Thinking of hiring a career coach? Smart move. But before you book that first session, you’ll want to ask the right questions. Not “Do you offer discounts?” — we’re talking about the deep, strategic questions that reveal how a coach actually helps you level up your career (or, let’s be honest, escape it altogether).

Here are the top 10 questions to ask a career coach — questions that will help you find the right coach for you and ensure they offer more than just motivational quotes and a well-lit Zoom background.

1. How can you help me identify my strengths and career goals?

This is coaching 101. A good career coach won’t just tell you to “follow your passion” (unless your passion pays rent). Instead, they should help you uncover your core strengths, work preferences, and career aspirations — and translate those into meaningful, achievable goals. Think of it as career counseling with a strategic plan and less incense.

2. What strategies do you use to help clients navigate career transitions?

Whether you’re jumping industries or stepping into leadership for the first time, career change is tricky. The right career coach will map out realistic pathways, avoid rookie errors, and manage the inevitable identity crisis that comes with leaving your job title behind.
Take Catherine, our hypothetical example — a mid-level IT Change Manager who wanted to transition into communications.

Her coach helped her identify transferable skills, reframe her experience for comms roles, and build a new network in the industry. Six months later, she landed a role in the HR department of a Telecom company doing internal comms for a change project— and no, she didn’t have to start at the bottom — or pretend to be passionate about IT projects ever again!

3. How can you support me in finding a job that aligns with my skills and values?

This one’s key. The best jobs aren’t just well-paid — they align with who you are and how you want to live your life. A good career coach helps you define your values, recognise your unique competencies, and find roles that reflect both — even if you’re still not sure what your “values” are beyond “coffee” and “Fridays off”.

4. What advice do you have for making my CV and LinkedIn profile stand out?

If your CV still lists “Microsoft Word” under skills, we need to talk. A professional career coach should help you tailor your CV and LinkedIn profile to clearly communicate your experience, strengths, and career goals — without sounding like a robot trained in buzzwords like “results-oriented team player”.

5. Can you help me improve my interview skills and confidence?

Great on paper but melt in interviews? You’re not alone. Interview coaching can boost your confidence and teach you how to handle curveball questions like “What’s your biggest weakness?

But you won’t just be rehearsing answers. The right coach will help you understand the psychology behind interview questions and build the kind of calm, clear presence that gets remembered (for the right reasons). Whether you’re struggling with storytelling, overthinking every answer, or battling last-minute panic, interview prep can transform the whole experience from terrifying ordeal to “Actually, that went pretty well.

6. How do you approach salary negotiations and career advancement?

I realise this one’s a bit thorny, and negotiation can feel like trying to parallel park in front of a crowd — you think you know how, but suddenly it’s all pressure and second-guessing. Your chosen coach will give you the strategies to advocate for what you’re worth, whether you’re asking for a raise or negotiating a new offer.

7. What techniques do you use to help clients overcome career roadblocks?

From imposter syndrome to job search fatigue, we’ve all hit a wall at some point. Ask your coach how they help people push through. Do they focus on mindset? Practical steps? Accountability? Ideally all three (and possibly chocolate).

8. How do you customise your coaching based on my unique challenges and aspirations?

You’re not a template, so your coaching shouldn’t be either. Your coach should tailor their approach to your goals, background, and professional life — whether you’re chasing a new role, switching industries, or wondering what happened to your motivation after 2020.
This personalised approach means your sessions aren’t filled with generic advice or one-size-fits-all worksheets. Instead, you’ll dig into your unique challenges and clarify what really matters, and as you grow, your coach will adjust their strategies to evolve with you.

9. Can you help me build a long-term career strategy, not just find my next job?

Career success is about building a fulfilling trajectory over time. A great coach should support your professional development with a long-term view, helping you clarify where you’re going and how to get there (even if right now you’d settle for just knowing what to do next Monday!).

10. What kind of support do you offer for networking and professional branding?

You don’t need to become a LinkedIn influencer (unless that’s your thing), but knowing how to build your brand and make meaningful connections is key to career growth. Ask how your coach helps with professional branding, networking strategies, and using tools like social media to stand out — without turning your feed into a stream of motivational quotes.

Bonus Tip: Don’t forget to ask yourself a question too

Something like: “Am I ready to invest in my future and take my career seriously?” If the answer is yes — or even just a cautious maybe — then it’s time to take the next step.

Want real answers to these questions? Book a free 30-minute call with Jane Piper, founder of Pipsy — a career coach who helps professionals get unstuck, get clear, and get ahead.

Or take the Mid-Career Audit — a quick, insightful quiz to help you figure out where you’re at and what’s next. Start here.

Whether you’re eyeing a promotion, planning a pivot, or just wondering if it’s too late to change careers (hint: it’s not), asking the right questions is the first step. The next? Finding a coach who gives you honest answers — and helps you build a career you actually want to wake up to.

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