Bright minds are driven by curiosity. And global expansion is a journey into the unknown. The right questions are your compass, helping you uncover not just the challenges but the hidden opportunities that lie within each new market.
This isn’t about simple answers. The questions you ask often matter more than the answers you expect. These 100 questions are designed to spark critical thinking, challenge your assumptions, and reveal potential blind spots in your strategy. They force you to consider the cultural, legal, and logistical nuances that can make or break your expansion efforts.
At Acumen International, we believe in the power of asking the right questions. We don’t just tell you the rules; we help you anticipate challenges, understand cultural nuances, and develop customised solutions that align with your unique goals. We support you at every step, ensuring your global growth is compliant, strategically sound and sustainable.
1. Strategic Expansion and Market Entry
Expanding into new markets involves more than just setting up operations, it’s about understanding the market, its potential, and the risks involved. Identifying the right entry strategy can save time and resources.
- What are the regulatory requirements for entering a new market without establishing a local entity?
- How do employment laws affect your ability to hire quickly in a new region?
- Are there specific sectors or industries that require different compliance measures?
- What are the risks of entering this market from a political, economic, and legal standpoint?
- How does local competition affect your hiring and compensation strategy?
- What is the best way to scale your workforce in a new market while managing risks?
- How do you evaluate a market’s potential before making a full commitment?
- What are the legal implications of running a pilot or test phase without setting up a permanent presence?
- How do you maintain operational flexibility while exploring new markets?
- What is the best way to pivot or exit a market quickly if it proves to be unviable?
2. Legal Compliance and In-country Employment Laws
Expanding into a new market comes with legal challenges that aren’t always obvious. Misunderstanding local laws, even in small ways, can lead to fines, operational delays, or worse. Getting ahead of these issues requires understanding each country’s employment, contracts, and employee rights rules.
- What critical employment laws differ between your home country and the new market?
- Are you aware of mandatory benefits and protections required for employees in that jurisdiction?
- How do local contract laws impact employment agreements?
- What are the specific notice periods and termination rights in the new country?
- What labour laws, if any, limit employee working hours and overtime?
- Are there any industry-specific regulations that need special attention?
- Do you understand how unionisation or collective bargaining laws could affect your workforce?
- What are the legal consequences of misclassifying workers?
- What are the requirements for severance payments and dismissal procedures?
- How will you address potential conflicts between corporate policies and local employment laws?
3. Legal Entities, Permanent Establishment Risk, and Worker Classification
Expanding into new markets introduces significant legal considerations that go beyond the surface. Choosing whether to establish a local legal entity or operate without one directly impacts taxation and compliance. Missteps in this area can inadvertently trigger permanent establishment (PE) status, exposing your business to unplanned tax liabilities and complex regulatory requirements.
Additionally, classifying workers correctly is essential, as misclassifying employees as independent contractors can lead to legal consequences, financial penalties, and reputational damage.
By understanding and addressing these risks early, you can structure your market entry strategy to be agile, compliant, and scalable while retaining the ability to pivot or exit the market when necessary.
- Do you need to establish a legal entity in each country where you plan to hire, or can you operate without one?
- What activities could trigger a permanent establishment status in the countries you’re entering?
- How can you assess and mitigate the risk of creating a permanent establishment inadvertently?
- Are you aware of the tax obligations associated with permanent establishment status in each jurisdiction?
- What are the legal and financial implications of operating without a local legal entity?
- How do local laws define the difference between an employee and an independent contractor?
- What are the risks of misclassifying employees as independent contractors in the countries you’re expanding into?
- What processes are in place to ensure correct worker classification across different jurisdictions?
- How will you handle payroll, taxes, and benefits for contractors to remain compliant?
- What alternatives exist for entering and testing new markets without long-term commitment or heavy investment in case you need to pivot, exit, or handle unexpected changes?
4. Taxation and Payroll Management
Managing payroll across different tax jurisdictions is a complex process. Mistakes can lead to financial penalties, unhappy employees, and damaged relationships with local authorities. Ensuring you meet payroll and tax obligations across multiple countries can protect your business from expensive surprises.
- How do tax regulations differ in each country you’re operating in?
- Are you clear on the specific payroll reporting requirements for each jurisdiction?
- What is the local tax withholding process for employees?
- How do you ensure proper tax deductions for remote workers across borders?
- Are there any country-specific payroll tax holidays or exemptions to consider?
- How will you manage currency exchange rates and cross-border salary payments?
- What are the social security and pension obligations in each market?
- How do tax equalisation and tax protection schemes apply to expatriates?
- What are the penalties for missing local payroll deadlines or tax filings?
- Are you prepared to handle tax audits across multiple jurisdictions?
5. Contracts and Agreements
International employment contracts need to account for local regulations. What works in one country may not hold up in another. Drafting contracts that protect your business while complying with local laws is crucial to avoiding disputes and ensuring fair treatment of employees.
- What specific clauses must be included in contracts to ensure they are enforceable locally?
- How do local contract laws affect the terms of employment agreements? What are the key differences between fixed-term and open-ended contracts in your target country?
- Are there mandatory contract terms or benefits that need to be reflected in your agreements?
- How do termination clauses vary between regions, and how should they be handled?
- What are the requirements for probationary periods in different countries?
- How do non-compete or confidentiality agreements differ from country to country?
- How will you manage contract renewals in regions with unique employment laws?
- What are the risks of using foreign-language contracts, and how should translation be handled?
- How do you handle local language requirements for contracts? What contractual protections do you need in case of disputes?
- How do you ensure contracts are compliant with regional collective bargaining agreements?
