by Mariia Shevchenko, CEO at Amy, Author at Amy | Career coaching platform for everyone

Your First Career Coaching Session: How to Prepare and What to Expect?

Thinking about career coaching but are not sure where to start and what to expect? A new job seems like a leap into uncertainty, career transition poses financial risks, and meaningless tasks drag down your brilliance? Even if you aim just for a little guidance on your way, career coaching sessions can be very helpful.

Here’s a look at what the first career coaching session typically involves, steps to prepare, and what makes a top-notch coach stand out from the rest.

First things first, what is the career coach’s role in your career development?

Career coaches help you achieve your career goals, and if you don’t know what your career goals are, they help you define them. A career consultant reframes experience at your current work to create a better work environment or smoothly navigates a career change. 

Career coaches are proficient in enhancing resumes, job search processes, and job interview strategies. With an expert, you will craft your career plan, define your skills, and map a timeline for upskilling. 

The image of a career coach at Amy

“Working with a career coach is a collaborative, strategic experience where clients gain clarity, self-confidence, and actionable plans. The benefits include personalized guidance in identifying strengths, setting realistic and inspiring career goals, and creating steps to advance while also addressing any blocks. Clients often walk away with a fresh mindset, which is a critical part of moving forward successfully.”

Jane Klymenko, a career expert at Amy with 10+ years of coaching experience and the main area of expertise in Work-Life Balance

Success story at Amy: from feeling undervalued to feeling fulfilled

Background

Kate approached a career coach with an issue: she struggled to secure a leadership role within her organization, feeling consistently overlooked despite her technical expertise.

Our approach

Kate, along with a career coach, focused on three primary steps: 

  1. Assessing her current skill set and the perception of her role within the company
  2. Identifying and amplifying her leadership potential through targeted personal branding
  3. Enhancing her network within and outside the organization to support her ambitions

Challenges faced

Kate had difficulty breaking through the “technical-only” perception her colleagues held, felt unsure about networking, and struggled with imposter syndrome.

Results achieved

We overcame her struggles by:

  1. Reframing her approach to networking as relationship-building
  2. Encouraging her to take on mini-leadership roles in projects
  3. Coaching her in developing the leadership style to make a strong impression in professional environments

Eventually, Kate secured her leadership role, and her confidence in personal and professional interactions grew significantly.

The image of a career coaching session

What makes a good career coach?

What qualities to look for in a great career coach? How to spot a career coach who is truly a great fit for you? The answer is to define what is your goal plus the following common strengths and competencies:

  • Has expertise in your career objectives. There can be a background in recruitment or management or even your industry. Can be experience in the work-life balance area. 
  • Has a portfolio of success cases and a trusted reputation in the market.
  • An active listener and a strong communicator. Clear communication builds comfy relationships and promotes an open environment in which you can share career preferences and challenges—be your true self.
  • Focused on setting measurable goals and taking actionable steps. A professional career coach guides you to grow and progress with specific, tailored strategies rather than generic, one-size-fits-all advice.

What are the preps for the career coaching session?

Here’s how you can start and get the most out of your career coaching session:

The image of a career coach at Amy

“The most important prerequisite for the first session is an openness to self-reflection and a willingness to commit to the process. While some clients prepare by reflecting on their career history or even journaling about their goals and challenges, it’s not a strict requirement. If they’re inclined, they could try some self-awareness exercises, like the “Wheel of Life” or “Values Assessment,” to bring a clearer sense of their current situation and desired direction.”

Jane Klymenko, a career expert at Amy with 10+ years of coaching experience and the main area of expertise in Work-Life Balance

  1. Reflection. Spend some time thinking about your past, present, and future aspects of work. What do you want from your career now and for the long term? What holds you back from achieving your aspirations? What motivates you in your work? What are your core values? Take careful note of your challenges. For example, you may experience imposter syndrome, burnout, or frustration with monotonous, never-ending activities. If you cannot find answers to your questions or miss something, it’s okay. A career coach will guide you in the right direction during the session. 
  2. Materials. To help your career coach get to know you better, think about bringing along your resume, cover letter, any certifications you have, your performance reviews, or feedback notes. Having these materials ready gives a career coach a clearer picture of your work history, skills, and accomplishments. Which means they can offer more tailored advice that fits your needs.
  3. Questions. Prepare questions for your coach and be ready to clarify any possible confusion on the call. This ensures you cover essentials during your session.
  4. Feedback. Be open to constructive feedback, reflections, and changes. Your willingness to grow and flexible mindset will make improvements.

What to expect from a career coaching session?

