Delivering Difficult Messages to Leaders

Navigating the complexities of workplace communication is a critical skill for executive assistants. This role often requires conveying feedback, setting boundaries, and expressing dissenting opinions to leaders in a way that fosters understanding, strengthens communication, and supports progress rather than conflict. Developing this ability helps executive assistants communicate with confidence while contributing to a more productive and transparent working relationship with leadership.

Mastering difficult conversations not only enhances a leader’s effectiveness, but also helps establish the assistant as a strategic partner. When executive assistants know how to choose the right timing, tailor their message to a leader’s communication preferences, and deliver it with the right tone, they are better positioned to provide elevated support. Without this skill, assistants may miss valuable opportunities to build trust, expand their influence, and strengthen the overall executive partnership.

• Learn how to strategically choose the right timing for discussion.
• Gain skills to craft messages that align with the communication preferences of your leader, ensuring your messages are received.
• Discover how to use verbal and non-verbal communication to convey the right tone.
• Understand how to demonstrate active listening, a key component of effective two-way communication.
• Explore how courageous conversations strengthen trust and foster a more transparent and supportive working relationship with leaders.

Attending this webinar will help you build the confidence to handle challenging conversations with greater skill and professionalism. You will walk away with practical communication strategies that can strengthen trust, improve partnership dynamics, and help you deliver support at a higher level.