Woman with glasses standing outside, looking at a clipboard

Upskilling and reskilling Baby Boomers for the future of work

Let’s dive into the world of upskilling and reskilling Baby Boomers and discover how workplace leaders can best support them through this new stage of their L&D journey. 
Courtney Norton, Content Writer

As some of the oldest members of the workforce, Baby Boomers have witnessed the workplace repeatedly transform before their very eyes. Experiencing all that change must have felt like quite a rollercoaster at times! 

Riding this metaphorical rollercoaster (whether willingly or otherwise) has meant that Baby Boomers have spent most of their lives learning at work. While many Baby Boomers are approaching retirement age, the learning hasn’t stopped yet, and they don’t want it to. There’s plenty of upskilling and reskilling left to do! 

Let’s dive into the world of upskilling and reskilling Baby Boomers and discover how workplace leaders can best support them through this new stage of their L&D journey. 

Asking the right questions 

Schools don’t use the same methods and materials to teach preschool students that they use to teach high school students. That just wouldn’t make sense. The same applies to those of different ages in the workplace. 

You may be thinking, “we’re all adults at work. Therefore, we should treat everyone the same at work regardless of their age.” That is partially correct. Everyone certainly does deserve to be treated with the same level of respect and have the same number of opportunities to progress at work. However, by accounting for age, businesses can tailor the workplace experience to suit the varying needs of employees of different ages. Tailoring the workplace learning experience is key to ensuring employees receive the most effective upskilling and reskilling. 


In the case of Baby Boomers, many are nearing retirement age and are likely to have much different workplace goals than members of younger generations. 

But how can employers be sure that they’re tailoring things correctly and not just formulating workplace learning based on assumptions about what Baby Boomers ‘probably’ want to learn? The answer is hiding in plain sight: asking questions. 

These questions can be divided into two important categories: ‘questions for employers to ask themselves’ and ‘questions for employers to ask their Baby Boomer employees.’. 

Some questions for employers to ask themselves include: 

  • When we look at our workplace demographics, are we tracking age?
  • Do we have any employees who are looking to retire soon? How many?
  • What processes, if any, do we have in place to help workers transition smoothly to retirement?
  • If Baby Boomer employees would prefer to transition to a role with less responsibility or change to a part-time schedule rather than full-time, do we have the capacity to facilitate that?

Some questions that employers can ask their Baby Boomer employees include:

  • What type of work makes you the most excited?
  • Are there any aspects of your role or the workplace in general that make you anxious or unsure?
  • What are your thoughts about retirement? (With this question, be careful not to make it seem as if you are trying to get them to retire soon. Rather, frame it so that employees can tell you want to help set them up with a path they’re happy with.)
  • What do you want to learn? 

Practical steps to tailor learning to Baby Boomers  

Even if learning content focuses on the most interesting or helpful topic in the world, it’s difficult to get employees enthused about completing it if the way the content is taught isn’t up to scratch.  

Similarly to how tailoring the content can help learners make the most of upskilling and reskilling opportunities, tailoring how that content is delivered to suit the strengths of Baby Boomers can make a significant difference in the success of that learning content. 

Additionally, when employees are interested in both the ‘what’ and ‘how’ of what they’re learning, they’re far more likely to retain that knowledge. ‘Work’ and ‘fun’ doesn’t have to be like ‘oil’ and ‘water’! 


If there’s one thing Baby Boomer employees love, it’s competition. Here’s where gamified learning can be vital for upskilling and reskilling Baby Boomers. Earning things like achievement badges, points, and rankings provides Baby Boomer learners with the intrinsic motivation required to continually upskill and reskill. This is because, combined with their competitive nature, Baby Boomers are typically motivated by personal growth and self-improvement. 

Likewise, creating goals and setting milestones for workplace upskilling and reskilling is something to which Baby Boomers respond positively. 

 Finally, including technology in learning is essential when considering the best methods to upskill and reskill Baby Boomers. While they may not have grown up with technology in the same way that Millennials or Gen Z have, Baby Boomers have used their dedication and resourcefulness to adapt and learn how to use technology as it has progressed.


Making full use of the technology available to them is upskilling Baby Boomers in itself. Being on top of the latest technology and knowing where to look to learn about technology developments that could affect them is an invaluable skill that can advantage Baby Boomers in the workplace and beyond. 


For more insights, be sure to subscribe to the Go1 newsletter to stay on top of all the latest L&D trends. Or, you can book a demo today to find out how Go1 can help with your team’s learning needs. 

Go1 helps millions of people in thousands of organizations engage in learning that is relevant, effective and inspiring.
Latest stories and insights