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Lessons Learned: Lawyers’ Biggest Career Mistakes and Successes

A lawyer’s day is filled with potential pitfalls—missed limitation periods, billing issues, misplaced files, problem clients—but, short of doing something that will get you disbarred, it’s those honest mistakes that can lead to some of the biggest learning experiences.


All lawyers have had experiences while practising law that they’d rather forget. But often it’s the worst experiences that can provide the greatest lessons, the ones you learn from and carry with you for the rest of your life. A lawyer’s day is filled with potential pitfalls—missed limitation periods, billing issues, misplaced files, problem clients—but, short of doing something that will get you disbarred, it’s those honest mistakes that can lead to some of the biggest learning experiences.

There’s one phone call a Toronto labour lawyer likely hasn’t forgotten. He made the mistake of forgetting to ask one simple, but very important, question. His would-be client recounts a call she made to the lawyer several years ago following a discussion with her manager. The woman, who worked for a large company, had been told she was being put on probation. “Basically, I was being fired.” A friend recommended a good labour lawyer.

“I called him and explained the situation: I’ve just been told by my employer that I only have a week to completely change or else I’m going to be fired, but for two years I’ve gotten outstanding job reviews. The lawyer expressed shock and said the employer had no cause. It was a strong case for wrongful dismissal.” The lawyer then asked her what company she worked for. “I told him and he said ‘oh.’ There was a long pause. ‘That’s the company I represent,’” he said, adding, “‘I guess that’s why lawyers should always ask the company’s name first.’” She says, “I actually heard his heart sink.”

We talked to several Canadian lawyers to find out some of the biggest career mistakes as well as successes that have shaped who they are today. Read on to benefit from the invaluable lessons they’ve learned along the way, without having to do it the hard way.

Own up when you’re wrong

“Be prepared to admit your mistakes,” says Paul Iacono, who practises in insurance, tort and personal injury litigation at Beard Winter LLP in Toronto. He advises lawyers to inform the client right away when something has gone wrong. Not long after he started practising law, Iacono got involved in a case after another lawyer made the mistake of missing an important legal principle. The lawyer called his client in and told him what had happened, then wrote down the names of five other lawyers and told him to choose one of them to consult with about the case. “So the man came to see me and I ended up having to sue this lawyer.” What impressed Iacono was the other lawyer’s professionalism about the issue.

Some years later, he remembered that lesson after missing a limitation period in one of his own files. He immediately told his client, “I’ve dropped the ball here, you’ve got to go and see another lawyer.” He reported it to his errors and omissions insurance, the other lawyer started an action and the issue was resolved in the client’s favour. As Iacono says, “You can’t try to run from a problem. You’ve got to face it. The worst thing you can do is sweep it under the carpet.”

And if you don’t deal with the problem right away? “It’s messier. The client is madder,” says Iacono. He advises lawyers to say, “‘I’m sorry that it happened, I did my best, I made a mistake, I’m human.’ You’ve got to be realistic about these things.”

Realize that what goes around, comes around

In the category of potential CLM (career limiting move), one lawyer, who didn’t wish to have his name used in this article, describes an experience he had as an articling student on a high-profile, hard-fought trial, which involved a number of senior counsel. His firm was appealing the case and he was given the task of ensuring the case was kept on the list. “My diarization system back then was not what it should have been,” he says. He missed the deadline and the appeal was struck off the list. “I had the not very pleasant task as an articling student of walking into the senior partner’s office, knees a-shaking, to tell him that by the way, this case, which has been much of the focus of your life for the last few years and which we are appealing, I just got it struck.

“I’m sure he was thinking all sorts of fairly negative thoughts, but he said, ‘all right, the thing about litigation is there are very few mistakes that can’t be fixed. Let’s get around to fixing this one. Let’s focus on what we do to get it back on the list.’ That involved me having the humbling experience of walking around to about six different lawyers’ offices, tail between my legs, asking for consent for the matter to be put on the list. And the other positive coming out of that was that everyone had the good grace to recognize it as an error, not to take advantage.” Everyone consented and it was put back on the list.

“In our business, we all make mistakes,” he says. “I really took it as a positive the way people responded to that error, both on my team—it would have been easy to jump down my throat—and on the other side of the fence. Everyone was very gracious about it. I’ve taken that as a good learning experience. I don’t seek to take advantage and fully recognize when other people make mistakes that that’s the course of the business and we all have to recognize that we’ll have our turn in those shoes.”

