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How To Prepare For Difficult Conversations

Having a difficult conversation is one of the most uncomfortable things people can imagine. It is no surprise, then, that many of us will go to great lengths to avoid them at all costs. However, there are many benefits to ‘killing monsters while they are little’ and getting unspoken truths out into the open. 

As an advocate, social worker and manager I have had my fair share of challenging conversations and have learnt a thing or two about how to keep your cool, see things for what they are and respond in a way that is more likely to result in a positive outcome. And because I learn best by sharing my knowledge I figured writing about it might just offer some utility to others! So let’s get started.

The situation

Let’s face it, we all know that feeling of ‘I think I need to say something’, as well as the dread and self-deceit that often follows – ‘I’m sure it’s just a blip, it’ll get better’. You might have one of these situations in mind right now! Often we talk ourselves out of saying something for the perceived benefit of keeping everybody (but really, us) happy, calm and the situation under control.

From an evolutionary perspective, this makes perfect sense – our brains and behaviour have evolved to maximize our chances of survival. Interpersonal conflict has the potential to seriously threaten our sense of safety and wellbeing, hence our hesitation to go there voluntarily. Framing it this way helps us to acknowledge that being uncomfortable with hard conversations isn’t a defect or a weakness, but rather a physical competence our body has developed to help protect us.

Challenging situations don’t often get better on their own.

However, challenging situations don’t often get better on their own and tend to get worse over time. What started as a little nuisance can quickly turn into a daily source of frustration and negative emotions. Our own fear of addressing the situation turns into anger and resentment towards the other person. Unfortunately, we think we are the world’s best poker players and have it under control, but really we don’t – we slip into passive aggressive behaviours and make critical judgments, snappy comments, eye rolls, pretend not to hear or misunderstand something they’ve said or withdraw from their presence altogether. This damages our self-confidence, sense of happiness and most importantly our relationship with the other person; it certainly doesn’t help to resolve any unspoken conflict. It’s a vicious cycle in which we shift our own responsibility of speaking up and improving the situation to blaming the other person, ultimately turning ourselves into helpless victims in the process.

When to say something

Unfortunately, there are no checklists for when to say something and when it’s best to sit back and wait for things to improve, but if you are radically honest with yourself you can usually tell whether you are intentionally shying away from a conversation. If that’s the case, there’s your first clue! Once you have identified that something needs to be talked about, you can follow the process outlined in the next few paragraphs to help you address the issue and hopefully turn the situation around.

Be radically honest with yourself

The first step in acknowledging any difficult problem is to start with what you have the most control over: yourself. Sit down and take some time to reflect on the situation. Surprisingly, that can sometimes be enough to solve the problem as you might notice facts you hadn’t considered before. But even if it doesn’t, it will prepare you for the conversation to come and will allow you to simulate different scenarios and outcomes.

Here are a few questions to help you get started:
  • What am I finding difficult right now? How long has this been bothering me?
  • What has led to it being a problem? Why am I finding this difficult now?
  • Who else is involved? What role are they playing?
  • Is the other person aware of this being a problem? If so, how were they made aware of the problem? Was that process helpful or hindering?
  • How have I contributed to this becoming/being a problem?
  • What else might be going on for them right now that could have an effect on/cause the problem at hand?
  • Do I know enough about this problem? What else do I need to know? What am I missing? Who else do I need to speak with?
Start by reflecting on the situation

In answering all of these, be as truthful as you can. Remember, you are doing this exercise by and for yourself, so you don’t ‘win’ by cheating. Getting it out on paper can help us to create some distance between thoughts and emotions, organize our arguments more clearly and look at more practical solutions, so I recommend you get writing or use a whiteboard to visualize.

Be especially honest about your own part in all of this. You shouldn’t take responsibility for other people’s negative choices or behaviour – everybody deserves to be treated with kindness, dignity and respect. However, being open to the possibility that we have contributed to the problem at hand can open us up to insights and potential solutions we might not have considered otherwise.

Preparing for the conversation

Once you have taken some time to reflect on the origins and causes of the problem it’s time to get underway with the next step in the process: preparing for the conversation.

