Six Common Challenges of Mentoring

Mentoring is a powerful tool for professional and personal development but there are a few challenges that can get in the way of its success. From vertical relationship hierarchies to unclear expectations, the Project Thrive team has learned a lot about what causes mentorship partnerships to sink or swim.

These are a few mentorship traps that could mean your mentoring relationship isn’t progressing as well as it could. Here’s how to identify these mentorship red flags, and what you can do about it.

1) You haven’t chatted about your expectations

Mentorship takes time and commitment. Before any mentoring relationship begins, both parties need to ensure they know what’s expected of them, and what they are taking on. This spans from logistical details, like when and where meetups will take place, to sharing what each hopes to accomplish through mentorship.

In terms of logistics, the following should be discussed at the outset:

1. The duration of the mentoring relationship
2. The length of each session
3. The frequency of meetups
4. The form meetups will take (formal/informal, in-person/online) and
5. Contingency plans in the event that either party can’t make a session.

When it comes to the nitty gritty of mentorship itself, each person needs to understand what they’re contributing to individual sessions, and how they’ll be involved in logistics and relationship management. For example, who will be driving the mentorship forward? Over at Project Thrive, we maintained that a mentee-led mentoring relationship—where the mentee is empowered to drive their development forward—is the key to success.

That means a mentee is responsible for:

1. Scheduling sessions
2. Preparing session agendas
3. Following up on previous discussion points
4. Circling back to any guidance they’ve implemented

With the practical details ironed out, you should discuss what you each hope to bring to and develop through mentorship. Aside from understanding each other's contexts more deeply, this will ensure both are ready for mentorship and prepared to put in the work needed.

On the mentor’s side:

1. Mentors should have enough time to commit to mentorship.
2. Mentors should be comfortable with their mentees driving the agenda forward.

On the mentee’s side:

1. Mentees should be ready to embark on professional development.
2. Mentees should have an idea of where and how they want to develop or be ready to figure this out together with their mentor.
3. Mentees should be prepared to put new skills into practice.

If you skipped this step, or are unclear on your responsibilities within the partnership, set up an expectation-setting session as soon as possible. Prepare an agenda so you can be sure you’ve covered all the areas mentioned above.

If you had this discussion but notice that mentorship logistics are frequently off track, this could be a sign that either party is not meeting their commitments. Since honest and open communication is a hallmark of effective mentoring, schedule a check-in session to reflect on expectations and problem-solve how you can get back on track.

2) You don’t know each other on a personal level

It’s tempting to dive right into goal setting and development work, especially for mentees who are extra motivated to begin their journey of growth. But mentorship is fundamentally relational, so it’s important to spend time building trust and establishing a solid foundation.

Before discussing professional goals, there should be space to get to know each other on a human level, and share interests, hobbies, backgrounds and values. Not only does this help to firm up the relationship between a mentor and mentee, but it breaks the ice and provides valuable context for the work that will take place later on in the partnership.

If you haven't already carved out time to get to know your mentoring partner, circle back and schedule some time to engage more informally. It’s also a chance to revisit the discussion around how you both see mentorship and to ensure your expectations are aligned.

3) You don’t feel comfortable disagreeing or setting the mentoring agenda

Since a mentoring pair includes one entry-level individual who’s looking to grow, and an experienced individual who is called on to share their expertise and guidance, you might expect this relationship to be hierarchical. But the most effective mentoring relationships are actually non-hierarchical.

While the mentor will be called on to provide their insights and help their mentee to upskill in targeted areas, it’s ultimately the mentee’s responsibility to drive the relationship forward and to set the development agenda. That means the mentee needs to feel comfortable taking charge, voicing their perspective and even disagreeing with their mentor. If this isn’t the case, it might be a sign of a power imbalance within the partnership.

Mentees should try to have an open and honest conversation about this with their mentors. If you don’t see an improvement, it might mean that you’re just not a good fit for each other and you could discuss dissolving the mentoring partnership.

4) Your confidences aren’t respected

Mentorship is built on a foundation of trust. At the beginning of each mentoring relationship, it’s important to establish the expectation of confidentiality. This equips both mentors and mentees to show up to the relationship openly and honestly, and express any vulnerabilities that might come up.

When trust is broken, it’s difficult to discuss development areas openly. For mentees to grow, they need a safe space to be honest about what they did well, and what they did poorly. The same applies to mentors. If a mentor feels they need to present an infallible front, the mentee loses opportunities to understand their mentor as a full and complex person who’s also worked through personal and professional challenges. In short, without trust, there are fewer opportunities for growth.

While this is important for all mentoring experiences, it’s even more important when mentoring is done within an organisation and where confidential topics could affect either party’s standing at work.

5) You don’t have clear goals

While mentoring is a more fluid approach to professional development than coaching, it should have parameters that are used to measure success. That’s why thoughtful and measurable goal setting is essential in mentorship.

By setting tangible goals and desired outcomes upfront, you can ensure you’re both working towards something concrete and achievable. It’s also a means for the two of you to outline specific steps and explore any obstacles or development areas where you may need input or guidance.

Moreover, to ensure mentees keep moving forward, they need a benchmark to measure progress against, as well as a shared understanding of what success looks like. Goal setting will help to establish both of these.

If you haven’t gone through the goal-setting process together yet, you can make use of two tools we used at Project Thrive: the personal SWOT analysis and the GROW goal setting model.

6) Communication is one way and critical

While the experience and expertise of the mentor is essential, if a mentor is always talking and never listening, something’s amiss. Even though a mentor has more professional experience, mentoring sessions should always be an open dialogue.

A mentor should be careful to listen to the experiences of their mentee and support them in their growth. While this might involve sharing professional insights or success stories, more often than not it calls for mentors to prompt their mentees to problem solve on their own, and for the pair to collaborate on new approaches to targeted goals.

At Project Thrive, we think of mentoring pairs as thinking partnerships where both parties have the opportunity to think out loud and problem solve together. In this dynamic, both mentees and mentors listen openly, and help each other to unpack their thinking.

We also train our mentors and mentees on both giving and receiving feedback . While a mentor shouldn’t gloss over development areas, feedback should always be supportive and constructive. Following this, feedback should focus on specific skills, approaches and areas for improvement.

If you think you might’ve fallen into one of these mentoring traps, now’s a good time for you and your mentoring partner to do a check-in to reestablish expectations, and to discuss your shared approach to mentorship.