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Planning difficult conversations, regardless of your role, can be managed much more effectively with preparation. Going into these conversations with intention and forethought can dramatically impact the outcome of the conversation and perhaps exceed your expectations.
Cloverleaf is a goldmine of information you can use to prepare for different conversations. In each of the scenarios below, we will consider various relationships: leader to direct report, direct report to leader, and peer to peer.
When using Cloverleaf to plan difficult conversations, consider the following steps. Set aside at least 15-20 minutes to prepare. It is time well invested!
Identify the best-case scenario for the conversation.
Creating your conversation opener.
Customizing your approach based on the conversation type using insights search, the Team Thinking Styles, and various aspects of the team dashboard. Consider asking…
What questions might you ask?
What might you do more of?
What might you do less of?
Step 1: Identify the Best-Case Scenario for the Conversation
This is a quick first step that you can do by just asking yourself the following questions:
If everything went better than expected, what would be the result?
What is one word to describe how I want this person to experience by the end of the conversation?
Step 2: Creating Your Conversation Opener
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:
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.”
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.”
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.”
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.
Step 3: Customize Your Approach Using The Insights Search, Team Thinking Styles, and Other Aspects of the Team Dashboard.
CONVERSATION TYPE: Performance Improvement/Leader to Direct Report
When performance drops or hasn’t yet elevated to where it needs to be, there are many areas you might consider exploring. One of the most common misunderstandings is that other people are not motivated in the exact same way that we are. People think and work differently than us, but we often try to understand people through the lens of what we would do if we were them.
As you go through the following steps, jot down notes for yourself that might answer the questions:
What questions might I ask?
What might I do more of?
What might I do less of?
Insight Search Prompts on My Dashboard
How can I motivate @ (tag your direct report)?
How can I discuss performance with @ (tag your direct report)?
How can I better connect with @(tag your direct report)?
This can also give you common ground and understand what is important to the other person.
Team Thinking Styles
Compare your DISC types to understand how your desired outcomes differ, how to customize your communication style, and how you can best create mutual understanding.
Compare your 16 types to understand how your personal preferences differ or are the same. What can you do more or less to effectively connect with this person?
Enneagram Triad
Go to the Enneagram triad that the person is (even if it's the same as yours) and review all the sections. What strengths can you tap into? What blindspots might be points for discussion? How does the “If Not” section inform your approach?
CONVERSATION TYPE: Performance Improvement Feedback Solicitation/Direct Report to Leader
If your performance recently has been an issue, you might want to solicit feedback from your leader as you work towards improvement. If you are concerned about how to go about the conversation, consider the following preparation process.
As you go through the following steps, jot down notes for yourself that might answer the questions:
What questions might I ask?
What might I do more of?
What might I do less of?
Insight Search Prompts on My Dashboard
How can I communicate more effectively with @ (tag your leader)?
What is the leadership style of @ (tag your leader)?
What frustrates @ (tag your leader)?
How can I share my strengths?
Team Thinking Styles
Compare your DISC types to understand how your desired outcomes differ, how to customize your communication style, and how you can solicit the most effective feedback.
Compare your 16 types to understand how your personal preferences differ or are the same. How can this shape how you’ll ask for feedback or share your strengths?
Enneagram Triad
Go to the Enneagram triad that your boss is (even if it's the same as yours) and review all the sections. What strength can you speak to when asking for feedback? What blindspots might frustrate you about their style? How does the “If Not” section inform your approach?
CONVERSATION TYPE: Collaborative Peer Friction
We’ve all had friction with peers at work. We often focus on differences rather than similarities or common goals. You might consider preparing for a conversation when a project is stalled, decisions are delayed, and misunderstandings are often happening.
As you go through the following steps for each scenario, jot down notes for yourself that might answer the questions:
1. What questions might I ask?
2. What might I do more of?
3. What might I do less of?
Insight Search Prompts on My Dashboard
What is the work style of @ (tag your peer)?
How should I avoid burnout alongside @ (tag your peer)?
What are techniques to motivate @ (tag your peer)?
How can I collaborate with @ (tag your peer)?
Team Thinking Styles
Compare your DISC types to understand how you can work best as a team and resolve conflict. How can you leverage each other's strengths?
Compare your 16Types to understand how your personal preferences differ or are the same. How can this influence how you might reorganize your work together to honor both of your workstyles?
Enneagram Triad
Go to the Enneagram triad that your peer is (even if it's the same as yours) and review all the sections. What strengths bring value to your collaboration? What blindspots cause friction that you want to resolve? How does the “If Not” section inform your approach?