Again, with pen and paper, ask yourself the following questions:
  • What is my ideal outcome? What do I want the other person to know/feel/understand?
  • What’s the absolute minimum of information I need to get across?
  • What preparations do I need to make to support this outcome? What do I need to know more about/understand better/learn before having this conversation?
  • What attitude/level of energy/attention do I need to bring to the conversation for this outcome to be realistic?
  • Am I willing to make concessions?
  • What is not acceptable?
  • What is difficult about this particular conversation? Why do I feel uncomfortable about addressing it? What buttons does it push? Why?
  • How will I remain calm, centered and focused on the issue when the conversation becomes emotional?
  • How is the other person going to feel when I share my views with them? What negative emotion or reaction will this create for them (defensive, angry, sad, anxious, etc.)?
  • How do I need to say what I want to say? How will I ensure they can actually focus on what I am telling them?
Writing your answers down can help you get a better perspective

Spending some time thinking about your ideal outcome, what’s needed to achieve it, personal motivations and limitations, and the other person’s perspective can help to see things through a new lens. Rather than focusing on frustrations and issues, you are directing your thoughts towards the impact you are having and solutions you can create.

The talk

You have taken some time to reflect on the issue and what changes you want to see. Now’s the time to do the hard part and get it out into the open! The most important thing to keep in mind is that your own attitude throughout the conversation will play a crucial role in creating positive outcomes. Even if the only positive thing to come from the conversation is the peace of mind of having spoken your truth with honesty, integrity and kindness! Before you start the conversation, try and find some time to get centered, calm and grounded. Entering the conversation from a place of balance, curiosity and with a motivation to share the exploration of new solutions will create a vastly different dynamic to focusing exclusively on perceived problems and shortcomings. Breathe, meditate, go for a walk, have a stretch, chew some gum, play with a fidget spinner – whatever helps you feel more centered and grounded. Personally, I like the box breathing exercise. Breathe in for four seconds, hold for four, out for four, hold for four – repeat. Do this for two to three minutes (or longer if you have time) and focus on your breath. When your attention goes elsewhere, bring it back to the breath.

A few additional pointers to help you stay on track:
  • The setting matters. Decide what environment will be most conducive to a successful conversation
  • Write down your key points you definitely want to bring across no matter what. This will help to keep you focus when you get nervous/anxious during the conversation
  • There will be some natural nervousness before and throughout the conversation, this is normal. Again, it’s your body doing clever things to keep you safe! Come back to your breath and relax. You’ve got this!
  • Make sure you stay focused on the intended outcome, not the perceived wrongdoing
  • Stay curios, balanced and open-minded. You’re trying to find a solution, not ‘win’ the argument
  • If you feel yourself becoming defensive and reactive, take a deep breath, try and find your way back to a calm center. If you can’t, it’s okay to acknowledge your feelings and take a break from the conversation!

It can be helpful to let the other person know that you would like to talk to them about the topic at hand in advance so they can prepare for the conversation. However, be mindful of not making them wait too long, or they might start to feel anxious and become defensive, which in turn can derail the conversation before it begins.

Reflection

Much like anything in life, working through difficult conversations are a skill that can be learned through repetition and reflection. Whether the conversation went well or not, it’s a great idea to look back on it to see what (if anything) could have been improved and what worked well. This will not only help you to better understand the outcome of the discussion, but also enable valuable learning and personal growth for similar future situations.

Here are a few questions you can work through afterwards to unpick what was said.
  • Do I feel the conversation was a success? If yes, why? If not, why not?
  • Was I able to bring across my main points? What worked? If not, why not?
  • Was I able to stay grounded and balanced? If yes, what helped? If not, why not?
  • Why did the other person react the way they did?
  • Where do I stand now with the other person? Do I need to follow up with them? When?
  • What could I have done better? What have I learnt?
  • How will I make sure I use the learnings from today for the next difficult conversation?
Reflecting on hard conversations afterwards helps to improve for next time

Conclusion

Difficult conversations are just that – difficult. However, with exercise, reflection and an honest desire to find solutions (rather than problems) you have all the tools you need at your disposal to become a successful mediator and negotiator of most hard talks that might come your way. Getting things out into the open can initially be painful, as our own anxiety about how the other person might react ramps up. Unfortunately, this unreleased negative energy will soon pile up inside of you and if left unattended will leak into other areas of your life that don’t deserve to suffer. Hopefully some of the suggestions in this article have helped you to reflect on how to speak your truth.

If you have successfully navigated difficult conversations, I would love to hear what you were up against and what helped you to negotiate positive outcomes!

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Nikita Picugin

Leadership and Team Consultant

I focus on how to get the best out of people, lead with integrity and courage, and create amazing teams.
I work as a consultant, project manager and lecturer. 

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