Legal support staff talk about their best (and worst) bosses // The Insider

“I find it hard to work for old-school lawyers, who expect you to grab their coffee, pick up dry cleaning and take dictation”

By Christina Gonzales

On Wednesday September 4th, 2019

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We all know that lawyers can’t do their jobs alone. On a daily basis, they rely on an army of legal support staff to complete a wide range of crucial tasks. This includes research, document drafting and client management. And a whole lot more.

Quite often, these working relationships run smoothly. But they can also spin out of control, especially if a lawyer has an intemperate personality or bad work habits.

Here, we’ve asked two legal assistants and one law clerk — who, collectively, have worked on Bay Street for almost a century — to dish on the highs and the lows of working with lawyers. As you’d expect, we’ve changed their names, mostly to protect their bosses.


ALISON | Assistant

Worked at 5 firms | 28 years of experience

Who are the best lawyers to work with?

“I currently work with three senior lawyers and one second-year associate. The second-year is my favourite. He’s so appreciative of my hard work. He’ll send me emails that say: ‘I know how hard you’ve worked on this. You rock!’ Sometimes, he’ll even bring me little gifts, like Timbits. These small gestures go a long way.”

Who are the worst lawyers to work with?

“I find it hard to work for old-school lawyers, who expect you to grab their coffee, pick up dry cleaning and take dictation.”


DAVID | Clerk

Worked at 5 firms | 30 years of experience

How can a lawyer make your job difficult?

“At my previous firm, I worked with a partner who would constantly change her mind about what she needed. Every time I delivered on her request, she’d say, ‘That’s not what I wanted.’ Things got so bad that I decided to leave the firm.”

How can a lawyer make your job easier?

“I like working with lawyers who show respect. You can spot them immediately. They can be gruff or abrupt, but they are professional and direct. They know what they want and can communicate it.”


ASTRID | Assistant

Worked at 3 firms | 33 years of experience

What do you like about your current boss?

“I’ve been working with the same lawyer for 16 years. And she’s excellent. She recognizes my skills and never treats me like an underling. On top of that, she understands that mistakes happen. When I make an error, I own up to it, and she appreciates that.”

Have you had a bad experience working with a lawyer?

“There is another lawyer who I worked with for 10 years. He was a nice guy, but he was a procrastinator. He would only get moving at the end of the day, and then he’d get annoyed that I didn’t operate on the same schedule. He would say things like: ‘Just when I’m getting going, you’re leaving!’ He would say it lightly, but it wasn’t really a joke. I sometimes had to stay late just because he didn’t look at something earlier. It was frustrating.”


This story is from our Fall 2019 Issue.


Illustration by Kyle Metcalf