6. Risk Mitigation and Dispute Resolution
Global expansion introduces new risks, such as unforeseen regulatory changes, employee disputes, and market instability. Planning for these challenges in advance helps minimise disruptions to your operations. The right strategy will keep your business stable even when problems arise.
- What are the most significant regulatory risks in the markets you’re entering?
- How do local laws affect your ability to resolve disputes with employees?
- Are there specific legal protections for employees that could lead to disputes?
- How will you prepare for changes in employment laws after expansion?
- What local arbitration or dispute resolution mechanisms are available?
- How will you manage conflicts that arise from cultural misunderstandings?
- How do local courts handle employment disputes, and what are the timelines for resolution?
- Are there additional risks due to political instability in the regions you’re entering?
- What contingency plans are in place for abrupt changes in regulatory requirements?
- How will you ensure compliance with laws regarding employee termination in the event of a dispute?
7. Immigration
Securing visas and work permits can slow down or even derail critical hires. Navigating each country’s requirements effectively ensures you can onboard the right talent without delays.
- What are the specific visa and work permit requirements for each country?
- How long is the average processing time for work permits, and how can it be expedited?
- What are the costs associated with securing work permits and visas?
- How do changes in local immigration laws affect your ability to hire foreign talent?
- How will you manage visa renewals and work permit expirations?
- Are there restrictions on hiring expatriates, or do specific quotas apply?
- What are the risks of hiring employees before their work permits are approved?
- How do dependent visas and family relocation affect your hiring decisions?
- What are the implications of hiring remote workers from countries where you don’t have a legal presence?
- How do you ensure full compliance with immigration rules for international hires?
8. Employee Benefits and Compensation
Creating an employee benefits package for global teams involves balancing mandatory benefits required by law and voluntary benefits that go beyond the minimum and make your company more competitive. While the legal requirements vary from country to country, offering benefits that employees value, like wellness programs, flexible working arrangements, or retirement plans, can help retain top talent across regions.
- What are the mandatory employee benefits in the countries where you’re hiring?
- Which voluntary benefits are most valued in the specific regions you’re operating in?
- How do local pension and social security systems affect your compensation packages?
- Are there tax-efficient benefits you can offer to attract local talent?
- How do you tailor voluntary benefits, such as wellness programs or flexible work options, to meet cultural expectations?
- What cultural differences in employee expectations around benefits do you need to consider?
- How do you handle holiday entitlements and local time-off policies?
- Are there any unique voluntary benefits you can offer that stand out from local competitors?
- How will you manage salary benchmarks and benefits across different markets to stay competitive?
- How do you offer flexible benefits packages that allow employees to customise their perks to meet personal and cultural preferences?
9. Employee Lifecycle Management
Managing international employees involves more than just hiring and firing. It’s about understanding the full employee journey, ensuring compliance at every stage — from onboarding to offboarding.
- What are the local onboarding requirements for new hires?
- How do you manage probationary periods and performance reviews across different countries?
- What specific local laws govern promotions and salary adjustments?
- How do you ensure smooth transitions when employees are promoted or transferred across borders?
- What are the requirements for managing employee terminations in different jurisdictions?
- How do you handle grievances and disciplinary actions while complying with local laws?
- What support systems can you implement to improve employee retention in international markets?
- How do you ensure local training and development programmes meet corporate and legal standards?
- What legal protections must be in place for employees resigning or being terminated?
- How do local laws affect severance packages, and what can you do to avoid disputes?
10. Global Workforce Coordination, Support, and Problem Solving
Managing remote and dispersed talent requires a robust support system capable of addressing both professional and personal challenges as they arise. Whether resolving regulatory or other unexpected issues, employees need reliable, timely, and human-focused support to keep operations running smoothly across borders.
- How do you handle urgent employee issues across time zones to ensure timely resolution?
- What systems allow employees to access immediate HR, technical, or personal support?
- How do you ensure employees in different regions receive localised support relevant to their location?
- What processes are established to address unexpected legal or regulatory issues impacting remote employees?
- How do you ensure employees feel supported during personal challenges while working remotely?
- What steps will you take to create an agile problem-solving framework for your global workforce?
- How do you maintain a personal, human touch in resolving issues remotely, ensuring employees feel genuinely supported?
- What systems ensure employees know exactly who to contact for urgent issues and can expect a timely, empathetic response?
- How will you manage sudden technical challenges that might hinder remote employees’ productivity?
- How do you ensure decision-makers are accessible and responsive when critical issues require escalation?
Acumen International: Enabling Confident International Hiring
International expansion demands more than standardised solutions or software platforms. It requires a partner capable of navigating the realities of each market, where employment law, tax risk, and immigration complexity are the rule, not the exception.
Acumen International operates as your legal employer in 190+ countries, ensuring every hire is locally compliant, audit-ready, and fully supported, whether in established, emerging, or high-risk markets. Our expertise covers every employment scenario: local and international talent, blue- and white-collar, executive or project-based roles, and every major sector.
Where other providers stop at templates or “best effort” compliance, Acumen delivers precise, role-specific employment solutions. We manage:
- In-country onboarding, payroll, and statutory employee benefits,
- Work permit sponsorship and global mobility for critical and senior talent,
- Contractor-to-employee transitions to eliminate misclassification risk,
- Country-specific audit, reporting, and ongoing local HR support,
- Clean market entry and exit strategies without permanent establishment risk.
Every client is backed by operational expertise and real-time advisory support, not just systems. Acumen’s Global Payroll Calculator and Global Compliance Guide provide instant cost and regulatory clarity before you commit, helping you compare, scope, and plan with confidence.
For organisations with serious ambitions or real complexity, Acumen International delivers the level of risk management, control, and local insight needed to turn global hiring from a gamble into a strategic advantage.
Grow with confidence, partner with Acumen International.