Navigating Difficult Conversations - For Mentors

Career
Pivots

Performance
Concerns

Misaligned
Expectations

Stalled
Progress

Ending the
Relationship

This guide is written for you. As a RISE mentor, you hold the experience, the perspective, and in many situations the responsibility to raise the conversations your mentee may not yet have the confidence or self-awareness to start. Withholding a difficult observation to protect the relationship is not kindness. It is a missed opportunity disguised as tact. This guide gives you language, framing, and principles to raise the five most common difficult conversations in RISE mentoring with the care and honesty that the relationship deserves.

Conversation Type One

When Your Mentee Wants to Change Direction

A mentee raising a career pivot is bringing you one of the most significant conversations in the relationship with one of the most delicate to handle well. They are sharing something vulnerable: a questioning of the path they are on, which may feel to them like an admission of failure. Your response in the first few minutes will either open the idea up for proper exploration or close it down before it has been properly examined. The wrong response is to project your own career preferences onto their decision. The right one is curiosity.

The trap to avoid The temptation is to respond from your own experience to say what worked for you, what you would do, or why the pivot might be risky. That is advice, not mentoring. A mentee who has come to explore an idea needs space to develop it before they need your opinion on it. Lead with questions, not conclusions.

How to hold this conversation well

Your job is to deepen the idea, not to approve or reject it. That means asking questions that help the mentee understand their own motivation more clearly distinguishing what is pulling them toward the new direction from what might simply be pushing them away from discomfort. A pivot made to escape something rarely lands as well as one made toward something specific and understood.

If you have relevant experience you have made a similar move, or have seen others do so share it as a story, not a lesson. RISE Module 3 covers the art of storytelling in mentoring: your experience is most useful when it illuminates the mentee's own thinking, not when it replaces it.

Questions that deepen the exploration

"What specifically is drawing you toward this direction not away from where you are?"

"How long have you been thinking about this?"

"What do you know about what this field actually requires day to day?"

"What would you need to learn or experience before you felt ready to commit to this?"

"Who do you know who has made a similar move could we get you in front of them?"

"If this pivot works out completely, what does your life look like in three years?"

If you have genuine concerns about the pivot

Ask before you advise: "Would it be helpful if I shared some observations from what I've seen including where pivots like this tend to go well and where they struggle?" This frames your concern as information rather than judgement, and gives the mentee the choice to receive it rather than having it imposed on them.

RISE tool to use: After the conversation, direct your mentee to the Three-Horizon Career Map in the RISE Career Development Framework. Offer to review their updated map in the next session it turns the exploration into a concrete plan you can both evaluate and build on.

Conversation Type Two

Raising a Performance Concern With Your Mentee

There will be moments in the relationship when you observe something in your mentee's behaviour, approach, or pattern that is getting in their way and that they may not be aware of. This might be a tendency to understate their achievements, a habit of avoiding difficult situations rather than addressing them, or a disconnect between the ambition they express and the actions they take between sessions. Naming it is one of the highest-value things you can do as a mentor. Staying in the comfortable zone of encouragement while seeing a significant problem is a failure of the role.

The trap to avoid Softening feedback to the point where it loses its meaning. A mentor who says "you're doing really well, but maybe just consider occasionally perhaps trying to be slightly more proactive" has said nothing. The mentee leaves feeling vaguely encouraged and changes nothing. Specific, honest feedback delivered with care is far more valuable than diplomatic vagueness.

How to raise it well

Use the SBI structure from the RISE Giving Effective Feedback guide: name the Situation, describe the specific Behaviour you observed, share the Impact with then ask for the mentee's perspective before offering your interpretation. This separates observation from judgement, which is what makes the feedback receivable rather than defensive.

Ask before you advise: "I've been noticing something I want to share -would that be useful?" When a mentee opts into receiving feedback, they absorb it far more deeply than when it arrives unsolicited. This one question changes the dynamic from something done to them into something done with them.

How to frame the concern using SBI

"In our last few sessions when we've discussed [specific situation], I've noticed [specific observable behaviour not a character judgement]. What I think the impact of that is [on their goals / on how others see them / on their progress]. That's my observation. I'd love to hear how you see it."

Then stop and listen before adding anything further. The pause after sharing a difficult observation is where the real conversation begins. Do not fill it.

When your mentee raises a workplace performance concern

When your mentee brings you a performance concern from their workplace, resist the urge to validate immediately. Ask for the facts before forming a view: "What specifically was said, by whom, and in what context?" A mentee who feels criticised at work needs clarity more than comfort. Your most useful role is to help them see their situation accurately -which may mean reflecting back things that are uncomfortable but true.

