Hana Akaike, Senior Associate at Osborne Clarke, has built a career at the intersection of employment law, cross-border advisory work, and organisational development. In this interview, she reflects on the experiences that shaped her path, the value of continuous learning and mentorship, and how practical legal guidance can support companies navigating an increasingly complex labour landscape.

Interviewd by Nini Gordadze

As a Senior Associate specialising in employment law, labour relations, and cross-border advisory at Osborne Clarke, what originally drew you to this field and what has kept it stimulating for you over the years?

My involvement in employment law began during my legal traineeship at the tribunal, when I was assigned to a judge in the employment law section. That is where I began approaching and learning about employment-related issues.

Employment law sits right where people, business and society meet that is what makes it so meaningful and dynamic.

Compared to other fields, labour rules are not abstract, they affect people’s working lives directly, and you can see their concrete impact. The field feels familiar, and it helps you understand how organisations work. Employment law is also constantly evolving with the economy, new technologies and social expectations. It is not static, which makes it interesting, but also demanding. Over the years, labour laws have changed frequently, especially when new governments take office, as the trend is to reform the sector. This makes continuous training and updating necessary, which can be challenging.

Another aspect I appreciate is working in an international environment. I often assist foreign companies and receive cross-border mandates, which is very stimulating. I interact with foreign clients who do not share the same legal or cultural background, and I have to make them understand how the Italian legal system works. This can be challenging because the legal system is complex in itself, and explaining it to someone who is not familiar with legal frameworks can be difficult. It requires empathy on one side and clarity on the other, because at the end of the day, we are people interacting with other people, and my task is to make them understand how the system functions.

Your role places you at the crossroads of labour law, business strategy, and cross-border client support. What does your day-to-day work actually look like, and what kind of impact do you aim to have through your role?

When I think about my day-to-day activities, I would say I sit between legal risk and business execution. I provide advice on risk exposure, helping companies understand the liabilities they might face, and at the same time I offer practical guidance to support them in implementing their decisions. I need to combine both aspects.

A typical day varies a lot. I might start with a call from a client asking for advice because they have an issue with an employee who is not performing well and they do not know how to handle the situation. After that, I might be required to review a contract to check whether it is compliant with Italian law. Later in the day, I may deal with a completely different topic, such as a restructuring or redundancy.

Another important part of my work is that it cannot be limited only to employment law. Often we need input from other departments, tax, corporate, privacy, so I interact with many different professionals. This interaction makes the work even more interesting.

You advise both Italian and international companies. From your experience, what are the most common cross-border employment challenges today, especially with companies expanding or restructuring across multiple countries?

One of the first cross-border issues is the hiring of employees in Italy by foreign companies. Many do not have a legal entity in Italy and want to understand how they can hire people here. This has become increasingly common with the rise of remote and hybrid work, especially after COVID, as these models allow companies to hire across borders without relocating employees. However, many companies do not know how to manage this process. In these cases, I provide step-by-step guidance on setting things up, meeting mandatory requirements, and complying with Italian law. It is not just about providing an employment contract; it is about giving practical guidance the company can use.

Another recurring challenge is restructuring across multiple countries. Restructuring, including redundancies and workforce reductions, is part of my job. Group companies often need to align timelines across jurisdictions, but different rules and requirements make alignment difficult. Ensuring consistent messages while remaining compliant with local laws requires flexibility and careful explanation so clients understand where their approach may expose them to risk.

Drafting policies for group companies is another frequent task. Many organisations want harmonised policies, but combining group-wide rules with local legal requirements is not always straightforward. Often, we create a general policy with separate local attachments, allowing the company to maintain uniformity while complying with each jurisdiction’s rules.

Your practice spans from drafting policies to handling disputes. How do these two sides of your work influence each other, and what principles guide you when you’re navigating such high-stakes situations?

My work is divided into two parts: advisory activity - providing consultancy and support to companies - and litigation, meaning disputes before tribunals and in court. For me, these are two sides of the same coin. Litigation, although it represents around 30% of my work, significantly shapes my advisory activity because it sharpens my ability to anticipate risks and potential claims.

