Great talent development via mentorship doesn’t just happen. It’s structured. While building connection and trust are essential, unstructured mentoring conversations often miss the mark when it comes to consistent and goal-oriented talent strategy.

Enter: structured mentoring discussion guides. 

Whether you're supporting early career employees, preparing future leaders, or upskilling people managers, structured conversations help ensure your mentoring program drives consistent results. With strategic mentorship discussion topics, mentors and mentees are empowered to have purposeful, outcome-driven conversations that align with your organizational goals. 

We know what you’re thinking…building this level of structure takes a ton of work. You’re not wrong. But you don’t have to do it all yourself. Mentorship platforms like 10KC offer pre-built, customizable mentoring discussion guide templates so HR, L&D, and Talent program leaders like you can easily support consistent, high-quality mentoring experiences across the organization.

Even if you're building your program manually or aren’t ready to invest in a platform yet, this article will help you easily create mentoring discussion guides, along with real-world examples and expert tips you can apply right away.

Why use mentorship discussion guides?

Mentoring programs are most impactful when they’re intentional. Without structure, mentorship can veer off course or remain surface-level, missing opportunities for skill-building, growth, and alignment with program goals. That’s where mentoring discussion questions come in.

Here’s how they support both you (mentorship program leaders) and mentorship program participants:

Enable consistency and equity across cohorts

Not everyone naturally knows how to be an effective mentor, or how to make the most of being a mentee. Discussion guides level the playing field by offering every participant (regardless of experience) a consistent starting point. 

This ensures that all mentoring matches and participants in the cohort are exposed to the same core development topics and opportunities. It also helps reduce bias or inequity in program delivery by standardizing the mentorship experience at scale.

Think of the discussion guides as scaffolding: structure that supports deep conversations towards a common goal without dictating every word.

“Some people are pretty experienced at being mentors or coaches, giving advice. A lot of people have never done it before. You want to make sure you've got as consistently high a quality of mentoring conversations. People will take it in their own direction, and that's part of the beauty of how it gets personalized. People make it relevant to them, but you want to give them enough of a starting point that there's common language. They're anchoring back on organizational resources, common language, and things that your HR leaders, your business leaders would want people understanding. And it becomes just a way to reinforce those topics.” - Christine Silva, Talent Advisor, former leader at RBC, Catalyst, Shopify

Keep the focus on key competencies and topics

Mentoring is most effective when it's aligned with the competencies and behaviors your organization is trying to build—whether that’s leadership, communication, adaptability, or time management, just to name a few. Discussion guides help anchor conversations in the priorities that matter most to your business.

By connecting sessions to internal frameworks (like your unique leadership model, for example), you reinforce what “good” looks like within your culture and give participants a clear path to get there.

Increase preparedness and reduce awkward starts

One of the biggest barriers to productive mentoring is that initial “what should we talk about?” moment. Without structure, sessions can stall or drift into casual chats that lack developmental value. Discussion guides help everyone come prepared, feel confident, and dive into deeper topics from the outset.

They should provide just enough structure to get the ball rolling while still leaving room for personalization and organic conversation.

📌 READ MORE: What Talent and L&D Leaders Need to Know About Structuring Successful Mentor-Mentee Relationships

Reinforce program goals and organizational priorities

The most successful mentoring programs are tightly connected to your organization’s learning and talent development priorities. Whether you’re focused on building leadership capability, strengthening collaboration, or improving manager effectiveness, mentoring discussion guides help steer conversations toward those outcomes.

By aligning discussion prompts and topics to your organization’s competency frameworks, career paths, or leadership models, you reinforce what success looks like within your culture and empower participants to actively grow toward it.

This approach also ensures that mentoring doesn’t happen in a vacuum. It becomes a direct extension of your broader talent strategy, helping you drive engagement, retention, and internal mobility in ways that are both measurable and meaningful.

📌 READ MORE: Effective Mentorship Programs Start with Strong Goals. Here's How.

How to build your own mentoring discussion topics

If you're creating mentoring discussion questions from scratch, the goal isn’t to script conversations. It’s to provide structure and direction that helps mentoring relationships thrive. A good guide sparks meaningful dialogue, reinforces skills, and aligns with your organization’s broader talent development strategy.

