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Upskilling & Reskilling for Creatives

Creatives stake their careers on imaginative work with a personal user experience. In the ever-changing business world, how can we make sure our products are impactful?

Staying up-to-date with new technology and the latest design thinking is essential for building the kind of experience that people crave and return to time and time again. Businesses can help their creatives by offering opportunities for consistent study.

Thanks to the constant influx of new technology and methods, there’s almost always something new to learn. Read on to learn how to upskill and some of the best upskilling and reskilling strategies for businesses who want to make sure their creative talent is first-rate.

What is Upskilling?

It might sound like a buzzword for normal learning, but upskilling describes a specific kind of skillbuilding. Upskilling is an effort by the employer to give employees time and resources to learn more skills and practice new methods.

Management might balk at the suggestion, but everyone at a company stands to benefit from more educated creatives. New software and streamlined production processes allow creative workers to be more productive in less time. Plus, they’re more likely to innovate when they have more information and experience.

Upskilling can be done through conferences, webinars, side projects, trial runs, or even visiting experts. It doesn’t always have to pull creatives completely away from their work, either. Most of the time, upskilling efforts can be integrated with ongoing projects so the workers can apply what they learn right away.

Upskilling Vs Reskilling

While upskilling improves existing skills, reskilling involves training employees in new areas. Usually, reskilling is used when a role becomes outdated or system-wide changes are made. Currently, automation is the leading reason for reskilling at most firms and businesses.

Just like upskilling, reskilling can be done while employees are still working at their old roles. Proactive reskilling will make for a more flexible workforce. Even if you have a ready talent pool available through icreatives, creative teambuilding to adjust to new challenges makes it more likely that talent will stay with the company for longer, boosting the retention rate and the company’s employment brand overall.

Imagine upskilling as a vertical progression and reskilling as a horizontal one. What scares some management teams about the prospect of horizontal education is that they might be inadvertently preparing their staff for a horizontal career change with a competitor. If you think about it, though, failing to reskill guarantees that your talent will jump ship if their current role changes or disappears.

A woman wearing a grey sweater works on a laptop from her bed.
Digital resources make upskilling and reskilling more convenient.

Identifying Skill Gaps: When Do Teams Need Upskilling or Reskilling?

Creating room and directing resources to upskilling is always a good idea, but how can you tell what skills need improvement and when people need to be moved into new roles?

Retrospective critique is the most important tool for identifying what worked and what didn’t for certain projects. Decision-makers should also be involved in regular appraisals of the staff and overall structure of the company. As goals are set for the coming months and years, talent gaps should be identified.

In one report, 75% of HR professionals complained about the lack of talented individuals on the job market. Insufficient upskilling opportunities for entry-level positions is the most probable cause. While creatives go to great lengths at universities and portfolio schools to learn the tricks of the trade, they still need time to learn the nuances of their work and reach a level where they’re comfortable with their individual strengths.

Remember that these upskilling opportunities don’t have to be separate from the work that employees do for the company. Slowly adding new responsibilities and tasks can be considered upskilling or reskilling provided the company also makes resources available to cover knowledge gaps.

Here are a few telltale signs that upskilling or reskilling might be needed:

  • Unclear Hierarchies

If delegating tasks and communicating up the chain of command is frequently confusing and team members are often pointing fingers or unsure about their responsibilities, it could be a sign that people are lacking important skill sets.

When there aren’t people with high-level skills, people often push work around to spread accountability out. Other skills that could help resolve the lack of clarity on teams, such as organization or leadership, are also prime areas for upskilling. They’ll always come in handy no matter what trajectory an individual’s career might take.

  • Performance Shortfalls

It almost goes without saying, but if people are missing their targets or failing to deliver enticing products to the client or stakeholders, it’s clear that some skills might be lacking to some degree. Pay attention to gaps between goals set in the brainstorming phases of projects and what comes out in the deliverables and the final product.

Head to the creatives or the people who manage them directly to find out how people are performing. If there are significant talent gaps, the creatives who brainstorm together are the ones most likely to be able to identify them. As an added bonus, the employees will have a chance to be heard if they have a role in the process, which will improve their view of the company overall and very likely improve retention rates.

  • New Possibilities

The vast majority of UX design and other creative work is commissioned by companies that are transitioning to online eCommerce or updating existing internet properties. As a result, new software and other technology are constantly being developed and introduced. Game-changers are now the name of the game.

Achieving new capabilities and streamlining business practices are always signs of progress. Your staff has to progress right alongside the technology, which is exactly where the majority of reskilling comes in. Old roles may no longer be necessary. Alternatively, existing team members might need to be upskilled so they can use the new technology.

Outsourcing & Reskilling

The world is becoming more international. For an increasing number of companies, that means offshoring or outsourcing sectors or the entire production process. Whether it’s for more favorable regulations or reduced labor costs, reskilling the staff that’s left behind is the best way to complete this outsourcing without destroying your credibility and tarnishing your employment brand beyond repair.

Offshoring leaves a bad taste in people’s mouths. But if manufacturing jobs are sent elsewhere and the workers who used to take care of that part of the operation are elevated to management, oversight, or other important roles, the outsourcing will seem like a victory for all parties involved.

It might not be possible to reskill every single worker, but the best of the best can be taught to oversee the exported operations. Since they have direct experience with the procedures, they know what to look for and should be able to help ensure everything goes smoothly. In cases like these, languages and cultural awareness are aspects of reskilling and upskilling that mustn’t be left out.

Aren’t Reskilling & Upskilling Expensive?

Why should your company pay for these training efforts when you can just look for a new hire that has the skillset you’re looking for?

Take it from a creative staffing agency: at icreatives, we’ve spent long enough connecting creative talent with companies that need them to say confidently that the dream candidate is not always out there.

