3 best examples of overcoming challenges in mentorship (with real-world twists)

Let’s start with the most common example of a mentorship challenge: mismatched expectations.

Scenario: The promotion-focused mentee vs. the big-picture mentor

Sara, a mid-level marketing manager, signs up for a company mentoring program. She wants one thing: help getting promoted in the next 12 months. Her mentor, James, is a senior director who loves talking about leadership philosophy, long-term career planning, and “finding your why.”

On paper, this looks great. In practice, both walk away from the first three meetings feeling frustrated.

• Sara thinks: “He keeps talking about leadership mindset, but I need concrete help with my promotion packet.”
• James thinks: “She’s so focused on a title that she’s missing the bigger picture of her career.”

This is one of the best examples of a mentorship relationship that looks fine but quietly fails. No one is angry, but neither is getting what they need. The challenge isn’t personality—it’s unspoken expectations.

How they turned it around

Instead of letting the mentorship fade out (which happens a lot—Harvard Business Review notes that many mentoring programs underperform because expectations aren’t clarified early on: https://hbr.org/2021/04/what-the-best-mentors-do), their HR partner suggested a reset conversation.

They tried three simple steps:

• Each wrote down their top three goals for the mentoring relationship.
• They shared those lists at the next meeting.
• They agreed on what this mentorship was and was not going to cover.

What changed:

• Sara admitted she wanted specific help: feedback on her portfolio, practicing for promotion panels, and navigating office politics.
• James admitted he was more energized by long-term development, but he was willing to commit to a 6-month “promotion sprint” if they blended it with broader skills.

They landed on a structure:

• First 15 minutes of each session: tactical promotion work.
• Last 15 minutes: leadership mindset and longer-term career strategy.

This is one of the clearest examples of overcoming challenges in mentorship: 3 examples like this often start with a simple reality—the problem isn’t the people, it’s the silence. Once they named their expectations, the relationship actually started working.

Other real examples of expectation mismatches

You’ll see versions of this everywhere:

• A mentee expecting job referrals, while the mentor thinks they’re just there to offer advice.
• A mentor assuming the mentee will drive the agenda, while the mentee waits for the mentor to lead.
• A mentee hoping for emotional support during burnout, while the mentor focuses only on skill-building.

Across all of these, the pattern is the same: nobody says what they actually want. These real examples show that the fix is usually not more meetings—it’s clearer agreements.

If you’re starting or restarting a mentoring relationship in 2024–2025, take a page from this example and:

• Write down your goals.
• Share them explicitly.
• Decide together what “success” looks like after 3–6 months.

Example 2: Communication breaks down—especially in remote and hybrid work

The second of our examples of overcoming challenges in mentorship: 3 examples is all about communication, especially now that so many mentoring relationships are remote or hybrid.

Scenario: The ghosting mentor (who doesn’t think they’re ghosting)

After the pandemic, Victor, a software engineer, was paired with a mentor, Priya, who works in another state. At first, things were great: monthly video calls, shared documents, and clear action items.

Then reality hit.

• Priya got pulled into a big product launch.
• Two meetings in a row were rescheduled.
• Emails started getting shorter.
• Slack messages went unanswered for days.

From Victor’s perspective, this felt like abandonment. From Priya’s perspective, she was juggling deadlines and assumed Victor understood it was temporary.

This is a textbook example of how remote mentoring can go sideways. According to a 2023 report from the Society for Human Resource Management (SHRM), many organizations have expanded virtual mentoring, but communication norms are often missing, leading to confusion and disappointment: https://www.shrm.org.

How they fixed the communication gap

Instead of quietly resenting each other, Victor sent a direct but respectful message:

“I really value our mentorship, but I’m not sure how to interpret the last few weeks. Are you still able to mentor me, or should we adjust our format or timeline?”

That message did three important things:

• It named the issue without blame.
• It gave the mentor an easy way to be honest.
• It opened the door to renegotiation instead of just ending things.

Priya responded with an apology and clarity:

• She explained her workload.
• She admitted she hadn’t communicated well.
• She suggested switching to shorter, more frequent 20-minute check-ins for the next quarter.

