Bridging Generations: Ambition, Influence, and Sustainable Success
Today’s legal workplace brings together women at different stages of their careers, shaped by different experiences, expectations, and definitions of success. While these differences can create tension, they also create opportunities for stronger leadership, deeper mentorship, and more meaningful professional relationships.
This interactive workshop explores how generational perspectives influence communication, feedback, career development, leadership, and well-being. Through discussion, reflection, and practical application, participants will gain insights into leading effectively across generations while building sustainable, fulfilling careers.
Dori Nelson-Hollis is the founder of Monarch Advisors LLC and a strategic advisor, executive coach, and fractional Chief Human Resources Officer with more than 25 years of leadership experience. She partners with CEOs, executive teams, law firms, professional service organizations, and nonprofit leaders to strengthen leadership effectiveness, align strategy, and build high-performing cultures.
Known for her practical approach, thoughtful facilitation style, and ability to ask the right questions, Dori helps leaders move from insight to action. Her work includes executive assessment, strategic planning, leadership development, and organizational effectiveness.
Dori is passionate about helping leaders build successful and sustainable careers while creating workplaces where both people and organizations can thrive.
Jennifer Osborn is the founder and owner of TalentSENSE, a human resources and recruiting firm that helps organizations attract, develop, and retain top talent while building strong, compliant workplaces. With extensive experience across manufacturing, professional services, legal, technology, healthcare, and other industries, Jennifer partners with business owners and leaders to solve people challenges and strengthen organizational performance.
Jennifer Osborn is the founder and owner of TalentSENSE, a human resources and recruiting firm that helps organizations attract, develop, and retain top talent while building strong, compliant workplaces. With extensive experience across manufacturing, professional services, legal, technology, healthcare, and other industries, Jennifer partners with business owners and leaders to solve people challenges and strengthen organizational performance.Known for her practical, results-driven approach and ability to quickly identify talent and opportunities for improvement, Jennifer provides expertise in executive recruiting, leadership development, performance management, employee relations, compliance, and HR strategy. She has successfully recruited hundreds of professionals and executives, implemented HR best practices for growing organizations, and developed processes that improve both employee experience and business outcomes.
Program Agenda
Wednesday, September 16, 2026
Group Dinner at the St. Julien Hotel & Spa (Redgarden Lower Terrace)
Thursday, September 17, 2026
Group Breakfast (Redgarden Lower Terrace)
Welcome and Introductions (Xanadu I)
The Legal Profession Through Different Lenses: How Experience Shapes Expectations, Communication, and Success
The practice of law has changed dramatically over the last several decades. This session explores how different generations of women lawyers entered the profession, how workplace expectations have evolved, and how those experiences continue to influence communication, feedback, engagement, and leadership today.
Leading Through the Tension: Maintaining High Standards in a Changing Workplace
Many leaders find themselves balancing high expectations with evolving perspectives on work, development, flexibility, and career growth. This session examines common leadership challenges, explores the gap between intent and impact, and provides practical approaches for accountability, communication, and feedback.
Refreshment Break
Influence Without Authority: Building Visibility, Credibility, and Strategic Relationships
Leadership opportunities are often created long before they are formally announced. This session focuses on strengthening influence, increasing visibility, and building the relationships that expand professional opportunities and enhance leadership effectiveness.
Burnout, Boundaries, and the Hidden Leadership Tax: Sustaining Performance Without Sacrificing Yourself
Women leaders often carry visible and invisible responsibilities that contribute to exhaustion and burnout. Explore how burnout manifests across generations, identify personal risk factors, and discuss strategies for sustaining performance while maintaining well-being.
Group Lunch (Redgarden Lower Terrace)
From Insight to Action: Applying Today's Lessons to Real-World Challenges
Participants will apply the day’s concepts through facilitated leadership scenarios involving retention challenges, influence opportunities, burnout risks, and generational tension. The session concludes with personal reflection and leadership commitments designed to translate insight into action.
Leadership Commitments and Closing Reflections
Participants will leave with a personalized leadership action plan focused on meaningful conversations, intentional leadership adjustments, and practical strategies to strengthen both performance and sustainability.
End Day One
Group Dinner at The Kitchen American Bistro
Friday, September 18, 2026
Group Breakfast (Redgarden Lower Terrace)
Leadership Plan Work Session
Revisiting the leadership action plans crafted on day one with fresh eyes, participants will consider revisions, challenges, goals, and support needed to execute their plans.
Refreshment Break
Closing Session: Ask and Give
Many accomplished women are eager to offer guidance, connections, and encouragement to others, yet may hesitate to ask for support themselves. Each participant will ask for a professional favor or support and may offer to give support to address another’s request.
In this interactive closing session, each participant will identify one meaningful professional ask—advice, introductions, resources, or accountability—and will have the opportunity to offer their own experience, expertise, and support to others in the room.