The Secret to Doing Reskilling Right: What Most Companies Miss
- Cara Heilmann
- May 1
- 8 min read
Reskilling has long been a strategy for smart HR teams. These initiatives boost retention, spark employee engagement and loyalty, and allow you to hire internally.
But we’ve reached a time with technology where building a reskilling program isn’t just smart, it’s essential.
AI and automation are coming fast. Already, we’re seeing a 27% drop in hiring for roles that are most exposed to AI, according to PricewaterhouseCoopers.
The point is, if you aren’t creating a program that actively reskills (and upskills) your employees, you might find employees, and even teams, becoming obsolete.
Having spent over two decades in HR, including serving as a VP of HR, I've developed numerous reskilling programs. In this article, I'll share the blueprint for reskilling success—and the pitfalls many companies stumble into—to help you stay ahead.
What Is Reskilling?
Reskilling is when you teach employees new skills so they can transition into different roles within the organization. A business will usually reskill its employees in response to shifting business needs, new technological advancements, or industry changes.
Take customer support as an example.
AI chatbots can now respond to messages and even take calls. So what should you do with your customer-support team whose roles are looking less and less necessary?
Don’t fire them!
Instead, reskill them. Turn your call center reps into customer success managers. Teach them how to outreach to customers, use CRMs, and manage accounts.
Now instead of a team becoming obsolete, they’ve turned into assets your business didn’t have before.
Before going into the “how,” let’s get a bit more clear on definitions, because I often see people confusing “reskilling” with “upskilling,” when they’re actually different.
What’s the difference between reskilling and upskilling?
Upskilling is when you teach your employees new skills that build on their existing roles, so they can stay effective as their jobs evolve.
Where reskilling prepares someone for a new role, upskilling helps them grow within the same role.
Got a team of marketers who are great at copywriting? Upskill them in social media content so they can stay effective as digital marketing evolves.
Here’s a table to clearly see the differences side by side.
Reskilling | Upskilling | |
Definition | Learning new skills for a different role | Learning advanced or adjacent skills for the same role |
Goal | Shift employees into new positions as old roles become obsolete | Improve performance and future-proof employees in their current positions |
Example | Call center rep → Customer success manager | Customer success manager learns data analytics |
Why Should I Care About Reskilling?
There are three very good reasons to care about reskilling.
1. Because skills are becoming obsolete—fast
In the past year, 60% of companies (and 84% of large companies) have automated tasks previously completed by employees.
Looking forward, the World Economic Forum predicts that 60% of workers will require upskilling and reskilling by 2027.
In other words: every job in every industry is getting impacted by AI. Analysts, marketers, and engineers. You name it.
If you don’t stay ahead of the curve in developing your team, then you may find yourself with employees whose skills are no longer useful. And then you’re in the no-fun position of choosing between excruciating layoffs or the pricey effort of new hires.
2. Because it’ll help you retain employees
94% of workers say they’d choose to work longer for companies that invest in their career advancement. And 74% of Gen Z and Millennials say they’d quit within a year if a job didn’t provide upskill opportunities.
That’s huge! If you’re not hearing that, let me make it loud and clear: if you help your employees build skills and future-proof their careers, they’ll want to invest their careers in your company.
Reskilling means you’re investing in your employees' long-term success and giving them more job security. It’s a win for them, and a win for you.
It’ll save you tons of money on hiring and training new talent. In fact, a report from PwC found that that reskilling an employee is about $50,000 cheaper than hiring someone new.
And ultimately, this approach makes your company known as a place where people want to work.
3. Because it gives you an agile workforce
If your company or team needs to pivot or redeploy, that’ll be much easier if you have reskilling systems in place.
Especially if you can integrate reskilling into your company culture, then you won’t need to create a big push when a role is threatened. Your team will be naturally adjusting and moving across roles within the company from the get-go.
And that point brings us to the key secret to reskilling well…
The Secret to Reskilling Successfully
Here’s the main takeaway I want you to leave with: for reskilling to work, you have to view it as a culture shift and not just a training program.
It won’t work to set up a few workshops and call it a day.
Reskilling needs to be woven into the fabric of your culture.
Plus, artificial intelligence isn’t going away any time soon. So, creating systems for internal mobility will only work to your advantage over time.
The way to do this is by making learning visible, accessible, and expected.
Practically, that looks like offering a wide variety of options to help your current workforce fill their skill gaps and grow. Such as:
Paid-for online courses and technical training
In-house workshops
Job shadowing across departments
Stretch assignments that build new competencies
Access to mentors and coaches
But you also need to help your current employees with career pathing within the company. And that might mean:
Personalized learning plans created with managers
Internal mobility pathways
Internal job boards
And let’s not forget one of the most powerful cultural levers:
Celebrating internal moves.
When someone successfully transitions roles after reskilling, make it visible. And give them kudos!