He adds that he has seen more files recently in which lawyers are picking on technicalities, “which are neither here nor there for the end result of the file. If you do that, you have to fully expect that it’s coming back at you and it’s going to backfire. And it’s not just going to backfire on this particular file—the last thing you want to do is get a name out there as someone who’s not reasonable to deal with because all of a sudden every other lawyer you’re dealing with knows that you’ve got that reputation and they treat you differently and you don’t get the courtesies at the time you require them.”

Make connections

“I wish I’d known earlier how important relationships are in the practice of law and to focus on building those connections early on,” says Soma Ray-Ellis, a partner and head of the employment group at Paterson, MacDougall LLP in Toronto, who is currently acting as counsel to Air India for the Air India Inquiry.

“When I began practising law, I thought it was just about working hard and producing good results,” she says, “but that’s the basic minimum. Beyond that, a significant portion of our time is spent managing clients and relationships, both within and outside of the profession, including the legal media, the media at large and the HR community.”

For Eamon Hurley, general counsel at Northrock Resources in Calgary, one of the best career moves he made when he left a major law firm was to stay in contact with lawyers he’d met there and to follow up on people’s offers. “When people said to me, ‘call me, we’ll go out and have lunch and play golf,’ I did call them.”

Hurley adds that far too many young lawyers he sees don’t work at building personal relationships with other practitioners. As the past-president of the Calgary Bar Association, he has often wondered why young practitioners aren’t taking advantage of opportunities to develop relationships with other lawyers at bar association get-togethers. They meet in collegial, non-adversarial settings, but participants tend to be what he describes as “the same old guard. Our events in Calgary should be overflowing with young lawyers, and it’s not the case … if your schedule doesn’t allow, if you’re too busy, then my advice would be make your schedules allow to come to these events.”

Avoid problem clients

Most lawyers have had this experience—clients you had a bad feeling about but you took on anyway. Sometimes there’s a gut feeling right from the beginning that something isn’t quite right, but often the realization doesn’t hit until the file is well underway. Family lawyer Lonny Balbi of Balbi & Company Legal Centre in Calgary tells the story of one client who suddenly made the decision to represent herself. “I got off the file and I was happy to get rid of her,” he says. She then came back to him several months later and needed his help right away.

“My sense was I didn’t want to take the file on,” but he did, and at a higher rate since he had to act quickly and move all his files to accommodate her. Although she agreed to the rate and the issue was resolved, “now she’s challenging my bill in court because she’s saying she paid too much.” He adds, “she was stuck in a bad place and needed help so I did it, and now it’s come back to bite me, so it wasn’t worth it.” When it gets to the point where there’s so much conflict and lack of communication between you and the client, refer them to another counsel.

“Not every lawyer is good for every client,” says Balbi. “It’s not personal. There are people you’re just not going to get along with.”

Maintain your integrity

Clients may come and go, but your reputation is invaluable. “Your reputation is built in little bits and pieces on every file and every telephone call and every dealing you have with other lawyers,” says Betty Johnstone, a partner at Aikins, MacAulay & Thorvaldson LLP in Winnipeg who practises construction law. “And it reaps rewards one way or the other.”

Johnstone often gets conflicted out of files, so over the years she’s had many opportunities to send work to people, but “my list of people that I send work to gets shorter with bad experiences.” She says that many young lawyers don’t realize “how much of their territory they burn by being sharp or inappropriately aggressive or doing a little sleight of hand. They have no idea what the impact of that is.”

Stay civil, advises Kathleen Peterson, a partner at Balfour Moss LLP in Regina who practises family law. “It’s worth it for your self-respect,” she says. “Sometimes you lose your temper and sometimes you behave in a way that you wish you hadn’t. I’ve breached this rule more than once…but that’s one of the rules I try to live by.”

Manage client expectations

Most clients who come to her door are going through a divorce, one of the most stressful times of their entire lives, says Peterson. Often, “you’re the closest thing they have to get mad at.” While she doesn’t advocate putting up with abusive clients, “I forgive a lot of bad behaviour from clients because I know what kind of stress they’re under. But if it crosses that line and I find the client starts to treat me like a doormat or a whipping post, then I tell them they need to go see another lawyer. Because that’s stress for both of us.”

A lawyer should be objective. Stay professional and keep your perspective while you’re helping clients deal with their problems. “You can give them objective advice without being swept along with whatever emotional stuff they’re going through,” says Peterson.

