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The Definitive Guide to Reskilling (Starts with Software Retraining)

The Definitive Guide to Reskilling (Starts with Software Retraining)

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💡 What is reskilling?

Reskilling refers to the process of learning new skills with the goal of transitioning into a different job or career.

Back in the day (read: pre-ChatGPT, pre-2023 tech layoffs, pre-COVID), many knowledge workers followed a predictable path.

  1. Early in their career → Developed skills suited to one area of interest. 
  2. Over time → Picked up more knowledge and specialization to deepen their subject matter expertise. 
  3. In time → Built a career by staying the course, upskilling, and improving their job performance.

Accumulating new knowledge happened in a T-shape, like this:

A T-shaped knowledge profile, acquired through upskilling.

Let’s take a marketer as an example. As a new hire, they decided to specialize in content marketing. Over the course of their next few roles, they became an expert on search engine optimization (SEO), getting certified in content automation, and taking a course on content marketing strategy. Their upskilling efforts eventually paid off, and they were promoted to a senior content marketing role in the same company.

That was—and still is—a perfectly fine way to approach career development. 

But these days, the people who set themselves apart have more of an M-shaped knowledge profile, like this:

An M-shaped knowledge profile, acquired through reskilling.

In this scenario, our marketer still specializes in content marketing out of the gate. But instead of learning everything there is to know about content marketing (and calling it good), they consider what skills they’d need to create a career path with a broader scope—via reskilling. 

They might see their biggest chance to make an impact overlaps with an emerging need for someone who can:

  1. Execute design work in-house → And teach themselves how to use InDesign, Illustrator, and Figma.
  2. Own all things website → And learn how to manage external partners, create an information architecture for web design, and scale a project management system. 
  3. Head up a new brand team → And launch a lightning strike category launch while learning on the job.

To fulfill those needs and achieve mastery in more than one domain, our marketer will need to reskill—and go through the process of learning how to do an entirely different job. 

In this guide, we’ll go beyond defining reskilling and explain:

The importance of reskilling (in the age of AI)

If you looked at your LinkedIn feed right now, how many posts would be about ChatGPT? 

If you answered “north of 90%,” you aren’t alone. 🤖 To say artificial intelligence (AI) is having a moment doesn’t quite do things justice. 

  • 77% of companies around the world are either currently using AI or exploring AI for future use. 
  • Goldman Sachs economists predict up to 300 million full-time jobs around the globe could be automated at least in part by AI. 
  • In the US and Europe specifically—two-thirds of existing jobs already involve AI, and up to a fourth of all work could be done completely by AI. 
  • AI is estimated to replace 85 million jobs by 2025. 

Depending on your personal outlook, these stats may be alarming, exciting, or both. 

What’s equally 🤯, no matter where you sit ? The 97 million new jobs experts estimate will be created due to AI. 

That means the best time to talk about reskilling and retraining was yesterday, and the second best time is today. 

Reskilling benefits for employers and employees 

While we’ve yet to come across a job description for a ChatGPT prompt writer, it’s only a matter of time. Innovations in AI are advancing at warp speed—and changing which skills are most in-demand just as quickly.

What should forward-thinking founders and employees both be thinking about? 

How to adapt to meet market demands, yes. But also: the fastest way to enable—and action—continuous learning.

"The ability to learn faster than your competitors may be the only sustainable competitive advantage."

Arie de Geus

Business Theorist

If acquiring and applying new knowledge is the key to long-term resilience, the (20+!) benefits to reskilling shouldn’t be underestimated.

Reskilling Advantages

For Employers 🏢 For Employees 👩🏻‍💼
Minimized layoffs and rehiring Better sense of job security
Improved retention Potential to make a career pivot
Less institutional knowledge lost More upward mobility
Fewer skill gaps—without adding headcount Broader subject matter expertise
Reduced recruitment costs Higher earning potential
Shorter onboarding process Increased productivity
More ability to adapt at speed More relevance
Better succession planning Opportunity to take on new responsibilities
Increased competitiveness Access to new tools and technologies
Stronger perception as an employer of choice Improved job satisfaction
Improved customer experience Higher confidence, self-esteem, and morale

How to reskill your workforce in six steps

Whether you’re a knowledge worker in a role that may be phased out or a functional manager looking for ways for your existing team to create more value, some degree of reskilling and retraining is likely in your future.

