I brought my intern on the podcast! She shares her first impression of me, what I did well as a boss, and what I can improve on. She also shares her advice for work, networking, and moving to a new city on her own. We also talk about competition among college students and the lessons she’s learned while working at a start-up. I think it’s pretty cool to have this type of conversation between a boss and an intern and hope you like this one!

The Mentor-Mentee Relationship: Honest Advice from a Boss and His Intern

Being responsible for someone else at work for the first time is a unique challenge. Whether you're the young professional suddenly managing an intern or you're that intern trying to make your mark, navigating this relationship can be tricky—especially when you're both figuring things out as you go.

In this candid conversation between a mentor and his intern, we explore what actually works in this dynamic, the mistakes made along the way, and how both parties can benefit from a transparent working relationship.

When You're Both New: Building a Relationship from Scratch

The most interesting mentor-mentee relationships often begin when both people are relatively new—either to their roles, the company, or the industry itself. This creates a unique dynamic where you're figuring things out together rather than following an established playbook.

Nina, a 20-year-old finance and entrepreneurship student from Northeastern University, joined our team as part of her university's co-op program, which allows students to take six months off to work full-time. What made this situation unique was that her "boss" had only started one week before her.

"We were both kind of starting at the same time. So that definitely brought in a different dynamic," Nina explains. "You were like, 'We're gonna figure this out together. I'm here to help you grow.'"

This mutual inexperience can actually be an advantage. Without established hierarchies or rigid expectations, both parties can build something authentic where learning flows in both directions.

What Makes a Great Mentor (According to an Intern)

What separates a good mentor from a great one? According to Nina, these were the game-changers:

1. Setting a Team Mentality from Day One

"The best thing was setting a precedent that we're a team," Nina shares. "That was made very clear to me and I really like walking into work having that culture."

Great mentors create a collaborative environment rather than reinforcing hierarchy at every turn. When your intern feels like a valued team member rather than just "help," they'll invest more deeply in the work.

2. Inclusion in Important Conversations

"I've been included on like every meeting, which has been huge for me, even when I shadow. Just to see how that stuff is done was very valuable."

One of the simplest but most effective things a mentor can do is bring their mentee into the room (or Zoom). Being present for important conversations provides context that no summary email could ever replicate.

3. Ownership Over Meaningful Projects

"It was exciting in those moments where I got to own things and say, 'Hey, this is mine. This is the work I did. I'm pitching it.' It allowed me to showcase my skills."

The fastest way to help an intern grow is to give them ownership—not just busy work. When they can take something from concept to completion, they develop confidence and critical thinking skills.

4. Asking for Their Input

"You asking me, 'What do you think about this deal? Do you think we should do it?' I'm the intern! You don't even have to ask me that. Just you asking makes me feel valued."

When you genuinely seek your intern's perspective, you signal that their opinions matter. This small gesture creates engagement and builds their analytical muscles.

What Every Intern Should Do to Stand Out

For those on the other side of the equation—the interns and mentees looking to make an impression—Nina offers these insights from her experience:

1. Ask How You Can Help

"I would do this thing where once I finished a task, I'd say, 'Hey, is there anything else I can help you with? Is there anything else I can do to make your day easier?'"

This simple question demonstrates initiative and signals your commitment to being valuable beyond your assigned tasks. Nina suggests the specific phrasing: "Is there anything I can take off your plate?" This approach focuses on how you can help rather than what they need from you.

2. Come in Ready to Give 100%

"I knew that because I was making big sacrifices [moving to a new city], I needed to give the job everything I had to make sure I got the most out of it. I had to. There was no choice not to."

The most successful interns approach their positions with intensity and purpose. They understand that the experience is directly proportional to the effort they invest.

3. Build Genuine Relationships, Not Just Professional Ones

"I've learned that if someone goes, 'Hey, I have an internship opportunity,' you should be sharing that because genuine connection comes from wishing other people well."

Nina emphasizes that real networking isn't transactional—it's relational. She maintains connections with previous mentors by checking in on important dates, celebrating their successes, and showing interest in their lives beyond work.

"What is success if you can't share it with other people?" she asks. "We should all have seats at the table. So we're actually not competing with each other."

Lessons for Both Sides

Some insights apply equally to both mentors and mentees:

Communication Style Shapes Culture

"Culture aligns directly with communication style," Nina observes. "The culture that we've created amongst our team is great and I think that has a lot to do with our communication style."

Small touches matter—from how you phrase emails to how you ask questions. Adding a "Happy Thursday!" to an otherwise formal email or expressing genuine curiosity about someone's perspective can transform the working relationship.

Trust Builds Excellence

"Giving people autonomy is so important. You have to trust your people because they will thrive."

When mentors demonstrate trust in their mentees, it creates a positive feedback loop. Mentees feel empowered to take initiative, which further builds trust, which leads to better outcomes.

Everyone Is Figuring It Out

"There are a few people who know what they're doing," Nina laughs. "It sounds crazy, but as much as people know what they're doing and people are trained, no one's a master at their game, really."

Recognizing that even seasoned professionals are constantly learning can be liberating for both mentors and mentees. It levels the playing field and creates space for genuine collaboration.

Finding Your Own Path

Whether you're a young professional navigating your first leadership role or an intern trying to make the most of an opportunity, the key is to approach the relationship with authenticity, curiosity, and a willingness to learn.

Nina's parting advice for anyone entering a new role or industry: "Set your intention and then figure out how the hell you're gonna get there. Once you start putting that intention out there, it's bound to happen."

The mentor-mentee relationship, when approached with the right mindset, can be transformative for both parties. It's not just about professional development—it's about creating connections that enrich both your career and your life.

Want to hear the full episode? Listen  on Apple Podcasts, Spotify, or wherever you get your podcasts. You can also follow along on Instagram and TikTok @theguyset for more content.

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