Understanding Both Sides of the Table - Simon Pelsmakher

QUESTION 1 OF 6

You sat on the employer's side of the table for years. What did it teach you about how employers assess a claim - and how do you use it now, on both sides?

Before founding my firm, I was in-house counsel at multinational companies, where I handled demand letters and resolved employment disputes on time and within budget. That taught me how employers assess claims: what they're prepared to pay, how quickly they want matters closed, and what it costs them to keep a file open.

I now bring that perspective to the other side of the table. At recent mediations for employees, I've been able to push files forward efficiently and obtain maximum value for my clients, without running up costs that eat into their recovery. When I act for employers, the same experience helps me anticipate what the employee actually needs to resolve the matter, so disputes don't drag on.

QUESTION 2 OF 6

You left in-house security in 2026 to found your own firm. What made you go, and what did you have in place before you jumped?

In-house taught me how businesses think about risk, budgets and their people, and that perspective still shapes how I advise clients. But I missed private practice: working directly with clients, the variety of industries and issues, and a practice that combines litigation with advisory and corporate work.

Having my own firm was a long-term goal, and I’m really happy to be doing it. It’s exciting to build a business while practising law full time. In many ways they’re two full-time jobs, and I am loving it.

QUESTION 3 OF 6

Pelsmakher Law advises employees and employers. Most boutiques pick a side. Why did you refuse to, and how do you sell both sides without losing trust on either?

I’ve worked on both sides, so it felt natural to keep doing that. My career has taken me from leading employment law boutiques on Bay Street to in-house roles at major multinational corporations, acting for both employees and employers. That gave me an appreciation for every vantage point, and I’m excited to carry that into my own firm.

As for trust, I don’t see it as a conflict. Whoever my client is, they get my full advocacy. Knowing how the other side thinks makes me a stronger advocate, because I can anticipate their arguments and pressures and advise my clients more realistically. And like any firm, I run strict conflict checks on every matter, so I never act against a current or former client.

QUESTION 4 OF 6

Your website runs a free severance calculator. What does giving away a tool like that do that advertising can't, and has it actually brought you clients?

The calculator is a helpful free tool for employees. Losing a job is stressful, and many people don’t know what they may be entitled to. The calculator gives them a starting point to assess their situation, and I’m happy to offer that.

The calculator also does something advertising can’t. It gives people something useful before they’ve spent anything or committed to anything. That builds trust and brings people to the website, where they can learn more and reach out if they want help.

QUESTION 5 OF 6

Employment law is Toronto's most crowded niche, and you launched into it this year. Where did your first clients actually come from?

Employment law is where I’ve spent my entire career, so there was never a question about focusing on it. It’s an area I find exciting. Labour and employment law touches on so many other areas of practice, from corporate and human rights, to privacy, tax, and litigation, and it’s always evolving.

My clients have found me from a mix of sources: referrals from colleagues, my personal network of family and friends; and people who found me online.

QUESTION 6 OF 6

You post case commentary nearly every week. What has posting that consistently actually done for your practice, and what turned out to be vanity?

I post regularly because I enjoy writing and staying on top of developments in labour and employment law. Writing about a decision makes me think it through thoroughly, and that makes me a better lawyer for my clients.

It’s also been good for the practice. It builds the firm’s brand, brings people to the website, and gives the public a free educational resource. Many people want to understand their situation before they speak to a lawyer, and the articles help with that.

As for vanity, I try not to focus on likes or view counts. What matters to me is whether a post is useful to someone trying to understand their rights or obligations.