Skip to main content

Planning a Learning Program to Reach a Multi-Generational Workforce

  • 6 Min Read

Melissa Stein, learning and development business partner for Tompkins Financial Corporation, shares the challenges she faced, the skills gaps Tompkins targets and her tips for creating an effective training program when working with a multi-generational workforce.


The 2020 pandemic ushered in a new era of learning. Suddenly, 90% of the workforce became remote employees. The long-term vision most companies had for digital learning came to a hard stop. They had to make it happen, right then. 

However, as companies began implementing their virtual upskilling offerings, they faced a significant challenge in reaching employees across generations. Tompkins Financial Corporation was one of the companies eager to expand training accessibility to all employees in this completely digital landscape. That’s when they found D2L for Business. 

We sat down with Melissa Stein, learning and development business partner for Tompkins Financial Corporation, to learn more about her approach to training a multi-generational workforce: the challenges she faced, the skills gaps Tompkins targets and her tips for an effective training program. 

What Does Today’s Training Landscape Look Like?

The pace and frequency with which companies have to deliver training has gone through the roof. Training needs to be delivered faster than ever, and employees are expected to perform better than ever—and for many, that came in a new and unexpected virtual package. 

Currently, Generation X is the generation with the smallest presence in the workforce. Throughout their decades-long careers, Gen X employees have taken a lot of time to develop and build their skills. And now we see millennials and Generation Zers stepping into the picture and completely uprooting the traditional learning framework.  

Companies like Tompkins had to put all their resources into the virtual learning basket to make programs come to life immediately. But with the reopening of facilities, we’ve also had to offer multiple training options—virtual, in person and hybrid—to suit learners of all kinds. 

What Are the Benefits of a Multi-Generational Workforce?

Because Gen Xers have those decades of workforce experience, they have a wealth of accumulated knowledge the younger generations don’t. On the other hand, millennials and Gen Zers generally have a better understanding of the digital space. When it comes to creating training programs, the challenge is successfully tapping into the strengths of these different generations so that they can learn from each other. At Tompkins, we provide open lines of communication plus resources for employees to express their uniqueness in how they learn, communicate, do business and build relationships. 

What Are Three Tips for Developing an Inclusive Learning Program?

Tip One: Start at the Top

This tip is true anytime you’re building a program, especially regarding multi-generational workforce development. A learning mindset comes from the top down, so my first order of business would be to talk to your leadership teams and devise a plan to align the learning strategy with the business strategy. 

Tip Two: Remain Flexible

What looks good on paper may not pan out in an actual learning environment. Stay in constant communication with learners and allow their input to help inform the best format for the end user. Designing an upskilling program is an iterative process; you might not get it perfect on the first go, and that’s alright. 

Tip Three: Have a Future-Facing Plan to Stay With Learners Throughout Their Careers 

Don’t just think about the here and now. The business landscape is bound to look much different 20 or 30 years from now, and your training course will too. Have a plan for what is to come, what the trends are moving forward and how you can develop a plan that guides lifelong learners with relevant, up-to-date content throughout their careers. 

How Does Tompkins Approach Multi-Generational Learning?

Making multi-generational learning possible all starts with meeting the learners where they are. What kind of values do they have? What are their learning preferences? What are their career goals? At Tompkins, we offer many virtual options, from WebEx meetings to YouTube videos and TED Talks, as well as in-person learning spaces. Virtual is by far the most popular option, but it’s important to offer in-person options too. 

Right now, the skills gaps Tompkins is most focused on revolve around leadership and management. Leadership looks different in a virtual environment. In the pre-pandemic era, it was more of a physical exercise. You’d walk into a room and establish how it feels. You’d have face-to-face conversations and gauge the mood of your team. Now, we’re in a virtual environment. It’s all about building relationships in the digital space. Still, as an added layer, we are applying emotional intelligence because the face-to-face factor has been removed from our interactions.  

We have new hire training at Tompkins, but we don’t stop there. We have managers who have been with the company for 35 years and in the banking industry for 40-plus years. And they’re still coming to training on emotional intelligence because we’re now operating in an environment where that is a requirement that some people might struggle with. We want to provide them with that continual learning as we enter a new workplace environment that spans the globe. 

And then, of course, there’s also culture. Employees are no longer walking through the workplace doors and experiencing the culture. They have to get that from their manager. So how is the manager exuding our Tompkins culture in their interactions with their peers? 

What Are Your Views on Upskilling and Lifelong Learning?

When you talk about lifelong learning and upskilling, it’s about providing content that continues the learner’s journey. You have to foresee what that path looks like and rely on subject matter experts to pave the path and move it forward. You have to know that learning doesn’t stop when you reach a certain milestone or hit the top. There are always new branches to explore. 

We recently held a poll asking employees what would be beneficial to learn at Tompkins and 40% of respondents said “learning about other areas of the business.” They’re interested in what other opportunities exist within the organization and how they can get there when roles open up. Or they simply want to gain a better understanding of other positions. 

We need to encourage lifelong learning, even for someone who’s been in the workforce for 25, 30 or 35-plus years. It’s about teaching them how to apply that learning in all avenues of life to keep them engaged. It’s also about providing them with the skills to adapt to the changing world and the demands of the individual. We’re keen on supporting this at Tompkins. It leads to team members who are more engaged and well-rounded because they understand what’s happening in other spaces. We’re seeing a trend where you might start your career in one department and end it in another. You have other opportunities if you’ve reached your potential in one space. 

Tompkins finds this approach to lifelong learning to be successful. I could see this trend increasing in the future working with D2L’s digital platform that offers flexible learning pathways. 

This interview has been edited and condensed for clarity.   

Two workers collaborating on a phone.

Ready to Maximize the Impact of Your Learning Investment?

Amplify your workforce’s onboarding speed, job satisfaction, retention and internal mobility with D2L for Business.

Written by:

Stay in the know

Educators and training pros get our insights, tips, and best practices delivered monthly

Table of Contents
  1. What Does Today’s Training Landscape Look Like?
  2. What Are the Benefits of a Multi-Generational Workforce?
  3. What Are Three Tips for Developing an Inclusive Learning Program?
  4. How Does Tompkins Approach Multi-Generational Learning?
  5. What Are Your Views on Upskilling and Lifelong Learning?