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What Should I Ask a Career Coach Before I Start Working with Them

What Should I Ask a Career Coach Before I Start Working with Them

A good coach can help you stop spinning in circles and finally take action. According to the International Coaching Federation, 80% of people who hire a coach report improved self-confidence, and over 70% see improvements in work performance and career outlook. [1]

Not all coaches are created equal. Some are great listeners, but lack strategy. Others are full of buzzwords but have never helped someone like you actually achieve results. That’s why it’s critical to ask the right questions up front, before you spend your time, energy, and money.

This is especially important if you’re stuck in a job that looks fine from the outside but drains you on the inside. This is your wake-up call. Maybe you’re torn between making a change and feeling guilty for not being satisfied. That foggy in-between is exactly when people need support the most but it’s also when they hesitate the most.

What Does a Career Transition Coach Actually Do?

Let’s be real. Changing careers, especially in your 30s, 40s, or 50s, isn’t as simple as updating your CV and crossing your fingers. There’s fear, doubt, overthinking, and a lot of “What if I screw this up?” swirling in your head. That’s exactly where a career transition coach steps in.

A coach helps you stop spinning and start seeing clearly. Their role is to support you in figuring out what you want next, why it matters, and how to actually get there. They’re not giving you all the answers. They’re helping you get to them with clarity and direction.

In midlife or during big transitions, feeling stuck is common and no, it’s not because you’re lazy or unmotivated. It’s usually because what used to feel like “success” doesn’t fit anymore, and you haven’t figured out what’s next. Coaching helps you slow down, reflect, and move forward with intention.

Here’s what you can typically expect from working with a career transition coach:

  • More clarity about what you actually want
  • Confidence to stop second-guessing every move
  • A real strategy that fits you, not someone else’s checklist
  • A path to change jobs, industries, or reinvent yourself entirely

Coaching works. More than 70% of clients report better performance, stronger relationships, and clearer communication. The numbers back it up. [2] 

Claire works specifically with women navigating big shifts, whether it’s a total career reinvention or just needing to stop feeling stuck. Her coaching style is calm, purposeful, and straight-talking. She helps you figure out what you want, then move toward it with less fear and more focus.

Ready to explore what’s next for you? Find out if career transition coaching is the right step for your journey.

Book a free discovery call with Claire Campion today!

10 Smart Questions to Ask a Career Transition Coach

Coaching isn’t cheap, but before you spend your time, energy, or money, ask the right questions. You’re not looking for a cheerleader. You’re looking for someone who gets you and knows how to help you achieve results.

According to Harvard Business Review, the best coaching relationships start with clear expectations and strong alignment between coach and client. That starts with asking smart, honest questions. [3] 

Let’s break them down:

1. What experience do you have helping clients in career transition?

Not every coach is built for change work. You want someone who specializes in helping people pivot especially if you’re shifting industries, returning to work, or starting over. Generic advice won’t cut it.

2. What’s your coaching style and philosophy?

Some coaches are soft and supportive. Others are direct and push you hard. Many are a blend. Make sure their vibe matches your needs, or it’s going to feel off fast.

3. What’s a typical coaching process like?

Ask what the journey looks like. How long does it last? What happens in each session? Will you get support between calls, or are you on your own between sessions?

4. Do you help with practical things like resumes, LinkedIn, or interviews?

Some coaches stay high-level, strategy, mindset, big-picture. Others help with tactical tools. You want to know what’s included before you start.

5. Can you share examples of past client results?

A solid coach should be able to share anonymized examples of real transformation. This isn’t about testimonials, it’s about proof that they know how to help people move.

6. How do you measure progress or success in coaching?

Coaching isn’t just “vibes.” There should be structure. Ask how they’ll help you track growth, outcomes, and shifts as you go.

7. What kind of clients do you work best with?

You want to be their ideal client, not someone they just say yes to. A good coach knows who they serve best and won’t hesitate to tell you.

8. Do you offer a discovery call or trial session?

Any legit coach will give you space to talk things through before committing. If they don’t offer a discovery call, that’s a red flag.

9. How do you tailor your approach to different career paths or industries?

Every journey is different. If they use the same cookie-cutter process for everyone, that’s a problem. Look for flexibility.

10. What should I expect to feel during this process?

Change isn’t all clarity and confidence. Sometimes it’s messy. Ask how they’ll support you through fear, doubt, and the uncomfortable middle.

Ask Yourself These Questions Too

Before you book a call, pause and get real with yourself. Coaching only works if you’re ready to show up and do the work.

Here are three questions worth sitting with:

1. “Am I ready to be coached?”

Coaching doesn’t need you to have it all figured out. It needs you to be open, open to being challenged, stretched, and maybe a little uncomfortable.  If you just want someone to tell you what to do, that’s not coaching, that’s outsourcing your life.

2. “Am I open to change, or just craving comfort?”

Wanting things to feel better isn’t the same as being willing to change. If you’re just chasing a job that feels safer, you might end up just as stuck. Change asks more of you, but it also gives you more back.

3. “What do I really want from this next chapter?”

Don’t overthink it. You don’t need a perfect answer. But you do need a starting point. A gut feeling. A sense of what matters more now than it used to. Your coach can help you shape it but they can’t choose it for you.

Self-reflection is a major part of coaching success. A study in the Consulting Psychology Journal found that clients who come in with a reflective, growth-oriented mindset tend to achieve stronger results. [4] 

So before you hire a coach, check in with yourself first. If the answer is yes even if it’s a nervous yes, you’re already on your way.

You don’t have to stay stuck. The right coach can help you move forward with clarity and confidence

Schedule a Call with Claire!

How Claire Campion Supports Career Transition

Claire Campion isn’t here to sell you hype, push a one-size-fits-all plan, or tell you to “just follow your passion.” Her approach is calm, thoughtful, and rooted in helping you move forward with purpose, not pressure.

She works best with women in midlife who are at a crossroads. Maybe your career looks fine from the outside, but something inside you is restless. You want more meaning. More clarity. Or simply something different, even if you’re not sure what that looks like yet.

Claire helps you cut through the noise and tune back into what you really want. Her coaching blends deep listening, smart strategy, and honest reflection. Just grounded support to help you move in a direction that feels aligned with who you are now, not who you were ten years ago.

If you’re ready to stop circling and start moving, Claire’s here to walk with you through the change with calm, clarity, and no judgment.

Don’t Just Choose a Coach. Choose the Right One for You

It’s more than okay to ask questions, it’s smart. Coaching is a personal investment, and you deserve to know who you’re working with, how they work, and whether they’re actually the right fit for you.

This isn’t about finding the most “qualified” coach on paper. It’s about finding someone who gets you, challenges you, and supports you in a way that feels right. So yes, do your research. Ask the hard questions. But also, trust your gut. If something clicks, pay attention. And if it doesn’t, keep looking.

You’re not stuck. You’re just one honest conversation away from movement.

Book a free discovery call with Claire and ask her anything.

 

References:

  1. https://coachingfederation.org/resources/research/global-coaching-study/  
  2. https://instituteofcoaching.org/coaching-overview/coaching-benefits  
  3. https://hbr.org/2004/11/the-wild-west-of-executive-coaching
  4. https://www.researchgate.net/publication/233682110_The_impact_of_life_coaching_on_goal_attainment_metacognition_and_mental_health