Their question stunned me because:

1. The Mentees in the program had just shared with me in a separate meeting that they were getting so much value from their Mentors already, and
2. The Mentors are the hospital’s executives… their insecurity was refreshing if not slightly surprising.

In its purest form, mentoring occurs when one person advises, guides, and supports another to help them professionally grow and develop.

However, Mentors – especially high-functioning, problem-solving, get-stuff-done leaders – often feel inclined to do more to support the success of their Mentees.

Beyond doling out advice, what could you do to improve your experience as a Mentor while nudging, not judging your Mentee? 

Here are 10 advanced mentoring techniques that you can use to up-level your mentoring and amplify your influence:

1. Strategic Inquiry: ask probing, open-ended questions to sharpen critical thinking skills and help your Mentee generate their own insights (ex: “What would happen if you…?”)
2. Pattern Recognition: instead of focusing on single incidents, identify repeating patterns (“I’ve noticed in our last three conversations that you…”)
3. Cognitive Reframing: help your Mentee reframe mistakes and setbacks as growth opportunities (“What can you learn from this?”)
4. Role Playing: work through forthcoming situations with a role-play exercise to provide real-time feedback and perspective
5. Stretch Challenges: assign your Mentee a “stretch” project or experience slightly beyond their comfort zone, and provide scaffolding (support, feedback, a safety net) while your Mentee takes the lead, building confidence and capabilities
6. Reflective Storytelling: share with your Mentee personal experiences of failure, recovery, and resilience to normalize struggle and highlight learning (“Here’s what happened to me when I was in a similar situation…”)
7. Network Brokering: expand your Mentee’s visibility by strategically connecting them with other leaders or peers to grow their network and accelerate their leadership readiness
8. Reverse Mentoring: ask your Mentee for advice to boost their confidence and create mutual learning, or encourage your Mentee to mentor a less-tenured colleague
9. Shadowing: invite your Mentee to observe you or other leaders on the job, and observe your Mentee in action to provide valuable feedback
10. Sponsoring: nominate your Mentee for opportunities on projects, committees, or new roles in the organization

When you want to make a difference beyond cheerleading and advice-dealing, experiment with an advanced mentoring technique to influence your Mentee’s behaviors, up-level their thinking, and catapult their confidence.

As Mentors, we can offer much more than “You should…”

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

He studied comedians on television, became a busboy at a comedy club to observe them perform live, and felt an urge to spend time with them – he wanted to learn their secrets.

But, he thought, what famous comedian is going to talk to a teenager?

Judd soon got his answer while working at his high school’s radio station.

One of his friends produced the music show for the radio and regularly took the train to the city to interview bands.

In Judd’s book Sick in the Head, he remembered thinking, “Wait, we could actually interview people we admired? They’ll talk to you if you ask nicely? It suddenly occurred to me that maybe I could do this with comedians.”

Judd’s first mentor, Jack DeMasi, was the radio station’s supervisor and the school’s film teacher. He treated the students like professionals, permitting them to produce their own shows.

Judd recalled, “Mr. DeMasi encouraged my voice and originality.”

When Judd approached him with the idea of starting his own show interviewing comedians, he agreed, and Judd recalls, “This moment changed my life.”

To get comedians to agree to an interview, Judd brazenly called their agents and said, “I’m from WKWZ radio on Long Island and I want to interview your client,” neglecting to share his age.

When Judd arrived with his AV squad tape recorder, the comedians were surprised but never turned him away. “They were gracious and generous with their time, knowledge, insights, and advice.”

His first interview? Jerry Seinfeld. Judd walked in and asked him pointedly, “How do you write a joke?” 

By the time he graduated two years later, Judd had interviewed over 40 comedic heroes, including: Lorne Michaels, Howard Stern, Al Franken, Sandra Bernahard, Jay Leno, Weird Al Yankovic, John Candy, Paul Reiser, Rodney Dangerfield, Rosanne Barr, Garry Shandling, and Jim Carrey.

He asked each of them for their perspective and advice: what they studied in college, how they got stage time, where they work out new material, how to keep momentum, what’s next in their career.

Reflecting on this experience, Judd wrote: “These interviews informed the rest of my life – they contained the advice that helped me attain my dreams.”

Judd discovered the power of the informational interview, one of the easiest ways to get mentoring.

• Have an intention
• Identify a role model
• Ask for a conversation
• Prepare questions in advance
• Bring a recording device
• Capture insights
• Express gratitude
• Review and reflect
• Take action
• Repeat

The world is bursting with advice just waiting for our fascination, courage, and initiative to collide.

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

Focused on his goal and determined to take action, Jeff joined his company’s mentoring community and invited 24 people to mentor him. Six of them responded immediately, agreeing to support him on his leadership path.

