A Better Way to Develop and Retain Top Talent

Author: Margaret Rogers

A Better Way to Develop and Retain Top Talent

Workers with capabilities that allow them to keep up with the rapid pace of change in today’s work environments—such as adaptability, technological literacy, and people management—are in steep demand. But employers are struggling to keep them on board.

One of your duties as a manager is to help develop and retain the top talent on your team. And in my experience, the most impactful development happens in small moments that occur within the workplace every day: on-the-job learning opportunities that are wholeheartedly catered to the worker’s unique needs and challenges.

It might seem impossible to offer every employee this kind of personalized training, but any company can do so at scale when managers create a learning environment. Here’s how.

Ask More Questions to Gain Insights on Employees

Just as a business must understand what its customers need to produce the most useful products, managers must understand what their employees need to give them ideal learning opportunities. Asking questions is the best way to do this.

Start by scheduling regular one-on-one meetings with each team member. In addition to using this time to check in on their current projects, ask them what skills they’re most comfortable with and which they would like to develop. Inquire about areas that feel especially challenging.

Here are a few examples you can use to kick-start that process:

  • What parts of your job are most interesting and rewarding?

  • What areas are you finding most challenging right now?

  • What are you doing to reach short- and long-term career goals?

  • Are there any other projects, committees, or additional responsibilities you would like to be a part of?

  • Is there anything else you’re curious about that you haven’t been able to explore yet?

In these meetings, practice active listening and try to come from a place of genuine curiosity rather than judgment. This means leaving your laptop closed and taking notes the old-fashioned way. It’s also helpful to repeat what employees say during meetings in your own words to ensure you are fully understanding their insights.

Create More On-the-Job Opportunities

Once you’ve identified the skills your team members want to learn, look for opportunities to help people develop them. Classroom-style training is a stellar foundation, but it can lose its effectiveness if it isn’t applied readily. “Learning moments” are an easier, quicker way to move the needle. These moments can be significant or small, but engaging employees in this way is key to helping them step outside their comfort zones, practice, and build confidence.

For example, imagine one of your employees is uncomfortable having tough yet necessary conversations. In a one-on-one meeting, he might express frustration about a peer whom he is struggling to collaborate with. You could take this opportunity to create a learning moment. This might be role-playing a tricky conversation or writing down a step-by-step plan of action. In this way, you are helping your team member practice and improve his communication skills in a safe setting (as opposed to simply sharing theoretical advice). The next time he comes across a similar situation, he will have tools to help him overcome it.

Treating every challenge your employees face as an opportunity for practice and growth—whether it is something personal, like improving communication skills, or practical, like learning a new technology—is critical to establishing an environment in which people believe they are valued enough as individuals to be given the time and space to flourish. It also gives managers the chance to help their employees effectively upskill and reskill on a case-by-case basis as new obstacles arise outside of formal trainings and in everyday work experiences.

Vary Learning Experiences

Consider which experiences will best cater to your direct reports’ needs. Factors such as the employee’s tenure, experience level, and adaptability are all variables that could impact your approach. Smaller opportunities—say, participation in projects where the employee can rely on more experienced peers for support—are best when a team member is unfamiliar with or new to a necessary skill. Bigger opportunities that require employees to take risks and stretch beyond their comfort zones are more suited to individuals who have prior experience carrying out a certain task; in these moments, they can put their skills to the test more independently and play a larger role.

Pretend, for example, you have two employees who express interest in public speaking and presentations. They both recognize it’s a valuable skill to develop as they work toward becoming leaders. From previous meetings, you know one of them is less experienced than the other and is therefore more nervous about speaking in public. This employee might benefit more from a small group setting, like a lunch-and-learn during which he gives a short presentation. Because the other employee has had more practice in this area, a lunch-and-learn would not be as valuable for her. Instead, you might have her fly solo and present on a topic at the next companywide meeting or at a conference in front of a larger audience.

Save the most significant opportunities for those who are ready. These have higher stakes—for the employee, the project, and the company at large.

The level of control employees have over their growth should also vary. You might encourage a more experienced employee to design or seek out their own opportunities for growth, but a less experienced employee often requires more structure in key learning areas. Either way, it’s crucial to allow employees a level of autonomy. When left alone, people will naturally find innovative ways to accomplish new things. Experimenting with autonomy also allows mistakes to be made—just as much as it allows successes to be had. This will help you identify skill gaps and brainstorm ways people can fill them.

Remember, safety is necessary when confidence is low, but pushing employees to the edge of discomfort results in real development.

Provide Regular Feedback

Feedback is perhaps the most valuable aspect of this process, and it starts with setting clear expectations. As your team continues to carry out on-the-job opportunities, work with employees to set goals to strive toward. Provide regular feedback on what they are doing well and where you see opportunities for improvement.

During this time, be patient. Reflect on the work your employee has done up to this point, making sure to discuss both successes and failures without judgment. If an employee tried something new and it didn’t pan out, recognize the effort. People are more likely to grow from their experiences when they aren’t punished for failure. (In fact, they’re probably kicking themselves already.)

In the same vein, you can ensure employees actively apply what they’ve learned by putting together a plan for improvement—whether that means creating clearer deadlines, helping them better manage their time, or thinking through difficult problems when they arise. Tracking personal metrics is also a helpful way for employees to measure performance and growth on their own time.

Manage Your Time

Employee development can be overwhelming, especially when you have a large number of direct reports. Take proactive steps to avoid ending up with an unmanageable workload. Before shaping opportunities, determine how much bandwidth you have. What level of involvement and support are you capable of giving as a manager, considering everything else on your plate? Setting realistic expectations for yourself is critical.

Not all coaching has to come from you. In some cases, you may be able to distribute employee-support tasks to informal mentors, other managers, senior leaders, or peers.


When leaders try to implement these user-centered principles in their interactions, experiment with them, and continually refine their coaching based on those findings, they not only will see astounding growth but will be able to effectively engage and retain top talent. Any company can begin by making a few changes to its managerial practices. It’s time for leaders to open communication channels and address each employee personally. Help your workers shape their learning and long-term contributions for the better.

QUICK RECAP

To develop and retain the top talent on your team, create an everyday learning environment.

  • Ask your employees what skills they’re most comfortable with and which they would like to develop.

  • Treat every challenge your employees face as an opportunity for practice and growth.

  • Consider which experiences will best cater to your direct reports’ needs.

  • Save the most significant opportunities for those who are ready, since these have higher stakes.

  • Provide employees with regular feedback on what they are doing well and where you see areas for improvement.

  • Set realistic expectations for what level of involvement and support you are capable of giving as a manager.

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