Here’s how to build a guide that works:

1. Start with mentoring program objectives and audience

Every guide should be built with a clear purpose. Ask yourself:

• What is the goal of this mentoring cohort—leadership development, early talent onboarding, manager capability?
  
  
• Where are participants in their careers?
  
  
• What behaviors or competencies are you hoping to build?
  
  

For example, an early talent guide might focus on productivity and workplace confidence, while a leadership development guide might center on topics like strategic thinking or leading through change. Tailoring the guide to the developmental context makes the session more relevant and more likely to drive impact.

“1.0 of mentoring was just ‘we're going to meet for coffee every quarter.’ You only get so far, and the conversations stay quite superficial. And just because someone's an executive doesn't mean they’re a good mentor. And so putting much more parameters and guidance around it in terms of what are we going to focus on, how are we going to make the conversations really meaningful and relevant with real curriculum and discussion topics I think really helps.” Manisha Burman, EVP and CHRO, CI Financial

2. Curate valuable resources to set the stage

Don’t rely solely on questions to guide the conversation. Providing pre-work (like a short article or video) can help participants show up informed and ready to engage.

This not only builds baseline knowledge, it ensures the session can go deeper faster. Internal content (e.g., leadership principles, culture decks) works especially well, while external materials can also help introduce fresh perspectives or frameworks.

“Think about what already exists in the organization that you can pull in. This is where you don't necessarily want to be reinventing the wheel. You want to be leaning on—like if you've got an LMS or an LXP, if there's, let's say a Leadership Model, capabilities, and competencies—lean on those to define the topics you want people talking about. So your curriculum becomes an opportunity to bring to life things that are deemed important in the organization.” - Christine Silva, Talent Advisor, former leader at RBC, Catalyst, Shopify

Plus, offering a variety of content and experiential mentoring formats helps engage a broader range of participants. Some employees may respond well to open-ended questions alone, while others find more value in reading an article to spark ideas or deepen understanding. For others, a short video or interactive tool might be what truly resonates and inspires a more meaningful conversation.

3. Add open-ended prompts and reflection questions

Include open-ended prompts that help both mentor and mentee reflect, share stories, and make connections to their current role or career path.

Example mentoring prompts:

• “How have you approached this challenge in the past?”
• “What would you do differently next time?”
• “What advice would you give your past self in this situation?”

These questions help participants move beyond surface-level chat into thoughtful, experience-based learning. Include prompts that invite both practical insight and personal reflection to balance action and awareness.

4. Evolve discussion topics over time

Not all mentoring sessions should look the same, and so neither should your discussion questions. As trust builds and the relationship deepens, the conversations should naturally evolve from foundational to more complex and reflective.

Let’s take a manager effectiveness mentoring program as an example. Here’s how you might structure discussion topics across the arc of the relationship:

‍​​Early sessions: Build trust and establish foundations. In the first few sessions, you might focus on building rapport and helping participants get comfortable. Choose discussion topics that feel approachable and relevant to all managers.

• Example topics:
  
  • Building trust and psychological safety with direct reports
  • Establishing effective communication habits
  • Giving and receiving feedback
• Example questions:
  
  • Tell me about your journey to becoming a people manager. What motivated you to take on a leadership role?
  • How do you like to communicate with your team? And how do you adapt your style for different people?
  • Think back to some of the best managers you’ve had. What did they do that made them effective?
  • Where do you feel most confident as a people leader, and where are you looking to grow?

Mid-program sessions: Develop skills and tackle core responsibilities. It’s time to go deeper into key management skills. Introduce more performance-oriented or coaching-focused topics.

• Example topics:
  
  • Coaching and developing team members
  • Delegation and prioritization
  • Performance management conversations
• Example questions:
  
  • “How do you approach goal-setting with your team, and how do you ensure alignment with broader business priorities?
  • What’s your approach to supporting team members who are struggling, and how do you balance empathy with accountability?
  • After watching [X video/resource], what new insights do you have about giving constructive feedback, and how might you adjust your approach going forward?
  • Can you share a time when your coaching had a measurable impact on someone’s growth? What made that interaction effective?

