How to Have Effective Career Conversations

How to Have Effective Career Conversations

By Jen Oleson, Manager, Operations, Career Management

A career conversation is a critical tool used to engage employees and support organizational development. Gallup suggests that leaders can increase engagement and productivity on their teams by providing more meaningful feedback and support. Holding effective career conversations is a strategic way to do this.

So, what establishes an effective career conversation? It’s crucial to understand that a career conversation is not a performance review or one-off chat. Each meeting should be an intentional discussion to learn about employee goals, align their aspirations with organizational goals, and enhance employee engagement. Exploring conversation themes that identify an employee’s satisfaction or dissatisfaction in their role, readiness for role enrichment, or new position supports having effective career conversations. People First Career Management consultants recommend considering the following elements to have more effective career conversations with your employees.

  • Prepare for the conversation
  • Ask the right questions
  • Move the conversation to action
  • Summarize next steps

Prepare for the conversation

Preparing for a career conversation sets the table for more meaningful discussions and ensures you can guide the conversation and keep it on track.

Plan to keep the conversation informal. Pick a setting that doesn’t give the impression that the employee is heading into a performance review. To do this, avoid booking a formal meeting room and instead consider going out for coffee or lunch. If you’re working remotely, you can host a virtual conversation. Arrange a coffee or lunch delivery to your employee to provide a similar feeling as going together in person. If you’re going to meet in the office, look for an informal meeting space.

To have a productive conversation, it’s also valuable to review the conversation themes ahead of time to determine the purpose and establish an outcome of the conversation. Providing the employee with a chance to prepare is also valuable. When you send the meeting invite, share an overview of the purpose of the conversation and the questions you plan to ask.

Coworkers talking at a coffee shop

Ask the right questions

Talking about an employee’s career plans can clarify uncertainty and align individual and organizational goals. It allows you to gather information, identify obstacles, and establish the next steps in their professional development. Asking the right questions and encouraging your employee to be accountable for their career development is key to a successful conversation. More importantly, it shows your interest in their career by building connections, identifying employee interests and opportunities, and fostering a learning environment within the organization.

Questions to consider in your next career conversation include:

  • What do you enjoy most and least about your current role?
  • In what settings or circumstances do you think you make the greatest contributions?
  • What would you like to learn this year and why?
  • What are some successes you’ve had in your current role that you’re most proud of and why?
  • What projects, responsibilities, or positions are you interested in and empower you to pursue your career goals?
  • What can I do to help you progress towards achieving your career goals?

Plan to ask open-ended questions centred around self-reflection and self-discovery to keep the conversation focused on the employee’s career development. This can provide insight and direction for what steps you can take to assist with the employee’s career development.

Move the conversation to action

To have an effective career conversation there needs to be action afterwards. After talking about the employee’s career goals, focus the conversation on what you can each do to help reach those goals.

Often these discussions result in a manager providing the employee with additional resources and information to support their career development journey. Whether you’re introducing them to other people in the company or providing development resources, you need to gather and share that information right away. Other follow-up considerations for managers include:

  • Providing constructive feedback and insights on how to proceed with career plans.
  • Looking for opportunities to align employee development with the organization’s goals, and
  • Offering information about potential career paths available within the organization.

Follow up considerations for an employee could include:

  • Finding professional development training opportunities that interest them and align with career goals.
  • Asking for feedback and putting it into action right away to enhance their development and take ownership of their career.

Assigning follow-up items to yourself and your employees shows them that you genuinely support their career development and care about their future with the organization. It also encourages the employee to take ownership over their career development.

Manager and employee talking at a table, with coffee cups and snacks. Manager is sitting causally with one leg crossed over his knee.

Summarize next steps in the wrap-up

As the conversation comes to an end, take a moment to summarize what you heard, confirm the next steps in terms of actions the employee should take, and set a date for a follow-up. Always close with encouragement and appreciation for the time and effort the employee took to prepare for the discussion.

Career conversations are an easy yet effective way to support your employees, learn about their goals and provide feedback. But an effective career conversation only happens when both the manager and the employee are prepared. Using the advice above, you can hold better career conversations with your employees. For additional support, contact us to learn how People First’s career consultants help managers and employees participate in effective career conversations.


Jen Oleson
Manager, Operations, Career Management

Jen believes that adopting an intentional and focused approach to one’s decisions and choices can lead to a more fulfilling and purposeful life. Her purpose and passion are to serve, inspire, and empower people and organizations to achieve their goals.

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