Navigating Difficult Conversations - For Mentees

Career
Pivots

Performance
Concerns

Misaligned
Expectations

Stalled
Progress

Ending the
Relationship

This guide is written for you. As a RISE mentee, you bring the agenda. You decide what to raise, when to raise it, and how deeply to go. That puts a real responsibility on you - and sometimes the conversations that most need to happen are exactly the ones that feel hardest to start. This guide gives you language, framing, and confidence to raise the five types of difficult conversation that come up most often in mentoring relationships. None of them require you to be perfect. All of them require you to be honest.

Conversation Type One

Telling Your Mentor You Want to Change Direction

Wanting to pivot your career - to a different industry, a different function, or a global opportunity you hadn't previously considered - is one of the most valuable things you can bring to your mentor. But it can feel exposing. You might worry that your mentor will think you've wasted their time, that the pivot sounds unrealistic, or that you'll be talked out of something that feels genuinely right to you. None of those fears should stop you from raising it. Your mentor is there precisely for the conversations that feel too big to have alone.

Why this feels hard to raise Sharing a pivot idea is vulnerable. It means admitting that the current path might not be working - which can feel like admitting failure. There's also a fear of being judged, or of getting advice you don't actually want when what you need is someone to think alongside you.

How to raise it

The most important thing is to separate the desire to pivot from the plan to pivot. You're not asking for permission - you're thinking out loud with someone who has seen more of the landscape than you have. Begin by describing what is pulling you toward the new direction, not just what is pushing you away from where you are. This frames the conversation around possibility rather than complaint, and gives your mentor something constructive to explore with you.

Tell your mentor upfront what kind of support you need. Do you want them to challenge the idea? Help you research it? Or simply hear you out first before offering any view? Naming this prevents your mentor from giving advice when what you actually needed was space to think.

Words you can use to open this conversation

"I want to think out loud with you about something I've been sitting with. I'm questioning whether I'm on the right path - not because something has gone wrong, but because something is pulling me in a different direction. I'm not asking you to talk me into it or out of it. I just want to explore it with someone who knows more of the landscape than I do."

After you've shared the idea, a useful follow-up is: "Before you respond - have you seen others make a move like this? What made the difference between it working and not working?" This signals that you want insight from their experience, not judgement on your decision.

What to do if your mentor is discouraging

A mentor's caution is worth hearing - they may be seeing something real. But caution is not a verdict. If your mentor expresses doubt, ask: "What specifically concerns you? What would you need to see from me to feel more confident about this direction?" This keeps the conversation open and turns their concern into useful information rather than a closed door.

RISE tool to use: After the conversation, complete or revisit the Three-Horizon Career Map in the RISE Career Development Framework. A pivot doesn't erase your map - it redraws it. Bring the updated version to your next session.

Conversation Type Two

Raising a Performance Concern About Your Role

When you are struggling at work - receiving critical feedback from your manager, underperforming against your own expectations, or feeling at risk in your role - bringing it to your mentor is exactly the right move. But it takes courage. There is a real fear of being seen as inadequate by someone whose opinion matters to you. The truth is that the mentees who raise difficult professional realities tend to get far more from the relationship than those who only share the highlights.

Why this feels hard to raise Admitting a performance difficulty feels like admitting inadequacy to someone you want to impress. There can also be shame in saying "my manager is unhappy with me" - particularly if you have been presenting a confident face in your sessions up to this point.

How to raise it

Be specific about what has actually been said, not just what you felt. Give your mentor the facts so they can help you understand the situation clearly - rather than validate a version of events that may be incomplete. There is a difference between seeking perspective and seeking reassurance. The first is genuinely useful; the second can give you false comfort without moving anything.

Your mentor's job here is not to agree with you or to defend you - it is to help you see your situation more clearly than you can on your own. That may include reflecting back things that are uncomfortable to hear. Receive that with openness. It is one of the most valuable things a mentor can do.

Words you can use to open this conversation

"I want to be honest with you about something that's been happening at work. My manager told me specifically that [X]. I'm trying to work out whether this is fair feedback I need to take seriously, whether there's a skills gap I haven't acknowledged, or whether something else is going on. I don't want you to just reassure me. I want to understand what I might be missing."