Later sessions: Reflect, apply, and lead through complexity. Challenge participants to apply what they’ve learned and reflect on their leadership style. These sessions can address more complex or emotionally nuanced topics.

• Example topics:
  
  • Leading through difficult times or change
  • Managing burnout (your own and your team’s)
  • Developing your leadership identity
• Example questions:
  
  • How do you support your team through ambiguity or stress? When do you find this is most difficult? 
  • How do you recognize signs of burnout—in yourself or your team—and what strategies have helped you manage it?
  • As you reflect on your mentoring journey, what leadership habits or insights have you started to apply in your day-to-day role?
  • “What kind of leader do you want to be known as, and what will it take to get there?”

By evolving your discussion guides across a program, you create a natural learning arc that builds on prior conversations, keeps engagement high, and ensures participants are growing.

5. Build in feedback loops on mentoring discussion topics

Even a well-crafted discussion guide can improve over time. Consider adding a post-session pulse check or a quick survey asking things like:

• Was the topic relevant?
• Were the resources helpful?
• Did the prompts lead to a meaningful conversation?

This feedback helps you continuously improve future mentoring cohorts and better understand what’s resonating with different audiences.

What to discuss in the first mentoring session

The first session between a mentor and mentee is arguably the most important. It sets the tone for the relationship, builds initial trust, and lays the foundation for the conversations to come. But without structure, it will likely feel awkward or aimless. 

It’s essential to set expectations and create alignment before the first session even happens, and then use that first conversation to build the foundation for success. Here’s what that looks like: 

Lay the groundwork for mentorship before the first session

Before your program officially kicks off, provide participants with a clear orientation around what to expect from your organization’s mentoring experience. This helps them show up with purpose, not confusion.

Key elements to cover:

• Participant expectations: What does being a mentor or mentee look like in practice?
  
  
• Fostering relationships: Tips for building rapport and creating trust quickly
  
  
• Meeting cadence and timelines: How often should they meet? What’s the program duration?
  
  
• Values and outcomes: What should participants expect to gain?
  

Orientation materials, kickoff events, or digital onboarding can all help reinforce these expectations so participants aren’t left guessing.

Use the first session’s discussion guide to build connection and intentionality

Once your program is launched, the first 1:1 session should focus on two things: establishing rapport and aligning on goals.

1. Build the Relationship: Start with low-pressure, personal prompts that help participants get to know each other and create space for authenticity. These may vary highly depending on your program goals and audience. Some high-level example questions include:

• “Tell me a bit about your career journey so far.”
• “What do you enjoy most about your current role?”
• “What are you hoping this mentoring experience will look like?”
  

This is also a good time to align on logistics like preferred meeting times or communication style between sessions. 

2. Define individual goals within the program framework: While your mentoring program should already be designed to drive clear strategic goals (e.g., mobility, retention, leadership development), the first session is where participants personalize those outcomes.

Encourage mentees to reflect on questions like:

• “What’s one skill or competency you’d like to build during this program?”
• “Where do you see your career going in the next 1–2 years?”
• “What would success look like for you by the end of this experience?”
  

For example:

• In a mobility-focused program, a mentee might aim to explore two potential career paths across departments.
  
  
• In a skills development track, they may want to build public speaking confidence or strengthen decision-making.

Early goal setting like this helps align expectations, spark momentum, and guide future sessions, turning big-picture objectives into concrete personal growth.

💡 Pro tip: The first session doesn’t have to cover everything. Focus on building a strong connection and walking away with at least one or two clearly defined personal goals to guide the rest of the mentoring relationship.

4 real-world examples of 10KC Mentoring Discussion Guides in action

Let’s look at some examples of discussion guides in practice and how they can create successful, outcome-driven conversations. These examples come straight from 10KC’s pre-built session discussion guides, which are designed to make it easy for program admins to deliver impact-driven conversations at scale.

Example #1: Early talent discussion on ‘Time Prioritization’

Designed for: Interns, co-op students, recent grads

Focus: Build foundational skills for workplace productivity

Outcome: Knowledge transfer + practical strategies

Consider a session within an early talent mentorship program geared toward recent grads, interns, or co-op students. Many of the sessions with this pathway are focused on building skills that are critical for early talent as they enter the first few years of their professional careers. 

