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13 Questions to Ask a Career Coach for a Game-Changing Session

Learn how to enhance your career coaching session with insightful questions curated by a career strategist.
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If you want to discover your true calling, accelerate professional growth, or seek expert advice for another career-related matter, finding a career coach is a wise way to gain clarity. However, a productive coaching session starts with asking questions that resonate with your career aspirations and align expectations. 

To help you prepare, we’ve leveraged our collective experience in career counseling to develop a list of 13 strategic questions to ask a career coach. By knowing what to ask, you can extract the most value from the coaching session, potentially redefining your career trajectory with newfound clarity and direction. 

Understanding the Role of a Career Coach

Career coaches (sometimes called career counselors) can have particular specialties, but their main focus is to help clients progress toward their career goals. They work with high school and college students, recent graduates, mid to late-career professionals, entrepreneurs, and anyone seeking informed guidance to grow in their professional lives. Here’s an overview of a career coach’s core responsibilities and what you can gain by working with one: 

What Does a Career Coach Do?

A career coach primarily gives clients personalized insights and informed feedback based on their aspirations. An expert career coach is familiar with helping people throughout all stages of the career journey, from discovering ideal professional paths to job searching, goal setting, enhancing job performance, changing professions, and more. 

While a career coach can help you navigate your career outlook, you shouldn’t expect them to single-handedly find you a job or remove the hard work from the process. Instead, they equip you with the right insights and perspective to make your ambitions attainable, ensuring you’re prepared and have a clear action plan.  

How Can a Coach Propel Your Career Forward?

Working with a career coach helps uncover the strengths, abilities, and unique values you bring to the workplace, giving you an informed picture of your future outlook and what you need to be successful. They provide actionable insights and constructive feedback to polish your professional persona, which helps you set strategic goals and navigate obstacles you otherwise might not foresee on your own.

Questions to Ask Your Career Coach

Your first career coaching session will likely have an introduction phase to determine what you hope to gain as a new client, but it’s helpful to consider your intended purpose beforehand. Here are 13 questions to help you prepare: 

1. How Can You Help Me?

When you ask how a career coach can help you, expect a response demonstrating empathy and a structured approach tailored to your unique needs. A skilled coach will outline how they'll assist you in identifying and achieving your career goals, overcoming challenges, and devising a strategic plan for success. This might involve a mix of assessment analysis, resume optimization, skills development, and interview practice. 

Additionally, they may offer access to their professional network. Their methodology should be geared toward pushing you beyond your comfort zone in a supportive manner while also respecting your individual risk tolerance. This personalized approach ensures that the guidance you receive is directly aligned with your career objectives and personal growth.

2. What is Your Coaching Philosophy?

When you inquire about a career coach's philosophy, expect an answer that reflects a deep understanding of the uniqueness of each career journey and a belief in your individual talents and potential. A thoughtful coach will emphasize their commitment to working collaboratively with you to explore careers that align with your strengths while also addressing any self-limiting beliefs. 

Their approach is about meeting you where you are in your journey, empowering you, and fostering self-awareness. Their philosophy should resonate with your values and career aspirations, helping you determine if their coaching style suits your personal and professional growth needs. This response gives you a window into their values, methods, and how they handle coaching relationships, ensuring their approach aligns with your objectives.

3. What are Your Strengths?

When inquiring about a career coach's strengths, anticipate a response that not only underscores their professional expertise but also their alignment with your specific needs. An effective coach will likely highlight strengths like empathy, insightful questioning, motivation techniques, and accountability strategies. They'll also talk about their extensive career knowledge and strong professional networks. 

You can expect them to share their proficiency in empowering clients through valid assessments, active listening, and personalized guidance. These aspects are crucial as they demonstrate the coach's ability to identify and leverage your unique strengths and experiences, contributing to their track record of helping clients achieve their goals. Such a detailed response will help you gauge if the coach’s strengths and methods are in harmony with your career aspirations and personal growth journey.