They also agreed on:

• A response-time expectation (e.g., “I’ll reply within 3 business days, even if it’s brief”).
• A backup plan: if they had to skip a meeting, they’d still exchange a quick email update.

This is another one of the best examples of how a mentoring relationship can recover. The challenge wasn’t that the mentor didn’t care; it was that life got busy and no one reset expectations until the mentee spoke up.

Other examples include cultural and style differences

Communication breakdown isn’t only about scheduling. Real examples include:

• Direct vs. indirect feedback styles in cross-cultural mentorships. A mentor from a very direct feedback culture may sound harsh to a mentee from a more indirect culture, and vice versa. The U.S. Department of State’s resources on cultural communication styles highlight just how different norms can be across countries: https://eca.state.gov.
• Generational gaps where a Gen Z mentee prefers quick texts and shared docs, while a Boomer mentor prefers long emails and scheduled calls.
• Neurodiversity differences, where one person thrives on structure and written agendas, and the other prefers free-flowing conversation.

In all of these, the examples of overcoming challenges in mentorship usually come back to the same move: talk about how you talk.

Try questions like:

• “How do you prefer to receive feedback—live, written, or both?”
• “What’s a realistic response time for you, given your workload?”
• “Is it okay if I nudge you if I haven’t heard back in a week?”

These tiny meta-conversations are often the difference between a mentorship that quietly fizzles and one that survives the messy middle.

Example 3: When growth stalls and both sides feel stuck

The last of our examples of overcoming challenges in mentorship: 3 examples tackles a quieter problem: the plateau.

Scenario: The “We just keep chatting” problem

A year into their mentoring relationship, Alicia and her mentor, Devon, realized their sessions had become friendly but repetitive. They liked each other. They checked in. They vented a little. But nothing was really changing.

This is a very common example of a mentoring challenge:

• No clear goals.
• No accountability.
• No real stretch.

In 2024, with so many people rethinking their careers, this problem is even more common. Surveys from organizations like the Pew Research Center show workers are increasingly focused on growth, purpose, and learning opportunities at work: https://www.pewresearch.org. When a mentorship doesn’t support that growth, people quietly disengage.

How they turned a “nice chat” into real development

Instead of ending the relationship, Alicia suggested they treat the next quarter like a mini-development program.

They did three things:

1. Picked one clear, measurable goal. For Alicia, it was: “Deliver a cross-functional presentation without reading from my notes.”

2. Designed experiments, not just advice. Devon didn’t just tell her to “be more confident.” They:

   • Co-created a simple presentation outline.
   • Practiced together on video.
   • Recorded and reviewed her practice runs.

3. Built in reflection. Every month, they answered:

   • What did you try?
   • What worked?
   • What would you change next time?

Within three months, Alicia had delivered two stronger presentations and received positive feedback from her director. The mentorship suddenly felt alive again.

This is one of the best examples of how to rescue a stagnant mentorship: shift from talking about growth to designing specific experiments that stretch real skills.

More real examples of stalled growth—and fixes

Other examples include:

• A mentee who keeps saying they want to switch careers but never takes a concrete step. The fix: agree on one small action between meetings (e.g., conduct one informational interview before the next session).
• A mentor who keeps giving the same generic advice. The fix: the mentee brings real artifacts—emails, slide decks, performance reviews—so the mentor can give targeted feedback.
• A mentee who’s burned out and has no energy for big goals. The fix: shift the mentoring focus temporarily to boundaries, energy management, and saying no. The National Institute for Occupational Safety and Health (NIOSH) has resources on workplace stress that mentors can use to guide these conversations: https://www.cdc.gov/niosh/.

In all of these examples of overcoming challenges in mentorship, the turning point is when both sides admit, “This isn’t working as well as it could,” and then consciously redesign the relationship.

2024–2025 trends that are reshaping mentorship challenges

Mentoring in 2025 doesn’t look like mentoring in 2015. The context has changed, and with it, the kinds of challenges people face.