After the conversation

Use the RISE SWOT template to examine your Weaknesses honestly - not as a source of shame, but as the raw material of your development plan. Every skill gap that is named can be addressed. Every gap that remains unnamed grows. Add the development priority to your RISE Goal Tracker and agree a timeline with your mentor.

RISE tool to use: The RISE SWOT Template helps you examine weaknesses and skill gaps honestly. The RISE Skill Gap Analysis in the Career Development Framework turns those weaknesses into a scored, prioritised development plan.

Conversation Type Three

When the Relationship Isn't Meeting Your Expectations

You entered the RISE programme with expectations - about how often you'd meet, what you'd cover, how much support you'd receive, and how the relationship would feel. If the reality is falling short, you have a responsibility to say so. Not because your mentor has done something wrong - but because an unspoken gap in expectations quietly erodes the value of the relationship for both of you, and you are the one who suffers most when it does.

Why this feels hard to raise Saying "I expected more from this relationship" to someone who is giving their time voluntarily feels ungrateful. There is a fear of seeming demanding, or of damaging a relationship that is still partly working. So the unmet expectation quietly erodes your enthusiasm instead of being addressed.

How to raise it

Frame it as a check-in, not a complaint. The RISE programme builds in formal check-in points at weeks 3 and 5–6 specifically to make this kind of conversation feel normal rather than critical. If you're approaching one of those moments, use it. If not, you can still initiate a check-in at any point - it signals maturity and self-awareness, not dissatisfaction.

Share your own experience first, before describing what your mentor has or hasn't done. This keeps the conversation non-accusatory and invites dialogue rather than defence. Be specific about what you need - more structure, more challenge, more contact, a different focus - so your mentor has something actionable to respond to.

Words you can use to open this conversation

"I want to be honest with you about how I'm experiencing our sessions - not to criticise anything you've done, but because I think we can get more from this relationship than we currently are. For me, [specific thing] hasn't quite been working. I'd love to understand your experience too, and to think about what we might do differently."

If the match genuinely isn't working

Sometimes the issue is fit, not effort. If you feel the relationship is structurally misaligned - different working styles, a sector gap that is too wide, or a personality mismatch - it is worth naming this openly with your mentor and, if appropriate, contacting the RISE Programme Coordinator at hello@riseglobal.co.uk to discuss whether a different pairing might serve you better. This is not a failure. RISE acknowledges that sometimes a mentor with a different background would be more suitable, and that recognising this early benefits both parties.

RISE tool to use: The RISE Learning Log contains reflection prompts for check-in conversations. Complete yours before the session so you arrive with specific, considered observations rather than a vague sense of dissatisfaction.

Conversation Type Four

When You Haven't Done What You Said You Would

This is the hardest conversation to initiate - and the most important. You committed to actions between sessions. They didn't happen. Maybe once, maybe repeatedly. The temptation is to show up, not mention it, and hope the session moves on. But your mentor will notice. And the longer the pattern continues without being named, the more it damages both your progress and the relationship. Naming it yourself - before your mentor does - is actually one of the most powerful acts of self-leadership in the whole programme.

Why this feels hard to raise Admitting you haven't followed through on commitments you made to your mentor feels embarrassing - especially to someone whose time you're using. There may also be real reasons behind the stall - personal circumstances, overwhelm, or a quiet loss of confidence - that feel too private or complicated to explain.

How to raise it

Open the session by naming it directly, before anything else. Do not wait for your mentor to bring it up. This signals that you take your commitments seriously and that you are willing to hold yourself accountable even when it is uncomfortable. That quality - in itself - is something your mentor will respect.

Focus the conversation on understanding why the stall happened, not on apologising for it. Apologies without insight do not prevent the same thing happening again. If you can identify the real obstacle - a competing priority, a gap in confidence, an action that felt too large to start - you and your mentor can do something about it together.

Words you can use to open this conversation

"I want to be upfront with you before we start. I committed to [action] and it hasn't happened - again. I could give you reasons, but I think what's more useful is to be honest that something is getting in the way and I haven't figured out what yet. Can we use part of this session to work out what it is, and to set something that I'm actually going to be able to do?"

