7 essential strategies for upskilling managers

1. Secure top leadership buy-in

HR leaders should make sure upper leadership is on board with managers' upskilling before the program starts. One way to convince them of the value of the training could be to discuss managers' effects on the company's success.

"[Managers are] absolutely critical to retaining talent, motivating talent, and keeping people engaged and on track to achieve goals and objectives for the organization," said Kacie Walters, people and development leader at Coalition, Inc., an insurance and cybersecurity company located in San Francisco and author of "Succeed From the Middle."

HR leaders should also ensure that upper management is aware of the topics discussed during the upskilling.

HR leaders should consult managers' own bosses to ensure that the upskilling is a good fit for managers' specific departments, said Susan Vroman, organizational and leadership effectiveness consultant at Chrysalis Coaching and Consulting, an HR consulting firm located in Boston. Doing so can help prevent post-upskilling conflicts, such as a manager going through training and then finding they are unable to apply their newly acquired skills.

2. Be selective

Like any training, upskilling requires an investment, so HR must work with other company leaders to decide which employees the company will target for development.

The best upskilling candidates fulfill the following criteria, according to Vroman:

• The employee is already doing great work.
• The employee is open to feedback.
• The employee has made clear efforts to improve their weak points.

HR leaders should also consider upskilling managers that the company is seeking to promote, which will link upskilling with the company's succession planning efforts.

"Upskilling, by its very nature, [means] 'I want to give you more skills so you can do more,'" Vroman said. "Who do you want to rise in the organization, right now or in the future?"

3. Consider cohort-based upskilling

When HR leaders decide on the form that upskilling will take, they should consider cohort-based training, in which training participants learn from one another instead of only learning from the person leading the training. Manager trainees may find it more valuable to hear about others' experiences instead of listening to a lecture.

Cohort-based upskilling programs provide an opportunity for managers to share their struggles and successes with their peers, Walters said. Cohort programs can also include traditional instruction but may add role-playing and assignments for training participants to apply their new learning to their day-to-day routines, then discuss how the material has played out in the real world.

"Workshops are great for laying [a] foundation, but people need time and space to apply these things on the job and then be able to connect with their peers and coach each other through those scenarios," Walters said.

4. Tailor training to needs

One size does not fit all for training, and HR leaders should make sure that any upskilling products that their company purchases are a good match for their organization.

"If you have something that is so generic that any company in the world could use it, it's not for you," Vroman said. "It's not for anyone."

For external events, a company's budget may only allow for a few employees to enroll.

In that case, a company could send some managers to a training event, then have them share their experience with other managers, Vroman said.

5. Ask about personal goals

HR leaders' best strategy for deciding on upskilling topics is to ask the managers who are participating in the training.

Managers should at least discuss their upskilling goals during their annual performance reviews, but those conversations could take place as frequently as every quarter, Vroman said.

"Make sure that there is an opportunity to hear from your employees," she said.

If a manager asks to upskill in an area that HR leaders had not previously considered, HR should make every possible effort to fulfill the request if possible, Vroman said.

6. Connect training to role

Managers will likely value upskilling more if HR leaders clearly link the training to the managers' everyday tasks.

Practicing for real-world situations they'll encounter helps training participants better apply what they are learning, said Colleen Adler, research director in the HR practice at Gartner.

For example, if a department is using new software, managers could learn how to help employees who may be struggling with learning new tech, including strategies for listening to workers who are concerned about the change.

7. Help managers find time for upskilling

Companies must prioritize upskilling for managers despite other demands on managers' time, which may not be easy to do.

"Most organizations are long past the point where they can afford to add one more thing to a manager's to-do list and expect everything to get done," Adler said.

HR leaders must ensure other leaders at the company make space in employees' schedules for the training.

A potential solution to this is making upskilling mandatory, Adler said.

Requiring training can help HR send the message to other leaders that they must find the time for managers to complete the training.

HR leaders must also ensure leaders plan for the time that training will take, including potentially removing other tasks from managers' workloads, so managers aren't overwhelmed, Adler said.

Carolyn Heinze is a Paris-based freelance writer. She covers several technology and business areas, including HR software and sustainability.