Managing a client’s expectations is important. Set them at a reasonable level and be very clear if the case is going to be very difficult. Then, says Balbi, “if we go in and I win, the client thinks I’m the best guy in the world and if we lose they kind of expected it.”

Don’t bury your head in the sand

Billing clients can be a very difficult part of the practice of law. Balbi says that when he was a young lawyer, “I was afraid to talk about what the legal fees were and I always tried to keep them within reason, thinking if I could keep them low, they would hire me.” Invariably the fees were more, “and I didn’t have the discussion and the clients always remembered the low number that I talked about.” When discussing fees, he recommends to “start at the high end and then quote each category and go down from there. I often would talk about the low amount. Of course we rarely ever achieved that. Stress the higher number. The first few times you say it it’s hard because you think that you’re going to choke just by saying this.

Balbi recommends phoning clients before sending out the bill. He describes it as common courtesy, plus your chances of getting paid are higher. “When you send out your bill to your client, the easiest thing in the world to do is just to simply sign the letter, sign the bill, and pop it in the mail. You kind of bury your head in the sand hoping that when the client gets it they’re going to be thrilled with it, they’re going to immediately write you a cheque for that exorbitant amount.

When he phones clients, Balbi tells them, “I’m going to be sending you a bill, here’s the amount, here’s how much is in trust. I just wanted to let you know it’s coming.” Listen for signals. “Does the guy fall off his feet? Does he have a heart attack? Or is he okay? If there’s a problem at that point you need to have that discussion with a client.”

Cope effectively with stress

If you don’t love what you do, find something else. That’s a hard lesson for a lot of lawyers, because once you spend years studying law and start making good money, it’s hard to think about making a change.

“There are days that I don’t enjoy some of the work I do or some of the people I deal with,” says Balbi, “but I do look forward to my work, I do enjoy it, I have a lot of fun in it. I think it helps me to be a much better lawyer when I love what I do.”

Take care of yourself mentally and physically. Have outside interests, exercise, meet with friends, eat well and get lots of sleep.

The stress of practising law “can cause a lot of problems, like addictions or depression,” says Peterson. “Don’t get so wrapped up in what you’re doing that you ignore the important things in life.” She’s seen lawyers crash and burn. “They literally feel like the weight of the world is on their shoulders and you watch them deteriorate day by day. A lot of them don’t recognize what’s happening to them but they may be falling into a depression.”

Peterson points out that articling students and associates are “being pulled by the partners to bill, bill, bill, it’s money, money, money. And of course you have four other files that have exactly the same stresses and they all have to be taken care of today. So it’s important to maintain a centre for yourself so you know who you are and where you’re going.”

Learn how to handle yourself in the courtroom

Be prepared. Peterson describes a mistake she once made in court. “I got up to talk to the judge and it was a complicated application and I brought the wrong file with me,” she says. “It was really horrible.”

She had to explain to the judge and other counsel why she wasn’t ready, then asked the court to put the case to the bottom of the list. Someone came from the firm with the correct file in a huge panic. “We did get to make our arguments. But of course I had to explain to the judge and other counsel why I wasn’t ready,” says Peterson.

Balbi says one rookie mistake he often sees in the courtroom occurs when “people don’t know how to address the court properly.” He adds that he frequently sees lawyers jump into an argument without explaining the background of the case first. “You can see the judge is really mixed up because he doesn’t know any of the context. You make the judge look bad and you don’t look like a very effective advocate.”

Spend some time in the courtroom. “Watch how other people do things, figure out what’s effective and what’s not,” says Balbi. “You learn a lot just by watching senior people.”

Get good mentors. Find a senior counsel that you can consult with regularly so you can learn from someone who knows what they’re doing. “Mentoring is deficient today,” says Iacono. “Thirty years ago young lawyers got to work with senior counsel, got to go to court with them, got to prepare their briefs. Today most young lawyers just get thrown into it.”

Finally, recognize when to stop asking a witness questions. Iacono gives a classic example. “You’re on your feet cross-examining a witness, you get a good answer out of the witness and you should sit down. But you make the mistake of asking one question too many and it gives the witness a chance to manoeuvre himself out of the answer he gave you.”

How do you know when you’ve said enough? “That comes from instinct and experience. And from being there, doing it, making the mistake the first time, and then knowing when to shut up.”