4. How Do My Skills Align with My Career Aspirations?

Understanding the relationship between your existing skills and career aspirations is a crucial step to achieving your professional goals. Asking this question of an objective professional helps you see which of your skills are assets, which ones need further honing, and what new skills you might need to acquire. 

A career coach can help translate your aspirations into tangible milestones, considering what you need to prioritize both in the short- and long-term. This process might lead you to realize that you already possess most, if not all, of the required abilities. Conversely, it can also show you if your career aspirations require more skills than you have the time or willingness to acquire. 

Once you understand how your skills align with your career aspirations, you can determine if you should seek additional education, training, or professional development to best position yourself for success. Likewise, you can ensure your development strategy matches the real-world demands of the job market and prospective employers in your chosen industry. 

5. Can You Help Me Set Realistic and Achievable Career Goals?

If you want to make your career dreams a reality, ask your coach for help with setting SMART goals (specific, measurable, achievable, relevant, and time-bound). This strategy helps you determine if your goals are feasible while also stretching your capabilities, encouraging you to think carefully about what you want to achieve and why. 

With this question, you can visualize your long-term career journey and the short-term objectives that will move you closer to this vision. Your coach can guide you in splitting broad goals into smaller, manageable milestones to make the path feel less overwhelming. This will also promote a sense of accomplishment as you progress, keeping you motivated and engaged.  

6. What Strategies Can I Adopt to Overcome a Specific Challenge?

When you face challenges, it’s crucial to address them head-on to keep advancing in your career. However, it’s not always clear how to approach these unique setbacks, which is where a career coach can provide invaluable guidance. They can help you understand the root cause and recommend personalized strategies to overcome the challenge, reframing it in a way that empowers rather than hinders you.

You should revise this question to fit your unique situation, whether it revolves around a lack of confidence, bridging skills gaps, addressing workplace changes, or any other obstacle you encounter. Additionally, you might ask your career coach for strategies to build a support system through networking, mentorship, or professional groups to work through future challenges. 

7. How Do I Navigate Professional Setbacks or Failures?

Although failure is never easy to work through, it’s one of the fundamental aspects of career development and human nature in general. With the right perspective and guidance, career setbacks can be transformative learning experiences, helping you avoid similar mishaps in the future. 

Addressing your failures with a career coach can show you how to process them with a constructive mindset, which could include reflecting on what went wrong and identifying corrective actions to implement going forward. A career coach can also advise you on communicating your setbacks to others, especially in interviews or discussing career transitions. 

Instead of viewing failure as a negative, you can demonstrate your resilience, ability to learn from mistakes, and commitment to continuous professional development. 

8. What Additional Skills Should I Acquire for My Desired Career Path?

Identifying the desired skills and certifications for your future career helps you create a robust development plan, but this goes beyond just reading job descriptions and application requirements. If you ask your career coach this question, they will likely give you an honest overview of the expectations, analyzing your existing skills and comparing them with industry demands. 

In addition to the industry’s desired hard skills, a career coach can recommend soft skills that set you up for success. Qualities such as communication, conflict resolution, leadership, problem-solving, and adaptability are universally valued and sometimes more sought after, as they’re not as easy to teach someone who doesn’t already possess them. 

9. How Can I Leverage My Existing Skills in New or Unexplored Areas?

There’s a good chance you already have a valuable set of skills that can meet the demands of different professional avenues (or at least give you a solid foundation to build on). If you aren’t satisfied with your current industry or professional line of work, you can ask a career coach about transferring your existing skills to something new, which could include professions you never would’ve considered. 

Your career coach will likely walk you through various compatible professional paths, and if you find something you like, they might even help tailor your resume to fit the role and highlight your transferable skills. Even if you’re unfamiliar with the recommended options, they can show you what to expect and why you’re a suitable match before you start the job search, similar to the insights provided by our free career test

10. Can You Provide Insights into Current Market Trends Related to My Field?

Every professional field is in a state of constant change, whether caused by market trends, worker shortages, or technological advancements. Since a career coach regularly studies these ongoing changes, they can help you stay ahead of them and align your career trajectory with the fluctuations of your chosen field. 

