How Great Leaders Make Difficult Conversations Easier

As a leader, it’s inevitable that you will be called upon to have difficult conversations. Whether it’s addressing a performance issue, dealing with conflict, or having a tough conversation with a team member, these types of conversations can be challenging and uncomfortable.

However, by following a few key strategies, you can make difficult conversations easier and less daunting:

Be clear on the intent: Before you even start the conversation, it’s important to be clear on your intent. What are you hoping to accomplish? What are your goals for the conversation? By being clear on your intent, you can focus on achieving your desired outcome and not get sidetracked by the conversation.

Ask open-ended questions: Rather than jumping to conclusions or making assumptions, ask open-ended questions to encourage the other person to share their perspective. This will help you gain a better understanding of the situation and build trust and understanding.

Embody emotional intelligence: Emotional intelligence is the ability to recognize and manage your own emotions and the emotions of others. By exhibiting emotional intelligence, you can create a safe and respectful environment for the conversation and build trust and rapport.

Foster openness and vulnerability: To build trust and understanding, it’s important to be open and vulnerable in difficult conversations. This means being honest and transparent about your thoughts and feelings, and being willing to listen to the other person’s perspective.

Listen to learn: It’s easy to get caught up in our own perspective and thoughts, but it’s important to listen to learn and gain a better understanding of the other person’s perspective. By actively listening and engaging in the conversation, you can build trust and understanding.

Use positive nonverbal communication: Nonverbal cues, such as eye contact, body language, and tone of voice, can convey just as much, if not more, than the words you say. Use positive nonverbal communication, such as maintaining eye contact and using a calm and respectful tone, to create a more positive and productive conversation.

Reflect and summarize: After the conversation, it’s important to reflect on what was discussed and summarize key points. This helps ensure that everyone is on the same page and helps to clarify any misunderstandings or miscommunications.

By following these strategies, you can make difficult conversations easier and more productive, leading to better outcomes and more successful relationships.

Lead From Within: Difficult conversations are not about winning or losing. They are about understanding and connecting with people you care about.


#1 N A T I O N A L  B E S T S E L L E R

The Leadership Gap
What Gets Between You and Your Greatness

After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR,, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

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