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Last week, I delivered my manager-to-leader program to an in-person audience of eager and engaged emerging leaders. When it ended, one of the participants, Sally, approached me for some advice about public speaking.

Sally asked if I ever felt nervous on stage. I shared, “Of course! I always get nervous initially – that’s how I know I care. But I’ve learned to tell stories to shift my focus from my angst to my audience.”

Feeling validated, Sally revealed, “When I get nervous, I ask ChatGPT to help me overcome my imposter syndrome. And it reminds me that I am better than I think.”

I felt punched. She turns to ChatGPT for mentoring?! Are human mentors obsolete now?

(ChatGPT is simply a version of AI that generates human-like conversational responses to questions.

Instead of spending hours weeding through websites and navigating a slew of derailing clickbait when we need information, ChatGPT filters the internet for us and produces answers in seconds!)

I decided to ask the culprit.

I typed the following into the prompt box in ChatGPT, “What advantages does a human mentor have over ChatGPT?” Here’s a summary of the results it generated for me:

• Personal connection
• Emotional support
• Empathy
• Accountability
• Personal guidance
• Motivation
• First-hand knowledge
• Practical experiences
• Real-world insights
• Moral and ethical guidance
• Tailored feedback
• Networking
• Advocacy
• Gut instincts
• Emotional nuance
• Tough love

Now, I felt validated!

Sally didn’t ask ChatGPT about my experience, advice, and insights – she asked me personally.

And Sally could have asked ChatGPT for information about managing vs. leading, but she opted instead to attend an in-person program to connect with and learn from others. 

While ChatGPT is indescribably efficient, providing us valuable information and even advice, it is a poor substitute for mentoring with a human.

• it robs us of the learning experience
• it doesn’t care if we grow, learn, or feel connected
• it doesn’t care about our autonomy, agency, relatedness, or belonging

Its sole job is to produce intelligence, not help us gain wisdom – that’s what Mentors do.

“We learn when we deeply process information. If we’re removed from that and we’re delegating everything to ChatGPT, we’re not connecting to that information.”

~ Gloria Mark, Professor of Information Sciences
at the University of California, Irvine,
and the author of Attention Span.

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

And then I discovered a way to join them: The Stoic Challenge – A Philosopher’s Guide to Becoming Tougher, Calmer, and More Resilient by William B Irvine.

Stoicism is a school of philosophy from the Roman Empire, emphasizing the “endurance of pain or hardship without the display of feelings.”

Irvine, however, argues that the Stoics were not anti-emotion. Rather, they were “eternal optimists who possessed a profound ability to put a positive spin on life’s events.”

Irvine recommends Anchoring and Framing to save us from the natural anger we feel when our expectations in life are not met. 

Anchoring
Anchoring is putting situations in perspective – zooming out to give the situation a better context.

• Does that broken link on the website really matter when my dog is sick? 
• Does that typo matter when my mom is battling dementia? 
• Do I really care that we lost a client after my dad was diagnosed with cancer? 

When someone on my team appeared distressed about a mistake, I reminded her (and me!) that no one dies in mentoring. And this has since become an anchor for my team.

Undeniably, we each care deeply about our work, but we remind ourselves that our work is a privilege and a passion (for us and our clients), but not a necessity.

Mistakes are inevitable, and they can be fixed. That perspective – that anchor – provides the space and grace necessary to grow and go together.

Framing
Framing involves seeing a situation in a way that prevents it from triggering anger.

At the crux of Irvine’s approach to stoicism is framing the stumbles, snags, and setbacks we experience as tests of our resilience and resourcefulness. He calls this the “stoic test strategy.”

Instead of being frustrated or angry, he approaches obstacles and aggravating situations with awe and occasional laughter.

When I shared this framing concept with my team, we started seeing “Stoic Challenges” everywhere – an angsty client, an impatient mentee, an irritating wait time.

We often text each other “Stoic Challenge!” to remind ourselves that we don’t need our frame to match their frame – we get to create a tougher, calmer, more resilient frame.

By implementing the Anchor and the Frame, I’ve witnessed and experienced the dissipation of stress and frustration, replaced by fascination, entertainment, and joy.

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

She confessed, “I want to be selfish this year. Can you find me a mentor?”

Yes and yes!! (Leaders who mentor and seek mentorship inspire me!)

Shortly thereafter, I ran into Priscilla, a recently retired nurse executive who agreed to mentor Michelle in the program.

When it ended, Michelle declared Priscilla the mentor she had been waiting for her whole career!

What was their secret?

Michelle came to the relationship ready to accomplish three concrete goals, eager for Priscilla’s guidance, support, and advice.

But Priscilla came with curiosity. Before tackling those goals, she wanted to understand Michelle as a human being and why she chose those goals. Priscilla first focused on Michelle’s needs and emotions.

And this pause in productivity gave Michelle permission to be vulnerable and transparent. 

Priscilla shifted the conversation from fact-finding to feelings.

In his refreshing new book, Supercommunicators, author Charles Duhigg explores how to effectively connect through communication.

He references a 2016 study by Harvard scientists who set out to understand the difference between successful and unsuccessful conversations. Studying hundreds of recorded conversations, they noticed that people interact in one of three ways:

1. Talk only about themselves
2. Ask fact-based questions
3. Ask feeling-based questions

Fact-based questions are simply a starting point, like small talk. The conversation ends when the responder answers the question.

• “What do you do?”
• “Where did you grow up?”
• “What is the first job you ever had?”
• “What are your hobbies?”

Many ice breakers, like “Fun Facts” and “Two Truths and a Lie,” often misfire because they simply exchange information without emotion.

Feeling-based questions go deeper. They draw out the other person’s needs, goals, beliefs, and emotions. They launch a discovery.

• “What caused you to change course?”
• “What was that experience like?”
• “How do you define success?”
• “What’s been weighing on your mind lately?”

To shift fact-gathering small talk into a deeper conversation, ask a follow-up feeling question steeped in genuine curiosity.

To further deepen the connection, the research concluded that when the other person reveals a need, goal, belief, or emotion, reveal something about yourself. Meet their vulnerability with yours.

The mutual sharing will demonstrate and cement trust.

Priscilla so masterfully pivoted their conversations from fact-gathering to feeling to revealing that Michelle ultimately referred to her mentor as her “soul friend.” 

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

An abundance of research evidences its impact:

• 75% credit their success to mentoring
• 90% with a mentor are happy at work
• 67% are less likely to leave their job
• 82% enhanced their sense of belonging
• 91% felt more confident
• 88% strengthened their leadership skills

But numbers lack emotion. And because we take action based on emotion, we are hungry to hear the stories behind the numbers.

Last week, I witnessed a profound one…

I had organized the final celebration of a leadership mentoring program so the mentees could reflect on their experience and acknowledge their mentors.

When it was Marianne’s turn to share, she captivated us!

Marianne had joined the program because she was feeling stuck in her career.

In her words, “I dreamt of returning to nursing school, but my quiet voice was whispering, ‘Maybe it’s too late.’ So, I found myself just standing still.”

Then, she was formally matched with Bridget.

“My mentor is the kind of person who listens with her whole being. Who asks you the right question at the right time. Who doesn’t just point you toward your potential but walks beside you until you believe in it for yourself.”

“Bridget listened and heard me. She didn’t just encourage me to go back to nursing school; she helped me remember why I wanted to become a nurse in the first place.”

“She inspired me with her own story, connected me to information, plugged me into the right people, and encouraged me. Her steady belief in me lit a fire I didn’t realize had gone dim.”

“She became more than a mentor. She became a guiding force and a beautiful example of the kind of nurse and person I want to be.”

Marianne concluded her reflection with: “I’m not just going back to school. I’m walking forward in my path toward leadership with purpose, clarity, and a whole lot of gratitude.”

From the surprised look on Bridget’s face, I could tell she was not expecting that.

When Bridget and I talked afterwards, I asked her what she did as a mentor that altered the trajectory of Marianne’s life.

Bridget reflected, “Honestly, I just listened to her, offered her a few suggestions, identified some potential opportunities, and shared my own story of feeling stuck.”

And then Bridget added, “I didn’t think I had done anything out of the ordinary.”

But she did. She created a safe, supportive space for Marianne to navigate life and take action. 

The numbers prove mentoring works. But the stories offer compelling reasons why it works.

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

In challenging times, “you want to have conviction, but not certainty. You need to have a steady hand on the tiller, but you can’t go back and forth all the time.”

“I thought of myself as the bus driver. If I try to avoid every pothole and everything in the road, everyone in the back of the bus will get pretty nauseous.”

Carl joined Autodesk when it acquired his start-up in 1993. Shortly thereafter, CEO Carol Bartz identified Carl as her successor and mentored him to take the helm upon her retirement.

During Carl’s tenure, he faced considerable challenges: a financial crisis, a recession, an activist investor, and the company’s new business model.

Carl met each challenge with bold decision-making. He forged a path forward with no guarantee of success.

“Conviction but not certainty” is clarity of purpose combined with a tolerance for ambiguity.

Ambiguity is tough, however, especially for leaders who like to be in control! When the unknown feels too risky, they tend to gather more evidence, produce surveys, overanalyze data, and seek consensus.

But people want to follow leaders who possess confidence, commit to some path, and are decisive. They don’t need a guarantee; they need vision in the midst of fog. They need leadership.

Moving ahead without certainty is where significant progress occurs, ideas are born, and trust is built – in ourselves and each other.

