about. Discussing the issue or not, can be the difference between a great outcome and a miserable problem.

Difficult conversations will present challenges, so T.A.L.K. to improve results.

T is for Time Take the time to prepare. Spend your energy preparing what you want to say, clarifying your message and planning your script.
Ask yourself specific questions, such as:

  • What is the purpose of the conversation?
  • What do you hope to achieve?
  • What would be an ideal outcome?
  • Try to remain as objective as possible beforehand and ask if you may be more emotional than the situation deserves. Fast forward into the future (3 months, 7 years…) to put the conversation into perspective. Will it still matter then? Prepare a cheat sheet if it helps you stay on track.

    A is for Ask and Acknowledge Ask for permission to have the conversation. Make sure that it’s a good time for the other person to talk to you. The last thing you want is to catch someone when they are in the middle of something else.
    Attempt to acknowledge and understand his or her position. This isn’t necessarily agreement; it’s about understanding perceptions. Genuinely inquire about how the other person is feeling so they feel heard and know you are also aware of their point of view.

    L is for List Think of a list of ideas of how to start the conversation. The first thing is to let the other person know that you want to have a conversation. Do not start with “We need to talk” though, that’s like a loaded Dear John letter that instils fear in the recipient. Don’t beat around the bush either as you may be interpreted to be saying “What I want to talk about is so bad that I don’t even know how to start”. Addressing the issue directly makes it less of a big deal. It’s alright to say upfront that this is not an easy conversation for you. Here is a list of ideas to help you get started:

  • I need your help with what just happened. Do you have a few minutes to talk?
  • By the way, if I still remember, I think you still owe me some money. Any idea when you might be able to pay it back?
  • I’d like to see if we might accomplish a better understanding regarding ____. I would like to hear your thoughts and share my perspective as well.
  • K is for Knowledge Know that you need to follow up. Before you do, end the conversation on a high note by letting the other person know what positive impact this will have. Now you are interested in finding out what future solutions look like. Highlight what you can or are willing to change. Clarify agreements or commitments for future behaviour (the good, the bad and the ugly).

    Remember that your attitude towards the conversation influences your perception of it. If you tell yourself it is going to go terribly it most likely will. If you are still feeling stuck or overwhelmed, get some support. Find an outside resource such as a colleague, friend or coach to discuss your options. An impartial third-party perspective may provide valuable insight and help you clarify and prepare.

    When done well, having a difficult conversation you have been putting off, clears the air and frees up energy to focus on something else. The results can be super positive on people, relationships and performance.

    Drop me a line to share your thoughts and experiences on having difficult conversations and to let me know if this article was useful.

    Good luck!

    Photos provided by Flickr users Tambako the Jaguar, Thomas Hawk, Reggie Bibbs, jek in the box and superhan.

    57 Responses to “How to Make Difficult Conversations Easier”

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