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How To Approach A Difficult Conversation

November 2, 2015


We all go through moments in life when we encounter a scenario we are dissatisfied with. We find ourselves in a situation with a partner, friend, colleague or other when we need a tricky talk.

Below I am sharing my tips on how to approach a difficult conversation, which I hope will help you navigate any awkward scenarios which may cross your path.


Identify why you are unhappy with ‘x’ situation

Write down on a piece of paper exactly why you are unhappy with a given situation; perhaps you are dissatisfied at work because a co-worker took credit for an idea of yours, or maybe you feel that your partner has been insensitive . . . if you are feeling unsettled, listen to that feeling. Try to unravel it in your own mind before taking the next step and approaching the person, or people, you need to discuss it with.

Talk through your concerns with a confidant

It is so helpful to have a sounding board – talk through your situation with someone you trust before broaching your difficult conversation. This confidant may be able to clarify the situation further for you, identify which areas you should focus on, and which perhaps, you should leave out.

Prepare for your conversation & bullet point your concerns

Whenever I am put on the spot, I pretty much forget everything I meant to talk about. I have learnt that in order to keep my thoughts on track, I need to have my discussion points to hand. Bullet point your concerns and try to be as specific as possible.

When it comes to location, try to find somewhere neutral for you to meet to discuss in person. Or if meeting in person is not possible, a convenient time to talk on the phone. Chose a location where you feel comfortable. If you are having a discussion with a colleague, you may want to explore the possibility of a Human Resources representative being there; certainly you can ask HR for advice ahead of time too (refer to the point above).

Invite the person, or people, you are wanting to talk to, in to a conversation and structure it

When approaching a difficult conversation, it can feel like you are gearing up for a fight. I have found that by switching your mentality from ‘this is going to lead to an argument’ to ‘this is going to lead to a solution’ you work towards a positive outcome.

Use your bullet points to structure the conversation, moving towards a resolution.

Introduce the topic of conversation

For example, “I would like to discuss something which has happened at work which has made me feel unsettled, I would like to find a solution for moving forwards which will work well for all of us”

  • Explain clearly, logically and firmly your concerns. 
  • State, again, that you would like to find a solution. 
  • Listen to the other party’s response. 
  • Put a plan of action in place for the next steps.
  • Thank the person, or people, in the discussion for their time. 

It always pays to be polite and positive. Approaching a difficult conversation can be just that – difficult – however I have found that the relief felt after said discussion far outweighs the worry or dissatisfied feeling before hand.

Whatever the scenario may be, if you are feeling unhappy or stressed, you have every right to bring it up. Things will only change if you put the groundwork in place to instigate it.

If you are unhappy at work, or home, or with something that has happened, don’t ignore it. We feel things for a reason.

Be brave! Remember, you are working towards a solution, not an argument.

What’s Your Take?

I hope that you’ll feel more confident approaching a difficult conversation in the future.

I would love to hear of any methods you have for working through similar scenarios. Have you had to broach a conversation which was particularly awkward or tricky?

Love, Monica x

Title image by Anna Shvets

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