This sends the message that reskilling into new positions isn’t just allowed, it’s encouraged.
Plus, when you broadcast success stories, it evokes hope and confidence that career growth within the company is possible.
The 4 Reskilling Pitfalls that Most Companies Miss
In a way, implementing a reskilling effort is kind of like creating a coaching culture in your workplace. To get it to stick, you need to know how to avoid a few killer pitfalls.
Pitfall 1: Treating reskilling as a one-time event
I’ve seen this time and again. A company hopes to make lasting change.
They launch a one-off bootcamp, workshop, or learning portal. And they think they’ve checked the box on reskilling, so then they put their efforts elsewhere.
Nuh uh. That isn’t going to work.
You have to think of reskilling as an ongoing project.
Make reskilling, upskilling, and continuous learning parts of your culture, and embody an environment of growth and talent development. And be cognizant of ways employees could find other roles within the company to put their skills to better use.
Then, when the market shifts and technology dissolves roles, you’ll be ready to adapt.
🧭 How to avoid this pitfall:
Create recurring learning opportunities.
That could look like quarterly workshops, ongoing stipends for courses, or internal mentorship programs.
Think about reskilling as a company habit.
It’ll also help dramatically to have regular career development check-ins with managers. That way, employees won’t feel like they’re stranded out on their own, hoping to save their careers from AI.
If their manager helps them plan their career, that’ll be the glue that holds the reskilling effort together.
If you want to learn more about how to teach coaching skills to your managers, check out this article: The Complete Guide to Employee Coaching for Intentional Leaders.
Pitfall 2: Failing to link learning to real career paths
Here’s a reskilling situation you want to avoid:
An employee takes a course and builds some great new skills. But there’s no clear next step. They don’t see a role to transition to. There’s no internal job board or available promotion.
And their next thought is, “Well shoot. That was a waste of time.”
If their learning feels disconnected from any tangible opportunity, their motivation will plummet. But we can make sure you avoid that.
🧭 How to avoid this pitfall:
Make it crystal clear how learning connects to real opportunities. Here are a few ideas:
Map internal career paths so employees can see where different skills can take them.
Look ahead at real roles that may open in the next 6–18 months, then reverse-engineer the critical skills needed, and build reskilling pathways that prepare people for them.
Create an internal job board and normalize applying internally as a key part of career development, not a sign of disloyalty.
Encourage career development conversations between employees and managers, especially during performance reviews or 1:1s.
Celebrate the success stories of employees who reskilled and transitioned into new roles.
When people can see what’s possible, they’re much more likely to put in the effort to get there.
Pitfall 3: Forgetting the emotional side of change
Let’s go hypothetical for a moment. Imagine you realize that a particular role in your company is going to be obsolete within the next year. So you approach those in the role and encourage them to reskill and chart a career path within the company.
Some of those employees take that news in stride and feel excited to keep growing.
But there are a few who freak out. The only thing they heard you say is “your job is going to disappear.”
Because here’s the thing—we all handle change differently. And if someone feels like their job is on the line, then you may need to offer more support than just teaching them new skills.
🧭 How to avoid this pitfall:
Pair your reskilling initiatives with 1-on-1 check-ins, coaching, or peer support so employees feel seen and like you’ve got their back.
And make sure your 1-on-1 sessions aren’t just strategic, but that managers also make room for empathizing and holding space.
It’ll also go a long way if you frame the shift as an opportunity for growth rather than a threat. Emphasize that these reskilling programs exist because the company believes in their long-term potential.
Pitfall 4: Not measuring the success of your reskilling efforts
It’s hard to improve what you don’t measure.
So many companies try to incorporate reskilling, but they never define what success means. That makes it impossible to know what’s working, what’s not, and where to invest next.
Just like any initiative, you won’t get the final version of your reskilling program right away. You start with a V1, see what works, then try out a V2, and keep improving.
Plus, if you track success, it’ll make it a lot easier to secure more budget, resources, and buy-in.
🧭 How to avoid this pitfall:
Define clear success metrics from the start. Try:
Internal promotion rates
Employee retention
Course completion and participation
What percent of current roles are filled by reskilled employees
Measure how those employees perform and how long do they stay
If you steer clear of these four pitfalls, you’ll be in great shape.
Want Support Bringing Reskilling Into Your Company?
Part of your reskilling strategy probably will involve encouraging managers to help employees plan their career path, set goals, and deal with the tides of change.
If that’s the case, then it’ll be extremely helpful if your managers have learned coaching skills. When a manager knows how to coach, they become a resource that empowers and develops their team.
If you’re interested in teaching your managers coaching skills, you might be interested in our in-house career coach training.
You’ll get to collaborate with me directly, where I’ll help you train your in-house team with state-of-the-art coaching tools.
Click the link above to book a free consultation to see if it’s a good fit.
