How To Begin Difficult Conversations

Precious few people enjoy having difficult conversations. Many of us full-out avoid difficult conversations for a number of reasons. We fear how people will react. We feel stressed about what we should or should not say. We worry we’ll lose a relationship that’s important to us.

The result of all this self-induced stress is that we often convince ourselves it’s better to avoid the conversation… except that in almost every case the pressure keeps building and everything keeps getting worse. So, lets look at how to begin difficult conversations.

Create A Foundation For Difficult ConversationsDifficult Conversations

Three of the most important things to remember when having difficult conversations are:

  • Be genuine and treat everyone with respect
  • Be honest and empathetic
  • Share your emotions (likely nervousness), but don’t be emotional

If you do these three things I promise, even if you have difficulties during the conversation you will likely be forgiven. In fact – not being perfect might help you build rapport as it demonstrates you are human just like they are.

Overcome Fear Of Having Difficult Conversations

Fear is a natural and understandable reason why we avoid difficult conversations. When we fear something we never fear the best case… we fear the worst.

For Example: If we fear falling down, we fear a broken hip not a light bruise. Same thing goes for having difficult conversations. The stories we tell ourselves almost always are worse than any outcome or the constant stress of not acting. Unfortunately, by not reacting we waste time and energy and never get to experience all the opportunities that COULD HAVE BEEN if we cleared the air.

Build Trust And Respect

In most cases, people who have difficult conversations build better relationships. Why? Because as long as those conversations are built on honesty and respect, the process teaches us that we can trust each other. Difficult discussions also often lead to creative and successful solutions – which adds team pride to your relationship.

Some conversations will be easy – some will be difficult – all will be worth it.

By having difficult conversations we:

  • Show the other people we care
  • Help everyone involved see a different perspective (creativity)
  • Tap into (and practice) empathy
  • Become better families, friends and/or organizations

Be Clear On Your Motive

Your motive is very important… and it requires self-reflection. If your motive is to support the other person, a project or even a whole team, you can mess up the conversation technically (I’ll share my 12 point steps in future blogs), and still have a great outcome. If your motives are honest and respectful your audience will realize your good intentions (maybe not immediately), and will cut you some slack. If your motive is selfish, your technique can be flawless and the outcome will be… well… you know… not so great.

Take Great Care With Timing of Difficult Conversations

Time and place are very important. Even if you only spend a few minutes preparing, your prep time is well worth it. You also want to make sure your audience is in a space they feel safe. Don’t try to have a difficult conversation just before they have to run out the door or before an important client meeting.

This is going to be a sensitive discussion so find a time and place where you won’t be interrupted, where everyone will feel safe and where an open/respectful discussion can take place.


How you manage the fear and stress associated with having difficult conversations will make you happier and more emotionally engaged… in the long run. Be confident and respectful in a way that demonstrates you are dedicated to being part of the conversation and a solution.

When your motives are true and when you are empathetic about their and your feelings, 9 times out of 10 you will end the conversation (or series of conversations), with a better relationship.

How you begin difficult conversations will always be an investment in your future.

Happy communicating.

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About Bruce Mayhew
Bruce Mayhew is a Leadership Coach, Keynote Speaker and Corporate Trainer who builds strong client and co-worker relationships that give clients a competitive advantage. Our training and development programs include: ■Generational Differences ■Effective Business Email Writing ■Email Etiquette ■Phone Etiquette ■Behaviour Event Interviewing (BEI) ■Mindfulness ■Using Linkedin to Build Client Relationships ■Objective Setting Made Easy

2 Responses to How To Begin Difficult Conversations

  1. Pingback: What Leaders Should Know About Intrinsic Motivation & Extrinsic Motivation | Bruce Mayhew Blog: Training And Development, Communication Training Blog

  2. Pingback: Embrace Your Night Owl Employees | Bruce Mayhew Blog: Training And Development, Communication Training Blog

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