How to Talk to Your Team About Career Development

Authors: Rebecca Fraser-Thill and Shuba Gopal

When you step into a leadership role, it becomes your responsibility to help your new team members determine their career goals, grow within your organization, and continue to feel engaged at work. But often career development conversations between managers and their employees don’t happen until it’s too late—only after the employee has already decided to leave the company. Since the pandemic, workers have been even more likely to leave their organizations if they cannot see ways to grow professionally. Lack of career development consistently ranks among the top reasons individuals leave their current positions.

Managers typically aren’t trained in how to talk about or foster career development, but it’s important that you make it a priority as you take on your new role. By discussing career development with your direct reports early and often, taking a personalized approach, and implementing small career-oriented experiments to support them, you can help retain top talent and put your team on a positive path forward.

Talk About Development Early and Often

In a closed study of three mid- to large organizations (1,000 to 10,000 employees) in the life sciences, one of us, Shuba, found that the best timing for career development conversations is when a person has been in their role for 12 to 18 months. By their two-year work anniversaries, 30% to 40% of employees at these organizations were already searching for the next steps to take in their careers. If they couldn’t take those steps internally, they left. On the other hand, when career development conversations were well-timed, employees’ tenure nearly doubled. For example, in one organization, the average tenure increased from 3.1 years to 5.4 years after career development programs were targeted to employees before the two-year mark. The impact was seen across all types of employees, regardless of role, seniority, age, gender, or otherher demographics.

It’s also important that these conversations are frequent and regular. Talking about development annually, or even once a quarter, can feel like a meaningless add-on at best. Instead, you should aim to have career development check-ins with each of your reports once a month. One easy way to do this is to set aside 15 minutes at the start of one of your scheduled one-on-one meetings. While 15 minutes doesn’t feel like a long time, it’s better to be consistent with these meetings and have them briefly than to put them off for a “better time.”

You should also consider the placement of these conversations within your meetings. Waiting until the end of a meeting can signal that the conversation isn’t important. It also makes it likely that the topic will be bumped to another day, perhaps indefinitely. Starting your meetings with career development reflection, however, shows that the importance of these discussions trumps the urgency of any short-term tasks.

At first, in the crush of deadlines, feedback needs, and productivity pressures, you may have to remind yourself to talk about career development with your team. With practice, though, these interactions can become more natural.

Ask Questions and Follow Up

Having your first career development conversation with a direct report can feel intimidating. If you’re anxious about it, think about how you would ideally like your manager to have this type of conversation with you. What would help you feel seen and heard? When in doubt, lean into what you already know about building rapport; express your interest in their passions, aspirations, and unique ways of doing things.

Every person has a different definition of what growth looks like. But many managers assume that everyone has goals tied to extrinsic rewards, such as upgraded titles and higher salaries. While these are important, for many people, they are not sufficient. In fact, most employees seek meaningful work—a combination of contribution, belonging, and purpose that is completely subjective. Given that meaningful work is highly specific to the individual, the key to supporting career development is getting to a person-centric understanding of each of your direct reports.

One way to start having more individualized conversations is to send out a prompt in advance of your one-on-one meetings with the goal of better understanding your direct report and their goals. Here are some questions you might include:

• If you were offered the finances and time to have work-related training on any topic, what type of course would you choose? Why?

• When you think about your typical workweek:

  • Which activities do you look forward to doing the most? Why?

  • Which activities energize you the most while you’re doing them? Why?

  • Which activities do you find challenging in the moment, but highly fulfilling after they’re done? Why?

• When you think about your skills, which do you enjoy using? Which would you rather not use frequently in the future?

• What outcomes from your work feel most fulfilling to you?

When you discuss their answers during your meeting, be curious. You can gather more information and help your direct report dig deeper by following up with questions like:

• Can you tell me more?

• Is there anything else?

• I hear you saying . . . Is that accurate?

• I’m wondering what you mean by . . . ?

• So, for you, what would it look like to . . . ?

The most important thing is to shift your mindset around the manager-report relationship. It shouldn’t be centered on performance supervision and task delegation. It should be about your individualized support of each team member.

Design Small Experiments

Once you understand more about your direct report’s individual preferences and goals, you can translate that into customized development plans. Try implementing small experiments, relatively simple changes to a person’s workweek that would allow them to try or learn new things. For instance:

• Consider inviting a team member to attend certain meetings that you typically attend solo, such as strategy sessions or IT-focused meetings. This can be an opportunity for them to learn new processes and make more connections across the organization.

• Think about any classes, conferences, or training that might match your direct reports’ interests, and encourage them to come to you with their own ideas. Ideally, these could be supported with organizational professional development funds.

• As new projects emerge, take a moment to consider who would be most excited to get involved. You can start to practice delegating based on a deeper understanding of your team members’ interests, instead of purely based on role or past habit.

• Consider light task swapping among members of your team. For example, you might say something like, “You want to develop a skill that Jon has, and you have a skill that Ella wants to learn. What might it look like for Jon to loop you in more, and for you to share more often with Ella?” (Read more about task trading in the next chapter.)

At some point, you may need to enlist the support of higher-level supervisors and HR, especially as these small experiments expand over time. Still, the most effective way to start is small. The goal isn’t to commit a direct report to a massive shift, such as a new role in a new team, but rather to give them brief opportunities to try out their career development ideas in practice.

Start designing these work experiments with your team members about a year after they join your team or have been in their current role. Your team members will feel more engaged in the moment, have the opportunity to gain hands-on data about the ways they most effectively add value to your team and organization, and feel highly supported as an individual. That’s a powerful recipe for long-term retention and productivity.

If and when your direct report gains the skills and experience they need to advance, you will have done your job: setting them up for success in a role they find meaningful and engaging.

Rebecca Fraser-Thill is an ICF-certified career design and leadership coach who owns a Maine-based private practice. Drawing on two decades of teaching and research in psychology, she coaches clients around the world on their management, delegation, and communication skills, and supports job crafting and career decision-making to optimize engagement and impact. Her coaching has been featured by the BBC, Business Insider, Forbes, and Bloomberg Businessweek, among other outlets. Shuba Gopal is principal at Glean Signals LLC, based near Boston. She applies data science and analytics to solve key challenges in the workplace, identifying patterns that help people thrive at work. She then works with organizational leaders to translate those patterns into high-impact actions with measurable outcomes. Her work has been showcased at the Wharton People Analytics Conference, NEHRA, LeapHR,and other venues.