The image of a career coach at Amy

“For me, career coaching is about empowering clients to see new possibilities and pathways in their professional lives, clarifying goals, and helping them take steps to achieve them. The biggest advantage is that it provides a structured approach to both personal and career growth, which can otherwise feel overwhelming. By having an objective perspective, clients can make intentional choices that align with their values and skills.”

Jane Klymenko, a career expert at Amy with 10+ years of coaching experience and the main area of expertise in Work-Life Balance

In the first career coaching session, you can expect to: 

  • Define objectives and assess your interests, needs, skills, values, background, or any other points
  • Discuss your current position
  • Outline any immediate concerns or challenges
The image of a career coaching process

The conversation sets the groundwork for the ongoing work to establish direction, identify focus areas, and outline initial action steps. You will get a sense of clarity, organize your thoughts, and solidify a starting point. So, the first session with a career coach is about laying the foundation. Regular check-ins or follow-up sessions are about tracking progress, addressing new challenges, and adjusting your plan.

Talk to a coach

Take your career to the next level with a personal career coach. Career coaching services will absolutely ease navigating the turns of your career path. With the right guidance, career coaching can unlock your potential and new opportunities, empowering you to achieve professional heights.

Self-Coaching or Guidance by a Career Coach—What Approach To Choose?

Choosing between self-coaching and working with a career coach is like choosing to fly solo or stay under someone’s wing. The first way stands for autonomy and flexibility. The second one means relying on the experience and support of a professional, especially when you lack time for self-management. After all, you may combine the two to gain diverse insights. 

How can you know what works best for you? We will give tips in this article so you can pick your option. And we will start with a self-coaching approach. 

Becoming your own career coach

Career self-coaching exists to self-reflect on your career path and set goals with free instruments available. Self-coaching instruments usually go in in the form of exercises to practice.

To understand if career self-coaching is a good fit for you, ask yourself whether you can navigate self-reflection questions, goal setting, and motivation for changes on your own.

Benefits of career self-coaching 

Self-coaching empowers to:

  • Take full control over your career without external influence 
  • Strengthen your self-awareness to make decisions with confidence
  • Cultivate self-development while looking at the skills you wish to master and the expertise you wish to build

Key self-coaching practices 

You might hit a point in your career where you are not sure what is next and need strategies to manage the unknown. You aim to balance personal fulfillment with professional growth or decide which path aligns best with your long-term goals.

Picture Nick. Nick is in his 30s, leading a team in a software company. While he is in a position of authority, he craves more—more impact, more fulfillment, and more effective use of his time. Despite Nick’s management opportunities, he misses direct involvement in the product cycle and cannot change the situation within the company. Nick is a project manager, not a product manager. He’s not quite satisfied, but thoughts about a new job bring uncertainty. 

The image of a man sitting at a desk, as an example of the career coaching process

What if he makes the wrong decision and ends up struggling financially? Why isn’t he getting better results in a new job search? Why does he feel stuck and unsure of himself despite his accomplishments? 

Nick’s story echoes the experiences of other professionals worldwide. It may even be your case. So, where can you start?

Self-assessment: reflect, realize, and evaluate 

  1. Write down or type your interests, needs, and values
  2. Analyze your work format: what your perfect workday looks like, what you enjoy most about your current role or job, and what drains your energy. 
  3. Think about your skills, mainly strengths and weaknesses. SWOT analysis (Strengths, Weaknesses, Opportunities, Threats) is a functional approach to explore your superpowers:
  • Strengths: What do you excel at? For Nick, it is technical knowledge.
  • Weaknesses: Where do you struggle? Nick needs strategic influence in his current position.
  • Opportunities: What external options could help? Are there leadership opportunities in other companies? What are the open vacancies Nick can apply for?
  • Threats: What challenges may happen? This could be fear of financial instability.

The most valuable insights come from understanding where you feel your impact is missing and what changes to your work environment could improve this.

Goal setting: draft your first career plan with goals and information from self-assessment

Define short-term and long-term goals to have a vision for today and the future. Include a goal, timeline, and how you will measure success. Break a goal into smaller and more manageable tasks for easier perception and to beat procrastination. 

In a new position, Nick can become more involved in strategic meetings or leading projects closely tied to a product’s core. Instead of generic intentions like “I want more impact,” Nick should aim for specific results. For example:

  1. Short-term goal: Start contributing to new projects that directly affect the product’s end result within the next six months. The success indicator: contributing to the monthly release of a product.
  2. Long-term goal: Fully transition into a career with more control over product strategy and development tasks within two years. The success indicator: taking the head of the product role.

