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The generational advice gap took center stage in a recent episode of the Apple TV series Shrinking.
In an early scene, Grandma, played by Candice Bergen, encouraged her grandson’s entrepreneurial passion, in direct contrast to the boy’s doting mom, Liz, who downplayed his fluky hobby. When the boy left the room, charged and excited by Grandma’s validation, Liz seethed, “I have one rule. Do not tell me how to parent.” As Liz stormed out of the room, Harrison Ford’s character, Paul, entered, finding Grandma deflated.
Wait! Do they not want what we have to offer, or are they simply distracted, navigating their insecurities, proving their independence, and oblivious to the power of thought partners? When I was in my twenties and the recipient of blindsiding advice from elders, I took it as a personal affront. Why didn’t they just shower me with praise for my brave but imperfect effort? I was young and unconfident. Decades later, I was surprised when the tables turned. A young person in my life wrote a book but never reached out for support or advice, even though I have authored five books. Was I hurt that my experience wasn’t called upon, or was I just feeling left out? Later in the Shrinking episode, Grandma and Liz reconciled.
And that’s how unacknowledged bravery bumps into thankless advice. So, how can we prevent our stubborn pride from blocking the thought partnership that could strengthen our relationships?
Regardless of generation, people are desperate to feel valued, respected, and relevant. © 2026. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved. |
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In his Netflix special American Boy, comedian Marcello Hernandez describes a scene in which he and his friends see a stunningly beautiful woman with a less attractive man.
Marcello: “When we saw this couple, my friends said, ‘I bet that guy’s rich.’ And I responded, ‘No, dawg. That guy probably listens like crazy. He probably says stuff like, ‘Wait, wait, wait, wait. Start again.’” Then Marcello adds, “That guy probably has…” At this, he inserts a dramatic pause and a smirk before dropping his punchline: “…follow-up questions!” Marcello gets it. According to Warren Berger, author of The Book of Beautiful Questions, we demonstrate our sincere interest in others by asking questions. Each question is an invitation to share themselves with us – their stories, experiences, thoughts, and feelings. And when they share, we begin to understand them better, strengthening our connection. My recent podcast guest, Selina Nazzaro, confirmed this strategy. I asked her how she manages those moments when self-doubt whispers in her ear as she is mentoring. She shared her secret: ask more questions. Brilliant! Through inquiry, we demonstrate our genuine interest in the other person’s success. To be a great leader or mentor, we don’t need to provide the right answer or life-altering advice. We need to become a thought partner. We need to engage and explore with more questions. If follow-up questions are our superpower, why isn’t every conversation bursting with them? Berger points to 5 “enemies of questioning”: Let’s add to his list: distraction and obliviousness. When we battle a constant assault on our senses, it takes effort to focus, let alone focus on someone else. But when we value the relationship, it’s worth the effort. Throughout the book, Berger offers lists of questions to help us decide, create, connect, and lead. His list of follow-up questions includes:
I use these follow-up questions to deepen conversations:
And when the other person offers follow-up answers, it’s vital to listen, engage, validate, and clarify using… more follow-up questions! An interested person is hard to resist. © 2026. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved. |
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Our mentoring podcast kicked off the year with a special guest, Jose De Guia, Chief of Staff at Kaiser Permanente’s Downey Medical Center.
From the very first question, Jose was vulnerable, engaging, and inspiring as he described his unconventional career path. He started as a retail manager before pivoting his career to healthcare and becoming the manager of a diagnostic imaging department at Kaiser. He worked hard, volunteered for opportunities, and consistently delivered results. Predictably, Jose was regularly recognized, praised, and promoted. During our exchange, Jose admitted that he had become overconfident, even a bit cocky, about his ability to execute and succeed in each role. He then revealed the arc when a promised promotion fell through. Jose became outwardly angry. His entitlement morphed into resentment, spilling into daily conversations. Jose finally scheduled a meeting with an HR Leader and challenged her, “Can they stop me from growing?” Unruffled, the HR Leader paused and asked Jose, “How did you get here?” He proudly shared his brazen and triumphant career journey. The HR Leader then gave Jose some career-altering advice. She said, “Jose, you need to remember that every day is an interview.” Jose shared his interpretation with our audience, “Every day, we earn our jobs. We aren’t entitled to them. We are privileged to hold them.” In the weeks that followed, I chewed on Jose’s insights, internalizing his wisdom. And, as I was about to meet with one of my team members to review her work on a project, I had an epiphany… every day is an interview for me too! Every day, my team interviews me to serve as their leader. I must earn their trust and commitment through my actions and behaviors. Every day, they choose where they invest their time and effort. I am not entitled to their service or their contributions. It’s a privilege to work with them. This revelation had me consider… how would I show up to this meeting with my team member if she were deciding whether to join my team? I would be:
I don’t always get it right. But every day is a fresh opportunity for me to practice earning my people’s trust and partnership, to demonstrate my gratitude, and to mentor. Every day is an interview, regardless of our role. © 2026. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved. |
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At the ACNL Conference recently, MJ confessed to me, “I have a bad habit. The older I get, the more I give people unsolicited advice! What should I do?”
