Let's be honest – some career conversations are just plain awkward. Whether it is asking for a raise, addressing feedback, or questioning your next step, these discussions are often dodged like a Zoom call from an unknown number. But avoiding these critical chats can stall your progress, limit growth, and keep you stuck in the same professional place you’ve outgrown.
It is time to stop side-stepping and start leaning in. Here is your guide to five uncomfortable (but necessary) career conversations – complete with scripts, strategies, and a cheeky bonus tip on how to get your boss to pay for your studies.
Covered in this article
1. The “I Deserve a Raise” Conversation
2. The “I Need Feedback” Conversation
3. The “I Want a Mentor” Conversation
4. The “What’s Next for Me?” Conversation
5. The “I’m Considering a Career Pivot” Conversation
Bonus: The “Can You Pay for My Degree?” Conversation
Courage Is Your Career Superpower
FAQs
1. The “I Deserve a Raise” Conversation
Why We Avoid It: Many people squirm when discussing money. They fear being seen as greedy, ungrateful, or even replaceable.
Why You Shouldn’t: Your compensation should reflect your value, contribution, and market rate, not your silence.
How to Handle it:
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Timing is key: Align your ask with performance reviews or after a big win.
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Do your homework: Research industry benchmarks and know your worth.
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Use this script:
“I’ve taken on additional responsibilities this year, including [example]. I’d like to discuss how my current compensation compares to industry standards and explore a potential adjustment.”
2. The “I Need Feedback” Conversation
Why We Avoid It: We fear criticism or being told something that knocks our confidence.
Why You Shouldn’t: Constructive feedback is a career accelerator. It helps you understand how you’re perceived and where you can improve.
How to Handle It:
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Be specific: Ask for feedback on recent projects, not just general performance.
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Show openness: Make it clear you’re looking to grow.
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Use this script:
“I’d appreciate your feedback on the client pitch last week. What worked well, and where could I improve?”
Bonus tip: Feedback can sometimes lead to a performance improvement plan, but don’t panic. These are not career death sentences – they can be reframed as structured opportunities for growth if tackled proactively.
3. The “I Want a Mentor” Conversation
Why We Avoid It: It feels like dating – what if they say no? Or worse, what if they say yes and it’s awkward?
Why You Shouldn’t: A mentor provides perspective, guidance, and access to opportunities you might not find alone.
How to Handle It:
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Choose wisely: Approach someone whose career you admire and who has time to invest.
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Be clear about what you’re asking for: Don’t just say “Will you be my mentor?”
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Use this script:
“I really respect the way you’ve navigated your career path. Would you be open to meeting monthly to discuss my development goals and share your experience?”
4. The “What’s Next for Me?” Conversation
Why We Avoid It: You don’t want to appear ungrateful or give the impression that you’re job-hunting.
Why You Shouldn’t: Asking about growth shows ambition and helps your manager plan your career trajectory.
How to Handle It:
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Frame it around contribution: Show how your goals align with the company’s.
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Tie it to a career development plan: Make your aspirations visible and structured.
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Use this script:
“I’ve been thinking about how to grow in my role and continue contributing to the team. Could we create a career development plan together to identify skills I should focus on over the next 6–12 months?”
5. The “I’m Considering a Career Pivot” Conversation
Why We Avoid It: Fear of burning bridges, losing trust, or being labelled a flight risk.
Why You Shouldn’t: Career shifts are normal. A transparent discussion might even lead to new internal opportunities.
How to Handle It:
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Be honest but diplomatic: Focus on your evolving interests and desire for alignment, not dissatisfaction.
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Use this script:
“I’ve been exploring how my skills could be applied in other business areas. Would you be open to discussing potential internal moves or learning opportunities?”
Bonus: The “Can You Pay for My Degree?” Conversation
Yes, this one does sound cheeky – but it’s more common than you think. Many companies allocate budgets for employee development. You just have to ask.
Why You Should Ask:
How to Handle It:
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Link it to company goals: Show how the programme supports your role and the company’s mission.
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Highlight ROI: Emphasise how new skills will improve your performance and output.
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Use this script:
“I’ve found an online programme through UJ Online that directly supports my current responsibilities and aligns with where I’d like to grow in the company. Would the organisation be open to subsidising or fully covering the cost of the course?”
Pro tip: Programmes like UJ Online offer the flexibility of studying while you work, which is a win-win for both you and your employer.
Courage Is Your Career Superpower
The most transformative conversations are rarely the easiest. But by stepping into them with clarity, preparation, and confidence, you turn discomfort into development. Whether it’s discussing a raise, asking for mentorship, or designing a career development plan, owning your voice is a crucial part of owning your career.
So here’s your challenge: choose one of the conversations above and schedule it this week. You’ve got the scripts. You’ve got the strategy. Now, all that’s left is the courage to speak up.
Thinking of levelling up your career through online learning? UJ Online offers world-class postgraduate qualifications you can pursue while working full-time. Explore your options here – and maybe even get your boss to foot the bill.
FAQs About Important Career Conversations
1. Why are career conversations often difficult to initiate?
Many people avoid these discussions due to fear of rejection, appearing ungrateful, or not knowing how to articulate their needs. However, proactive communication is essential for career growth.
2. What is a performance improvement plan, and should I be worried if I'm placed on one?
A performance improvement plan (PIP) is a formal document that outlines specific goals and supports improving job performance. If approached constructively, a PIP is not necessarily a bad sign—it can be an opportunity to refocus and grow.
3. How do I ask for a raise without sounding entitled?
Prepare by gathering evidence of your achievements and industry salary benchmarks. Align your request with the company’s goals, keeping the tone professional and data-driven.
4. What’s the best way to ask someone to be my mentor?
Choose someone whose career path you admire and be clear about what kind of mentorship you’re looking for – monthly chats, project feedback, or general career advice.
5. How do I know if it’s the right time to talk about a career development plan?
Ideal times include performance reviews after a significant milestone or when company planning cycles occur. It shows foresight and initiative.
6. What if I want to explore a different role within my organisation – how do I bring it up?
Frame it positively: highlight your interest in growing within the company and how your skills can add value in another capacity. It’s about alignment, not dissatisfaction.
7. Can I ask my employer to fund my studies?
Yes! Many organisations offer education benefits or reimbursement. Just make sure you demonstrate how your studies (like a UJ Online programme) align with your role and the company’s goals.
8. What if my request is denied – should I stop trying?
Not at all. If you receive a “no”, ask for feedback on what would make a “yes” possible in the future. Continue to show growth, and revisit the conversation when the time is right.
