If AI can teach people almost anything, what is the role of mentoring now?

Imagine a new hire, fresh from college, top talent recruited for a high-performing team. We can call her Whitney.

Whitney is six months into her role. She is bright, capable, and resourceful. When she gets stuck, she opens an AI tool.

She asks it to explain the new market she is working in. She asks it to draft an email to a senior stakeholder. She asks it to summarize notes from a meeting she barely understood. It does all these things, well and quickly.

In many ways, Whitney is moving faster than she could have a few years ago. She is not waiting for someone to teach her the basics or wondering where to start.

Her company sees this as a win. They are so pleased with the efficiencies of AI that, instead of investing in mentoring, they have invested in AI coaching as their primary development tool. The message, though no one says it quite this plainly, is: Why build mentoring when people can get answers instantly?

For Whitney, something is missing.

AI can’t identify which stakeholder really needs to be consulted before the proposal goes forward. AI can’t help her understand why one very influential leader nodded enthusiastically in the meeting but sent a skeptical email afterward. It can’t help her discern whether her colleague’s stony reaction is par for the course or a sign of misalignment. It can’t teach her, in context, how to raise a concern without sounding difficult, or how to tell whether silence in the room means agreement, resistance, or fatigue.

She feels disconnected from context and isolated by her independence. AI cannot help her with that.

Whitney’s manager holds her accountable for performance: the report, the deck, the deadline, the client response. But no one is holding her accountable for her growth. No one is asking what she is learning, where she is stretching, what patterns she is noticing, or what kind of judgment she is developing.

Whitney’s work looks good enough that everyone assumes she is fine.

She isn’t fine. Her skills are underutilized. She is producing without developing. She is answering questions without building confidence. She is surrounded by tools and still has nowhere to turn.

Eventually, Whitney realizes she needs more than answers. She needs people.

She reaches out to someone in another department whose judgment she admires. Not with a grand request to “be my mentor forever,” but with a specific invitation: “I’m trying to get better at reading stakeholder dynamics. Would you be willing to talk with me once a month for the next few months?”

That relationship changes something.

Her mentor does not simply give her advice. She provides context. She helps Whitney see the organization more clearly. She challenges Whitney’s assumptions, shares her own mistakes, and points out patterns Whitney had missed.

Over time, Whitney begins to use AI differently too.

Instead of asking AI for the answer, she asks it to help her prepare: What questions should I bring? What assumptions might I be making? How can I reflect on what I heard? Where do I need more context from a human being?

AI becomes a tool for preparation and reflection. The relationship becomes the place where judgment is built.

This is where the question gets real: If AI can teach people almost anything, what is the role of mentoring now?

The answer is that mentoring was never just about teaching.

At its best, mentoring is about development. It is about connection, reciprocal learning, shared sense-making, feedback, encouragement, perspective, accountability, and access. It is not merely the transfer of knowledge. It is a relationship that helps people interpret experience, build judgment, navigate complexity, and become more capable than they would be on their own.

In an AI-shaped workplace, that role becomes more important, not less.

This relationship is just a starting point for Whitney. She does not need one all-knowing mentor to hand her every answer. She needs a developmental network: a mentor who can help her make sense of experience, a connector who can help her understand the unwritten rules, a challenger who will sharpen her thinking, a sponsor who will say her name in rooms she is not yet in, a peer who will compare notes honestly, and a manager who sees development as more than task completion.

Organizations need this too. They cannot simply give people AI tools and assume growth will follow. Output is not the same as development. Efficiency is not the same as judgment. Access to information is not the same as access to wisdom.

AI does not replace the human relationships that help us make meaning, build courage, exercise judgment, and contribute fully.

AI hasn’t made mentoring obsolete. It has made human intelligence and connection even more essential to ensuring talent is fully realized.

For more information and resources, visit:  www.centerformentoring.com or www.lisazfain.com

AI and mentoring

Is Anyone Else Alarmed by the Decline of Civility?

Civility is disappearing. Public meetings turn into shouting matches. Social media feeds overflow with personal attacks. Customers berate service workers. Even in workplaces, people talk past each other instead of to each other.

And it’s not just about rudeness. It’s how quickly conversations escalate, how little space there is for listening, and how disagreement turns into hostility. Civility isn’t about being well-behaved or avoiding conflict. It’s about how we engage—even when challenging norms or shaking things up.

Real change has never come from people simply being “nice.” It has come from people speaking up and staying in relationship with one another. Civility allows us to break barriers without breaking connections.

Civility Creates Community and Strengthens Peer Networks

When incivility takes over, people disengage, avoid tough conversations, or retreat into echo chambers. Over time, this fuels loneliness and isolation.

