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

Condé Nast announced this month that Anna Wintour, Editor of Vogue magazine since 1988, has identified her successor, Chloe Malle.

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.

[Flash] Enterprise CEO Chrissy Taylor Used Personal Invitations to Whisper “You Belong Here”

When Chrissy Taylor became President of Enterprise Rent-a-Car, she set out to connect the female leaders in her 80,000-person organization.She started with the Level 4 Leaders – the highest level at Enterprise – and invited them to happy hour. She called it “Cocktails with Chrissy.” These events fueled intentional networking and mentoring conversations among senior leaders.

Chrissy then asked the Level 4 Leaders a favor: bring people forward. She requested that they each invite to the next happy hour a high-performing Level 3 Leader who could use an introduction and visibility.

For the next year, Chrissy invited a small group of Level 4 Leaders to Cocktails with Chrissy each month, and they each invited a Level 3 Leader. During that year, Chrissy reached every Level 4 and Level 3 Leader in the organization.

Chrissy’s Extend-an-Invite approach is the key to igniting a mentoring culture. It relies on personal invitations, rather than general announcements.

A personal invitation activates what psychology calls “self-identity.” Your brain perks up when it hears your name. A general announcement doesn’t trigger that same cognitive priority.

Whether it’s a happy hour or a mentoring program, people are constantly evaluating, “Is this worth my time?” “Is this for people like me?”

To launch new mentoring programs, my team designs beautiful promotional flyers. Sadly, they are marginally effective in recruiting participants. Why? Because they aren’t directed at anyone in particular.

Flyers scream, “Everyone is welcome!”  A personal invite whispers, “This is for you.” It feels exclusive, even when it isn’t.

Flyers work to generate awareness. But people pay attention to and take action when something feels individualized.

  • “Sam, you would make a great mentor. Have you considered the new mentoring program? It would give you exposure and develop your leadership skills. Here’s the flyer with more information.”

When we extend personal invitations, people feel acknowledged and seen, which activates a mild sense of obligation to respond. Flyers and posters alone don’t create that same relational pull.

How to deploy a bring-them-forward approach in recruiting mentors and mentees:

  • Encourage each current participant to invite one peer to join them in the program.
  • Urge every former participant to nominate one colleague for the new cohort.
  • Ask senior leaders to recommend one of their team members.
  • Request that executives send targeted email requests.
  • Send that sparkling flyer to someone with a personal invitation to join the program.

Finding participants for a mentoring program can be challenging.

But if we are determined to create you-belong-here cultures, then recruiting needs to become an effort of the village, not an obligation of the program leader.

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

[Flash] How Adam Sandler Found Comedy Confidence by Modeling Heroes

I became an entrepreneur by modeling Piyush Patel and Robert Siegel, two of my favorite clients when I was a start-up attorney – I revered their audacity! As I fumbled into my new chapter, I emulated them until I felt confident leading my business.

When David Letterman interviewed Adam Sandler for his Netflix show My Next Guest Needs No Introduction, Sandler revealed a similar strategy that gave him the courage to perform on comedy club stages as a teenager.

“I was 17. I didn’t know what I was yet. I would watch so many great comedians and think, ‘I guess I’ll be like that guy.’ More like Steve Martin, for example.”

Sandler tried on comedians.

“Colin Quinn, a great comedian and a nice guy, was the emcee at a club where I was doing standup and bombing on stage. He commented, ‘You know, you make me laugh a little bit more off stage.’ Of course, I got my feelings hurt”. 

Quinn added, “What I’m saying is when you tell me stories about growing up Jewish in New Hampshire, that stuff makes me laugh. Maybe you should talk about that a little more on stage…”

While Quinn’s contribution felt raw, it validated Sandler’s comedic gift and helped him confidently become himself on stage.

Modeling helps us navigate the nefarious power of imposter syndrome.

Like covert mentoring, we observe the behaviors of those we respect and admire to mold our own. In psychology, this observational learning is referred to as “Social Cognitive Theory.”

