Worker classification must be treated as a defensible process with rigorous, sequenced review that begins with structured fact-gathering before contractual scrutiny. Safeguard Global’s Wanda Prewitt examines how teams need to understand who directs the work, how integrated the role is into core operations and whether the worker is financially dependent on the organization, and why visible internal challenge, a named decision owner and a clear escalation path indicate a serious, repeatable process rather than box-ticking.
Global expansion creates opportunities for HR compliance leaders to build robust decision-making frameworks that scale across jurisdictions. When worker classification decisions are grounded in local law, tested against operational context and clearly documented, organizations can confidently manage cross-border workforce complexity while maintaining compliance. For example, analysis from the Economic Policy Institute estimates that when workers in misclassified occupations are treated as independent contractors instead of employees, they can lose thousands per year in combined income and employment-based benefits, while social insurance programs lose hundreds to thousands of dollars per worker annually.
As this occurs alongside new platform work reforms and more active enforcement in many countries, HR compliance teams have an opportunity to bring greater structure to how cross-border worker decisions are made. The most effective teams focus on decisions they can explain and defend, grounded in local law, tested against real-world context and documented clearly.
Train for defensible judgment
Knowing the legal requirements is table stakes. Most global HR compliance teams can identify the right test or statute, but what separates them is how they think when the guidance isn’t obvious. That starts with what the business is really trying to accomplish and then weighing legal, operational and people risks against those goals.
Senior compliance officers can equip their teams with methods for ongoing learning and improved risk identification by standardizing a simple judgment method that guides them through complex cross-border questions.
I recommend “the 5 Whys,” attributed to Taiichi Ohno of Toyota, as a tried-and-true, non-technical approach that helps practitioners drill down level after level. Short practice reps on real past cases help people move beyond “What does the rule say?” to “What is this actually about, and what happens next if we’re wrong?” That same mindset carries into documentation, where a short decision brief that captures the facts gathered, sources consulted (ideally down to article, section or government guidance), alternatives considered and the rationale for the final call will strengthen your position during an audit.
This evidentiary record can be strengthened by a “weather of the day” check, assessing how the situational context has changed since the initial intake, which could now alter guidance. We know that the sky is not always blue, but it’s in our nature to rely on the universal, technical answer, rather than adjust based on the immediate context. This ability to take knowledge and transform it into something understandable is a cornerstone of effective HR compliance.
Over time, this combination of simple root-cause analysis, curiosity and disciplined record-keeping will help HR compliance teams make well-reasoned judgments they can back up with facts.
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Read moreDetailsMake worker classification a process
Worker classification itself must also be treated as a defensible process with a rigorous, sequenced review that begins with structured fact-gathering before diving into contractual scrutiny. Just like in an investigation, teams will need to understand who directs and supervises the work, how far the role is integrated into core business operations, whether the worker is financially dependent on the organization and which party provides the equipment, IT systems and other tools needed to perform the work. While government questionnaires and tools (like HMRC IR35 assessments in the UK) provide valuable starting points, they may not capture your specific operational context. This makes it critical to document your fact-based analysis rather than relying solely on automated assessments.
To maintain consistent diligence, organizational leaders should set clear criteria for when worker-classification decisions are escalated to senior internal reviewers or compliance specialists with country-specific expertise. Situations like large contractor populations in a single country, gray areas in how work is organized or recent regulatory attention in a jurisdiction may warrant that extra review. Whatever triggers you choose, document them in advance and capture the reasoning in your memo. Visible internal challenge, a named decision owner and a clear escalation path indicate a serious, repeatable process rather than simple box-ticking.
Align policies and contracts across the employee lifecycle
Defensible cross-border decisions start long before a termination, restructuring or carve-out hits your desk. For any non-US exit or divestiture, consider running a structured alignment check well in advance. Focus on determining if corporate policies, template contracts and local laws match in the jurisdiction and whether individual agreements quietly include obligations (or rights) you cannot meet in practice. This is especially important during transitions or organizational restructuring, where inconsistencies between inherited contracts and new structures can lead to claims.
That same discipline applies at the front end of the lifecycle. In a remote and hybrid hiring market, basic identity and right-to-work verification is now a compliance control that will require a second-step verification as best practice. That could be a live video or phone verification aligned with local law, with clear documentation of who verified what, on what legal basis, and for how long.
As AI tools become more common in recruitment and worker management, they should be handled like any other regulated control. The EU AI Act, for example, places certain systems in a “high-risk” category with clear expectations around transparency, data quality, human oversight and documentation. Practically, that means knowing where AI is in the process, confirming it aligns with local equality laws and documenting how those tools are used and monitored using the same defensible decision templates they would apply elsewhere.
Position people continuity at the center of compliance
Business continuity isn’t only about systems and facilities; it’s also about having the right people available when something goes wrong. A practical first step is to identify, country by country, the roles that keep you compliant for payroll approvals, statutory reporting, day-to-day operations and key customer support functions. For each of those roles, set clear coverage expectations and designate trained backups (including who can sign what), instead of relying on informal handoffs.
To assess the robustness of people-continuity protocols, run a quarterly test under plausible disruptions, such as a local weather event or power outage. The purpose is to confirm, in writing, how decisions will flow, who informs workers, who informs clients and how quickly you can reassign work across borders without violating local labor, privacy or immigration rules.
If done well, those exercises will generate metrics your C-suite cares about. For example, you can illustrate coverage gaps that were identified and closed, time-to-recover for critical processes, the percentage of key roles with documented backups and how often the plan prevented an interruption or protected employees in real events. This is a critical step in reframing HR compliance teams as the operators responsible for keeping the business and its people standing when an unexpected event occurs.
Conclusion
HR compliance teams are facing a moment when a few slight adjustments in how they operate can move the function from being seen as reactive legal interpreters to proactive, indispensable drivers of business stability. Decision-making around cross-border workers is a critical component as teams build out continuity plans for 2026. The HR compliance leaders who become trusted partners are the ones who can show they went beyond surface-level, purely legal answers; asked deeper questions; and turned that thinking into a clear process with documented reasoning.
Just as importantly, they build people continuity into risk planning instead of treating it as an afterthought. Those habits are what will matter most when a regulator, a board or a worker says, “Show me how you got there.”
Wanda Prewitt is the chief operating officer at Safeguard Global, with over 25 years of experience in payroll, HR operations and global service delivery. Her background includes executive leadership roles at ADP, Alight Solutions and NGA Human Resources. 