On the other hand, civility builds strong teams, workplaces, and neighborhoods. It makes people feel heard, valued, and more willing to participate.

Peer networks—professional, academic, or social—depend on civility. A thriving workplace or grassroots movement requires an atmosphere where people feel safe to share ideas. Civility paves the way for individuals to connect and form a true community.

Civility and Diplomacy: Learning From One Another

Civility and diplomacy go hand in hand. Diplomacy isn’t just for world leaders—it’s a skill we all use in daily life. Whether negotiating at work, leading diverse teams, or collaborating across cultures, diplomacy requires listening, thoughtful communication, and relationship-building—all hallmarks of civility.

Diplomacy isn’t about avoiding conflict; it’s about navigating it productively. The best diplomats don’t just argue their points—they learn from others. Civility enables that kind of meaningful dialogue.
When civility is abandoned—whether in politics, business, or everyday interactions—trust erodes, relationships break down, and opportunities for cooperation are lost.

Where Civility Has Gone Off the Rails

We see examples of incivility daily:

  • Breakdowns in Diplomacy: Dismissiveness and hostility in high-stakes negotiations weaken global cooperation and stall progress.
  • Social Media’s Callout Culture: What was meant to connect us often turns into a space where a single misstep—sometimes even a misunderstood comment—leads to public backlash.
  • Toxic Workplace Cultures: When people don’t feel respected, collaboration and innovation suffer, and disengagement rises.

Where Civility Has Made a Difference

Despite the challenges, civility still drives meaningful change. It is evident in processes like Open Space Technology (OST) and Restorative Justice (RJ), which create environments where people can engage in honest, respectful dialogue and tackle big issues through a shared sense of ownership and problem-solving. It also shows up in these contexts:

  • Programs That Foster Dialogue Across Divides: Organizations like Tomorrow’s Women, which brings together young Israeli and Palestinian women, and The Sustained Dialogue Institute, which fosters conversations in divided communities, show that structured, civil dialogue can bridge deep divides.
  • Cross-Industry Collaboration in Business: Successful multinational companies prioritize civility-driven negotiation, strengthening partnerships and decision-making.
  • Diplomatic Success: The Colombia Peace Agreement – In 2016, the Colombian government and FARC rebels ended five decades of conflict through civil negotiations, trust-building, and diplomacy. Instead of relying on force, leaders engaged in dialogue, proving that even deep divisions can be healed through civility.

Civility Starts with Small Choices

We can draw on these successes and make a difference in our workplaces and our relationships.

Civility isn’t about avoiding hard conversations. It’s about ensuring they remain productive. And while large-scale change matters, the real shift starts at the micro level—in everyday conversations, workplaces, and interactions.

So before sending that dismissive email, interrupting a colleague, or shutting down a different perspective, let’s take a beat. A single moment of civility—a pause, a question, an act of listening—can change the tone of a conversation and create space for connection.

Civility isn’t about pretending we all agree—it’s about ensuring we don’t lose each other in the process.

Where have you seen civility make a difference in your workplace, team, or community? 

Civility

The Quality of Your Questions

The best mentor-mentee relationships thrive on curiosity and powerful questions. Mentors should resist the urge to “fix” problems and avoid prescribing specific actions. Mentees should focus less on being who they think their mentor wants and more on approaching interactions with a willingness to learn, grow, and discover how to think.

I am always seeking great questions to facilitate these interactions. Recently, I discovered three excellent questions while listening to the audiobook Clear Thinking* by Shane Parrish. Parrish suggests that when seeking advice, your goal should be to understand how the other person thinks, not just what they think. Although his book is not specifically about mentoring, the questions he proposes can be highly beneficial for both mentees and mentors.

Questions Mentees can ask their Mentors
Mentees might ask….

1. What variables would you consider if you were in my shoes?
How do these variables relate to one another?

2. What do you know about this problem that I don’t?
What can you see based on your experience that someone without it cannot?
What do you know that most people don’t?

3. What would your process be for making this decision if you were in my shoes?

Questions Mentors can ask their Mentees
These questions are also valuable for mentors. Instead of offering solutions or suggestions, mentors can prompt their mentees to reflect by asking:

1. What variables in this decision are important to you?
Who else or what else does this decision impact?

2. What are you most worried about in making this decision?
What possibility excites you the most?

3. What have you tried so far?
What do you think is the best process for this decision?

These questions encourage reflection and empower mentees to solve both the current problem they are facing and future problems. They also enable mentees to develop authentic solutions that fit their unique needs, values, and learning styles.

What questions have you used to encourage clear thinking in your mentoring relationships?

*Clear Thinking by Shane Parrish: (Farnam Street, 2023, ISBN: 0593086112)

The quality of your questions