It’s not dissimilar to asking for advice and then experimenting with recommendations offered. Imitation gives us the courage to take action, while action gives us the confidence to evolve into our own version.

We mirror people we admire until we determine who we want to be.

  • I stepped on stage as a speaker by modeling Tony Robbins.
  • I made friends after law school by modeling Dale Carnegie.
  • I became a stepmom by modeling my mom.

Even Warren Buffett believes in the power of modeling and mentoring.

Buffett once told a young shareholder, “It’s better to hang out with people better than you. Pick out associates whose behavior is better than yours, and you’ll drift in that direction.” 

In his final letter to shareholders as the retiring CEO of Berkshire Hathaway in November 2025, Buffett mused, “Choose your heroes very carefully and then emulate them. You will never be perfect, but you can always be better.”

Choose heroes. Emulate them. Always improve.

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

[Flash] Navigating Sharp-Edged Advice – When Blunt Mentors Jolt Mentees

In his weekly “Social Qs” column in The New York Times, columnist Philip Galanes addresses social etiquette dilemmas with his straight-shooting, suffer-no-fools approach.

But recently, he missed an opportunity to mentor a Mentor.

A reader submitted this question: “An older Uncle told a young Nephew that he talks too much. The Nephew told me how hurt he was by the comment. But I don’t disagree with the Uncle – the Nephew does talk incessantly. Should I get in the middle?”

Philip’s response: “I hope you expressed compassion for your Nephew’s hurt feelings. Learning to stand up for ourselves is important, especially for young adults. Encourage him to communicate his feelings to his Uncle. You can help this young person set boundaries and process unwanted criticism.”

But by focusing on the Uncle’s sharp tongue, we risk encouraging the Nephew to avenge an insult instead of identifying an opportunity to develop.

Shortly after reading this column, a Mentee in one of our programs reported feeling jarred by the blunt advice her Mentor delivered. The program leader wanted my guidance – should she address the Mentee or the Blunt Mentor?

My response: Both!

Of course, Mentors can always finesse their approach, be more empathetic, and improve their communications. But we must assume that Mentors are well-intended in their offered contributions. 

And even if we suppose the Rude Uncle had not intended to mentor, and the Blunt Mentor was acting venomously, it’s remiss to focus only on their flaws.

Doing so hampers the growth of the Nephew and the Mentee – the whole point of mentoring!

According to Adam Grant, author of the book Hidden Potential, one of the most essential character skills we can develop is “Absorptive Capacity – the ability to recognize, value, assimilate, and apply new information.”

Absorptive Capacity entails two essential components:

  1. how you acquire new information
  2. how you filter new information

When we are reactive and driven by our ego, we tend to reject any information that threatens our image, like “you talk too much.” Instead of seeking wisdom, we prioritize protecting ourselves from judgment or offense. 

Conversely, when we are reactive and growth-oriented, we are like “clay” (Adam’s word), responding to any input as potential development. We’re not afraid to get our feelings hurt. We’re not afraid of criticism. We’re afraid to miss the opportunity to improve.

Want to be a great Mentee? Remember that mean people don’t mentor and insulted people don’t grow.

Want to be a great Mentor? Help people sidestep the criticisms and look for the contributions. 

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

[Flash] Ditch Opinionated. Become a Thought Partner.

Over my 25 years of running businesses, I’ve paid numerous consultants to give me their advice (secretly hoping they would absolve me of the responsibility of making a decision!). Too often, I ended up ignoring their advice, grumbling that they didn’t understand my situation.

The irony of asking for advice about an important decision is that we don’t necessarily want someone telling us what to do. Research shows that advice-seeking decision makers are actually seeking validation, perspective, and sense-making support.

When people ask for our advice, we tend to lead with our opinion, which is typically informed by our experiences, not theirs. It often sounds like “You know what you should do…” 

In sharing our opinion-cloaked advice, we risk robbing people of the ownership of their decision.