RISE tool to use: The SBI Model, GROW Model, and WWW/EBI framework in the RISE Giving Effective Feedback guide are your primary instruments here. The RISE SWOT Template can be used with the mentee after the conversation to turn a named weakness into a development priority.

Conversation Type Three

When Expectations Are Not Aligned

Misaligned expectations are among the most common sources of friction in a RISE mentoring relationship with the least likely to be named directly. Your mentee may have expected more structure, more challenge, or more frequent contact than the relationship has delivered. Or you may have expected more initiative, more follow-through, or more preparation from your mentee. Both are legitimate concerns. Both become problems only if they are absorbed rather than addressed.

The trap to avoid Absorbing the imbalance quietly to preserve the relationship. If you are finding that sessions lack energy, that the mentee is not driving the agenda, or that you are doing most of the work to make the relationship feel valuable -naming that is not a criticism. It is a reset that serves both of you.

How to raise it well

Use the RISE check-in structure as your natural opening. The programme builds in formal check-in points at weeks 3 and 5-6 specifically for this purpose. If you are approaching one, use it. If not, you can initiate a check-in at any point it normalises the conversation and removes the sense that you are raising a complaint.

Share your own experience first, before describing what your mentee has or hasn't done. This keeps the conversation non-accusatory. "I've been finding that..." is more productive than "You haven't been..." Describe the gap, invite their perspective, and then problem-solve together.

Opening the check-in conversation

"I want to take a few minutes to check in on how this relationship is working not just what we've covered, but whether the shape of it is right for both of us. I'll share my honest experience first, and then I'd love to hear yours."

This framing normalises the conversation it is a calibration, not a complaint. Both parties want the same thing: a relationship that creates real value. Naming a gap is the first step to closing it.

If you think the match isn't working

RISE explicitly acknowledges that sometimes "a mentor with a different background would be more suitable." If you have come to that conclusion, name it with care it is not a failure, and saying so protects both of you: "I want to be honest with you, because that's what this relationship is for. I'm not sure the match between us is serving you as well as it could. That's not about your effort or mine it's about fit. I'd like us to be able to talk about that openly, including whether the Programme Coordinator might help us think about a different arrangement."

RISE tool to use: The RISE Learning Log contains reflection prompts for check-in conversations. Complete yours before the session. If the relationship needs restructuring or rematching, contact the RISE Programme Coordinator at hello@riseglobal.co.uk.

Conversation Type Four

When Progress Has Stalled

When the actions agreed between sessions consistently do not happen when the same ground gets covered again and again without deepening when the relationship feels comfortable rather than useful something has stalled and it needs to be named. The RISE programme explicitly acknowledges this possibility, noting that progress may not happen due to "a lack of commitment from one party, a clash of personalities, or that a mentor with a different background would be more suitable." Your job is to notice the stall early and raise it before it quietly kills the relationship's potential.

The trap to avoid Avoiding the conversation to protect the mentee's feelings. A mentor who watches a stall developing and says nothing is choosing their own comfort over their mentee's growth. The relationship exists for the mentee's development. If it is no longer serving that purpose, naming it is the most caring thing you can do.

How to raise it well

Lead with curiosity, not confrontation. You are not delivering a verdict you are opening a conversation about what has been happening. The most useful framing is to name what you have observed specifically, explain why you are raising it (because you care about the relationship being genuinely useful), and then ask a question that invites the real answer.

When you understand why the stall has happened, you are in a position to do something about it whether that is resetting the goals, changing the format of sessions, addressing a personal obstacle the mentee has been reluctant to name, or deciding together whether the relationship still has productive life in it.

Words to open the conversation

"I want to raise something I've been noticing, because I think it matters. Over the last few sessions, the actions we've agreed haven't been moving with our conversations feel like they're covering familiar ground without going deeper. I'm not raising this to make you feel bad. I'm raising it because I care about this relationship being genuinely useful to you, and I don't think it is right now. What's been going on?"

Then listen fully before responding. The answer to "what's been going on?" is often the real conversation that has been waiting to happen.

Resetting after naming the stall

If the stall is due to the actions being too large, set smaller ones. If it is due to something personal, acknowledge that and adjust accordingly -a mentee dealing with a significant personal difficulty may need a different kind of session for a period. If the stall is due to a loss of motivation about the goals themselves, revisit the RISE Goal Tracker and the Career Development Framework together to understand whether the direction still feels right.

