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A Users Guide to Important Conversations

This article provides a set of distinctions and frameworks for preparing and holding important conversations. These conversations are often thought of as ‘difficult’, not because they are difficult to hold, but because we often feel negative emotions, and imagine awkward, uncomfortable moments arising in them. The prospect of having important conversations can have us feeling anxious, especially if the conversation involves making or responding to a complaint or criticism.

By Stewart Ramsay, Vanry Associates

Examples of challenging conversations include:

  • A performance review of a person or deliverable that hasn’t met expected performance standards.
  • Negotiating contracts that could make/break your business.
  • Project review meetings where the project is not going well.
  • Presenting proposals to key customers/clients.
  • Discussing a new job opportunity, or new role.
  • Informing a person that their current role or employment is ending.
  • Seeking support from a person with whom you have a contentious relationship.

If conversations have been avoided over time, the distress of having the conversations is multiplied – difficult conversations become seemingly impossible.

We tend to imagine or be fixated on the potential ‘worst case’ outcomes from the conversation, e.g.:

  • An emotional blow up, shouting, or dissolution of the relationship
  • Making a bad presentation, or not being awarded the project
  • Being fired

Even if we understand intellectually that the conversation is needed and likely will be valuable, we may feel negative emotions and physical discomfort when anticipating the conversation.

Applying the approaches described below, you will likely find yourself better prepared, more confident and successful in achieving the results you want (need) from these conversations.

Assumptions that make conversations seem ‘difficult’ or ‘high risk?’

We tend to predict – and act in the belief – that a conversation will be difficult because we are holding one or more of the following assumptions:

  1. I am right, they’re wrong.
  2. The other person cannot handle this conversation.
  3. I’m not fully prepared. Needing answers for every possible scenario equals never being fully prepared.
  4. The other person cannot be trusted.
  5. ‘I need to already have the solution’, often means you aren’t open to other, maybe better options.
  6. I need to win this conversation.
  7. I must teach the other person.
  8. This issue needs to be solved today.
  9. We don’t share much in common and won’t understand each other.
  10. Our relationship is not strong enough to have this conversation.

Instead, make declarations that enable conversations to be productive.

  1. We each have perspectives which are valuable to uncover and explore.
  2. We are each competent and aware enough for these conversations.
  3. I understand my concerns. I’m open, focused, and compassionate in my listening for the other person and what matters to them.
  4. I trust the other person to be honest, to do what is in their best interest, and to consider my interests as well. I will treat them the same as I wish to be treated.
  5. We will create options in our conversations.
  6. We will each get value from the conversations. We will each learn, become more aware and benefit from each other’s perspectives.
  7. We can both learn.
  8. We probably need multiple conversations over time.
  9. We have much in common as human beings and share common concerns.
  10. We will strengthen our relationship.
Summary of Typical Limiting Assumptions vs. Enabling Declarations
# Aspect Limiting Assumptions Enabling Declarations
1 Assertion vs. Assessment I am right, they are wrong We each have perspectives which are valuable to uncover and explore
2 Competence The other person cannot handle this conversation We are each competent and aware enough to have these conversations
3 Preparation I'm not fully prepared I am clear about my concerns and I am open, focused, and compassionate in my listening for the other person and what matters for them
4 Trust The other person cannot be trusted I trust the other person to be honest, to do what is in their best interest, and to consider my interests as well
5 Solution I need to already have the solution We will create one or more options in our conversations
6 Winner I need to win this conversation We will each get value from the conversations
7 Learning I have to teach the other person We will each learn and become more aware
8 Urgency This issue needs to be solved today We will likely require a number of conversations over time
9 Commonality We don't share much in common We have much in common as human beings
10 Relationship Our relationship is not strong enough to have this conversation We will streghten our relationship in these conversations
11 Risk/Reward The risks are high, and the value is low The risks are manageable, the potential for mutual value is high. The highest risk is not having the conversation
12 Resulting Action No conversation avoidance The conversations will start and continue

Outline for Productive Conversations

Using the above yields a simple outline for productive conversations.



  • What is important to you, the other person, your organization(s)? How will you find out? Practice expressing these concerns.
  • What specific outcomes, do you hope to accomplish in the first meeting, and beyond?
  • What are your assessments of the situation? What’s your basis for them? Make notes.
  • What do you see that is desirable and possible in the future? What additional value can be produced, for the other person, you, your organization(s)?
  • What waste/frustrations are being produced now that could be avoided for the other person, you, or your organization(s)?
  • What skills do you need to exercise for this conversation? Are you sufficiently competent in these for the sake of this conversation? Should you ask for help?


  • Note the declarations you make regarding any of the points above for future reference.
  • Document your proposed purpose and desired outcomes of the conversation as a whole, and the purpose of the first meeting. Be ready to amend these based on listening to the other(s) in the discussion.
  • Invite the other person to have a conversation with you, starting with an initial meeting. Do this in person if possible. Review your desired outcomes and treat this as a genuine request with options for the other person to accept, decline, or an alternative.
  • Schedule the meeting for a time and place which is supportive of your desired outcomes and that will be supportive of the other person’s concerns.
  • Decide what you will do or not do in the days before the meeting to be in an appropriate mood and physical state, think mind, body spirit.
  • Take time. Do the following immediately before the meeting:
    • Review the purpose and outcomes.
    • Grant legitimacy to yourself and the other person(s) as both being without need for change, accepted as you and they are, and legitimate participants in the conversation.
    • Adopt a productive mood, including elements of curiosity and wonder about yourself, the other person(s), and what might be produced in the conversation.
    • Ensure you are relaxed, open, and focused.

During the Conversation


  • Encourage the other person to speak first and more often than you, suspend your assessments about what is being said in the moment (you can always revisit your assessments later).
  • Listen for the concerns behind what is said, and inquire to learn more.
  • Regularly check your intended state of mind, shift if required.


  1. Open: Describe the purpose of the meeting, what you hope to achieve, and why
  2. Ask for the other person’s views on:
  • What is working well, not working well?
  • What is being achieved now and not being produced now?
  1. Describe your views, making connections or links with what you have heard so far:
  • What is working well, not working well?
  • What is being achieved now and not being produced now?
  1. Collaborate in describing a better future.
  • What would each of you be doing differently?
  • How would each of you feel?
  • What new results and value would be produced for each of you and your organization(s)?
  • What old results would not be produced for each of you or your organizations?
  1. Collaborate on describing what it might take to create this future.
  • Being and Structure
    • Resources and Budgets
    • Skills/Capabilities
    • Authorities/Accountabilities
    • Relationships/Attitudes
  • Doing
    • Actions/Commitments
    • Projects/Programs
    • Routines/Processes
  • Having
    • What results?
  1. Close
  • What next steps will you take?
  • What value was produced in this conversation?
  • Areas to improve in these types of conversations?

Future conversations

  • What results and actions do you each commit to?
  • What’s the action plan?
  • How will we meet and overcome the challenges?
  • How will we measure progress?

We invite you to apply these approaches and learn what works and what doesn’t for you.

Remember, the only difficult conversations are the ones you don’t have.

Banner & thumbnail credit: Christina @ wocintechchat on Unsplash


Global Connections

Global Connections Section includes invited articles and interviews along with CIGRE articles to broaden global power system expertise. Invited authors and interviews approved by the Electra Editorial Board may express opinions solely their own.

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