Career discussion with your employee - Deepstash
Career discussion with your employee

Career discussion with your employee


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Career discussion with your employee

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1. Don’t cancel or reschedule the career session

This tip is easy – unless unavoidable, do not cancel or request to reschedule the career discussion meetings. Your report has most likely spent time planning for the meeting, and this meeting is probably on the top of their mind. By cancelling or rescheduling, you are essentially reflecting priority of this meeting to be lower for you, which will impact the trust the employee has in the team or company. In a survey of 10.5K job changers, conducted by LinkedIn, “concerns for career development” was cited as the top reason of leaving the job.


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2. Prepare for the professional development meeting

It is usually the report’s responsibility to share the agenda for this meeting, however, don’t be a silent spectator. Familiarize yourself with the agenda and come prepared to the meeting for an active discussion. Take the time to review the agenda ahead of the meeting and contribute to it, if needed. This is a great way to show that you care and would like to invest in your report’s career growth (which you should!).


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3. Provide feedback during the meeting

Career discussion meetings are a great forum to give informal feedback to your reports. The idea of the meeting is to work together towards achieving your report’s career goals and retrospective feedback is a key component to that. If needed, gather feedback from your report’s co-workers and stakeholders ahead of the meeting and combine that with your own personal feedback for them. The feedback should be well rounded and should clearly outline their superpowers (something that they are good at), accomplishments and scope of improvement (skills that they should be improving).


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4. Understand your report’s motivation

‍Every individual is motivated by different things – working towards the next promotion, getting to flex a specific skillset, the team vision, the people, or money. Knowing what keeps your report going will help you customize your discussion and opportunities to fit with your report’s vision and their professional growth. If your report wants to build a product, then presenting them with opportunities to build a team will not help them achieve their goals.


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5. Drive the meeting agenda to arrive at expected meeting outcome

It is very easy for career discussion meetings to turn into mentoring sessions or philosophical – this often does not lead to actionable results. While this is a good time to mentor your report or share relevant feedback, it is important to stick to the agenda and ensure that you’re driving towards achieving the expected outcome. If you think the end outcome cannot be achieved, communicate that to your report as soon as possible to reset expectations.


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6. Build SMART goals

SMART (Specific, Measurable, Achievable, Relevant and Time-bound) goals ensure that the employee is setup for success and the goal will be met in a certain time frame.

You can create SMART goals by using the following mental model –

  • Use specific wording
  • Include measurable goals
  • Aim for realistically attainable goals
  • Pick relevant goals that relate to your business
  • Make goals time-bound by including a timeframe and deadline information


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7. Implement a follow-up mechanism

This holds the key to a successful career discussion. Once you and your report have outlined the career development plan, discuss what mechanisms should be set to enforce the plan. The type of mechanism can be a personal choice. A few ideas of a follow-up mechanism are 

  • The classic - Monthly check-ins: Setup 30min monthly check-ins 
  • Asynchronous meeting: Use a collaborative tool to capture the milestones and next steps discussed in the career discussion meeting and keep updating the document as progress is made.


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