Agreeing to mentor is conviction without certainty. We invest in a mentee’s potential before they can show us results.

Taking a new job is conviction without certainty. We invest our career in a new team with no assurance of success.

Even getting married is conviction without certainty. We invest in a union with the promise of forever but not a warranty.

Why? Because we believe in the possibility of the future. And that belief is louder than our fears.

That belief emboldens us to improvise, innovate, iterate, and improve. Undeterred by the unknown, we navigate, adapt, and adjust, eager to discover and learn as we go.

So, when we don’t take action, it’s not the guarantee we are missing. It’s the belief.

And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom. ~ Anais Nin

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

Our monthly conversation started strong: I re-established trust, and when she regaled me with the latest in her ongoing saga, I practiced loud listening.

But suddenly, I heard the rescuer in me proclaiming, “You should…” “You must…” “Here’s what you need to do….” and “Go! Now!”

And like an over-eager, compliant Mentee, she “Yes!”-ed me, agreeing to implement my advice immediately.

I left the conversation feeling like a rockstar – I changed my Mentee’s life! I almost strained a muscle, patting myself on the back.

So when I received a disappointing text from her a week later with a sheepish update replete with excuses and apologies, I realized what I had done – I had broken a few cardinal rules of mentoring:

• I acted like she needed fixing
• I told her what to do
• I became invested in her executing my advice
• I failed to consider her people-pleasing nature

Cardinal Rules

1. Water Don’t Weed.
Mentees don’t need fixing. Mentees seek guidance and support as they traverse change and grow their careers.

2. Slow to Yes, Fast to Maybe.
Mentees often want to indulge us, which can rob them of critical thinking. Our position allows us to observe this need-to-please and encourage them to exchange their fast-Yeses for strong-maybes: “That’s an idea.” or “I’ll consider that.”

3. Challenge Don’t Cheer.
When a Mentee expresses a concern, we attempt to boost their confidence by gushing, “Don’t worry! You’re amazing! You’ve got this!” But doing so inadvertently invalidates their concerns.

They don’t need cheerleading. They need a thought partner who helps them navigate their worries: “What is causing this concern? Is there another way to frame the situation? What can you do to mitigate it? Here’s what I’ve tried …”

4. Question Marks Before Periods. 
Question marks help us dig deeper to ensure any story or advice will be relevant and valuable. Our job is to explore options with our Mentees, not flood them with platitudes and proverbs.

5. Improv Not an Orchestra.
The conductor of an orchestra knows precisely who is going to play which instrument at what time. Conversely, a comedian on an improv stage has no idea what words will appear next.

Treat mentoring like an improv exercise, not an orchestra performance. Be present, agile, and accepting, with a splash of levity.

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

But in the middle, she takes a surprising pause to share a poignant, seminal mentoring moment with Jane Fonda.

As Chelsea describes the encounter, Jane invited Chelsea for dinner: “I need to talk to you.”

When they sat down to eat, Jane did not hesitate, “You might have noticed that I’ve been icy toward you since the fundraiser, and I want to tell you why.”
[Jane demonstrated accountability for her actions.]

“You behaved badly at my party. From the moment you came in, you had a black cloud hanging over you. You insulted people, and it brought the whole party down. A few people told me you were horrible to them.”
[Jane directly shared her experience, condemning not Chelsea but her behavior.] 

“I don’t get it. Why did you even come if you were in that kind of mood?”

[Genuinely confused and curious, Jane paused to allow Chelsea to engage and explain.] 

Chelsea met Jane’s candidness with humility. She revealed her recent journey into therapy to work on her deep anger.

[Rather than defend her behavior, Chelsea leaned into Jane’s invitation, not with excuses but with vulnerability.]

Encouraged, Jane responded, “Good. Your gifts are plentiful. Sometimes, people with the most gifts have the easiest time throwing them in the trash.”

[Here, Jane disclosed the compelling reason she summoned Chelsea to dinner. And doing so validated Chelsea’s talent.]

“Don’t be a product of your environment, Chelsea. Make your environment be a product of you.”

[Like a female Obi-Wan Kenobi, Jane concluded with watershed wisdom.]

It was risky. Without obligation, agenda, or permission, Jane confronted Chelsea despite the unpredictability of Chelsea’s reaction.

Jane dared Chelsea to be better than her behavior. It was audacious.

And Chelsea could have easily missed the moment.

She could have avoided the altercation, accused Jane of offending her, justified her actions, and then unloaded it all on stage in a future comedy sketch disparaging Jane.

Instead, she recognized Jane’s generosity, a raw display of humanity.

Chelsea concluded, “Jane will never have to talk with me about my behavior again – that kind of honesty deserves action!”

Audacious mentoring moments can be formative when our courage with each other meets our commitment to each other.

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