Preparing for a difficult conversation

Taking a few moments to reflect on your assumptions and intentions before beginning a difficult conversation can set you up to be more effective.

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A difficult conversation usually means one or both parties experience strong emotions, like anger, fear or frustration. Difficult conversations may involve conflict or differences of opinion.  

The following list of questions can help you reflect before you begin a difficult conversation. They can help you think about your own mindset, your intended outcome and potential consequences from the conversation. 

Consider your own needs

  • Do you have time to do this properly, or will you have to rush through it?
  • Are you responding to hearsay or assumptions, or do you know all of the facts?
  • Are you in the right frame of mind to do this, or should you wait until you feel less emotional?
  • Are you considering your own role and responsibility in the situation, or do you believe you’re blameless?

Explore potential outcomes

  • Are you looking for solutions and a way forward, or are you just rehashing the problem?
  • Will this conversation help bring about positive action or focus on what’s wrong?
  • Will this conversation bring about long-term improvement or only short-term results?
  • Are you thinking about the bigger picture or just this particular situation?
  • Will the potential solution energize the other person or drain them?
  • Can you preserve the dignity of all involved, or will someone feel shamed or blamed?
  • Will your approach encourage the other person to take control and responsibility for their well-being and success, or are you retaining all control?
  • Will you adequately address others’ fears and concerns, or will you minimize and dismiss them?
  • Will you help the other person develop their own plan for a solution rather than impose your plan on them?
  • Will you focus on actions and behaviours rather than on personality or characteristics that may be outside of the other person’s control? For example, rather than asking someone if they’ll be stronger, you may ask them what action they’ll take when things get difficult again. 
  • Do you plan to follow up, or will this conversation be the end of your involvement?  

Collaborate on solutions

Don't offer solutions unless and until you've given the other person a chance to come up with their own. If you believe their solution isn’t practical, don’t just shoot it down.  Instead, ask how they would deal with potential challenges, such as those you’re concerned about. For example:

If you do [whatever their solution is], how would you deal with:

  • juggling work and family
  • the additional expense
  • others’ reactions, etc.

Help the other person think it through, rather than lecturing them about your concerns.

Questions to help explore the situation

  • How have you coped so far?
  • What do you wish could be different right now?
  • What are you finding most stressful right now?
  • What is most important to you right now?
  • How can I be helpful to you right now?

Questions to wrap up

  • What do you need right now?
  • What will you do first? (And then what? And then what?)
  • Can we set up a time to talk again?


Communicating with emotional employees offers strategies can help you have supportive conversations with employees and avoid triggering negative reactions.

Check out the Supportive conversation library for questions and strategies to help you have a supportive conversation with someone you care about on difficult topics, like mental health, stress, addiction, anger, abuse or lying.

*Adapted with permission from source: Baynton, M. (2011). Resolving Workplace Issues. Waterdown, Ontario: Self-Published.

Contributors include.articlesMary Ann BayntonWorkplace Strategies team 2007-2021

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