Skip to main content
All CollectionsWebinars
December 2024: From Awkward to Awesome: Using Cloverleaf for 1:1s and Tough Conversations
December 2024: From Awkward to Awesome: Using Cloverleaf for 1:1s and Tough Conversations

Explore how Cloverleaf equips you to navigate challenging situations with confidence and care.

Jason Miller avatar
Written by Jason Miller
Updated over a week ago

Planning Difficult Conversation Openers: Cognitive Function Pairs

To help create your conversation opener, consider the individual’s Cognitive Function pair using 16Types on Cloverleaf. The two middle letters of one’s 16Types profile highlight how a person mentally consumes, organizes, and decides upon information.

When preparing for a difficult conversion of any kind, consider who you are speaking to:

  1. ST(Sensing-Thinking)

    This pair is logical, practical, and wants to know the details up front. With STs, you can get to the point quicker without making small talk.

    A conversation opener may look something like “I wanted to take some time to discuss ________. I’ll share my perspective, but first, I’d like to get your take on things.”

  2. NT (Intuition-Thinking)

    This pair is logical, idea-focused, and seeks out the general idea of expectations leaving room for independence to design their own system that serves their vision. NTs may be attached to their ideas and vision for how things get done, so lead off by expressing your desire to learn.

    Consider starting with “I’d like to understand your thinking on_______ so that I can support you/we can work better together.”

  3. SF (Sensing-Feeling)

    This pair is people-oriented, practical, and seeks out the details and expectations on the front end. Like STs, they appreciate the details upfront but are also harmony seekers and value harmony in their relationships.

    You might start by saying, “Because I value our working relationship, I’d like to discuss___________ to see if we can come to a place of shared understanding.”

  4. NF (Intuition-Feeling)

    This pair is people-oriented, idea-focused, and seeks out the general idea of expectations leaving room for autonomy while serving others. Being so others-focused can sometimes result in minor errors.

    NFs will internalize what you say, so you may want to note their intention by opening with, “I know you have a deep commitment to ____________, which I appreciate. Can we discuss________ together so you can continue to fulfill your intention?”

Obviously, the situation may warrant reorienting these openers, but understanding how someone takes in information can help you customize a conversation opener that sets the tone for the entire conversation.

Leveraging Enneagram Insights For Preparing for Tough 1-1 Conversations

The Enneagram doesn’t just identify personality types; it also reveals unique thinking styles that influence how individuals process information, solve problems, and approach challenges. By using Cloverleaf’s Enneagram Thinking Styles Comparison feature, you can uncover actionable insights into how you and the other person approach situations, helping you navigate tough 1-1 conversations with empathy and clarity.

Step-by-Step Self-Coaching Guide:Using Enneagram Thinking Styles Comparison for a Tough 1-1 Conversation

This self-coaching guide is designed to help you prepare thoughtfully and strategically for a challenging conversation, using the Enneagram Thinking Styles Comparison as your blueprint.

1. Initial Reaction

  • First Impressions: Review the analysis and note your initial thoughts. What is your gut instinct about how best to start this conversation?

    • Ask yourself: Does my instinct align with what I know about the person? Could it be influenced by my own preferences rather than theirs?

    • Consider if your approach feels collaborative or self-focused.

2. Communication Style Alignment

  • Are You Similar?

    • If your communication styles are the same, what approach could leverage this commonality?

    • Reflect: What approach do I typically appreciate when others address tough conversations with me?

    • Recall: When has someone handled a conversation with me in a way that resonated? How can I adapt that strategy here?

  • Are You Different?

    • If your styles differ, what adjustments are needed to meet the other person where they are?

    • Reflect: What about their communication style might they value most? How can I use that knowledge to open the conversation effectively?

      • What specific word choices, tone, or framing might help bridge the gap between your style and theirs?

3. Source of Conflict

  • Conflict Triggers: Review the other person’s sources of conflict.

    • Ask: What specific actions or language should I avoid to prevent escalating tension?

    • Think: What could I do instead to create a safe and constructive environment?

  • Strengths-Based Approach: Consider how to frame the conversation in a way that aligns with their strengths.

    • Example: If they value precision, can I present feedback with clear, actionable examples?

    • Question: How can I affirm their strengths while addressing the issue at hand?

4. Conflict Resolution Advice

  • Resolution Insights: Review the narrative on conflict resolution provided in the bottom section of the thinking styles comparison

    • Ask: What specific actions or strategies does this person appreciate in resolving disagreements?

    • Reflect: How can I use this insight to ensure the conversation feels like a partnership, not a confrontation?

      • What specific adjustments can I make to my body language, tone, or phrasing to create trust and openness?

5. Personal Reflection and Action Plan

  • Your Mindset: How does understanding this person's thinking style influence your mindset going into the conversation?

    • Reflect: Am I prepared to listen as much as I speak? How can I signal collaboration and respect?

  • Scenario Preparation: Play out the conversation in your mind.

    • Ask: What potential responses might they have, and how can I handle them constructively?

  • Planning for Outcomes: How will you measure the success of this conversation? What would a positive outcome look like for both of you?