Stepping out of your comfort zone: networking and extra activities

Engaging in new activities or meeting new people can take you out of your comfort zone and help you discover new sides of yourself. In Nicks’s situation, new activities may be around developing a growth mindset. Nick feels demotivated by difficulties, such as not landing a new job or failing to shift into a more impactful role immediately. Self-coaching will boost resilience through a growth mindset. This means viewing failures as learning opportunities rather than barriers.

An external feedback is usually a missing piece in self-coaching. If you can ask friends, family, or colleagues for feedback about your behavior, grab the opportunity. For example, conversations with industry leaders provide insights Nick might not learn on his own, specifically about career transition moves.

“In the absence of the ability to pull regular feedback, I would recommend tracking the progress of goals set up at the beginning of each week/month by identifying three categories: what goals were achieved, what was the key learning from working on the goal, review of mid-term goals and their relevance to potentially changed circumstances.”
Pasha Cherednychenko, a career expert at Amy, with two years of coaching experience and the main area of expertise in Work-Life Balance 

Being consistent: stick to the plan, measure results, and celebrate your success

Be consistent with your career plan and goals-related activities. Practice makes perfect. Acknowledge every achievement, small or big. These wins can provide a sense of accomplishment and encourage you to keep up with the pace, no matter how gradual the progress seems. As the cherry on top, treat yourself to a cherry cake, to celebrate.

When career coaching is more beneficial

While self-coaching offers autonomy, there are moments when working with a professional career coach is more beneficial. You may feel stuck and lack confidence in your job search strategy, like Nick.

In general, if you face any difficulties you cannot handle alone, try guidance from a career expert who will help you throughout the journey. 

“When I think of career coaching, acceleration and dynamic learning come to mind. In my experience,  regular and focused work with the coach creates a sense of urgency and accountability, which is much harder to achieve when you work by yourself.”
Pasha Cherednychenko, a career expert at Amy, with two years of coaching experience and the main area of expertise in Work-Life Balance 

Here’s when it makes sense to collaborate with a career coach:

The image of when it makes sense to collaborate with a career coach
  1. If self-doubt is overwhelming and you can’t cure imposter syndrome, a coach helps boost your confidence as they use evidence-based techniques. This is crucial for Nick as he feels he is underqualified for roles in his goals. A career coach will help him recognize and communicate his strong sides. 
  2. If you have assessed your skills and set your goals but still don’t know the next step, a career coach helps you gain clarity. They will ask questions that uncover recurring or hidden patterns in your experiences and provide insights for the future. Nick can’t see why his job search is ineffective. Together with a career coach, they will identify that he is applying for roles that don’t match his skillset and reveal fears holding him back.
  3. Motivation to follow your commitments affects the results. Successfully coaching yourself requires the discipline to confront problems on the way. Moreover, you may feel isolated. If you face a particularly tough challenge—like changing a career direction—having a career expert and personalized guidance can make the difference. In Nick’s example, a career coach will help him explore side gigs or transition gradually while maintaining income.
  4. We are often too hard on ourselves. We tend to abandon well-being and only focus on achievements, running faster and reaching more. Such an approach results in burnout over time. A career coach can help you escape the harmful, unhealthy cycle of self-criticism and overthinking. You will focus on small, actionable steps rather than jumping into huge tasks that can lead to further anxiety and frustration. By breaking down your goals into manageable parts, you can progress steadily toward your expected results. “A bird in the hand is worth two in the bush,” they say.

The primary benefit of a career coach is the accountability they provide. A career coach ensures you stay on track by holding regular sessions and navigating you through challenges, specifically to revise and follow through with your strategy.

A hybrid approach: self-coaching with professional guidance

Self-coaching and professional coaching don’t have to work in isolation. You have a choice to begin with self-coaching, gain valuable insights through self-reflection, and then turn to a career coach when you hit a roadblock.

A hybrid approach could look like this:

  1. Self-coaching to reflect, set initial goals, and start making small changes at work.
  2. Collaborating with a career coach when challenges occur, such as financial fears or a lack of confidence in making a change.
  3. Returning to self-coaching techniques regularly while using a coach periodically for significant transitions.

Give it a go! Start with career self-coaching

A career coach can highlight what you may not notice, offer an objective view, or give you a hand at a difficult moment. Besides, you can first consider the library of free self-coaching exercises at Amy with timing and expected outcomes after completion. The good news is that we also save your progress on the platform. After all, if you feel confused about your career path, setting goals, and which strategies to implement from the number of resources, professional career coaches are here for you.

Personal SWOT Analysis: How to Identify Strengths and Weaknesses for Career Growth

The SWOT analysis defines your strengths, weaknesses, opportunities, and threats. SWOT helps you understand your capabilities and areas for development. And uncover your superpowers! On top of that, you will be prepared for obstacles. Identifying threats lets you strategize solutions in advance and cope with a clearer vision.