So what’s the best way to lean in and get a jump on the inevitable transitions ahead? 

A list of the six steps needed to stand up a successful reskilling program.

Step #1: Identify the skills needed to stay relevant. 🔭

We’ve talked about identifying skill gaps before, while explaining how to stand up an upskilling program. It’s equally foundational here. 

To get started, first think about the knowledge gaps that are [already] all too clear. Then think about which areas of the business are likely to have the greatest need over the next 3-5 years. 

Consider questions like:

  • Where has our competition been beating us to the punch? 
  • Where are we most likely to be outpaced and outperformed? 
  • What skills would we need to keep up? 
  • What knowledge would we need to lead the pack?
  • What do we anticipate growth will look like for us? (New markets, new products, new target customers, etc.)
  • What should we stop trying to train on?

You can do this individually or with others. The key? Keeping an open mind.

💡 Tango Tip

Rather than focusing on which jobs might next be replaced by AI, think about what humans can bring to the table that AI can't.

Step #2: Decide which roles may no longer be necessary—or should be reconfigured. 🔍

This topic of conversation isn’t the easiest—but knowing that the goal of reskilling is to equip existing team members with the skills to succeed in a different role can help create some psychological safety.

To guide the conversation in a group setting, you might ask questions like:

  • Which parts of the business are impacting our key performance indicators (KPIs) the least?
  • Which team(s) have too little—and too much—to do?
  • What processes and tasks could (and should) be automated?
  • Which of our standard operating procedures are no longer necessary, or won’t be soon?
  • Who owns those workflows today? 

Note: Changing “jobs to be done” may be one outcome of digital transformation and AI for knowledge workers. But in many cases, roles may not be eliminated altogether. For example—a customer support rep may no longer handle as many Tier 1 tickets, but could be responsible for auditing the Tier 1 automation and creating more help content to drive self-service.

Step #3: Make a list of candidates for reskilling and roles to meet new needs. 🗒️

Steps #1 (desired skills) and #2 (obsolete jobs to be done) should give you a good starting point for assessing how you can most effectively leverage your existing team.

Some career transitions may be synergistic, with clearly transferable skills. For example—say you need to make a change in Sales, and you know there’s a Business Development Representative (BDR) who creates all of her own prospecting materials and has a great pulse on customer pain points. She might be a logical addition to the marketing team, and be uniquely equipped to help bridge the gap between Marketing and Sales. 

Other transitions may be more of a stretch (and a harder sell). Say you need to double-down on improving your customer experience, and with the introduction of ChatGPT, you don’t need as many full-time content writers. Being retrained to succeed in a customer-facing role may not be your writer’s first choice—but it would give him a way to maintain his income, and a way for you to speed up the onboarding process for a more mission-critical role.

💡 Tango Tip

Reskilling can result in more than just a lateral movement from one role to another. It's also a great opportunity to promote people with more mastery to higher level positions—and retrain others on any responsibilities that need to be backfilled.

Step #4: Determine your reskilling methods of choice. 📌

The success of your reskilling program hinges on the success of your reskilling strategies. 

E-learning. Job shadowing. Cross-functional training. Since reskilling methods mirror the best practices for training new hires and upskilling employees pretty closely, we won’t run through them all in detail here. 

Interested in our top two recommendations for closing the gap between learning and applying? Check out these posts on learning on the job and microlearning

Want to help people capture and access knowledge in the flow of work? 

Step #5: Create, socialize, and adapt the game plan. 🧡

At the risk of stating the obvious—change is hard. And it’s even harder when it’s happening *to* you, it feels like you don’t have much of a say, and the silver linings aren’t immediately obvious.

To handle all reskilling conversations with care, create a plan to give people as much information—and agency—as you can.

A few tips for each one-on-one:

  • Explain the “why” behind the decision. (Focus on their strengths, and why they came out on top as the best choice to help the company move forward.) 
  • Shed light on the company’s overall philosophy on reskilling. (Emphasize the benefits for employees mentioned above!)
  • Share an overview of the new role—ideally with a formal job description.
  • Present your roadmap to help them hit the ground running (without leaving their current team high and dry). 
  • Invite their feedback on their preferred ways to learn (both digital skills and soft skills).
  • Ask what additional resources they might need to succeed (access to a subject matter expert, an online course, how-to guides, a new mentor, etc.).
  • Talk about timeline, priorities, and desired outcomes.
  • Use your conversation as a springboard to talk about career pathing.
  • Reiterate all you’ll do to help ease the transition.