What to do? Contribute differently. Become a Thought Partner. Help people think and make sense of their choices by posing probing questions:

  • What would it be like for you if you…?
  • How do you feel about…?
  • Are you willing to…?
  • Are you ready to…?
  • What if you do nothing? 
  • What might you regret?
  • What alternative options have you considered?
  • How will you measure success?
  • What’s the worst that can happen?
  • What’s the best that can happen?

For example, if your Mentee asks for your advice on her lingering decision to change jobs to end her strenuous relationship with her boss, fight the urge to impose your opinion.

Instead, be her Thought Partner – help her think through the decision.

Thought Partners don’t have an agenda. Ultimately, it doesn’t matter what decision your Mentee makes – it only matters that she feels supported as she gallops and grows.

You might ask:

  • What would it take to improve the experience with your boss?
  • How will you feel about your position if the situation with your boss doesn’t change?
  • How could you leverage this challenging situation?
  • Which role will help you best develop and grow your career?
  • Are there other options besides these two?
  • Is there any urgency to this decision?
  • Are you prepared if your next boss is similarly difficult? 

After twisting the kaleidoscope a few times, you could share your own insights and wisdom“When I was in a similar situation, I found it helpful to…” “The best advice I ever received was…”

When Mentors help people think and grow, they become valuable Thought Partners.

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

[Flash] Put Yourself in the Path of Your Future (Advice from Jamie Lee Curtis)

“You have to put yourself in the path of your future. It’s not going to come find you just sitting on your phone.”

Jamie Lee Curtis shared this advice on the Sunday Sitdown podcast last month.

Acting for 48 years, Jamie’s career continues to thrive. When the host asked about her secret, she responded emphatically, “I put myself in the path.”

Definitive wisdom for our new year, but what does “put yourself in the path” practically mean?

Readiness + proximity with a sprinkle of hustle.  

Instead of waiting to be discovered or chasing every shiny object, “put yourself in the path” is deliberately stepping into rooms, conversations, collaborations, and creative ecosystems where interesting work is happening.

Jamie’s favorite “get in the path” strategy: she never leaves the movie set during production. Instead of hiding between her big moments in a script, Jamie engages with the director, always ready to contribute.

The result? She lands more on-screen time in a film because she doesn’t retreat to her trailer.

Jamie stands where opportunity is occurring. 

Reflecting on this advice, I “put myself in the path” every time I exhibit at a conference. By immersing myself in the community, I participate in conversations, discover priorities, and communicate solutions to the problems I hear from attendees at our booth.

Readiness. Proximity. Hustle.   

Why does it work? Trust.

People trust people they see, know, and experience. They trust people who consistently show up. They trust people who support their projects and ideas.

People want to engage with people who want to engage with them.

Embarrassingly, I once took myself off the path when I became disenchanted with a former boss. Instead of working to improve our relationship, I petulantly moved my office to the other side of the building.

At that point, I was no longer visible, engaged, or relevant. But I was successfully righteous. Not surprisingly, my boss stopped including me in decisions. And one day, he hired someone to replace me.

Some suggestions to “put yourself in the path” of your future:

  • Prepare – hone your communication and your craft
  • Be intentional and confident, but not entitled
  • Eagerly volunteer to participate in meetings, projects, and teams
  • Stay curious – observe, ask questions first
  • Commit to contribute – offer to improve situations 
  • Maintain strategic presence – don’t hide behind cameras or keyboards
  • Employ a thoughtful “yes!” to ideas and conversations

Place yourself where passion, people, and possibility intersect, again and again. Opportunities favor the involved.

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

[Flash] 2025 Fan Favorite Roundup

The conclusion of the year offers us not only respite but reflection.As I reflect on the Flash! Mentoring articles I wrote for you each week in 2025, I’m resharing the 9 that generated the most conversation:

