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The Employee Career Conversation: You've Got This, Manager

One statement I hear a lot from managers is “How do I go about developing my employee’s career? I know they’re going to come to me soon…” (accompanied by a panicked look.)

The panic is a result of the myth that managers have to have all answers ready for an employee who comes to them looking for their next step. This is simply not true, and not even possible without knowing their focus in the first place.

The key is open dialogue on career aspirations. These conversations build trust and demonstrate a genuine interest in the employee’s development. As an added bonus, employees are more likely to feel committed to an organization when they have a manager who is engaged and supportive of career development activities. Below are some tips and key questions you can proactively use to create a rich career discussion.


Career Development Prep Questions – Give these to your direct report before the scheduled conversation so they have time to prepare their thoughts.

  • Tell me about the projects you have worked on that make you most proud.

  • What activities in your job motivate you to excel? Which activities are most interesting to you?

  • What do you think your talents and skills are?

  • What are your short-term and long-term career goals?

  • What values are important to you? Can you apply your values at work?

Career Awareness – In the conversation, share the broader perspective that you have as a leader. You know more about opportunities in the organization; ask some key questions to see how you can connect the employee to the right projects and people.

  • Let’s talk about the organization’s and our department’s goals so you can see how yours ladder up.

  • What projects, committees or other responsibilities would you like to be a part of in order to develop your career?

  • Who are the people I know that could be helpful to you? If you don’t know them, would you like me to introduce you to them?

Skill Development – if they are looking for more ways to learn, ask specific questions to narrow the focus on resources.

  • What developmental experiences might help you progress toward your career goals?

  • What education or training might help you progress? Have you looked into tuition reimbursement possibilities?

Conversational Tips for You

Some employees may not feel comfortable fully sharing their career goals and aspirations with a manager. You can help put employees at ease by using the following tips:


Explain how your role as their manager can help them with career development and planning. As mentioned earlier, you may know about upcoming projects or experiences they are not privy to. Help open their world.

Demonstrate your comfort with exploration of opportunities outside their current role or team. The important thing to remember is that you are helping your employee grow. Would you rather have them grow into a different role or watch great talent walk out the door? Stay open.

Be supportive of an employee’s goal to remain in their current position. Not all employees immediately want a promotion or to shift departments. Help them (and yourself) think more horizontally than vertically about opportunities. Work with them to identify new goals and/or restructure current responsibilities.


Make silence your friend. If you’re asking the right questions, you’re going to make people think. They will be digging through experiences, making connections, and reflecting deeply on who they are. This might take more than a few seconds. Often managers don’t allow more than a few seconds for a response before jumping in with their own responses or more questions. Give employees the space and silence to consider the question and formulate a thoughtful response. You’ll realize a rich return on your investment of time.


Prove that you’re listening. Many employees have been conditioned to expect career conversations to go nowhere. The really important piece? What you do after the conversation. Make notes after even the most informal of career chats. Follow through on promises you made to talk to others and explore projects. Revisit the conversation with your employee, holding them accountable as well as yourself.


Be prepared that an employee may not have a career goal. Many people struggle to articulate where they see their careers going. Despite all the talk about employees needing to drive their own careers, many still look to their boss to light the way. If you’re not regularly connecting with your staff on how they want to develop with your company, you’ll risk having them look for the answer outside your organization.


It’s not necessarily about a title. In Dan Pink’s book Drive: The Surprising Truth About What Motivates Us, he shares that once money is off the table, humans are motivated by autonomy, mastery and purpose. If you focus your energy on giving your staff maximum autonomy around their roles, if you encourage them to develop their strengths and there’s a bigger reason “why” they are coming to work every day (beyond a pay check), chances are you’ll have people who feel like they are growing and developing.


Have an open-door policy. Being open to chatting with your employees about their career growth outside of an annual performance review can make the conversation more relaxed. You'll generate better strategies if the subject is regularly on the radar.

Today’s leaders need to be a combination of career coach (asking the right questions), career realist (balancing what a business needs with what an individual wants), and career ambassador (looking for opportunities beyond job descriptions and departments). Retaining key talent is really an exercise in shared success. Don’t let the pandemic or Zoom fatigue be excuses. Schedule some time today.










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