Here are a few real examples of new pressures that show up in mentoring conversations:

• Remote and hybrid work. Many mentees have never met their mentors in person. That changes trust-building, visibility, and networking. Mentors now help mentees navigate “being seen” in a virtual workplace.
• AI and automation anxiety. Mentees are asking, “Will my role exist in five years?” Mentors are guiding them toward adaptable skills—communication, problem-solving, learning agility—rather than just technical tools.
• Diversity, equity, and inclusion (DEI). There’s more awareness that mentoring can either reinforce existing inequities or help counter them. Cross-race and cross-gender mentoring pairs may need to talk explicitly about bias, sponsorship, and psychological safety. Research from organizations like the American Psychological Association discusses how mentoring can support underrepresented groups when done thoughtfully: https://www.apa.org.

These trends don’t replace the classic issues, but they do color them. When you look at modern examples of overcoming challenges in mentorship: 3 examples might now include:

• A remote mentee learning to advocate for themselves with a manager they rarely see.
• A mid-career worker retraining with their mentor’s support to stay relevant in an AI-heavy industry.
• A first-generation professional navigating unspoken norms in corporate culture with the help of a mentor who “translates” those norms.

Putting it all together: How to apply these examples to your own mentorship

We’ve walked through several examples of overcoming challenges in mentorship: 3 examples in depth, plus additional real examples woven throughout. Here’s how to translate them into action in your own mentoring relationships.

If you’re a mentee, you can:

• Start or reset the relationship with a clear statement of your goals.
• Ask your mentor how they prefer to communicate and share your own preferences.
• Speak up when something isn’t working—ghosting, vague advice, or stalled progress.
• Bring real work to your mentor so feedback is specific, not theoretical.

If you’re a mentor, you can:

• Ask your mentee, “What does success look like for you in 6 months?”
• Be honest about your time and energy so you don’t overpromise.
• Suggest concrete experiments instead of only offering high-level advice.
• Invite feedback: “What would make our conversations more helpful for you?”

The best examples of mentoring success rarely look perfect. They look like two imperfect humans adjusting, renegotiating, and staying in the conversation long enough to grow.

FAQ: Examples of mentoring challenges and how to handle them

Q: What are some common examples of challenges in mentorship?
Common examples include mismatched expectations (the mentee wants promotions, the mentor wants deep reflection), communication breakdowns (slow responses, missed meetings, unclear feedback), and stalled growth (lots of friendly chats, not much progress). These real examples show up across industries and career levels.

Q: Can you give an example of how to reset a struggling mentoring relationship?
One example of a reset is sending a candid message like: “I value our mentorship and want to make sure it’s working for both of us. Could we use our next meeting to revisit my goals and how we’re structuring our time?” Then, in the meeting, share your goals, ask about theirs, and agree on a simple plan for the next 3–6 months.

Q: What are examples of boundaries that help mentorship work better?
Examples include agreeing on response times, setting a realistic meeting cadence, deciding what topics are in or out of scope (for instance, career strategy is in, detailed personal therapy is out), and being clear about whether the mentor is comfortable making referrals or introductions.

Q: How can mentors and mentees handle cultural or generational differences?
Use curiosity instead of assumptions. Ask, “In your culture or generation, how is feedback usually given?” or “How do you like to communicate—short messages, calls, longer emails?” Real examples of overcoming challenges in mentorship often start with these simple questions that surface unspoken norms.

Q: Are there examples of when it’s better to end a mentoring relationship?
Yes. Examples include when the mentor no longer has the time and can’t realistically support the mentee, when the mentee’s goals have shifted far outside the mentor’s expertise, or when there’s a persistent lack of trust. Ending respectfully—by thanking each other, sharing what you’ve learned, and, if possible, helping the mentee find another mentor—is itself a healthy example of professional growth.

If you remember nothing else, remember this: the strongest mentoring stories—the best examples of overcoming challenges in mentorship—aren’t the ones that started perfectly. They’re the ones where both people were honest enough to say, “This isn’t working yet,” and patient enough to stay and fix it together.