The conversations that always come back.. how to prepare for difficult conversations




Difficult, uncomfortable and emotionally loaded conversations are everywhere. Oftentimes what makes us worried is not only how to go through them, but actually how to even get started with them. It goes one layer deeper even, because we do not know whether we should tackle them at all, and just avoiding them altogether seems easier because “who I am to tell people how I feel?” or maybe because “the consequences of such talk could be horrible”. Usually though is the person who wants to initiate the conversation and decides to censor her/himself the one who suffers the most for the lack of that conversation. And the consequences are much more far-reaching when we do not have those conversations, especially because we know that they always come back.


I cannot count the times where participants of my masterclass “How to navigate difficult conversations with assertiveness”, or during corporate assertiveness trainings, have mentioned that they are dealing with the indecisiveness about having a conversation that has been daunting them for years. Or how many times they have tried to have that conversation with the same person for a very long time, only to find themselves frustrated and not able to go through it or feeling not heard.

These conversations can go across topics, are multi-layered and complex. But this is exactly what we are going to do now, we are going to unpack them, put them into context and self-reflect. You will be surprised how half of the work of having these conversations resides in your ability to know what YOU want out of that conversation, rather than performing it. And more often than not we will discover that the very terrible reaction we feared from others when having the conversation is usually never happening.


Three things we need to work on when we talk about difficult conversations:

- The preparation phase: with ourselves mostly

- The communication skills required: assertive and non-violent communication tips to get started

- The aftermath of the conversation: is guilt creeping in? How to keep that at bay


Being an expert of the intersection between communication and mental wellbeing at FindYourWay Coaching, I find it key that we also talk about a specific territory where these conversations are important: mental health. Why? Because conflicts which are not articulated, or a conversation held with the wrong tone or even an e-mail sent with poor consideration takes a toll on our mental health. But that is not the only reason: people who are struggling with their mental health at the workplace really want to talk about it but feel the stigma and the shame and recent research has shown that people who use assertiveness in their communication style are less anxious and are more open in their communication and in their sense of purpose. In organizational contexts, assertiveness training is also a powerful tool to promote team functioning.


But wait. What type of conversations are difficult conversations though?


- Think of something that has bothered you for a very long time, and you never managed to tell your spouse or your parents or siblings or any family members. That could be a type of difficult conversation;

- Disagreements. You so want to disagree with your colleague or manager on a topic, but you feel you are not “allowed” to do that (or maybe you do not allow yourself) or fear not to be liked anymore right after the disagreement has taken place?

- Any conversation that has a taboo or stigma attached to it: money, mental health or health in general, asking for forgiveness, gender discrimination, injustice, war.


The preparation for the conversation


Since I was a kid I have been journaling my thoughts and emotions away. I do the same now, but I also use that journal to prepare my difficult conversations with people. So get your pen and paper and prepare this conversation in a very practical way.

- Write down the topic of the conversation. Is it something you want to have or stop having? Is it a specific request or a general idea on something that needs to change? It is a tough topic that might required other two or three mini-conversations? Reflect on this.

- Write down the goal of the conversation first. YOUR goal/goals first. What is your desired outcome of the conversation?

- Now, write down possible scenarios of how the conversations could go, keeping in mind also what the other person’s goal could be.

- If many emotions are involved and it is difficult to process everything, take a break and use some simple distraction or self-care technique. Breathe and be patient with yourself. It takes courage to have those conversations!

- Tell yourself that most of the catastrophic anticipation of the bad outcome of the conversation might be just only a fear. And that we might experience great relief and satisfaction afterwards.

Also, you don’t have to write a long paragraph or anything. You can simply use keyworkds for each point.


Assertive communication tips to get the conversation started


Usually naming the elephant in the room helps with getting started. And we all know how powerful “I statements” are for conflict management. Examples of a good introduction can be:

- I know we never talk about these things, but it is important to me to be able to mention...

- I would like to have a conversation with you about something. Whenever you have time it would be important for me.

- I feel it is time for us to tackle an elephant in the room that has been there for some time. Do know that this is not an easy conversation for me to have, so thank you for giving me the time and space to expressing a few important points.


The principles named in the non-violent communication guidelines say that it is possible to have any conversation, as long as it it non-jugdemental and it is honest about how we are feeling and it is based on factual observation. And if we care about the relation with the person we talk to, accusing them would not result in us meeting our goals, but it would do the opposite. This is why instead of saying “you are always interrupting me in meetings, ”, but we better say “I have noticed that you have interrupted me a couple of times today during the meeting, and that has left me feeling frustrated, especially because it is not the first time that happens”.

Another good example is making a request. We never know how to start. Well, what about we start by stating that we have a request about something that it is important to us. And remember, a request is not a demand, so it would need to be met by our interlocutor, so we need to give him/her the space to express their requests as well and see how we can meet half way.

You can rehearse the conversation in your head or in front of the mirror if you foresee extreme difficulties in going through it. The more you prepare and the more compassion you have for yourself, the better the results. If the conversation does not go as planned, remember that you can always have another chance!


After the conversation has taken place

Yes, we managed to have that conversation, we found the courage and it went well. Now what? Will the relationship with the person being ruined? We ruminate. Maybe it was better to avoid that altogether. STOP 😊 And ask yourself the following questions:

- What would be the consequences of never having that conversation?

- What would be a positive outcome of the conversation that would change my life for the better?

- What if an entire team could be positively affected by having real conversations instead of feeling angry at each other for feedback gone bad?

- What if we have improved the team’s mental health because of this conversation?


Mental Health

As I mentioned before, talking about mental health is important when it comes to difficult conversations. At the workplace it seems to be still a taboo, despite being a topic that now has seen a lot more interest and care. Sometimes it is because people fear that naming their own mental health could make them feel worse. Some other people think that it is offensive to talk about someone else’s mental health. And just for simpler reasons: we don’t know how to talk about mental health. This is changing though, and many people are getting more and more interested in doing something called “first aid for mental health”, and have meaningful conversations with others in distress.

What if we would be worried about someone’s mental health because of the pandemic or because of the war? Maybe we notice changes in behavior and a general sadness and want to help? Asking how are you does not have to be difficult. Here some few tips which have a lot to do with the introduction I was mentioning before. They can be used at the workplace between colleagues but also by managers with their reports.

- We never talk about our mental wellbeing and I think the time has come for us to start doing that

- How are you really feeling? How can I support in the work environment to feel safer?

- What do you like to have in place here at work for your mental health? I am struggling myself sometimes too with all that has been happening.

- What do we need as a team to have a more meaningful conversation?

You would be surprised but how disarming and powerful these questions are. Your next difficult conversation or healthy disagreement is around the corner, what about tackling it? Because, as Susan David once said: “Courage is not the absence of fear, it is fear walking”.


FindYourWay next public Masterclass on difficult conversations will take place on May 20th. Click here to join


Alessandra Patti

Founder and Mental Wellbeing Strategist. Working at the intersection of Mental Wellbeing and Communicaton Traininings. Committed to mental distress prevention.

38 views0 comments