Building Confidence for Critical Conversations

Leadership is as much about perception as it is about reality. One of the biggest challenges many leaders face is managing their inner critic, especially when preparing for critical conversations. Feeling nervous or anxious about these discussions is common, and instead of feeling confident in your abilities, you might worry about getting it wrong and end up putting it off.

Imagine a situation where you are presented with a problem and need to talk to a peer or direct report. Now, picture entering that conversation feeling sure and capable, ready to navigate whatever comes up. You’re curious, asking a lot of questions to build connection and understanding. Both you and the other person walk away feeling heard and understood, with a clear plan to course-correct and be more effective. Sounds great, right?

We often see other leaders doing a great job with this, making it look simple, or doing a poor job, making us feel intimidated and nervous to tackle similar conversations. Here’s how you can prepare yourself to manage your inner critic and approach these conversations with confidence:

1. Think About the Other Person

Remember, you’re talking to a human being. What motivates them? How do they typically show up or communicate? Do they seem prepared when you schedule a huddle, or are they comfortable with drop-in conversations? Understanding their communication style and motivations can help you tailor your approach to make the conversation more effective and less intimidating.

2. Check Yourself

Get really clear on what you hope to accomplish in this conversation. Be specific. Don’t try to tackle everything at once—focus on one or two key points. Also, check any assumptions you might be bringing into the conversation. Based on how you hope to move forward collectively, consider how you might need to adapt your approach to meet them in the middle. If they prefer starting with small talk, investing some time in this could build trust and psychological safety.

3. Be Curious

Don’t make assumptions about what you think they might be experiencing. Ask open-ended questions and listen actively. This approach not only helps in understanding their perspective but also in building a connection. It demonstrates that you value their input and are committed to finding a collaborative solution.

4. Define Levels of Success

Determine what would be good, better, and best outcomes in terms of how you collaborate and agree to move forward. Try to remove any ambiguity about the next steps and create a space for open dialogue. Setting clear goals for the conversation can help you stay focused and measure success.

Practical Steps to Prepare

  1. Pre-Conversation Reflection: Take a moment to reflect on the upcoming conversation. What are the main points you want to address? How do you think the other person might react? How can you create a supportive environment?

  2. Role-Play: If possible, role-play the conversation with a trusted colleague or friend. This can help you anticipate potential responses and refine your approach.

  3. Practice Active Listening: Really focus on listening to connect and make a conscious effort not to interrupt. Listening to connect can help you look past just the content of what they’re sharing and pick up on more clues and body language to help you better understand one another.

  4. Manage Your Body Language: Be mindful of your body language and non-verbal cues. Open, relaxed posture with active eye contact can convey confidence and warmth.

  5. Post-Conversation Reflection: Afterwards, take a little time to reflect on what went well and what could be improved. This can provide valuable insights for future conversations and help you continuously improve your communication skills.

By managing your inner critic and approaching critical conversations with curiosity, clarity, and confidence, you can transform these discussions into opportunities for growth and connection. Remember, becoming a better leader doesn’t just happen—it takes intentionality and practice. So, take these steps to prepare, and watch how your confidence and effectiveness in critical conversations improve.

How do you prepare, and what strategies have worked for you? Send me a DM with your takeaway and I’ll share my communication audit.

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