Don’t Run From Career Conversations

Talking to employees about their abilities, interests, and opportunities is critical. These five steps can help.

Why do so many managers steer clear of career conversations? Our research tells us that there are a variety of reasons. Do any of these sound like the familiar words you might say to yourself when one of your direct reports asks for such a discussion?

  • No one, let alone me, knows what the future holds.
  • It is just not the right time.
  • I’m not prepared.
  • I wouldn’t know what to say.
  • We’ve just reorganized. It will be a while before anyone knows anything about career possibilities.
  • I would never open something I couldn’t close.
  • I don’t know enough about what’s outside my department to offer advice.
  • I don’t want anyone blaming me if they don’t get what they want.
  • Why should I help? Nobody ever helped me.

These thoughts are understandable. However, this is such a critical conversation that it should not be avoided. What your employees really want is a chance to talk to you about their abilities, interests, and possibilities. They want you to listen. They don’t expect you to have the answers, but they expect (and really want to have) the dialogue. Here are five simple steps that will support your employees’ search for a good career fit and demonstrate that you care about developing your people.

Step One: Identify Their Abilities

The primary objective of career conversations is gathering information that will tell you more about your employees. It is frequently difficult for employees to talk about their skills, values, and interests. Open up a dialogue that gives you and your employees an opportunity to become more aware of who they are both professionally and personally.

To get them talking, ask questions that help them to think more deeply about their unique capabilities. Your job is to listen while they answer, as a diligent researcher would. Probe, inquire, and discover more. Here are a few questions you might ask:

  • Which assignments have most challenged you? Least challenged you? Why?
  • What part of your education or work experience has been the most valuable to you over the years?

Step Two: Offer Your Feedback

Helping your employees to reflect on the feedback they’ve gotten from others, and on the areas they need to develop is essential. Frequent feedback is critical.

Think back to that last performance review you gave. It probably was based on past performance and connected to that employee’s salary. Development feedback is different. It is future-oriented and focused on areas where the employee can improve.


Employees want specific feedback with examples of their performance and the effect on their future goals. Have them seek out people in other parts of the organization who can give them a more realistic self-portrait to help them develop faster and smarter.

Think about all the awkward conversations you’ve had with employees whose career goals are simply out of sync with reality given their strengths and weaknesses. Remember, the absence of honest feedback probably caused this in the first place. Employees continually tell us that they want straight talk. Want to keep them? Level with them. Here are some questions you might try:

  • If you asked three people in the organization to give you feedback on your greatest strengths, what would they say?
  • What would you say are the most critical areas I would select as essential in your current position? How would you rate yourself in these areas?

Step Three: Discuss Workplace Changes

Helping your people consider their options means helping them look beyond your department to detect shifts and changes that might impact their careers. You will need to be aware of your company’s growth areas and limitations as well as changes in the skills that your industry will require.

You don’t have to take this all on your own shoulders. You do have to ensure that your employees know what’s going on in your organization. By suggesting others who can provide additional perspectives on these issues, you open channels for your employees and give them a closer look at the key business needs of the organization. Have you done this lately? Perhaps these questions will stimulate a good dialogue:

  • Are you optimistic about the organization’s future? What are the specific reasons you feel this way? Do you see new opportunities for yourself?
  • What do we need to get better at? Faster at? Smarter at? What implications does this have for your career?

Step Four: Discover Multiple Pathways

Helping your employees consider multiple career goals while they grow within their current positions is a key element in development. When employees analyze their potential development goals in terms of business needs and the strategic intent of the organization, everyone wins.

One caution: The employee is still primarily responsible for his or her career. Our suggestions do not mean telling the person what to do. Instead, offer choices for employees to analyze and consider. This is important, but sometimes difficult. For generations, the only acceptable career direction has been up. But there are several ways employees can move their careers along. You can help your employees consider lateral moves, exploratory assignments, and opportunities to grow on the job as well as the traditional vertical moves.


You can give your employees permission to discover the possibilities based on their abilities, their values, and what they can contribute to the organization. The more career goals your employee identifies, the better. The biggest career frustrations (and the most exits) occur when an employee’s only goal is thwarted.

Once you have helped your employees look at options they will feel as if they have more leverage to manage their own careers. You might ask one of these questions:

  • Which goals seem most in sync with where the organization is going?
  • Which goals will position you best for the future?
  • Step Five: Design a Course of Action

    A course of action increases your commitment and the employee’s commitment to the plan. Collaborate and brainstorm all of the steps your employee would have to take to realize the best choices. Develop contingency plans for each. Then, if one is blocked, the other paths will already be laid out. Work with your employees to identify the obstacles to each path, then brainstorm ways around the obstacles. During the process, help them to maximize the assets they already have.

    Remember, your job is to stimulate your employees into identifying skills, development opportunities, and knowledge areas required for each alternative. Your job is not to build their plans, but to support them! Try using one of these questions:

    • If you could give yourself the perfect assignment, what would it be?
    • Who would you like as a mentor or coach? How can I help you enlist his or her support?

    Keeping your employees on a continual path of growing, developing, and adding new skills will help you keep your competitive edge. You must help them discover the inevitable barriers that will get in their way. But they must overcome them and do the work. Help them build alliances and relationships to meet their goals. Any organization that ignores the ambitions of good people can’t expect to keep them engaged and productive.