But why did Jeff need six Mentors? He didn’t. What he needed was advice, guidance, and perspectives. He found it in various mentoring conversations.

Jeff set up 20-minute meetings with each Mentor every other month for a year. The result? An assortment of practical ideas, connections, resources, thought partners, and champions… and ultimately a promotion!

Jeff didn’t just work with six Mentors on his learning journey; he engaged in six different mentoring conversations.

You can’t step twice into the same river.

The Greek philosopher Heraclitus (535-475 BC) originated this metaphor as an expression of his core philosophical belief that everything is in flux at all times.

The river is continually changing. Stepping into it offers one experience. Step into it again, and the river is no longer the same – the water has flowed past along with any fish and debris. The water is never the same from one moment to the next.

Life, like the river, is in constant motion; its impermanence renders repetition impossible, making each encounter unique.

Even our mentoring conversations flow like the river, in flux, always evolving, never to be repeated.

• As a Mentee, we can ask the same question of various Mentors, and it will generate different advice based on the Mentor’s experiences, gained wisdom, and particular viewpoint.
• As a Mentor, we can offer the same advice to various Mentees, and it will be received and acted upon differently depending on the Mentee’s situation and specific goal.

This brevity affords us freedom. Instead of searching for the perfect Mentor, the right answer, or the precise solution, we can engage in possibility. The possibility of our connections.

The possibility that wisdom can be gleaned from anyone in any conversation, provided we stay present, curious, and engaged.

To leverage the metaphorical flowing river:

• Look for mentoring instead of a Mentor.
• Tackle goals by seeking advice from a range of people.
• Offer your advice, perspectives, and ideas to anyone seeking guidance.
• Say yes regularly to formal mentoring programs, either as a Mentor or a Mentee – your experience in the program will never be repeated.’

You can’t step twice into the same river or the same mentoring conversation.

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

According to a report in The Information, Nadella’s morning routine consists of exercise, gratitude, and two phone calls. Who is he calling? Leaders in companies outside of Microsoft, like Pete Carroll, an NFL coach, and Aravind Srinivas, the CEO of Perplexity AI.

Why? He wants their perspective and advice. And to ensure the conversations are purposeful, he starts with these two questions:

1. What new startups are you excited about?
2. What new people have you met who would be good to know?

This routine ensures Nadella stays apprised of threats and opportunities in the market while also expanding his network.

Seeking wisdom in this way is a form of peer mentoring – Nadella is leaning into his network to learn from them. He’s cognizant that his colleagues are connected differently, possess unique insights, and are privy to knowledge he doesn’t yet have.

Even if The Information’s report is exaggerated and Nadella only reaches out to leaders once a month or once a quarter, it’s still a remarkable commitment to connect, listen, and learn from his peers.

To make these peer mentoring conversations work, Nadella must suspend any steadfast opinions, predetermined answers, and established solutions.

Instead, he must approach the conversation with an open mind, willing to explore and discover new possibilities.

One of his peers might be excited about a company that Nadella had already unearthed and dismissed. By engaging with curiosity, he can hear his peer share a perspective or an insight that he had initially overlooked.

Peer mentoring is an exercise in intentionality, humility, wonder.

If the CEO of Microsoft invests time, effort, and energy into being mentored by his peers to grow and develop, we can too!

How?

• Connect with new people on LinkedIn.
• Make phone calls for wisdom instead of simply texting for information.
• Share goals and aspirations.
• Ask peers to contribute: “How would you approach this?” “What am I missing?” “Who should I know?”
• Frame conversations with a clear objective.
• Lead with thoughtful questions that drive that objective.
• Request introductions to new people.
• Seek connections beyond your department, job level, organization, and industry.
• Join formal mentoring programs to practice turning strangers into friends.

Network science research suggests that connecting to peers in diverse industries and social groups is a predictor of career success.

Makes sense! The more conversations we have, the greater the chance of colliding with promising ideas, opportunities, and people.

Intentional peer mentoring is the gateway!

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

During the interview, Amor shared the influence his Mentor has had on his success…

While at Yale as an undergrad, Amor took a seminar with his hero, writer Peter Matheson, who enthused, “Based on the three stories that you’ve submitted, Amor, I think there’s a possibility that you may be gifted at writing.”

Amor reflected, “That was a major turning point in my life.”  It was the first time an outsider – someone who Amor admired and respected – acknowledged his talent.

Peter continued to mentor Amor in the years following graduation, encouraging Amor’s writing pursuits.