Making the next commitment stick

Ask your mentor to help you set a smaller, more specific action than the one you missed. The RISE framework is: "I will [action] by 2026 so that [outcome]." Write it in the RISE Goal Tracker before the session ends. The act of writing it in a shared document raises the commitment level - it moves it from intention to accountability.

RISE tool to use: The RISE Goal Tracker. Use it to write every committed action before you leave the session, and review it at the start of every session. Making your commitments visible to both yourself and your mentor is the single most effective accountability practice in the programme.

Conversation Type Five

Closing the Relationship Well

The RISE programme has a defined 8-week arc, and the closing session is not just an administrative formality - it is one of the most significant conversations of the whole experience. Done well, it leaves you with a clear sense of what you have built, what has changed, and where you are going next. Done poorly - or not at all - it leaves both of you with a sense of incompleteness that can diminish something that was genuinely valuable. You have a role in making the closing great.

Why this feels difficult Endings can feel like losses, particularly if the relationship has been genuinely meaningful. There can be anxiety about losing the support structure, or uncertainty about whether it's appropriate to ask to stay in touch. Some mentees rush through the closing to avoid the discomfort of naming what is ending.

How to engage with it fully

Start preparing for the closing in week 7, not week 8. In your penultimate session, raise the ending explicitly - say that you want the final session to feel intentional, and ask your mentor what they think it should cover. This signals that you take the relationship seriously enough to close it properly.

Before the final session, review your Goal Tracker. Look at where you started and where you are now. Identify the specific moments of growth - not just the outcomes, but the conversations, the decisions, the shifts in how you think about yourself and your career. Come prepared to name them. Your mentor cannot give you recognition for things they don't know you are aware of.

What to bring to your closing session

☐ Your completed Goal Tracker - reviewed and annotated

☐ Three specific things that changed during the programme

☐ One thing you are still working on - and your plan for it

☐ What you are grateful for about this particular mentor

☐ A clear question about what comes next - your next step

☐ Your view on staying in touch - expressed honestly

On staying in touch

Be explicit rather than assuming. If you would like to maintain some contact, say so directly - and be specific about what that might look like: an occasional message, a LinkedIn connection, reaching out when something specific comes up. This respects your mentor's time and avoids the ambiguity of an implied relationship that neither of you has actually agreed to. And if your mentor has gone beyond what the programme required, a genuine, specific thank you is one of the most meaningful things you can offer.

RISE tool to use: The RISE Session Agenda Playbook includes a full Week 8 Closing Template. If you feel you still need support after the programme ends, contact the RISE Programme Coordinator at hello@riseglobal.co.uk - they will help you identify what is available.

Five Principles for Every Difficult Conversation You Start

Regardless of the specific conversation, these principles apply every time. They reflect the 2026 RISE cohort theme - Becoming by Design - which calls for intentional growth through deliberate choices rather than drifting around the conversations that matter most.

Raise it early, not late

A concern raised at week 3 is a speed bump. The same concern raised at week 7 is a problem. Use the RISE check-in points as your natural moments to surface things - they exist precisely to make this feel normal rather than confrontational.

Describe your experience, not your verdict

Start with what has been true for you, not with a conclusion about what your mentor has done or hasn't done. "I've been finding it hard to [X]" opens a door. "You haven't been giving me [Y]" closes one. Your experience is yours to share. Your verdict on someone else belongs in a conversation, not as an opening statement.

Seek perspective, not permission

You are not asking your mentor to approve your decisions. You are using their experience and perspective to make better-informed decisions yourself. There is an important difference. One makes you dependent; the other makes you smarter. RISE is designed to build the second kind of relationship.

End with something concrete

Every difficult conversation should close with a next step - a decision made, an action agreed, a plan to revisit, or an understanding reached. A conversation that simply airs feelings without producing any direction is a missed opportunity. Before you leave the session, name what changes now.

Know when the conversation needs to go further

Some of what you are carrying may go beyond what a mentoring relationship is equipped to hold - serious personal difficulties, welfare concerns, or situations that require professional support. Your mentor is not a counsellor, and asking them to act as one is not fair to either of you. If something in your life is significantly affecting your ability to engage with the programme, it is worth naming that with your mentor, and contacting the RISE Programme Coordinator at hello@riseglobal.co.uk to discuss what support is available.