Inside Flexible Engagement Work

Legal careers take many forms—and flexible engagement work is increasingly part of that conversation.

In this episode of Leveraging Latitude, Candice Reed is joined by Amber Hilliard and Cynthia Cutler Moon for a candid conversation about how contract engagement work shows up in practice today. Drawing on their own experience as attorneys who have worked in and alongside these roles, they talk through how flexible engagements fit into today’s legal careers and legal teams.

Together, they explore:

• What draws attorneys to flexible engagement work at different stages of their careers—and how those choices can open new avenues for growth over time
• What hiring leaders look for in engagement experience and how attorneys can position that experience effectively
• How contract engagement lawyers contribute meaningful value to legal teams during periods of change and growth
• The depth of responsibility, judgment, and leadership that flexible engagement opportunities can offer

This episode is for attorneys who are curious about contract engagement work, and for legal leaders looking for a clear, experience-based perspective on how flexible legal talent can support today’s legal teams.

A podcast by Latitude Legal - Flexible Legal Talent.

Chapters

• 0:53 Meet Amber Hilliard and Cynthia Cutler Moon
• 8:21 Why Experienced Attorneys Explore Contract Engagements
• 12:10 How Perceptions of Contract Work Have Evolved
• 14:32 What’s In Demand Right Now: Healthcare, AI & Tech-Focused Roles
• 17:44 Leadership Roles in Contract Engagements
• 22:30 How Contract Engagements Can Open New Opportunities
• 24:13 Compensation and Benefits in Engagement Roles
• 28:30 What Flexibility Makes Possible
• 34:31 Exploring Options as Your Priorities Change
• 43:47 What Makes an Effective Engagement Attorney
• 47:40 How to Explore Flexible Engagement Opportunities