Career Development Conversations: Why and How to Hold Them

According to a study by Ipsos Karian and Box, recent studies showed 29% of Singaporean workers are planning on leaving their current employer, with only three in five workers proud to work for their current employers.

Some of the reasons cited include lack of career progression, manager behaviour, and lack of motivation, which really seems such a pity given that these can be alleviated through quality career development conversations between bosses and workers.

After all, good staff leaving for such reasons is a lose-lose situation on some level: the employee has to take time and energy to look for a new role and adapt to another working environment and job.

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On the employers’ end they lose someone who is already well-versed with the job scope, could be incentivised by simply being made aware of their value to the organisation, and also having clarity on how staying could be beneficial to them and their career development.

Here’s some advice for both sides of the fence.

How employers can have career conversations to engage and motivate your workers

Before a career conversation meeting

Make sure this meeting agenda is specifically for your employee or staff, rather than an addendum to another meeting, so they know the importance of having such career conversations, and that your goal is to understand their career aspirations and how your organisation can support them.

Ahead of the meeting, ask your employee to think about the answers to these four questions:

1. What is your career goal? (This is where you want to be, in the future. It may be in 5-10 years’ time, or it may be the ultimate destination for your career.)

2. What are the best possible next steps towards that goal, in terms of job roles? (There may be only 1 clear option, or there may be 2-3 possibilities.)

3. What are your development needs, to prepare for your next role? (Try and be as specific as possible.)

4. What’s the one development need to focus on, that will really make a big difference?

Start considering what you and the organisation can do to help your workers reach their expected goals, as well as the job descriptions, career paths, and skills they would need to consider to get there.

During the career conversation with your employee

This meeting should be pillared around those four key questions you asked them. Listen to their responses carefully, and make sure to get these 3 points across:

• You are the employer/manager, and you want to help your worker/subordinates develop their career. But ultimately, they are also responsible for taking the steps to get to where they want to be.
• The point of this conversation is to discuss and agree on how your organisation can help them in a structured and clear way. This way, both parties can track the staff/employee’s career progression. Your role is to be a coach, manager, and mentor, and as such, there should also be regular feedback systems in place for you to learn how to do these roles better as well.
• Whatever career aspirations you have to factor into the overall company/organisation’s business needs.

After the career conversation with your employee, what next?

With your employee, work out the actionable insights and the short, medium, and long-term actions to take to reach their goals. Then, schedule further career conversations to track this. Usually, once a year is sufficient, but for some workers, it may be good to meet every six months or even quarterly.

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How employees can have career conversations to ensure their jobs can better help reach their personal career aspirations and personal goals

Before a career conversation meeting

• Start having a clear understanding of where you are professionally, and where you want to be in the future. This will help you verbalise your career and personal goals and build a development plan towards hitting them.
• If your bosses don’t have any questions ahead of the meeting, try answering these questions ahead of time:
  • Where are you now, and what tasks in your job do you find energising and draining?
  • What are your professional skills currently, and are they at the level you need to be at for your current goal? If they are, what other skills do you need to take your career to the level of progression?
  • What’s important to you in the long term? What are your values, and how do they fit into your career?
  • What is success to you? Do you prefer to be an individual contributor or a manager of others? Defining this will help your manager/employer understand your ambitions and create a better progression path for you.

During the career conversation with your employer/manager

• Try to start the conversation on a positive note, along the lines of giving appreciation for them taking the time to speak with you on this, and state clearly that you’d like to build a plan to develop your career in a way that aligns with your team and organisation’s goals.
• Share the realisations you have about your career aspirations and personal goals that you reflected on earlier, what you’ve found fulfilling, and what you’d prefer to change and develop in new ways.
• Mention your achievements so far and how they’ve helped your team and organisation, and then discuss how you can do more in the same vein and what you might need to do so.

After the career conversation with your employer/manager, what next?

• After the conversation, write up what was agreed upon in an email and send it to your manager. Try to do this soon while what was discussed is still fresh in everyone’s minds.
• Ask if you can check in on progress, either in additional follow-up meetings or during performance reviews throughout the year.