Meet Cheryl: Legal Assistant Grad Reflects on Her Career Journey

Cheryl Michaud’s original plan was to become a teacher. But when she was partway through her education degree, a change in her personal circumstances made her realize she needed to get job-ready more quickly. So she enrolled in the legal assistant program at Herzing College.

That was back in 2004. Since then, she has supported lawyers in both small and midsize firms, worked as an executive assistant to a couple of chartered accountants, assisted a group of provincial court judges, and played a key role in the legal services department of city government.

Along the way, she kind of fell into office management, developing systems and processes to keep operations running smoothly. That eventually led her to management positions supervising other legal assistants. Today, as part of her position she’s in charge of hiring and training assistants for a firm that offers legal support in more than 20 different areas of law.

We interviewed Cheryl recently to learn more about her career journey and what advice she has for people considering this line of work. Read on for the highlights.

Q. Cheryl, could you share a bit about your educational and professional background?

Cheryl: I actually started university thinking I was going to be a teacher. Then I wound up taking a few courses in conflict resolution studies, which was fascinating to me. I wanted to get involved in some type of work that would follow from a degree in conflict resolution.

But unfortunately, my personal circumstances dictated that I needed to get a stable job to support my family quickly. I was only a year and a half into my university career and didn’t feel that I could complete it and support my family at the same time.

Legal assistant sounded like something that was still going to satisfy what I wanted from a career and get me in a stable job faster. I started the legal assistant program at Herzing in 2004 and after a few months worked part time at a law firm at the same time. That led to a full-time job when I graduated.

Over the years I’ve worked in both small and midsize firms, as well as a few larger corporations. I’ve done general practice, family law, even finance.

At one point I had a job with the province of Manitoba working in judicial services. That was always a bit of a dream for me. I think for a lot of legal assistants that’s a career option that’s really inspiring—you’re sort of at the top working for the judges. It’s a role that doesn’t come up very often because most people who get into it tend not to leave it.

I continued to expand my education with courses related to finance, project management, and business analysis. That helped me to move into more of a management role.

Currently, I’m the Manager of People and Operations at Tapper Cuddy. I’m responsible for recruiting, hiring, and retaining staff in addition to working on the operational business side of the office.


Q. What was it that drew you to the legal assistant field?

Cheryl: At the time, I think what appealed to me about it was the link between that and the conflict resolution studies I’d been taking in university. The thing about law is that there are a lot of people coming to you in a state of conflict, and you get to try to help them sort that out. I saw it as an interesting opportunity.


Q. What’s the most challenging aspect of the work?

Cheryl: The most challenging part was learning to prioritize—that is, learning to understand what could wait and what couldn’t wait when everything feels like it needs to happen right now. There’s a lot of pressure to complete a task quickly, but the reality is that these things take time to do and often require a very high level of attention to detail. Learning to cope with the pressure and maintain a high attention to detail and accuracy in what you’re working on is very important.


Q. What special skills or traits would you say you need to succeed as a legal assistant?

Cheryl: The number one trait is that you need to pay very close attention to the process behind the task that you are completing. You’re not just pushing paper. You need to understand why this document is being created, what its purpose is, and what next step is coming after it. Having very high attention to detail is critical; I can’t stress that enough.


Q. You’ve worked for private law firms as well as municipal and provincial governments. How do those settings compare?

Cheryl: They’re both really interesting in their own ways. The part I found most challenging in government is that you’re a little bit more stuck in a process. There are processes that are predefined and there’s different layers of approval that are absolutely required. There might be opportunities to implement continuous improvement, but more than likely you’re going to be told what to do and you’re going to be expected to meet those standards to an exceptionally high level. That’s a challenge.

When you’re in a private firm, depending on the firm, you can have a little bit more flexibility. But having that flexibility comes with its own challenges because you have to be able to adapt quickly.

In my opinion, if you like to innovate and be more creative, a private firm might be a better fit. But if you crave a little more structure, government might be a better place for you.


Q. What advice would you give aspiring legal assistants? What should they know upfront about starting a career in the field?

Cheryl: You’re working with people who have high expectations of themselves and high expectations of those around them. So you want to make sure you’re totally focused on performing your role well. Take lots of notes, review them, and ask questions. When you are in the role, you need to be 100 per cent focused on what you are doing and make sure you are doing it well.


Q. Any final thoughts?

Cheryl: I think back to when I first started out as a legal assistant and how I was stumbling along trying to learn new things after I left the security of school. It was tough. One of the things I’m trying to do at Tapper Cuddy LLP is develop mentorship and training programs for new legal assistants so that they too can have careers where they’re involved in the files and enjoying the work they do.

I think it’s an amazing career. Yes, there’s an opportunity to follow my path and move into different areas, but also being a legal assistant is pretty great.



Herzing College’s online legal assistant program is just nine months long and includes a four-week internship for real work experience. Many of our grads get hired straight from their internships.

Need more info? Reach out to admissions. An advisor would be happy to walk you through the program and answer any questions you have about course schedules, application procedures, career paths, and more.

Click below to get more details on the legal assistant program and chat live with an advisor. We’re here to help!

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