10 Tips to Make Challenging Conversations Easier

Do you avoid what you perceive might be a difficult conversation? I confess that I do! I am a person who likes to keep the peace; I dislike confrontation or upsetting anyone so I therefore find I am the queen of avoidance when it comes to speaking out about something that may cause angst for myself or others.

Once I had an ‘argument’ with a flatmate about something he said that upset me. But he didn’t even know I had fallen out with him! For at least two weeks following the incident I did everything I could to avoid coming into contact with him in our flat and secretly seethed every time I heard him even so much as clear his throat. But the argument was completely in my head and the only person it bothered was me; he continued happily with his life completely oblivious to my feelings.

Years ago I read the book ‘Feel the Fear and Do It Anyway’ by Susan Jeffers. At the time it helped me move forward with a situation I had been avoiding. Despite the fact that I can’t remember the content in detail, the phrase ‘feel the fear and do it anyway’ has stuck with me and often comes to mind when I’m feeling anxious about a situation. This phrase is great advice for when you find yourself avoiding a potentially difficult situation. (Notice I said ‘potentially’ difficult situation - it is more often than not a situation that isn’t difficult at all; it is just our perception which has been blown out of all proportion by our overactive imagination). Remembering this phrase, I did finally face my fear and confront my flatmate with how I was feeling. As I suspected, he had no idea how his behaviour had made me feel but he was incredibly grateful to me for raising it and allowing us to clear the air.

I have a personal belief that when you hold onto negative feelings they impact on your physical body in the form of ailments of varying types and severities. Therefore, it is crucial to ensure that you find a way to express yourself and not continue avoid it.

So here are some tips for preparing and managing the conversation:

1. Purpose

Knowing why you want to have the conversation, what you want to accomplish and what would be an ideal outcome is the best place to start.

2. Past experience

Consider what in your past experience may have led you to feeling the way you do about the situation. Has the other person triggered something in you that has led to you reacting in a certain way? Are you more emotional than the situation would normally warrant?

3. Point of view

Think about the situation not only from your point of view but from the other person’s point of view as well. What assumptions are you making about them? Could it be possible that your assumptions are incorrect? Do they perceive the situation in the same way? Are they aware of what you want to talk about? How are they likely to feel about what you are going to say?

4. Preparation

It’s important to spend some time thinking through and maybe even writing down what you would like to say.  Some suggestions for how you could open up the conversation to ensure the most favourable and least defensive response are:

I’d like to share with you something that has been concerning me and then it would be great to get your take on it so that we can discuss it.

I’d really like to understand what just happened – do you have a moment to talk?

I get the sense we have different perceptions about ___________ and I’d like to hear your point of view.

I’m keen to see if we might reach a better understanding about ___________. I really want to hear your feelings about this and share my perspective as well.

Always approach the conversation with an attitude of curiosity; by stating up front that you’re interested in what the other person has to say, they are more likely to take the time to listen and engage in the conversation.

Once you have explored the other person’s point of view a good way to calmly express yours is by using the ‘UHT’ technique:

I understand… (recognise the other person’s point of view); however, … (outline your point of view), therefore I’d like… (outline your proposed solution).

5. Plan

Think about the possible outcomes and plan how you are going to handle different responses or emotions that may be triggered in you or the other person. Also consider the best time and place to initiate the conversation to ensure the other person is in the most receptive state.

6. Practice

Sometimes when you hear your words for the first time out loud they can not only sound strange, but they may not come out quite the way you intended or with the right tone. Therefore, take some time to practice out loud, ideally with a trusted friend or colleague who will be able to support you and give you feedback as to how what you’re saying is coming across.

7. Position

Where you are situated in relation to the other person can make a difference to how the conversation pans out. If you are sitting behind a desk this can create a barrier between you and the other person may feel intimidated. Consider whether it is best to be standing or sitting and aim to be at a 45 degree angle to each other rather than facing each other directly.

8. Pay attention

One of the most important aspects of any conversation is the ability to listen to the other person without interrupting. Pay attention to what the other person is saying, listen with an open mind and let them know that you understand. Take a moment to clarify anything that isn’t clear. Notice their body language and tone of voice as well so that you can get a sense of how they’re feeling when either of you speak.

9. Personal power

It is crucial to remain calm and centred as this is where you have most control.  Before you approach the other person take a few deep breaths and focus on managing your emotional energy. If you feel yourself (or the other person) moving off-centre, concentrate on bringing yourself back to centre as this will ensure you stay in control and help the other person to remain centred as well.

10. Positive outcome

Aim for a positive outcome from the conversation. Even if it’s not the outcome you had hoped for, at least know that you did everything you could to communicate effectively and keep the relationship on positive terms.

What about you? Are you a person who avoids what you perceive to be difficult or challenging conversations? Or are you always up front about what's on your mind? If you’ve got some techniques that have worked for you I’d love to hear them – just add them in the comments section.

If you enjoyed this article, click here to access Mel Sherwood’s ‘Top 5 Tips for Public Speaking Success’

Mel Sherwood is a pitch and presentation specialist who prepares ambitious entrepreneurs and business professionals to take centre stage, embrace the spotlight and present with more confidence, credibility and conviction.

Mel's book 'The Authority Guide to Pitching Your Business - how to make an impact and be remembered... in under a minute!' is available on
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