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How Employee Retention Can Improve With Upskilling 

  • 6 Min Read

Steve Cadigan, LinkedIn’s first CHRO, shares how building upskilling into your learning strategy can encourage internal mobility, career security and growth.


Do you remember classified ads? You know, where you used to be able to find open jobs in the newspapers? 

They’re a reminder of how skills were assessed in the past and provide a stark contrast to the rapidly changing world of skills we’re living in today. 

In a podcast interview with D2L, Steve Cadigan, LinkedIn’s first CHRO and founder of Cadigan Talent Ventures, shared how he views the evolution of jobs from the days of classified ads. 

“When I started out of school—this was pre-internet, pre-cellphones. Back in those days, you found something through a classified ad,” said Cadigan.   

“Now on my phone I can see thousands of pathways that I never even considered before. Not only that, we have an increasing set of platforms where people don’t have to work for someone else,” he explained. “They can create value for themselves, whether it’s producing a YouTube video or music on a SoundCloud or being a TikTok influencer for example. That proportion of opportunity is growing, and it’s getting a lot of attention.” 

In the modern workplace, it’s less about the job and more about the skills. You need to be able to clearly document the current skills that exist within your company and define the future in-demand ones you want or need. This will allow you to provide the right upskilling opportunities for your staff to increase employee retention. 

Creating a Culture of Learning to Fuel the Future of Work | Steve Cadigan | Part One 

Steve Cadigan shares tips and advice on how your business can become a place where people want to stay and grow.


Unpacking Upskilling

Before you jump into the world of upskilling, it’s important to know what skills already exist within your company. A skills matrix will show where you’re missing expertise in your business. From there, you can create a map between existing talent sets that can be upskilled to fill these gaps and show your employees you’re investing in their future. 

“Before we can really get to the learning, I think we have to solve something even more important that should have been solved already. And that is determining what skills our people have now,” said Cadigan.  

In the past, companies have come to Cadigan saying they have a recruiting problem. When these same companies are asked to show all the skills their current employees have, the information doesn’t exist. 

“You can’t tell me you have a recruiting problem if you don’t know all the skills, abilities, capabilities and experiences of your existing staff,” Cadigan explained. “You have an awareness problem, and we need to solve that quickly.” 

Enter upskilling. 

“So many people walk out of a company when they could have done something else, but the company doesn’t know that they could have done it. The business isn’t aware that there’s a place they could have applied their skills in a different way,” said Cadigan.  

Let’s dig deeper into how upskilling can improve employee retention. 

How Employee Retention Can Improve With Upskilling

Investing in Internal Mobility 

One way you can improve employee retention through upskilling is by considering internal mobility. This might include following a traditional career path or involve digging into skill mapping and personal interests, a less expected route. 

Cadigan recalls an example of unconventional internal mobility at LinkedIn that promoted employee growth in a new field. The organization needed a large number of Python developers, yet people able to write the code were hard to come by. 

“The people who are doing Python now, what skills did they have before? And is there a correlation that we could draw between those skills to give us a higher level of confidence that prospective Python developers could be good with it and enjoy it?” he explained.  

“And we found a pattern. We mapped that to our employees and found about 15 people that had the attributes that gave us a good level of confidence that they could do this really well and learn it really quickly.” 

The identified employees were asked if they’d like to take part in a six-week bootcamp in lieu of their normal work to get them upskilled. 

“That capacity to grow is one of the most core muscles any organization should be focused on right now,” said Cadigan. “You’re not going to find that fully baked skill out in the open market anywhere near as fast as you used to, so you’ve got to be in the business of growing skills.” 

Identifying and sharing current or future high in-demand skills needed at your org can provide upskilling opportunities in unexpected places, giving you a chance to increase employee retention. 

Creating Career Security

We’ve all heard the term job security. But when you consider that phrase in the workforce’s current rapid rate of change, it can seem a bit narrow-minded. Why not think bigger and aim to provide your employees with career security to encourage their tenure at your organization? 

“I believe that learning is now part of the rewards compensation stack. The more you grow me and make me more capable for an uncertain future, the more likely I am to stay compared to my other choices,” said Cadigan. 

“If you promise that you’ll never let me go, I’m not going to believe you. But if you promise you’ll make me better and you’ll do everything you can, whether I get fired or laid off or the company goes under, I’m okay,” he explained. “This is where I think the challenge is. I believe increasingly talent wants to grow and learn more than anything … Don’t promise me job security. Promise me something bigger: career security.” 

When you start to show staff that you’re thinking of them being part of your business long term and are willing to help them get there through learning, employee retention can improve. 

Leaving Room to Grow

When you build out a job description, what are your expectations for the number of checkboxes an applicant will fulfill? When looking to the future, it might be better to look for people who have the capacity to grow. 

“A job description is a snapshot of the job yesterday,” said Cadigan. “What I’m trying to really help people understand is the need to hire for learning velocity because the job and market that we’re in is going to change.” 

When you start looking and leaving room for learning velocity in new hires, you’re giving them a reason to stay with your company. You can improve employee retention by investing in their future and showing them you want to see them grow with your organization. 

Cadigan also sees this as a solution for companies who say they can’t find people with the skills they need. 

“Do you think you’re going to be able to do that better in the future? Probably not,” he said. “Why? Because skills are always changing. So why don’t we hire for learning velocity? Why don’t we hire by measuring someone’s capacity to grow and learn?” 

Future-Proof Your Business With Learning

For your business to keep up with the evolution of skills, you need to invest in a culture of learning and growth. 

Building upskilling into your learning strategy will show your staff that they’re more than a number by encouraging internal mobility, career security and growth—and can have a positive impact on employee retention. 

Ready to become an organization where people want to come, stay and grow? Learn more about D2L for Business

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Table of Contents
  1. Unpacking Upskilling
  2. How Employee Retention Can Improve With Upskilling
  3. Future-Proof Your Business With Learning