Step #6: Launch the program—and consider it ongoing. 👀

It may be tempting to think of reskilling as a one-time tactic. But it’s far more effective to create a culture of continuous learning and collaboration. 

After all, new technology is going to continue to take off. Business models we can’t imagine now are going to take center stage. Opportunities to increase productivity through automation are going to keep appearing. Consumer behaviors are going to continue to change. Roles and responsibilities are going to remain in constant flux. 

The companies that can adapt to change the fastest are the ones that will survive. And the people with the most well-rounded capabilities (who can step into new or expanded roles in less time) are the ones who will thrive.

Software retraining: The gateway to reskilling success

When was the last time you started a job without learning any new technology? 

For many, learning new software is the biggest hurdle to developing deep subject matter expertise in a new domain (and the hardest part of going from a T-shaped learner to an M-shaped learner).

That’s why we see software as the gateway to reskilling for most knowledge workers. It’s next to impossible to master the most important and impactful parts of a new career without first learning how to navigate all the systems that come with it.

Say you’re switching from a marketing role to a sales role, and your company uses Salesforce for customer relationship management. Until you understand all the tasks you need to perform in Salesforce, it’ll be hard for you to focus on much beyond gaining basic competence in the tool. 

So how can you raise your floor faster? 

By finding a way to:

  • Start gaining hands-on experience *while* you go through big picture learning.
  • Learn in context, on the job, with readily available answers, insights, and shortcuts from co-workers.
  • Apply the knowledge you need, when you need it—without rewinding long videos, sifting through outdated PDFs, or sitting in a classroom. 

Would you believe us if we said we had just the thing? 😁

💃🏽 Learn new software, in seconds
Tango how-to guides make working and learning a team sport—with step-by-step guidance to make capturing and accessing knowledge easy, fast, and fun.

See how it works:

Overcoming obstacles to reskilling

Learning new software is clearly one (significant) obstacle to reskilling. What else should you keep an eye out for?

Common Reskilling Challenges

What’s Tricky 🤔 What To Do About It 😎
Lack of time or resources Leverage free tools that make learning in the flow of work easy and fast.
Lack of support Learning a whole new set of skills usually doesn’t happen overnight—or on an island. Create a plan to ensure working and learning can take place in tandem, with access to additional support when needed.
Fear of failure Normalize how hard it is to be a beginner (especially for any perfectionists), and set achievable goals with opportunities to celebrate small wins along the way.
Age and experience biases Make a point to challenge stereotypes and highlight the value, unique skills, and knowledge various members of the team bring to the table.
Fixed mindsets Explain the importance of a growth mindset—and help people understand why their current beliefs may be limiting their potential.

The bottom line

Looking for the top three takeaways? 

  1. Reskilling is one of the most highly effective talent development tools available today. 🎯
  2. In the age of automation, the cost of inaction seems especially steep. ⚠️
  3. For knowledge workers, making software easier to learn is the key to reskilling success. 🙏

With as many benefits for employees as there are for employers, a six-step framework to reskill your workforce, and ideas to overcome the top five reskilling obstacles, there’s no reason not to embrace a new, more agile way of working now.


What is upskilling vs reskilling?

Both upskilling and reskilling refer to the process of learning new skills, but with different end goals. Upskilling aims to improve job performance in the same role, whereas reskilling intends to tee up a successful transition into an entirely different job or career.

What are examples of reskilling?

Here are a few examples of reskilling in the workplace:

  • Accounting to data analysis → May warrant deep expertise in data mining, data visualization, statistical analysis, and programming languages like SQL or Python.
  • Administrative assistant to HR → May demand recruitment, employee relations, payroll, benefits administration, and employment law skills.
  • Sales to marketing → May require retraining on market research, social media marketing, content creation, and digital advertising.
  • Customer service to project management → May involve reskilling in project planning, risk management, budgeting, and communication.

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