  1. When a TSA Agent and the Sixt Manager Helped me
    https://mentorlead.com/blog/flash-when-a-tsa-agent-and-the-sixt-manager-helped-me/
  2. You Can’t Step Twice Into the Same River (or Mentoring Conversation
    https://mentorlead.com/blog/flash-you-cant-step-twice-into-the-same-river-or-mentoring-conversation/
  3. Am I Doing Enough? Asked the Mentors
    https://mentorlead.com/blog/flash-am-i-doing-enough-asked-the-mentors/
  4. Wisdom from the Cornfield – Great Corn Comes from Great Mentors
    https://mentorlead.com/blog/flash-wisdom-from-the-cornfield-great-corn-comes-from-great-mentors/
  5. Are Human Mentors Obsolete in the Age of ChatGPT (Spoiler: No!)
    https://mentorlead.com/blog/flash-are-human-mentors-obsolete-in-the-age-of-chatgpt-spoiler-no/ 
  6. No One Dies in Mentoring (the Stoic Challenge in Action)
    https://mentorlead.com/blog/flash-no-one-dies-in-mentoring-the-stoic-challenge-in-action/
  7. When Lily Tomlin Astutely Mentored SNL Lorne Michaels 
    https://mentorlead.com/blog/flash-when-lily-tomlin-astutely-mentored-snl-lorne-michaels/
  8. When Mentors Become Wise (Are You a Loud Listener?)
    https://mentorlead.com/blog/flash-when-mentors-become-wise-are-you-a-loud-listener/
  9. How Do I Get Your Job? (When Mentoring is the GPS for our Lives) 
    https://mentorlead.com/blog/flash-how-do-i-get-your-job-when-mentoring-is-the-gps-for-our-lives/  

March 2025 marked 10 years of my weekly Flash! articles. And in September, I published my 5th book, a compilation of Flash! articles organized around the art, science, and magic of mentoring. You can find this and all of my books at: www.mentorlead.com/books

It is a delight to be on this bigger-better-bolder adventure with you! Thank you for reading and rooting! 

I look forward to circling the sun with you again! Happy New Year!

© 2025. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved.

[Flash] Making Holiday Conversations Count – 12 Hip Pocket Phrases!

[reprinted from 2023]

Holiday gatherings offer a valuable opportunity to practice connecting with curiosity and compassion – a coveted skill that makes us better mentors, leaders, and human beings.

Here are 12 phrases to help us connect, not just cope:

1. “You look terrific!”
People are constantly critiquing themselves, especially during the holidays. We can instantly reassure them with a (genuine) compliment.

2. “That’s amazing!”
Ask people about their recent adventures or experiences – everyone deserves a spotlight!

3. “How can I help?”
Swap “Do you need help?” with “How can I help?” to indicate your commitment to making a difference. Better yet, start helping!

4. “What’s your perspective?” 
Everyone has a perspective, and their view of the world is inevitably different than yours. Get ready to discover what they see!

5. “Tell me about…”
Demonstrate an interest in their experience. “Tell me about your perspective – how did you arrive at that?” Or “tell me about your job change, college decision, vacation…”

6. “That’s wonderful, frustrating, or interesting.”
People have an innate desire to be understood. No matter the story they share, validate their experience and make them feel heard by mirroring their feelings with your words.

7. “Have you considered…? What about this idea…?”
If they ask for your advice or get stuck venting, offer an idea for consideration. Doing so with a question allows you to contribute without judgment, expectation, or pressure.

8. “Not yet.”
“No” halts conversation, whereas “Not yet” fuels possibility.

9. “Say more…”
As in, “I’m curious about that idea. Say more about what you’re thinking.”

10. “To change the subject…”
Not every conversation needs to be exhausted over a fruitcake. Conversations can change, and this phrase signals your intent to change it.

11. “Grateful!”
Using an alternative to “thanks” causes people to hear it and ourselves to mean it. Options: “Grateful!” “Appreciate you!” or “Much obliged.” For more significant impact, add context: “I’m grateful that you…” “I appreciate you for…”

12. “Pleasure.”
I worked with a woman from South Africa who always responded to my “Thanks” with “Pleasure!” as in, “It was a pleasure to help.” This cheerful response made me delighted that we partnered.

Regardless of the conversations you create this holiday, guests will appreciate your effort to engage. And who knows… you might feel more connected and compassionate as you savor the celebration.

Wishing you Happy Holidays!

© 2025. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved.