How Managers Can Help Reskill Your Organization

Bruce Tulgan
September 06, 2019

Bruce Tulgan

Founder of RainmakerThinking, Inc. and Top Expert on Leadership Development and Generational Issues in the Workplace

We are on the brink of a reskilling revolution in the workforce, and it has already begun in organizations such as Amazon and Wal-Mart. The increasing pace of change has made it clear to workers of all ages that in order to remain competitive they must continually improve. Skills that were relevant a week ago may no longer apply today. Conventional industry wisdom fluctuates every few months. Adapting and evolving are the only options, whether you're an entry-level employee or the CEO.

When it comes to employee retention, many organizations have recognized the incredible power of reskilling--most employees today will leave an otherwise good job if there are no opportunities for training or career advancement. Of course, when employees leave, that means spending a lot of resources on finding a new hire. And there is always the possibility that new hire may not stick around for very long, resulting in even more hiring costs. Employers that can effectively harness the power of reskilling in their organization will be much better off when it comes to retaining both old and new employees long-term.

But the problem facing most organizations is cost and time: how can they possibly afford to provide training for their entire organization? After all, the work still needs to get done. The solution is to turn every manager into a Chief Retention Officer by involving them in an ongoing reskilling process at every level of the organization.

Make Reskilling Manageable by Identifying Goals

The only way to manage improvement--whether it's a behavior problem or a performance problem--is to find a way to monitor and measure it in concrete terms. Then the manager has a way to directly compare past performance to current performance and evaluate the difference over time. Of course, that comparison is meaningless if there is not a specific goal to achieve.

Have managers start the reskilling process by identifying employee skill gaps in their 1:1s. This will be a whole lot easier if managers have already been practicing the fundamentals and tracking employee performance over time. In any case, have managers ask each of their direct reports good probing questions to get at the heart of any skill gaps or deficits:

  • What best practices and standard operating procedures are you currently following?
  • Are there any industry standards you are aware of that you are not following? Why not?
  • What apps, tools, or software would make doing your job a lot easier?
  • What apps, tools, or software would make the quality of your work higher?
  • What are the skills you believe will be most helpful and relevant to your work today?
  • What are the skills you believe will be most helpful and relevant to your work in five years?
  • What new skills will be easy for you to learn?
  • What new skills will be difficult for you to learn?
  • What new skills can you learn and improve on in the course of your everyday work?
  • What new skills will require you to set aside special time and effort?

Managers and their employees may have to work together to find answers to these questions. It may require a little research from both parties. But if managers can identify the reskilling goals they have for each person, they will be able to create an improvement plan.

Reskill One Step at a Time

Once reskilling goals have been identified, it is time for managers and employees to develop a structured improvement plan. That plan is going to serve as both a management tool and a checklist for the employee, comprised of intermediary goals along the way.

Say one of an employee's reskilling goals is to become an expert in a new CRM platform. Start by defining what "becoming an expert" means: what does the employee need to accomplish with this new software? What problems is the new platform intended to solve? The answers to these questions will build a checklist of intermediary goals right away. Then, organize those goals into a logical order: which goals must be accomplished first, second, third, and so on?

Once the manager and employee have created a list of intermediary goals, then it is simply a matter of breaking down those intermediary goals into concrete steps. This is where managers can really engage direct reports' enthusiasm and creativity by asking them to create a list of resources--books, videos, even other people within the organization--that they can use to support their self-directed learning efforts.

This process should create a robust reskilling improvement plan that managers can use as a guide in the coaching-style conversations they have with each employee 1:1.


1:1s Are Where All the Action Is

Armed with a plan and actionable goals, the hope is that employees make consistent, steady improvement on their own. But the reality is that even the most self-starting, reliable employees need guidance, direction, and support in order to stay on track and do their best. That's where the importance of regular, ongoing 1:1 meetings comes in.

After following the improvement plan for a while, it may become clear that an employee's reskilling efforts would actually be better spent elsewhere. A manager may realize that one employee's efforts are interfering with another's, or that there is unnecessary redundancy. Employees may simply get stuck, go off track, or lose momentum. Unless managers focus on reskilling as part of their everyday management responsibilities, there will be no one else to identify or solve these problems along the way.

Involving your managers in this process won't help you meet every reskilling challenge--some heavy lifting will likely still be required. But it will help to get you most of the way and undoubtedly transform the culture of your organization into one of continuous improvement, with reduced employee turnover and increased retention.

To book Bruce Tulgan for your next event, please visit his profile at

Bruce is the author of several books including It's Okay to Be the Boss: The Step-by-Step Plan to Becoming the Manager Your Employees Need. To order in bulk for your next event, go to

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