RISE tool to use: Open the RISE Goal Tracker together in the session and review every committed action honestly -both what has happened and what has not. Use this as a shared diagnostic rather than an accountability document. The Learning Log check-in prompts help both parties name what is not working before deciding what to do about it.

Conversation Type Five

Closing the Relationship Well

The RISE programme has an 8-week arc and a structured close. As a mentor, you have a particular responsibility in the closing conversation not just to participate in it, but to shape it with intention. The mentee is looking to you for a model of how to end something well: with recognition, honesty, and forward momentum. The RISE framework -Acknowledge, Prepare, Recognise, Celebrate, Review -gives you the structure. Your experience and care give it the meaning.

The trap to avoid Letting the closing session arrive without preparation, or treating it as a tidying-up exercise. The closing conversation is not administrative it is developmental. A mentee who leaves the final session with a clear sense of what they have built, what has changed, and where they are going next is far better equipped for what comes after than one who simply waves goodbye.

How to lead the closing well

Begin the closing conversation in week 7 not week 8. Raise the ending explicitly in your penultimate session. Tell your mentee that you want the final session to be intentional, and ask what they think it should cover. This gives both of you time to prepare what you want to say, rather than arriving at the last session and realising you have run out of time to close properly.

In the closing session itself, be specific. Do not give generic praise -name the moments. "At the start you described yourself as someone who found it hard to [X]. I have watched you [specific behaviour that demonstrates growth]. That is real, and it is yours." The more specific the recognition, the more deeply it is felt as genuine rather than ceremonial.

The RISE closing framework your checklist

Acknowledge	Name the transition in week 7. Discuss what the ending means and what you both want the final session to achieve.
Prepare	Review the Goal Tracker together. Identify what was achieved, what is still in progress, and what sources of support the mentee will have after the programme ends.
Recognise	Name specific moments of growth not just outcomes, but decisions, shifts in thinking, and moments of courage. The more specific, the more it lands.
Celebrate	Consider a LinkedIn recommendation, a warm introduction, or a nomination for the RISE Celebrate Success Awards. Make the celebration concrete, not just verbal.
Review	Reflect on what you each learned. Complete the RISE mentor report and Learning Log. Share what you are taking from the relationship your mentee needs to hear that the growth was not only theirs.

On staying in touch

Be explicit. Staying in touch is a personal choice outside the programme's formal terms -neither party is obligated. Name what you are open to: "I'm happy to be a resource if something specific comes up. I'd also encourage you to build your network beyond this one relationship rather than relying on me as your primary support. What would feel right to you?" This respects both parties and avoids the ambiguity of an implied relationship that neither of you has actually agreed to.

RISE tool to use: The RISE Session Agenda Playbook Week 8 Closing Template gives you a session-by-session guide. Complete the RISE mentor report before the relationship closes it feeds back into RISE's ability to improve the programme for future cohorts, and it closes the loop on your contribution.

Five Principles for Every Difficult Conversation You Hold

These apply across every conversation type. They reflect the RISE values of honesty, care, and action-orientation with the role of the mentor as someone who helps their mentee see themselves and their situation more clearly than they could alone.

Name it early, not late

A concern raised at week 3 is a speed bump. The same concern raised at week 7 is a crisis. The RISE check-in points at weeks 3 and 5-6 exist precisely to give you a legitimised, normalised moment to raise things before they compound. Use them.

Address behaviour, not character

Every difficult conversation has a higher chance of landing well when it addresses a specific behaviour or pattern rather than a character judgement. "You are unreliable" closes a conversation. "The actions we agree on haven't been happening and I want to understand why" opens one.

Ask before you advise

RISE Module 3 teaches guiding without telling for a reason. Asking permission before offering a challenging perspective -"Would it be helpful if I shared an observation?" -transforms feedback from something done to your mentee into something done with them. That shift changes how it is received.

End with a concrete next step

A difficult conversation that ends without an action or a clear understanding is a missed opportunity. Before closing every hard session, ask: "What are we each going to do with this?" The answer becomes the next entry in the RISE Goal Tracker.

Know when to refer on

The mentor role has boundaries, and knowing those boundaries is itself a form of care. If a conversation surfaces something that goes beyond professional development -serious mental health concerns, safeguarding issues, or situations requiring professional support -acknowledge what you have heard with compassion and refer the mentee to the RISE Programme Coordinator at hello@riseglobal.co.uk, or to an appropriate professional. The RISE Code of Conduct sets out these limits clearly. Holding within your role is not abandonment it is responsible mentoring.