A great example of one key talking point is time prioritization. Your discussion guide might include resources that highlight time prioritization strategies and frameworks. 

Meanwhile, including discussion questions like, “How do you currently prioritize your work?” can encourage both mentors and mentees to share their own experiences. 

Additional prompts, such as, “Are there productivity tools, tricks, or systems that work well for you?” also provide an opportunity for mentors to share their own knowledge and advice that mentees can adopt for their own prioritization strategies.

📌 LEARN MORE: Give fresh professionals the tools, network, and support they need to thrive with 10KC's Early Talent Pathway.

Example #2: Career development discussion on ‘Embracing Change’

Designed for: Mid-career employees, ERGs, or function-specific tracks‍

Focus: Navigating change with confidence‍

Outcome: Self-awareness + resilience-building

Continuing career development pathways can be leveraged for ongoing mid-career development of a variety of talent segments, from specific departments and to employee resource groups. One skill and challenge that employees often face across different stages of their careers is navigating change—both professionally and personally. 

In a discussion guide for a mentoring session on embracing change, you might start by introducing participants to relevant concepts through internal or external reading materials and videos. This helps set the stage with expert insight into embracing change. Then, following up on these materials with prompts such as “How do you typically react to being uncomfortable?” or “Do you tend to embrace the concepts presented in the pre-reading?” gives space for participants to dive into the topic and skills on a more personal level.

This type of discussion can often feel vulnerable, making it a great topic for the later stages of a mentoring program, once mentors and mentees have had the opportunity to build trust and safety in their relationship.

‍📌 LEARN MORE: Give employees the mentorship structure, guidance, and relationships they need to drive their own development with 10KC’s Career Development Pathway.  

Example #3: Manager effectiveness discussion on ‘Communication and Feedback’

Designed for: Current and aspiring people leaders

Focus: Sharpening communication and feedback techniques

‍Outcome: Confident, empathetic management

Mentoring can be a valuable tool for providing current and emerging people managers with the skills and resources to engage, motivate, and build high-performing teams.  One major skill that all managers can benefit from is effective communication and feedback.

In this instance, discussion guides are a great opportunity to provide strategies and techniques for providing effective feedback ahead of a mentoring session. Then questions like “How do you deliver feedback?” can prompt participants  to provide actionable insights and examples in their mentoring session. 

More personal questions, like “How do you handle difficult conversations?” can also provide a platform for self-reflection so participants  can set themselves up for success the next time they come across a difficult conversation.

“Don't be afraid to get really tactical with people, especially with frontline managers. The amount of people who don't know how to run a good one-on-one is astounding. [...] Training people on some of the basics can go a long way and giving them the content and materials. You've got to build communities around this in two forms: Managers have to have communities where they can turn to each other, as well as to you for support.” - Brian Elliott, Co-founder, Future Forum; Author of "How the Future Works”; Former Slack & Google Executive

📌 LEARN MORE: With ongoing peer connections and structured mentoring experiences, managers get the guidance they need with 10KC’s Manager Effectiveness Pathway. 

Example #4: Leadership development discussion on ‘Leading Through Change’

Designed for: Emerging leaders and high potentials‍

Focus: Building change leadership skills‍

Outcome: Strategic thinking + leadership growth

Leaders are expected to guide their teams through all kinds of waters. And being that beacon during times of change can be an invaluable skill, which is why it’s an important mentoring conversation for leadership development. 

In a discussion guide for leading through change, you might provide resources and expert-led exercises for mentors and mentees to work through ahead of their live session. Then prompts like, “What did you learn from a time in your career where you led a significant change?” And “What new ideas or thoughts do you have about leading change after reading the resources?” can help mentors and mentees look back and forward to hone their change leadership skills.

📌 LEARN MORE: Give both emerging and established leaders the skills and business acumen they need to lead through change with 10KC’s Leadership Development Pathway.

Scale mentoring discussions with 10KC

The best mentoring programs don’t leave connection and development to chance. Structured discussion guides help mentors and mentees engage in meaningful, outcome-driven conversations. 

With 10KC, you don’t have to build these guides from the ground up. Our platform includes a library of customizable discussion templates aligned to career stages, skills, and program goals, so you can spend less time creating content and more time delivering impact.