What I see in litigation, I can apply to my advisory work, not only in managing employment relationships but also in negotiating settlements. A part of my job is finding solutions to disputes with employees by identifying settlement terms that represent a fair compromise for both parties. To do this, it is important to understand risk exposure, points of leverage, and weaknesses on both sides, what the company can use as leverage and what the employee might rely on against the company. Litigation is a good way to train this analytical skill.

Regarding principles, I try to maintain the same values in both ordinary and difficult situations: fairness, transparency, consistency and accuracy. I aim to work with commitment, providing clients with enough information so they can make decisions consciously and with full awareness of potential risks. When situations are more complex, I offer more detailed scenarios to help companies understand all possible outcomes. Accuracy is important, but so is practicality. Advice cannot be purely theoretical; it must be actionable and tailored to the company’s business context.

With digitalisation and the rise of new forms of work, from remote and hybrid models to platform work, what major legal trends do you expect to shape the labour landscape in the coming years and which issues do companies most often underestimate when managing cross-border or distributed teams?

I think one of the major trends is the implementation of AI systems in our everyday lives, and this also has an impact on employment law and HR matters. I believe this development is inevitable, and it will change our lives not only in our field but in many others as well. In the context of labour law, AI might play a role in areas such as recruitment processes and performance monitoring systems.

AI brings significant opportunities, but it must be handled with caution. Its value is clear, yet full reliance can expose us to risks.

Another aspect is remote work and hybrid work. This has also been a significant trend over the last few years, especially after COVID. One of the difficulties companies face is managing the relationship with employees who work remotely. Sometimes companies struggle with how to interact with employees they have never met in person. Of course, remote and virtual work can be very efficient, and employees are not required to be physically present at the office or at meetings, which saves a lot of time. However, at the same time, important aspects such as building trust and developing relationships with colleagues can be jeopardised by this type of work arrangement. I think this will remain a challenge in the coming years.

Another topic that is currently very prominent in the employment law landscape is the Pay Transparency and Equal Pay Directive. This European directive sets out certain rules and general principles that each jurisdiction must implement through national legislation. Italy has not yet transposed the directive, but many organisations have already started working on it, preparing policies and governance systems that can align with the requirements of the EU directive.

As someone who has built an impressive career in a demanding field, what advice would you give to young women entering the legal profession today, especially those considering employment law?

To be precise, I am still in the middle of my career progression, so I consider myself a work in progress. Based on my experience, I would advise young professionals to stay curious and eager to learn. It may sound old-fashioned, but mastering the legal framework is essential; without this foundation, it is difficult to apply the law or offer solid support.

Another key lesson I’ve learned is the importance of finding the right mentors. In our profession, technical skills and strong competencies matter. For young people entering the field, it is crucial to work with the right team, not necessarily the biggest or highest-paying firm, but the one that helps you grow and learn. Today, studying can feel more challenging because AI provides quick and convincing answers. These tools are advanced, but they can also make it difficult to tell what is accurate. When I started working, I could already find information online, but I still needed to verify and deepen my understanding. With AI now even more sophisticated, the ability to question and check information remains essential.

My personal background has also shaped my perspective. I have Japanese origins but grew up in Italy, between two cultures, and later studied in Innsbruck. These experiences helped me understand different cultural nuances, which is especially important for anyone working on cross-border mandates. Finally, it is essential to work in an environment where your efforts are recognised. You may be an exceptional lawyer, but if no one notices your work, growth can be difficult. Having colleagues and mentors who recognise your value makes a real difference.

Given the growing role of networks such as WIL Europe, I’m interested Has being part of similar networks influenced your own career or perspective?

Yes, being part of the network is really helping me reshape my approach to networking. Before joining this training programme, I was not the kind of person who would naturally go to others, connect or try to establish new relationships. However, since I started the WIL programme, I have realised how important networking actually is, and my approach has changed over the last months.

Networking is essential, not just for meeting people, but for creating opportunities for yourself and taking an active role in shaping your professional path.

My aim is not to rely solely on what the law firm or the company provides me, but to also take initiative myself and look for opportunities independently. The WIL programme has helped me understand how important this approach is.