Even with the cost savings that come from sourcing talent through a creative staffing agency, bringing in new talent every time you need someone with a new skill isn’t always the most inexpensive way to go about things. The money and time spent interviewing and onboarding new people may as well be spent on upskilling existing staff. You just need to know how to upskill without breaking the bank.

This creative teambuilding will also do wonders for the workplace culture. When people have pathways for career advancement within a company, they have a vested interest in the company’s long-term health and performance. If employees see the only opportunity for advancement is outside the company, retention rates will plummet and you can bet they’ll be delaying the hardest jobs for the next person to take on their role after they jump ship.

How to Upskill for Creatives

Training creatives in new areas can be difficult when management and other stakeholders aren’t in creative roles. When the higher-ups aren’t familiar with the latest trends and tools for creative work, they won’t know exactly what the creative team needs to learn.

Luckily, creatives themselves are generally very good at identifying skill gaps in themselves and other members of the team. Critique is an important part of creative work from graphic design to content writing, so the creatives who need upskilling are very likely going to be able to point out skill gaps right away.

Use some of these tips to upskill and reskill creative employees and teams in the most constructive and least obtrusive ways possible.

1- Empower the Team

As we just mentioned, the creatives are likely already aware of skill gaps on the team. A major concern for management when it comes to reskilling and upskilling is that it takes time away from stakeholders who need to organize sessions. You can address both of these issues by putting creative teams in charge of their own upskilling and reskilling.

Set goals and concrete deliverables for training and make it a consistent part of every creative role. If you can turn the upskilling into a creative teambuilding exercise, you win twice. The last thing creatives want is a boss coming in and arranging a speech that doesn’t do much for their professional education, so let the creatives lay out a plan for their upskilling plan that can then be reviewed and approved by upper-level decision-makers.

2- Be Candid

When you set these training goals, there’s no reason to beat around the bush about the company’s desires. Although management may personally appreciate upskilling from a human perspective, it’s vital to communicate a business-oriented agenda to the people going through the training so they know what to aim for.

This is just good behavior from a teamwork angle. Like it or not, if the upskilling doesn’t help accomplish business goals then it can’t continue. No company wants employees working on ineffective tasks while they’re on the clock, and creatives especially want to be engaged in meaningful work more than they just want to collect a paycheck.

3- Empathize

You might have heard creatives preaching about design thinking, a structure for building user-centered products. Empathy is the first stage in design thinking and management can benefit greatly from including it in their business practices, too.

Decision-makers should understand that each team member – not just the ones in creative roles, either – has their own professional goals. The same solution isn’t always suitable for everyone and management should understand that. Attempting to build one-size-fits-all solutions is unlikely to work, especially for larger teams.

Combine the business goals identified when setting up an upskilling program and ask the creatives who will go through the program to ensure it aligns with their personal goals. Leave a mechanism for feedback and make the upskilling program flexible enough to make everyone happy.

4- Use Existing Talent

Seminars and training materials from experts are both great for upskilling and reskilling. But if you have in-house talent that can provide new information or mentor the creatives you need to train, why not use it?

If you want to know how to upskill and do some creative teambuilding at the same time, establishing a mentor program or allowing senior talent to aid in the upskilling of creatives is the best tip we can give. Not only will it increase communication and create a sense of camaraderie throughout the office, but it will also introduce different aspects of the business process for all parties.

Incentivize these training sessions for the senior talent. Make sure no one’s schedule is interrupted by getting the mentor to join the creative team while they’re working on a project. If that’s not feasible, then buy lunch for everyone and let them talk informally about what’s going on. That’s also a great way to find out what the creatives think is the biggest skill gap on the team and what they would like to concentrate upskilling and reskilling efforts on.

5- Make Upskilling Remote-Friendly

Remote work was skyrocketing in popularity even before the unexpected events of 2020. Nowadays, it’s hard to find a fully traditional team. At least part of most creative teams is remote and it doesn’t appear that it will change anytime soon.

Whatever method you use to upskill creative talent, make sure people who are accessing the material from a remote location get the same fulfilling experience. Otherwise, you risk the remote parts of the team falling behind, which will create division and make the work that much harder.

Time changes make coordinating these training efforts a bit difficult, but if your team is spread out through different time zones you can make your remote-friendly materials accessible at any time. Recorded seminars and materials enable workers to access the training on their own schedule.

Make sure there are concrete deliverables to make sure the training is done. It shouldn’t feel like another work assignment, though. You can prevent this by making the deliverables part of a larger piece and get the whole creative team together to discuss the results of the training in a relaxed setting without a specific agenda.

6- Begin Upskilling ASAP

The earlier employees begin some kind of upskilling, the more it becomes a feature of their role at the company rather than an annoying temporary chore. It also shows that the company values continuing education, innovation, and imagination.

Why not start upskilling slowly when new team members are being onboarded? They’re already in a learning mode for the first few months of their employment at the very least. It’s never too early to start upskilling and it will leave the workforce much more prepared for whatever comes next.

Make sure this immediate upskilling is clearly defined as general skill-building and not simply education that is required to work the job. That way, the creatives will understand that upskilling plays a major role at the company and expect it throughout their career there.

A girl holds a book over her face near a brick wall.
Creatives should always keep studying but need to take a break sometimes, too.


Businesses that know how to upskill creative talent effectively are in a much better situation to meet the ever-changing demands of modern business. If you start upskilling efforts during the onboarding process and make sure they continue consistently, employees won’t even view them as an interruption.

In many ways, these training efforts can build a better office culture if they’re used as a creative teambuilding effort in addition to teaching new skills. Mentor programs and upskilling or reskilling that empowers the creatives to design their own process will keep talent happy and boost retention rates. All in all, there’s no reason not to implement a flexible reskilling and upskilling plan as soon as possible.

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