6. Post-Conversation Reflection

  • After the conversation, reflect:

    • What went well?

    • What could I have done differently?

    • Did the adjustments I made improve the dynamic?

Use these reflections to build on your understanding for future interactions. Tough conversations aren’t just challenges—they’re opportunities for growth, trust-building, and collaboration. By applying these insights, you can turn conflict into connection.

Understanding the Value of Insights Search for Preparing for Tough 1-1 Conversations

Detailed Scenario 1: Manager Perspective

Situation: A manager addresses a team member who is over-analyzing and missing deadlines. The manager wants to be able to provide feedback but also support the person in setting a goal to complete necessary work.

  • Search Prompts in Action:

    • "How can I approach giving feedback to @employeesname?"

      • Goal: You are looking for ways you can craft conversation openers here.

        • How can you open the conversation in a way that creates partnership and alignment?

        • What about how this person relates to or processes feedback can inform how you present the feedback?

    • "What motivates @employeesname to accomplish goals?"

      • Goal: What about how this person is motivated to complete work can you leverage to help accelerate goal completion?

        • What strength can you tap into to encourage meeting deadlines?

        • Where can you support or encourage their own motivation style to help drive task or goal completion?

    • "How can I acknowledge @employeesname?"

      • Goal: What value does this person’s attention to detail bring to the team?

        • How can you best acknowledge the person for their strengths?

        • How does this person prefer to be appreciated for their work?

    • Outcome

      • The manager uses insights to frame the conversation around measurable outcomes and clarity using the unique way the employee is motivated, while valuing the team member’s unique contributions to the team

Detailed Scenario 2: Individual Contributor Perspective

Situation: An individual contributor feels their input is being overlooked in team discussions. They want to be able to assert themselves in team discussions but also address the issue with their manager.

  • Search Prompts in Action:

    • "How can I assertively express ideas without creating conflict?"

      • Goal: How can you have your ideas be heard in a collaborative way when you go into your next meeting?

        • What approach might get you the best result?

        • What natural strengths can you lean into?

        • What strengths might be laying dormant that you could be using more often?

    • “How can I ask for support from @managersname?”

      • Goal: This is about crafting your approach to ask for support from your manager on this issue. Maybe they see things differently and can share some perspective with you

        • What about your manager’s communication style might help you start out the conversation?

        • How could your manager best support you in this situation?

    • Outcome

      • The contributor gains confidence and communicates their ideas in a way that aligns with team goals while also getting support from their direct manager.

Detailed Scenario 3: Manager Perspective

Situation: A manager needs to address a team member who dominates discussions, making others feel unheard. The manager wants to address the behavior and help the team member collaborate more effectively.

  • Search Prompts in Action:

  • "How can I encourage balanced team discussions with @employeesname?"

    • Goal: Understand strategies to help the employee balance their natural enthusiasm with team collaboration.

      • How does this person typically engage in team settings?

      • What insights about this person’s communication style can help guide a conversation on creating space for others?

      • What coaching tips can help frame this as an opportunity to elevate the team’s dynamic?

  • "What drives effective collaboration for @employeesname?"

    • Goal: Identify motivators that align with teamwork and emphasize the value of shared success.

      • How can this person’s natural leadership tendencies be reframed as facilitation rather than control?

      • What incentives resonate with this person to adjust their behavior without diminishing their enthusiasm?

  • "How can I leverage the strengths of @employeesname?"

    • Goal: Use their strengths as the foundation for constructive feedback.

      • How can this person’s energy and enthusiasm be celebrated in a way that encourages buy-in for behavioral changes?

      • How does this person prefer to be acknowledged, so they feel supported during the conversation?

  • Outcome

    • The manager uses the insights to guide a conversation that reinforces the value of the employee’s energy while positioning active listening as a critical leadership skill, fostering better team collaboration.

Detailed Scenario 4: Individual Contributor Perspective

Situation: An individual contributor feels frustrated about misalignment with their manager’s expectations for task prioritization. They want to share feedback with their manager and be able to create more alignment with their workstyle.

  • Search Prompts in Action:

    • "How can I share constructive feedback with @managersname?"

      • Goal: Understand how to frame concerns in a way their manager is receptive to.

      • What is your manager’s communication style, and how can it inform the way you bring up concerns?

      • Are there specific preferences for how your likes issues to be presented (e.g., directly, with data, or through a collaborative tone)?

  • "What motivates task prioritization for @managersname?"

    • Goal: Gain clarity on the reasoning behind the manager’s prioritization to frame your input constructively.

      • How does your manager’s motivational style influence their decision-making process?

      • What language or framing might help you align their perspective with your manager’s goals?

  • "How can I adapt to the workstyle of @managersname?"

    • Goal: Explore actionable strategies to meet in the middle.

      • What specific coaching tips could help you bridge differences in work preferences?

      • How does understanding your manager’s work style help you clarify misunderstandings?

  • Outcome

    • The individual contributor uses these insights to approach their manager with empathy and strategic language, reframing the conversation as a collaborative effort to align priorities and enhance productivity.

Did this answer your question?