5 Steps to Successfully Navigating Cringy Conversations

By Sydney Robinson

August 22, 2023

Having difficult conversations is never easy, but you can navigate them with empathy and effectiveness by following a structured approach. In this guide, we will explore five key steps to help you have those uncomfortable conversations in a way that promotes open dialogue, collaboration, and growth. Implementing these steps can foster a safe and productive environment for discussing challenges, finding solutions, and strengthening relationships.

Step 1: Set the Stage and Establish Safety

Consider the timing and environment of the conversation to ensure the person is receptive. Create a safe and non-judgmental space where they feel comfortable expressing themselves openly.

Example: “[Person A] Hey [Person B], can we chat about a few challenges I’m having and how we can create a few solutions together that can benefit the team? Is now a good time?” Or if the timing isn’t right, say, “Can we schedule some time later today or tomorrow? “

[Person B] “Yes, we can chat. What can I help with?” Or “Yes, but can we chat after….?”

[Person A], “This is great: before we begin, can we establish our goal to have an open and honest conversation where we both feel safe and understood? Together, we can create great solutions. Is that okay with you?”
Note: If this conversation is to correct actions, consider having this conversation later rather than in the moment. Also, think about your surroundings. You want to avoid correcting actions in front of a team member or publicly. Publicly calling someone out could spark their defense system. You do not want to come off as nagging, and the person may need to be in the mindset to receive your message well.
Step 2: Actively Listen, Recognize, and Observe

Engage in active listening, demonstrating genuine interest in the Person’s perspective. Acknowledge their emotions and observe their body language to gain deeper insights into their feelings and reactions.

  1. Use their words.
  2. Point out their emotions.
    1. “I see this is upsetting you; how can I fix this while still accomplishing our goal?”
  3. Do not say things you do not mean or have no control over.
  4. Being vulnerable is okay.

Step 3: State Challenges and Collaborate on Solutions

Articulate the specific challenges or issues that need to be addressed, framing them as shared problems rather than blaming the individual. Invite the person to participate in finding solutions, encouraging their input and ideas for resolution.

Example: “I’ve noticed that we’ve been having some difficulty with [state challenge], which has affected the overall [state the effects of actions]. I believe we can find a solution together. What are your thoughts on this challenge? How do you think we can fix it together?”

Note: Remember to be open to hearing what they say and ensure the solution will create a win-win.

Step 4: Seek Feedback and Set Clear Expectations

Ask for feedback on the conversation and their thoughts on how the discussion could have been more effective or how to move forward positively. Reflect on their input and consider what adjustments can be made to improve future interactions.

Note: Take extreme ownership and set clear expectations moving forward. If a check-in is needed after the conversation, schedule a time to chat and hold each other accountable for keeping the time.

Step 5: Use Distance When Needed

If the conversation becomes too intense or unproductive, create some distance. Creating distance could involve redirecting the discussion to a previous situation to highlight progress or suggesting taking a break and reconvening later.

Note: Use this pause to reflect on the person’s perspective and consider alternative approaches.

Statement Key:
  1. “I want to understand. Can you tell me more? “
  2. “Are you open to tough love right now?”
  3. “Where do you think we can go from here?”
  4. “Can you tell more about your experience and the challenges you’re having…..?”
  5. “What could we/I have done differently?”
  6. “It’s important to me that you feel supported; how can I support you, or what tools can I provide to support you.”
  7. “I don’t know how to say this without my next statement being taken personally; I want you to understand I want to help and move past [X]; can I be direct?”
  8. “Now that we understand the challenge, what are a few solutions you suggest to overcome these challenges? “
  9. “I see I could have done [X] differently. Moving forward, I will…”
  10. “I understand I should have set clear and realistic expectations. In the future, if [x} is ever an issue, you will let me know right away.
  11. “What tools can I provide so that you….”