Unsolicited advice is well-intentioned support. We feel compelled to contribute wisdom that could help someone rather than selfishly hoard it. MJ followed her confession with a reflection, “I feel like a historian. I want to tell people what I know.” Brilliant! That fueled my suggestion to her, “Then share your stories and hard-earned wisdom like a historian, not like a parent.” Parents often lead with an agenda.
But historians don’t have an agenda – they analyze, interpret, and communicate past events to understand human evolution over time. When you show up like a historian, you share stories about events in your past and how they’ve shaped your evolution. Your audience can then translate and apply your experience and insights, tuck them away for future use, or ignore them altogether. I practiced being a historian recently when a friend admitted that her oven has been unusable for two years – she’s been cooking for her family using only the stovetop! This friend is younger, so the urge to respond like a parent was hard to resist. I caught “You-know-what-you-should-do” in my throat before it tainted her trust. Instead, I responded with a story: “When we lived in a 100-year-old house, things broke often, like the screens on the porch. Eventually, we couldn’t use the porch. And then a realtor friend offered, ‘You’re going to have to fix those screens before you sell the house, so you might as well do it now and enjoy your porch.’ So, we did, and I loved sitting on that porch for three years before we sold the house.” I have no underlying motive to get my friend to fix her oven. Whether she gets it fixed does not impact me. But I wanted to help without inadvertently expressing disapproval. Showing up as a historian allowed me to offer my curated wisdom free from lecturing, judging, or pressuring her to take action. By sharing a story with transformative-to-me advice, I made a difference, my friend preserved her power to choose, and our relationship strengthened. As a historian, I can transform my unsolicited advice from condemnation to contribution. © 2026. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved. |
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When Gaon Choi of South Korea received a snowboard at age 7, she searched for tricks on YouTube and discovered the iconic US snowboarder Chloe Kim.
“She was so cool, and I wanted to be like her. Chloe is my idol,” gushed Gaon. Chloe is considered the world’s greatest female snowboarder, having won gold in the halfpipe at the 2018 and 2022 Olympics and being favored to win another gold this year! They met ten years ago when Chloe discovered Gaon’s promising talent. (“I saw something in you” is a powerful validation!) Chloe took Gaon under her wing, helping her master snowboarding tricks and introducing Gaon to Chloe’s coach in California. Last week at the 2026 Olympics, Mentor and Mentee became rivals in the women’s halfpipe finals: Chloe aiming for a three-peat; Gaon seeking her first gold. When Gaon crashed on one of her runs in the competition, Chloe reminded her, “You got this. You’re a badass snowboarder.” And Gaon proved her Mentor right. Her final run earned her a score that beat Chloe’s, awarding Gaon the gold medal and her Mentor the silver! Chloe embraced Gaon in a celebratory hug and beamed at her Mentee throughout the medal ceremony. At the press conference, Chloe reflected on the full-circle moment, watching Gaon progress felt like seeing a mirror reflection of herself. Mentees often surpass their Mentors.
A Mentee’s triumph is not an indication of a Mentor’s weakness or failure; it’s an indication of their influence. But why bother expanding wings to mentor a potential rival?
Mentoring Gaon didn’t diminish Chloe; it enriched her. It made her a stronger snowboarder and a healthier human being. Competing against her Mentee over the past decade pushed Chloe to dominate her sport, while mentoring Gaon expanded her empathy, emotional security, and leadership. Following the competition, Chloe gushed with pride on social media, “I feel like a proud mom. The future of snowboarding’s in good hands.” Healthy mentors operate from abundance with Chloe-level confidence and generosity. © 2026. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved. |
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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?
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:
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. |
| 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.
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:
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. |
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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.
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. |