An image of two men sitting and chatting new a river to represent the topic of the article - Difficult Conversations: How To Have A Convo We'd Rather Avoid

Difficult Conversations: How To Have A Convo We’d Rather Avoid

I was inspired to write this article on how to have difficult conversations that you’d normally avoid after a session with one of my clients. I’d noticed for a while that there was an issue that kept popping up with having these kinds of chats. Because of that, I wanted to create an article to help people outside of my client’s list.


Contents show


Why Is It Important To Have Difficult Conversations


Having difficult conversations can be nerve-wracking, but they’re an essential part of life. They help us establish and maintain boundaries that protect our mental wellbeing. They’re also an important sign of a healthy relationship. If you or your partner(s) aren’t able to have an open and honest conversation, then that could be a red flag regarding your relationship.


According to Meyer et al. (2009), a common concern is worrying about not being able to find the right words, saying too much or not enough, or saying the wrong thing altogether. Because of this, people can often avoid or delay having these difficult conversations, worsening the situation within that relationship.


Difficult conversations can be broken down into two types: those with your romantic partner and those with everyone else. Having difficult conversations with loved ones can be even more challenging because emotions often run higher. We don’t want to upset our partners or do anything we think might hurt them. But if you’re having the right kind of dialogue, no one should feel like that when the conversation comes to an end.


In the workplace, conflicts of various magnitudes occur frequently, which could be the result of a lack of clarity with expectations, poor communication, personality differences, competing interests, and changes within an organisation (Overton and Lowry, 2013). This can even lead to bullying.


Some of you may be aware of the ‘criticism sandwich‘. You may have experienced that method during your working life at some point. I know I have. However, the criticism sandwich method no longer leads to constructive conversations, because people are too aware of the method, and thus focus on the unsavoury middle layer of the criticism sandwich.


According to Weinstein, Itzchakov, and Legate (2022), difficult conversations, although they may start from a place of disagreement if done right, can lead to positive outcomes for everyone involved. And this positive outcome can be reached regardless of the relationship between those having the difficult conversation.




Before Having The Difficult Conversation With Other People


The reason for the conversation

The first thing you should probably do is ask yourself, “What do you hope to achieve from the conversation?” (Ringer, 2019).


Gather information

Is there any relevant background information you need to share? If this is a conversation with a colleague, then there might be policies that need to be referred to and reviewed before having the conversation.


Anticipate the other person’s perspective

Sometimes it can help to consider how the other person in the conversation with you might react or what their concerns might be. Spending time to consider this can help with having a more manageable conversation, and help you feel less anxious.


Practice what you want to say

Practising what you want to say can help you stay calm and collected during the conversation. This reminds me a lot of how I used to have to prepare to make a phone call.


Choose the right time and place

Aim for a private, quiet environment where you can speak freely without distractions. Consider both your and the other person’s schedules (especially in a work setting) and emotional states. If you try to have a difficult conversation with someone who is already visibly upset or stressed, then trying to have that conversation knowing that, will reduce the likelihood of a positive outcome.




How To Have A Difficult Conversation With Other People


Start with empathy

Much like having a difficult conversation in a healthcare environment, you want to have that conversation in a caring and empathetic way (Svarovsky, 2013). Therefore, acknowledge the potential difficulty of the conversation and express your desire for a respectful dialogue.


Use “I” statements

Focus on your feelings and observations instead of blaming or accusing the other person. However, although using “I” statements is common advice, especially to avoid the blame game, still be careful to use these statements with respect. While studying for my postgraduate counselling degree, I saw firsthand how people training to be therapists quickly became defensive when others directed “I” statements at them during our experiential group work.


Actively listen

Give the other person your full attention, listen without interrupting, and try to understand their perspective. A good listener is someone who has a non-judgmental attitude, can provide some form of validation, and can convey interest with their body language (Weinstein, Itzchakov, and Legate, 2022).


Open-ended questions

Use open-ended questions (questions that can’t be answered with a, one or the other, binary answer, like yes or no) to encourage sharing so you can have an honest and open conversation.


Avoid “why” questions

Starting your questions with what, how, who, where, etc. are better options than starting a question with a “why”, as this can cause people to become defensive.




Communicate clearly and concisely

Be specific about your concerns and what you would like to see happen.


Focus on solutions

Instead of dwelling on the problem, work together to find a solution that works for both of you. Problem-solving is your friend in such situations, as it helps avoid rumination on the negative aspect of the problem you’re discussing with them.


Be respectful

Even if you disagree, maintain respectful communication and avoid personal attacks.


Be flexible

Often the best outcomes involve compromises, so be open to being flexible and be willing to adjust your expectations.


Take breaks if needed

If emotions start to run high, take a short break to calm down and collect your thoughts.




After The Difficult Conversation


Reflect on the conversation

Reflecting on the conversation can be a good learning experience so you can become better at having these kinds of difficult conversations. Therefore, consider what went well and what you could improve on for next time.


Follow up

If you agree on any actionable items, then follow up to ensure they are implemented. It will also allow you to clear the air and provide support to help them complete the items.




Additional Tips



If the conversation becomes unproductive or disrespectful, let the other person know you need to end it.


Seek support

If you’re struggling to have a difficult conversation, consider talking to a trusted friend, family member, therapist, or counsellor. In a workplace setting, you may want to involve someone more senior to work as a mediator.


The picture is split in two, with the top image being of a two women sitting down and having a conversation. The bottom image being of a two White women sitting on a set of playground swings, having a conversation. The two images are separated by the article title - Difficult Conversations: How To Have A Convo We'd Rather Avoid


Before Having A Difficult Conversation With Your Partner(s)


What’s the reason for the conversation

Just like with having a difficult conversation with someone you’re not romantically involved in, you’ll want to ask yourself, “What do you hope to achieve from the conversation?” (Ringer, 2019).


Choose the right approach

It’s important to try to promote constructive conversations, as you’ll want to consider your partners’ needs and factor in their emotions, by trying to get everyone to speak non-defensively (Weinstein, Itzchakov, and Legate, 2022). By that, I mean to encourage those involved to ask questions in a sincere way and without trying to control how people respond. You may also want to consider your loved one’s personality and communication style. Some people prefer directness, while others need a gentler approach.


Outline a plan

It’s a good idea to go into a difficult conversation with an idea of what you want to talk about, otherwise, your concerns might not get a chance to be heard, leaving you deflated by an unfulfilling outcome.


Attitude towards the conversation

Our attitude can influence almost everything we do, and your attitude towards having this difficult conversation is no different. If you think this is going to go badly, it probably will (Ringer, 2019). Self-fulfilling prophecies are annoying like that. Approach the conversation with a mindset that seeks a positive outcome through a cooperative conversation.




Focus on love and concern

When talking to your partner(s), try to frame the conversation as coming from a place of love and concern for their wellbeing and the wellbeing of the relationship(s).


Acknowledge their feelings

Validate their emotions, even if you disagree, and avoid defensiveness. Just like when having a difficult conversation with another person, such as a colleague from work, you’ll still want to approach the conversation with caring and empathy (Svarovsky, 2013).


Pick a neutral topic starter

Sometimes, it can help to start with a neutral topic to ease into the conversation and gauge their receptiveness.


Choose the right time and place

It goes without saying, that there’s a good and bad time to have these difficult conversations. The moment your partner(s) walk through the door, isn’t likely to be a good time. Nor would it be a good time to have such a conversation if you or your partner(s) have been drinking.


Disentangle intent from impact

What your partner(s) might have intended and what actually happened, can be two different things (Stone, Patton, and Heen, 2023). It’s worth reminding yourself of that when having difficult conversations with your partner(s).




How To Have A Difficult Conversation With Your Partner(s)


Use “I” statements

Using “I” statements to express your feelings and observations, such as “I feel hurt when…”, helps with avoiding blaming or accusing. However, be mindful of how you use your “I” statements, as they can still trigger people’s defences.



Make sure your partner(s) have time to express their thoughts, needs, and wants. A one-sided conversation isn’t going to lead to the best outcome.


Open-ended questions

Again, the use of open-ended questions will encourage participation in the difficult conversation, and allow them to be heard, which is important. Consider questions like: “How do you feel when…?”, “What are your thoughts about…?”, and “What do you like about…?”.


Summarise and paraphrase

Another useful skill when having a difficult conversation with your partner(s), is to summarise and paraphrase what they’ve said. This shows you’ve been listening to what they’ve said and can be useful to get confirmation or clarification.


Dropping the “why” question

When I was training to be a counsellor, we were told to avoid using questions that start with “why”. This is because it’s associated with accusations and anger. For example, “Why are you such a…?” is common when someone is angry. Thus, that association can cause people to become defensive, which isn’t what you want to happen when trying to have a difficult conversation with your partner(s).




Listen actively and empathetically

Much like with having a difficult conversation with other people, you’ll want to approach the conversation from a non-judgemental place, provide validation when appropriate, and have engaging body language (Weinstein, Itzchakov, Legate, 2022). However, you’ll also want to remember, that with your partner, you’re also going to be an important part of their social support network.


Simply put, show genuine interest in understanding their perspective without interrupting and encourage your partner(s) to ask questions to help them better understand.


