The design industry is rapidly evolving with new technology, overall speed of practice, and the challenges adapting to hybrid work. As designers, we embrace continuous learning and growth at all stages of our careers to advance and navigate change. The journey is difficult alone, so strong professional mentoring relationships become critical. Mentors are key in a thriving multigenerational workplace to nurture emerging talent, provide professional development opportunities, and share best practices for success. A good mentor is a trusted resource and advocate, invested in a mentee's growth and professional development. The best mentoring relationships are mutually beneficial and create empathy across generations. Success is achieved through open, honest two-way conversations which strive to understand unique experiences and challenges. Fostering a great mentoring culture will inspire others to become mentors and engage the next generation of design talent. Join this roundtable discussion between two mentor/mentee pairs from leading Chicago design firms sharing how mentoring relationships have supported and help guide their career paths.