Leadership Under Pressure: Practicing Difficult Conversations with AI

Discover how virtual coaching creates a safe space to hone your ability to engage in high-stakes academic conversations

Academic leaders are routinely expected to handle complex, high-stakes conversations. However, they rarely have a safe space to practice and prepare. Although role-play with colleagues is often not an option, role-play with realistic AI personas, in a private, virtual environment can be a real opportunity. Join our live webinar on Thursday, April 23, to explore:

  • Why role-play is such a powerful learning tool

  • Where AI-enabled practice can complement human coaching conversations

  • How to build capability and confidence in safe, judgement-free spaces

Special guest: Rachel Cosar, Co-Founder & CEO, Virtual Sapiens

Hosted by: Dr Jenny Stine, Founder and President, Academic Leadership Group

Join the discussion, pose questions, and learn from short demonstrations.

Date: Thursday, April 23, 2026
Time: 11:00 AM PT / 2:00 PM ET / 8:00 PM CEST
Duration: 1 Hour

Reserve your place now

 

Rachel Cosar, Co-Founder & CEO, Virtual Sapiens

Rachel Cossar is a leader in AI-enhanced coaching and training, learning innovation, and leadership development. Her work sits at the intersection of behavioral science and emerging technology, helping individuals and organizations build lasting skills through adaptive practice and data-driven coaching. A former nationally ranked athlete and professional ballet dancer, Rachel has a long-standing ability to translate complex human behaviors into teachable, measurable, and actionable competencies. Her approach bridges embodied performance, psychological safety, and modern learning design.

Virtual Sapiens, Rachel’s latest venture, leverages AI roleplay, automated feedback, and scalable practice environments to transform how professionals build communication mastery in high-stakes contexts.



 
 

Dr Jenny Stine, Founder and President, Academic Leadership Group

Jenny leads the Academic Leadership Group, helping academic leaders and their institutions navigate change, design effective organizations, and build leadership capacity. Jenny spent over a decade leading executive and professional education programs at MIT and Harvard, where she also taught master's-level courses in organizational behavior and executive courses in leadership and teamwork. She worked for ten years in global HR at Accenture, where she played a key role in major corporate-university partnerships.




 
 
 
 

Our Empowered Leader webinars bring together leading voices in the world of academic leadership to discuss the biggest issues facing institutions today. Join us to gain insights and connect with other academic leaders.

 

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Past Webinars

Here are some past webinars we’ve offered. Interested in seeing a recording? Just fill out our contact form, including the name of the webinar you would like to see, and we will send you a link.

How Can You Manage Yourself To Lead Others? Margaret C. Andrews shares why great leadership begins with self-understanding

Margaret C. Andrews, renowned leadership expert and author of Manage Yourself to Lead Others, shares insights into:

  • Harnessing the power of self-understanding to become a more authentic, successful leader

  • Slowing down to speed up: Why leadership learning is not linear, and growth is an S-curve

  • What’s holding so many academic leaders back, and how we can move forward with confidence and resilience.

How Do Top Universities Grow Globally?  Proven strategies for your institution to succeed in international markets

Hear how our distinguished panel of leaders are pioneering new approaches to global strategy, innovation, and growth, including:

  • Emerging trends in program delivery to prepare for now

  • How to navigate complex markets and explore new gateways to growth

  • What leading institutions are doing differently to engage, compete, and thrive.

Panelists included Kelly Bean (Moderator), Carissa Little (Stanford), Marco Serrato (ASU), Mike Malefakis (Emeritus) and Paul Marco (Parallax Global Advisors)

Lead Forward: Real Tools for Real Challenges in Higher Education

Higher education leaders face increasing expectations, often with fewer resources and more complexity. In this interactive session, Dr. Jenny Stine, author of The Empowered Leader, offers practical tools and insights grounded in real experience working with academic leaders across top institutions.

Innovation Alchemy — Building and Sustaining Partnerships in Higher Ed

Join Lori Glover, author of Innovation Alchemy, for a dynamic conversation on how to move beyond transactional collaborations and build partnerships that truly last. Drawing from her book, Lori shares insights and strategies for creating high-impact, values-aligned engagement in higher education—whether you're launching a new initiative, strengthening community ties, or reimagining stakeholder relationships.

Navigating Higher Education Leadership in Uncertain Times

Today’s uncertainties require next-level leadership in higher education institutions. Understand key practices and skills that will help you and your institution to adapt and grow through uncertainty and change. In this webinar, we will explore themes in Jenny’s upcoming book, “The Empowered Leader”, including practical approaches to critical leadership themes. Featuring Jennifer K (Jenny) Stine, President & Co-founder, Academic Leadership Group.

Empowering Future Leaders: Creating High-Impact Mentorship Programs for Graduate Success

Discover the secrets to creating transformative mentorship programs for graduate students in professional degree programs. Join our webinar to discover innovative strategies for bridging the gap between academic learning and professional application while fostering personalized growth, expanding professional networks, and enhancing leadership skills. Featuring Raquel Cabero Quiles, IE University Academic Director & Professor, Marta Revilla Patiño IE University Program Coordinator – Sci-Tech School, and Charles Lagemann, Senior Consultant and Coach, Academic Leadership Group.

Elevating Executive Education with Award-Winning Strategies

Many top universities overlook the strategic advantage of earning external awards for their executive education programs. In this 60-minute interactive seminar, join our experts to uncover why prestigious accolades matter and how they can elevate your program’s reputation and impact. Featuring Deb Arnold, Chief Winning Officer at Deb Arnold Ink.