How Freelance Talent Can Change the Failure Structure of DX

The Pattern of DX Failure Blamed on “Talent Shortages”

“We want to push DX, but we don’t have any IT talent in-house.” “Our IT department is too busy to even consider new systems.” I hear these kinds of comments from business owners all the time. The solution that’s been gaining attention recently is leveraging freelance IT talent.

Recently, a company called TechBiz exhibited at the “Digitalization & DX Promotion Exhibition (ODEX),” proposing DX promotion through the use of freelancers. At first glance, this seems like a perfectly reasonable approach: “accelerate DX by borrowing external power.”

However, I want to pause and consider something here. Isn’t the use of freelancers just ending up as “filling a talent shortage”? Isn’t management trying to use external talent to paper over the consequences of failing to define IT and leaving everything to the front lines?

In this article, I will organize, from a management decision perspective, the cases where using freelancers is effective for DX promotion and, conversely, the cases where it leads to failure.

Conditions Where Using Freelancers is the “Right Answer”

First, let’s clarify the situations where you should use freelance IT talent. It’s when “management defines the purpose of IT and only outsources the implementation expertise to external parties.”

For example, let’s say management decides on a policy to “visualize the sales process and create a system that prioritizes deals with a high probability of winning orders.” In this case, the goal is “improving sales reproducibility,” and IT is just a means to that end. In this state, you can entrust freelance engineers with tasks like implementing a CRM (Customer Relationship Management) system or setting up automation using Zapier.

Because management has defined “what IT is for,” external talent can focus on implementation without hesitation. This is the ideal form of using freelancers.

The Vicious Cycle of External Dependence Caused by “Design Abandonment”

The problem is the opposite pattern. It’s when management brings in external talent with the mindset of “we want to push DX for now, so let’s leave it to the freelancers,” without defining the purpose of IT.

In this case, freelancers just complete the tasks given to them and don’t think about the overall optimization. Why? Because management hasn’t provided the overall blueprint. As a result, the following vicious cycle emerges:

• The tools introduced by freelancers don’t integrate with existing systems.
• When the person in charge leaves, the system can no longer be operated.
• Multiple freelancers build systems in silos, and data cannot be integrated.

This is exactly the pattern where the “fragmentation of IT’s objective function,” mentioned in the editorial policy, is accelerated by using external talent. As a result of management failing to define IT, different tools are introduced in different departments, and no overall value is created. This structure is no different from when IT is handled internally.

The Management Challenge of “Freelance Management Costs”

Another thing management tends to overlook is the cost of managing freelancers. When entrusting work to external talent, the following management overhead occurs:

• Defining work requirements and managing progress
• Quality checking deliverables
• Establishing rules for security and information management
• Creating systems for handovers and knowledge sharing

Who in the company will be responsible for this management? In many small and medium-sized enterprises, it ends up being the business owner themselves or an already busy IT department member who takes on this role in addition to their existing duties. As a result, a counterproductive situation arises: “We were supposed to outsource, but now we’re spending so much time on management that our core business is suffering.”

While using freelancers has the advantage of “converting labor costs into variable costs,” you need to understand that management costs will then become a fixed expense.

Small Successes, One Step at a Time: The “Business Card Management App” Example

The case of “Nexsta Meishi,” a business card management app for corporations that also exhibited at ODEX, offers a different insight. Digitalizing a simple but easily personalized task like business card management. This kind of “small DX” can often be completed in-house without relying on freelancers.

In fact, using Power Automate or GAS (Google Apps Script), a system to automatically import business card information into a CRM can be built with a certain level of IT literacy. What management should do is not suddenly outsource a large-scale DX project to external parties, but rather define for themselves “which tasks, if digitalized, would reduce the burden on the front lines and provide data useful for management decisions.”

Three Questions Management Must “Define”

Before considering using freelancers, you, as a business owner, need to answer the following three questions:

1. What management issue do you want to solve with IT?: Is it increasing sales, reducing costs, or speeding up decision-making?
2. How do you define “success” for that issue?: Have you specifically set KPIs or target values?
3. What scope should be outsourced, and what decisions should remain in-house?: You can entrust implementation, but management must retain the definition of purpose and evaluation criteria.

Only after clarifying these three points does using freelancers become a “strategic option.” Conversely, if you bring in external talent while these are vague, DX will end up being just a “we did it” feeling, with no return on investment.

Freelancers are a “Means,” Not an “End”

The news about TechBiz shows that using freelancers is one means of promoting DX. However, the means should not become the end. What management should be thinking about is not “how to use external talent,” but “what to achieve with IT.”

Freelancers are skilled craftspeople who implement the blueprint management has drawn. However, drawing the blueprint itself is the role of management. Even if you gather craftspeople without a blueprint, you’ll only end up with scattered parts; you won’t build a house.

The success or failure of DX depends not on the quality of the tools or talent used, but on how seriously management has defined IT. Before using freelancers, why not first put your company’s IT strategy on the agenda of your management meeting?