This technique is valuable at any career stage, whether just starting, looking to advance, or navigating a career transition. Drawing SWOT may take time in addition to saving notes in an appropriate place, but you can simplify the process by practicing on the Amy platform.

The image of the Personal SWOT Analysis exercise on the Amy platform

What do you need to do for the SWOT analysis?

When taking the exercise on the platform, consider strengths and weaknesses as internal areas. Opportunities and threats belong more to external factors.

  • For strengths, you will be asked to recall at least three situations you were successful at, what motivated you, what made you proud of yourself, and what was the best part of this experience. For weaknesses—in what areas do you feel you lack expertise?
  • Opportunities shed light on what options are open to you now. How can you turn your strength into opportunities, given your life context? Threats are about the points that may affect your role, job, or industry. And any personal challenges that may slow your progress.

How can you benefit from SWOT?

As a result of the SWOT analysis, you have:

  • Your strengths and opportunities mapped
  • Steps you can take to address threats
  • Action items to progress in achieving your career goals
  • Overview of your values

For a detailed analysis of values, the platform correspondingly offers two exercises, Your Life Values and Your Work Values, to identify what truly matters to you in your personal and professional life.

SWOT analysis example

The example of Emma, a UI/UX Designer, might support you in your SWOT.

Strengths

What was the situation in which I was successful and proud of myself?

“In a limited amount of time, I delivered a user-friendly design mockup to a demanding client. They came back with great reviews and recommended me to the company they collaborate with.”

What are my strengths?

  1. Vast experience in product design, particularly in big tech companies, which enhances credibility and expertise.
  2. Consistent positive feedback from clients and customers, indicating a solid ability to create user-friendly designs that simplify their experiences, especially in the FinTech sector.
  3. Demonstrated success through proven use cases, which can be showcased in my portfolio to attract new clients or employers.
  4. High level of dedication and commitment to my work, resulting in high-quality outcomes.

Weaknesses

In what areas do I lack expertise? What tasks do I find challenging?

“I aim to improve at trending design and AI technologies but lack effort for learning activities. I sacrifice all my time for projects, and I cannot say “no” to them because of the many tasks on my plate already.”

What are my weaknesses?

  1. Struggle with assertiveness, which may affect communication and collaboration with team members or clients.
  2. Tendency to overwork and prioritize responsibilities and reputation over personal well-being, leading to potential burnout.
  3. Difficulty tolerating criticism, which can impact professional growth and feedback acknowledgment. 
  4. Preference for stability and reluctance to take risks, making it challenging to transition to new roles or environments.

Opportunities

What opportunities can you take advantage of?

  • Exploring freelance opportunities could provide flexibility and improve work-life balance while leveraging my extensive experience.
  • Moving to a smaller company with fewer responsibilities may reduce stress and provide a supportive environment for growth.
  • Investing time in developing assertiveness and coping strategies for criticism could enhance interpersonal relationships and professional growth.
  • Engaging with other professionals in the UX/UI field could open doors to new opportunities and collaborations.

How can you connect your strengths and opportunities?

“My extensive background in design will make me a preferred candidate in the job market, particularly for smaller companies needing self-management and freelance clients seeking a trustworthy collaborator.” 

Threats

What external and personal factors could pose threats to my career path?

  1. Overworking and sacrificing personal life for career responsibilities may lead to burnout, impacting performance and overall well-being.
  2. Changes in the job market or industry standards may require adapting to new skills or roles, which could be challenging, given my preference for stability.
  3. Being inflexible about career changes might prevent me from adapting to new job market trends and opportunities.
  4. Increased competition in the UX/UI design field, especially with the rise of freelance platforms and remote work, may make it harder to secure desirable positions.

How can I address the threads with three small steps today?

  • I can write down my 5-10 work achievements to boost my confidence and add those items to my CV. 
  • This week, I can practice saying “no” to set boundaries without feeling guilty. For example, if my colleague asks for help with something I can’t take on, I will politely decline and explain why (because I am extremely busy with three other projects). 
  • I can talk to a career coach to figure out the reasons and patterns for my poor work-life balance and start following a smooth approach to enhance it.

This SWOT analysis highlights strengths in experience while addressing areas for improvement, such as assertiveness and work-life balance. By taking opportunities like freelancing and skill development, Emma can navigate the threats of burnout and competition while progressing in her career.

Take a step forward for your career plan

Identify your unique skills, recognize areas for improvement, expand your reach, and prepare for challenges—it’s all about SWOT, and you can nail it with a career self-coaching exercise. The analysis will then serve as a trustworthy groundwork for a career plan or roadmap we will discuss in later articles.