In this exchange, your coach might recommend various strategies to stay up-to-date and agile, such as subscribing to a reputable industry publication, engaging with professionals in your network, or acquiring in-demand skills and crucial tools for accelerated growth in a turbulent market. They can also help you prepare for shifts in industry demands that could potentially impact your career pathway, ensuring you’re ready to respond. 

11. How Should I Adapt to the Changing Dynamics of the Professional World?

In recent times, we’ve seen a growing need for continuous learning, a rapid transition to remote or hybrid work cultures, and the emergence of new workplace norms, especially since COVID-19. These are testaments to the fluidity of the professional landscape, making it essential to take a proactive stance and embrace evolving dynamics.

Your career coach can share insights to help you navigate these changes, including how to create a productive work-life balance, improve communication skills, and find new ways to market your skills to new employers. Beyond workplace skills, they can also help you align with the growing emphasis on diversity and inclusion, mental health awareness, and flexible work arrangements, among other advancements in the professional world.

12. What Networking Strategies Would Be Most Effective for My Career Growth?

Many working professionals can attest that who you know is often more important than what you know. Networking is a cornerstone for career advancement, and it’s much more than collecting business cards or gaining new LinkedIn connections. Effective networking means building meaningful, mutually beneficial relationships that open doors to new opportunities, knowledge, and mentorship, which takes time and effort. 

However, a career coach can help you figure out the best way to build your professional network based on your personality, career goals, and chosen industry. For instance, if you’re introverted, your coach might suggest strategies that focus on building one-on-one relationships with professionals you trust. Moreover, your coach might highlight the importance of following up and maintaining the relationships you form, as networking is a two-way street that requires consistent maintenance. 

13. How Can I Develop and Promote My Personal Brand?

If you want to stand out in a crowded job market, developing your personal brand is an effective way to share your unique professional story and make it memorable. Your personal brand should be tailored to your audience while aligning with your career goals, which is a delicate balance that can take trial and error. 

Your career coach can help you identify the core values, skills, and experiences that set you apart, honing in on what makes your professional narrative unique. They can also help you develop channels for communicating your personal brand, whether through social media, a personal website, or a blog where you share insights on topics you’re passionate about.

Maximizing the Benefits of Career Coaching with JobTest.org

Career development is an intricate process, as no two career seekers have the same goals, personal situations, or available time and resources. Navigating this process often calls for a holistic approach, blending self-awareness and outside perspectives to develop a strategic plan for advancement. 

This is where our assortment of resources and one-on-one coaching services at JobTest.org shines. Our career aptitude test is built with the latest technology in the industry, uncovering your intrinsic strengths, interests, and potential career paths in less than twenty minutes. It provides personalized insights and constructive feedback to help you move forward, giving you a reliable starting point before your first coaching session. 

By leveraging the career tests and resources on JobTest.org alongside the personalized guidance from our career coaches, you equip yourself with a robust framework for informed decision-making and strategic career advancement. Whether you’re exploring new career paths, seeking to climb the corporate ladder, or striving to overcome professional setbacks, JobTest.org is your companion for the journey. 


The path to career success often begins with asking the right questions, and we hope our list helped you find inspiration. Discussing topics relevant to your unique career aspirations and challenges enables you to extract the most value from the session, laying a solid foundation for actionable strategies and advice. 

When you meet with a career coach, we encourage you to use these probing questions to enrich the dialogue and propel you closer to a fulfilling professional journey. Strive to be authentic, tailor them to match your unique situation, and be sure to ask follow-up questions to fully understand what you hope to learn. 

In addition, we encourage you to take our free career test to enhance the quality of your coaching session, ensuring you show up prepared and well-versed in your career personality. 

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