[Flash] When Vogue Editor Anna Wintour Became a Mentor and a Mentee

Not eager to retire (despite 37 years at the helm!), Anna has become the magazine’s Chief Content Officer and Chloe’s Mentor.

When asked about passing the reins to Chloe, the famously intimidating Anna declared, “I’m excited to continue working with her as her Mentor, but also as her student, while she leads us and our audience where we’ve never been before.”

With this public proclamation, Anna nodded to the power of mutual mentoring.

While she will draw on her own experiences, judgment, and institutional memory to guide and support Chloe, Anna indicated an intent to learn and grow through the process.

What does 76-year-old Anna stand to gain from mentoring 40-year-old Chloe? 

• Fresh perspectives and new ideas
• Exposure to generational influences
• Understanding of an ever-evolving digital landscape
• Awareness of emerging challenges
• Reinforced wisdom
• Renewed professional purpose and relevancy

Declaring an eagerness to learn from a Mentee is not only graceful but strategic. Anna knows the future will not look like the past, and she’s intent on learning from Chloe, who will shape it.

In addition, and more significantly, Anna is cognizant that intentionally bestowing upon Chloe the power to teach Anna will accelerate Chloe’s confidence. Exactly what Chloe needs for success in her new, highly visible role.

Finally, the vulnerability required to invite Chloe to contribute to Anna will bolster Chloe’s trust in Anna, essential for their relationship to thrive.

While mentoring is often framed as an act of altruism, its value runs deeper – for the Mentee and the Mentor.

For even the most confident people, growth requires power, purpose, and a lack of pride, especially when carrying impressive titles or tenure.

Announcing an eagerness to be our Mentee’s “student” communicates and reinforces our own:

• intellectual curiosity
• openness to change
• respect for emerging leadership
• ongoing commitment to improve

At the conclusion of formal mentoring programs, Mentors often express surprise and delight at the value they received from their Mentees. This inevitably surprises and delights the Mentees, who then reveal an increase in their confidence as a result of working with their Mentor. They each then credit their success to the trusting relationship with their mentoring partner. Amazing!  

The magic of mentoring often works covertly. But first, we need to let ourselves be taught.

© 2026. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved.