5 Career Conversation steps for you to engage your supervisor

Talking about your future aspirations and career direction with your supervisor is usually a conversation of walking on egg shells or avoiding pitfalls. Some common concerns include:

Concern 1: You are concerned about sending the wrong signal of disinterest or disloyalty when talking about your career.

Concern 2:  You are unsure about what you want in your career, so you wonder how much should you reveal to your supervisor.

Concern 3:  You don't feel comfortable or safe to discuss about your career with your supervisor.

Given these concerns, how can you have an honest career conversation yet not ruin your prospects in your current job? Read on to learn more about how to have effective career conversations with your supervisor.

Step 1: Clarify your own career aspirations

Step out of the "hamster wheel" of work and life for a moment to take stock of where you are and where you hope to be. Your career aspiration is not about the next job or the next industry; it is about the next enhanced version of you!

Recall your past experiences and how you have grown through them in terms of self awareness and proficiency. Start to connect your past with your present to create a future by digging up past ideas, dreams, hopes and pairing them with your experiences, proficiency to create possibilities for the future.

Pro Tip:

1. Create a Personal Career Map comprising:

   1. Tasks that you enjoy, your strengths, what matters to you and what you want to be known for.

   2. Recurring patterns and themes that have been there in your life.

   3. Current life stage, priorities and obligations

   
   

2. Use objective measures like profiling tools, inventories to help you frame your thoughts

   1. RIASEC career assessments

   2. Gallup StrengthsFinder

   3. Workplace Big 5 OCEAN

      
      

Step 2: Engage your closest, most important people first

Every good performance comes as a result of many practice rehearsals. Therefore, the first person to talk to with regard to your career aspirations should not be your supervisor! Instead, consider the many other important people (eg. family, spouse, partner or even friends) who are part of your life and can be part of your conversation, especially if they will be impacted by your career decisions.

Speak with the people who are close or important to you about your emerging and preliminary thoughts about your career aspirations. Encourage them to question and enquire further about your motivations. Be open and honest as you clarify your own desires and hopes. This process will help you clarify and sharpen your own thoughts and translate your thoughts into a vocalised expression of language.

Pro Tip:

1. Consider to involve people outside of your close circle too, they could bring different perspectives too.

   1. Your peers, former bosses, colleagues

   2. Your network, mentors, advisors

      
      

2. Share your Personal Career Map with those who know you, working together to:

   1. Validate your thoughts and contents

   2. Pose questions to you about your thoughts using "what", "who", "when", "where" and "how"

   3. Seek out blindspots and unknown areas

Step 3: Examine your workplace

Every workplace is not just a place where you work and contribute. It is a place of resource support and growth opportunities. Every new business goal, new project, new process, new department that brings about uncertainty also creates opportunities to learn and grow.

Reach out to your HR or learning development team to understand more about learning pathways, career tracks, learning and development programmes and support within your organisation. Pay attention to how the business and the priorities of your organisation is changing - what is emerging and where is the company headed?

Pro Tip:

1. Look beyond your organisation, tap on public resources and information to explore opportunities

   1. Stay aware of emerging and transferable skill in various industries (Eg. SkillsFuture SG's dashboards)

   2. Utilise learning subsidies, training vouchers, credits (Eg. SkillsFuture Credit, UTAP)

   3. Explore career conversion programmes (Eg. Workforce SG career conversion programmes)

   4. Reach out to someone from the industry or sector you are interested to learn about (eg. Workforce SG's Volunteer Career Advisor)

      
      

Step 4: Consider the psychological safety of discussing your career aspirations

Supervisors typically avoid discussing career aspirations because they fail to see how it could translate into immediate outcomes for the business. They may also be worried about creating disappointment and losing you if your career aspirations cannot be fulfilled by them or the department's direction. Hence it is possible that some supervisors may apply avoidance, tokenism towards your career conversation.

Test the receptivity of your supervisor by enquiring their comfort level to discuss about your career aspirations. Remember that they may not have had conversations about their career aspirations with their own past and present supervisors hence this may be something new for them. Make an effort to explain how having this career conversation will help you to become a more productive and effective worker for your present job role.

Pro Tip:

1. Read the room by assessing your workplace environment and culture and how others fared in their attempts to engage supervisors for career conversations.

   
   

2. Observe the personality, management style, work load of your supervisor to gauge an appropriate time to reach out

   
   

3. Utilise AI to generate some conversation prompts to help you assess your supervisor's receptivity and increase the chances of having the career conversation

Step 5: Engage in career conversations, starting with the big picture, ending with actions

Career conversations differ from performance appraisals in terms of focus, with the former being developmental, forward looking, exploratory in nature and the latter being retrospective, evaluative centric. Therefore it is important for you to take the driver seat and set the right context for your career conversation.

Start by sharing the big picture of your life, your circumstances and your emerging thoughts about your work in future. Overlap your work experiences in your role and how you see your current role / department / organisation to be places to help you move towards how you see yourself in the future. Invite your supervisor to share feedback, ideas, opinions as honestly as possible. Express tangible and practical ideas you came up with to be applied within your role / department / organisation and invite your supervisor to validate them or co-create new ones with you. Set some timelines and agree on a followup arrangement to monitor your progress.

Pro Tip:

1. Use a framework to guide your career conversation structure and flow.

   1. Refer to guide references created for employee career conversations (eg. Workforce SG's Career Conversation Guide)

      
      

Remember that while it is good for you to engage your supervisor in a career conversation, it is not a deal breaker if it is not possible to do so with your supervisor. Your life ahead and your future career aspiration is yours and it deserves to be deliberated and discussed with many people beyond your supervisor, such as mentors, your network, your family, friends. The more you engage in thinking, discussing about your career aspirations, the more likely that you will receive feedback, advice, guidance, support, validation to finetune and refine your aspirations.