Focus on specific behaviours, not personality

Your partner(s) aren’t their behaviours, so if it’s their behaviour you want to talk to them about, then make it clear that your focus is that specific action that’s bothering you, not their overall personality.


Use “we” language when possible

When suggesting solutions, use “we” language to emphasise shared responsibility and finding a solution together. Although it may be subtle, the lack of using “we” language may have them assuming all the blame, or in extreme cases, they may see this as a breakup, thus making it harder for them to engage. Using “we” language highlights that this is something to work on collectively.


Validate their feelings

It doesn’t matter if you agree or not, their feelings matter. So even if you disagree, acknowledge their emotions and show understanding. However, that doesn’t mean their feelings supersede yours.


Be patient

Most importantly, these conversations may take time, so be patient and understanding. You may have to have this conversation more than once so your partner(s) can become accustomed to how these conversations work, helping them to bring their defences down.




After The Conversation


Give them time to process

Don’t expect immediate agreement or resolution. Give them space to process the conversation and emotions.


Stay open to further discussion

A part of being patient is to be open to continuing the conversation later if they need more time. It also means allowing your partner(s) to be able to talk about things that might be on their mind as well.


Focus on the positive

Appreciate their willingness to have the conversation and build on areas of agreement.


Seek support if needed

If the conversation is particularly difficult, seek support from a trusted friend, therapist, or counsellor. Couples counselling is always a good idea if you’re struggling to work out difficulties in the relationship, especially if you’ve already had several difficult conversations.




Additional Tips


Offer specific suggestions

Rather than just venting, propose specific solutions you’re willing to work towards together. Or, an even better approach would be to seek solutions together to work on, using the “we” language.


Remember your own goal

Try not to forget what the purpose of the conversation was. Stay focused on the desired outcome of the conversation, even when emotions run high.


Maintain healthy boundaries

Because of the nature of romantic relationships, there can be a lot of feelings involved that you wouldn’t encounter when having a difficult conversation with a colleague. Thus, if emotions run high or the conversation becomes toxic or disrespectful, take a break or end it politely. Boundaries are always important, even in a romantic relationship. Those boundaries, if in a healthy relationship, should be respected. If they’re not, there may be a bigger problem to address.


Follow up

Unlike having a follow-up when you have a difficult conversation with someone else, when it comes to your partner(s), you may want to check up on them sooner. Not because you want to follow up on progress, but to check that they’re ok.






Difficult conversations are an opportunity for growth and understanding. By approaching them with preparation, empathy, kindness, and respect, you can navigate them effectively and build stronger relationships. Also, remember, that having difficult conversations with loved ones is an act of love and care, with the aim being to strengthen your relationships and work towards positive outcomes.


As always, leave your feedback in the comments section below. Also, please share your experiences with having difficult conversations in the comments section below as well. Don’t forget, if you want to stay up-to-date with my blog, you can sign up for my newsletter below. Alternatively, click the red bell icon in the bottom right corner to get push notifications for new articles.


Lastly, if you’d like to support my blog, then there are PayPal and Ko-fi donation payment options below. Until next time, Unwanted Life readers.







Meyer, E. C., Sellers, D. E., Browning, D. M., McGuffie, K., Solomon, M. Z., & Truog, R. D. (2009). Difficult conversations: improving communication skills and relational abilities in health care. Pediatric Critical Care Medicine10(3), 352-359. Retrieved from

Overton, A. R., & Lowry, A. C. (2013). Conflict management: difficult conversations with difficult people. Clinics in colon and rectal surgery26(04), 259-264. Retrieved from

Ringer, J. (2019). We Have to Talk: A Step-By-Step Checklist for Difficult Conversations. Retrieved from,, and

Stone, D., Patton, B., & Heen, S. (2023). Difficult conversations: How to discuss what matters most. Penguin. Retrieved from

Svarovsky, T. (2013). Having difficult conversations: the advanced practitioner’s role. Journal of the advanced practitioner in oncology4(1), 47. Retrieved from

Weinstein, N., Itzchakov, G., & Legate, N. (2022). The motivational value of listening during intimate and difficult conversations. Social and Personality Psychology Compass16(2), e12651. Retrieved from

7 thoughts on “Difficult Conversations: How To Have A Convo We’d Rather Avoid

  1. Really great post, thank you for taking the time to research and share with us all. I think it is so important we learn how to have and have to navigate difficult conversations. So many of us suffer in silence, and/or don’t feel like we can speak up. I love all the tips n this post and think they are really helpful for me to reflect on, and I hope they reach others who need it too! 🙂

  2. Great article! I find it hard to deal with confrontation or difficult conversations. However, they’re very important – and these are helpful tips. You need to find the right time to have your conversation, and following up is a great suggestion.

  3. I always learn something new on your blog. Keep writing and growing.

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