When Amor finished his first draft of Rules of Civility, he sent the manuscript to Peter with a note: “I feel really good about it. This is the first book I’ve written that is worthy of submission, and I’m interested in your feedback. It’s about a 25-year-old woman set in the 1930s.”

Peter responded brusquely: “Amor, I can’t understand why you continue to write about the 1930s. To be honest, this is a terrible thing. And I find that spunky, opinionated, witty women are boring in fiction.”

Amor was undeterred. He fine-tuned his book and sold the publishing rights at auction.

When Rules of Civility hit the bestseller list, Peter sent the following note:

“This is what we call eating crow. My sister, who’s one of the greatest readers I’ve ever known, said that the minute your book ended, she was sad it was over and wanted to start again. That’s as much as you could ask of a book.”

Amor reflected that having his Mentor dislike his manuscript was almost as valuable as having his Mentor validate his talents at age 19.

“It meant that this book worked even though my hero didn’t like it. It was a lesson to me as an artist that I have to have confidence in my work, even when my mentors or my friends don’t care for what I’ve created.”

Mentors don’t have all the answers – their value lies in recognizing and supporting our potential as we find our own answers.

The edge we get from mentoring is confidence. And that confidence gets revealed when we start believing in our work when others don’t.

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

There was an Indiana farmer famous for growing the finest corn in the valley. Year after year, his corn won the blue ribbon at the State Fair for “Best Corn.”

One day, an enterprising reporter made an interesting discovery while interviewing the farmer – he learned that the farmer shared his seed corn with his neighbors. 

Stunned, the reporter asked, “How can you afford to share your best seed corn with your neighbors when they are entering corn in competition with yours each year?” 

To which the farmer replied, “Why, sir, don’t you know the wind picks up pollen from the ripening corn and swirls it from field to field? If my neighbors grow inferior corn, cross-pollination will steadily degrade the quality of my corn. If I am to grow good corn, I must help my neighbors grow good corn.”  

In mentoring, we share our best knowledge, experiences, and insights to enrich others, helping them grow stronger. As the farmer demonstrated, doing so doesn’t threaten our success but sharpens and strengthens us.

If the farmer had hoarded his best seeds, cross-pollination would weaken his corn. Similarly, if we hoard wisdom, we not only limit our potential, but we also threaten the caliber of our team and organization.

Leaders regularly ask me about the return on investment (ROI) of mentoring – can I help them justify the costs associated with launching a formal mentoring program? And of course, I have a slew of literature, metrics, and results that point to the indelible impact of mentoring.

But shouldn’t we also be considering CONI – the cost of not investing? Because the cross-pollination of unmentored team members leaves its own lasting mark. As the farmer noted, inferior corn outlasts a single season, thereby undermining future crops.

Mentees are a reflection of our investment in their success. Only when they thrive can we possibly win “Best Corn.”

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

She knew I could do more. And when she wondered it out loud, I realized I could do more, too. So, I picked up heavier weights.

She was nudging, not judging me. She was inviting me to see what she sees – a stronger version of me.

Instructor Jen cleverly used the Proposal Question to communicate her belief in me to reach for more while leaving the decision to take action in my hands.

When Peter Cuneo, former CEO of Marvel Entertainment, was interviewed on the How Leaders Lead podcast, he reflected:

“I’ve had people who came into my life at certain times who believed in me even more than I believed in myself. I’m not lacking self-confidence, but there were certain heights I just didn’t think I could reach. And they pushed me, encouraged me, and I made the effort just to please them, never thinking I’d get there. And they all worked out, actually.”

While research shows that we view advice as more valuable when we ask for it, our blind spots often cause us to miss opportunities to seek the nudge we need to stretch, reach, and grow.

And even when we know we need some support and encouragement, our pride often prevents us from asking, “Instructor Jen, could you encourage me to lift more?”

So, we count on people like Instructor Jen to notice opportunities to encourage us.

(More arguments for the power of the formal mentoring structure: mitigate the trappings of the ego and create opportunities to intentionally notice and encourage others!)

But the words these Mentors choose will determine if we receive that nudge with gratitude or a grudge.

Luckily, the Proposal Question operates stealthily – an invitation cloaked in a compliment.

It whispers, “I believe you could do more or do better. Want to try?”

The Proposal Question works by suggesting possibilities. Ultimately, the power to choose to do something and the ownership of any action remains at all times with the Mentee.

• Is that goal big enough for you? 
• Is that dream compelling enough for you?
• Will that plan stretch you?
• Are we thinking broadly enough?
• Have we explored all the career options?
• What about…?
• What if…?

Believing in people’s greatness before they do supports their ego, which then strengthens the trust they have in the relationship. Bottom line: we tend to like people who believe in us.

A little nudge goes a long way!

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