About this page:

This page supports Spearfish Innovation's workshop on Managing Difficult Conversations. It is designed to help you have more successful conversations, especially when they are the ones you’d rather avoid.


Should I Bother Having a Discussion?

People often ask themselves if it’s worth having a difficult conversation. In general you have four choices:

  • Address it directly - talk it over as soon as possible – initiate a conversation
  • Address it indirectly - talk about it with your boss, a mentor, or an influencer
  • Leave the relationship – simply sever contact with the other party
  • Do Nothing – lump it and just accept the situation


The bottom line is: trust your instincts. If you think you need to have a conversation, then have the conversation.

Managing Difficult Conversations

Stages in Managing Difficult Conversations

Preparing for the Conversation

5 Steps to a Successful Outcome

  1. Envision a desired outcome: Think about what you want out of the conversation. What would be the best possible outcome? How will things be different as a result? How will you know if things have really changed?
  2. Capture observable data: We can climb up the ladder of inference very quickly. Ask yourself what assumptions you’re making about the other person’s intentions. While you may be feeling disrespected, or belittled, be careful about assuming the other person meant to make you feel that way. Recall what you saw and heard as objectively as possible.
  3. Your thoughts and feelings: Using an Empathy Map (see our quick reference guide) review your earlier conversations. Write down your thoughts and how you felt in the moment. Ask yourself why you didn’t speak up, say certain things, or why you were feeling the way you were at the time.
  4. Take a walk in their shoes: Think about how they might have felt, what they might not have said. What might you have done to make them feel or say certain things? Consider things you may have done to contribute to the current situation. Have you avoided the person, made yourself unavailable, acted in a way that could be considered antagonistic? Consider different scenarios that could explain what’s going on.
  5. Develop a 3rd Story: Think about the situation as though you are a mediator with no stake in the result. By stepping back from your story, and theirs, you will be in a much better position to state the facts as you understand them. A good 3rd Story will also help you see how you may have contributed to the situation and how you may have made the other party feel.

Holding the Conversation

Before You Begin

The majority of the work in any difficult conversation is work you do on yourself. No matter how well the conversation begins, you’ll need to stay in charge of yourself, your goals and your emotions. Breathe, calm yourself, and keep focused on your outcome. At the same time you will need to be responsive to the other party and their emotional state.


Check in on your attitude toward the conversation – is it influencing your perception of it? If you think it is going to be terribly difficult, it probably will be. Focusing on a positive outcome will help you approach it much more confidently.

Quick Reference Guide

For details on each of the steps above, download our Quick Reference Guide


Practice, Coaching, Learning

As with any new skill, practice makes all the difference. Find a coach or mentor to help you through the process. Talk with folks you think are good at handling difficult conversations and seek their advice. Be willing to share with others what you’ve learned and what’s worked for you in a given situation.

Want More?

Book a Custom Workshop

Spearfish Innovation will be happy to work with you and your team to design a workshop tailored to your needs and your environment. Our highly interactive, engaging sessions provide you with the tools, frameworks and plenty of practice to help build your skills and your confidence.


If you'd like to know more contact Mike Northcott: mike@spearfishinnovation.com and he'll be happy to answer any questions you may have.


© Spearfish Innovation, LLC

© Spearfish Innovation, LLC

© Spearfish Innovation, LLC