November 17, 2025
5 Min Read
If there’s a tougher job in the corporate world than a human resources professional, Natalie MacDonald has yet to find it.
“They have to be coaches and mediators, liaising between the company’s employees and the senior leadership. And on top of that, they have to know the law, without ever having gone to law school,” says MacDonald, co-program director of the Osgoode Certificate in Advanced Human Resources Law for Senior HR Executives.
The four-day course, which MacDonald runs with co-program director Stuart Rudner, helps HR leaders take their legal skills to the next level through an in-depth case study method that makes extensive use of breakout rooms, practical exercises and real-life scenarios. The program also counts towards the Human Resources Professional Association’s continuing professional development requirement for members.
Each of the four modules is based on a different stage of the employer-employee relationship lifecycle, from the job posting and hiring, all the way through to termination and potential litigation.
Every day starts with an initial demand letter from Plaintiff’s counsel, which is dissected throughout the class. At the end of each module, a senior HR panel comes in to discuss the hot button issues raised during the day in a Fireside Chat.
“We say that we’re taking them through a day in the life of an HR professional. Hopefully none of them will ever have a day exactly like this, because it’s quite an extreme scenario, but the idea is that we work as a group through all the issues they could face at each of those stages,” Rudner explains. “It’s very hands-on.”
Rudner’s connection to Osgoode goes back some way, having graduated from the school with an LLB in the 1990s. Despite his initial interest in criminal law, Rudner found his true calling in employment law at a large full-service firm, where he worked under the tutelage of practice area heavyweight John Sproat, now a judge of the Ontario Superior Court of Justice.
Rudner eventually returned to Osgoode as the founding director of the Osgoode Certificate in Human Resources Law for HR Professionals. MacDonald was a speaker at the inaugural event, before Rudner brought her on as his co-program director – a few years prior to them founding their own law firm together in 2013.
When MacDonald was admitted to law school in the early 1990s, she had seen her future in family law, but quickly realized that this was not the only way she could make a difference in society.
“Employment forms such a significant part of our identities that when it is negatively impacted in any way, it creates all sorts of issues. I see employment law as a way to really assist in terms of an individual’s and an organization’s wellbeing,” MacDonald says.
Within years of her law school graduation, MacDonald had joined the partnership at a leading employment law boutique. Meanwhile, she quickly established a name for herself in the wider employment law bar as a leading authority on the subject of extraordinary damages through her textbook, Extraordinary Damages In Canadian Employment Law, followed by a series of landmark court decisions in favour of her clients.
In 2017, Rudner and MacDonald went their own ways professionally, each forming their own employment law firm catering to both employees and employers. They both continue with Osgoode, thanks to the advanced human resources law certificate, which they designed together as a follow-on from the earlier certificate program in HR law.
“That program is really geared towards making sure that they understand the basics, including things like employment standards and entitlements, occupational health and safety, workplace harassment investigations and termination with or without cause,” MacDonald says. “Then they step it up a notch with the advanced certificate for senior HR executives, where we really go deep into the issues.”
Completion of the original Osgoode Certificate in HR law is not a pre-requisite for the enrollment in the advanced course, according to Rudner, who explains that many mid-career and seasoned HR professionals will have a solid foundation of HR law knowledge. Returning graduates of the original certificate will notice a difference, Rudner adds, due to the extremely practical focus of the advanced certificate program.
“There’s no lecturing and very little PowerPoint,” he says. “One thing we try to emphasize is that HR executives are not making employment law decisions; they’re making business decisions.”
“Our role is to let them know what the employment issues are and where the risks are, but then take a more holistic approach to figure out what the right decision is. The case studies help us do that,” Rudner adds.
For MacDonald, the highlight of the advanced HR law program comes on the fourth and final day, when attendees turn their attention to the litigation process and what they can expect if one of their HR matters ends up in court.
“It ties together everything they have learned to that point,” she says. “Most HR professionals have not been through litigation, so they don’t always understand the critical role they play. I think it gives them a lot of confidence to go back to their role and address these issues with some authority.”
“I’ve learned as much from attendees over the years as they do from us, because the people in the class have a lot of experience and we always make time to hear from them about the problems they face in their workplaces throughout the day,” MacDonald adds.
Rudner says the networking opportunities arising during the program are another point of pride.
“I’ve seen so many personal and professional relationships develop between participants. And I’m very happy to say that many former students have become friends and clients,” he says.
Want to learn more about OsgoodePD’s Certificate in Advanced Human Resources Law for Senior HR Executives?