Lessons from my Loony Early Days of Practice

When I started practicing business law immediately after being called to the Bar, I had just been rejected for hire-back with the firm where I had done my articles. I was told that the reason that I was not hired back was that I had not shown sufficient self-confidence. Compounding my insecurity was the fact that I was younger than most first year lawyers, having entered law school after just one year of university. Worse still, I had no prior business experience.

The firm that I joined had a number of very capable commercial real estate, condominium, and litigation lawyers, as well as a fairly sophisticated client base. What they did not have was an experienced business law lawyer. So, the corporate department was to consist of just me and one other very junior associate, who also had a limited background in business law. While I had access to some senior lawyers in other areas in practice, none of them had corporate experience, so their ability to help me was limited. I would have to figure most things out on my own.

Another interesting thing about my first job was that the most influential partner in the firm was a significant shareholder in a large family business, and that family business gave much of its legal work to the law firm. As a result, I was often working on fairly sophisticated files which a more independent client would likely have hesitated to entrust to a junior lawyer.

During my first year of practice there were many times when I was not sure that I was going to make it. What I did have going for me was that I was reasonably smart, and I was willing to work as hard as I had to in order to get things right. While those early days are long past for me, I do understand that many lawyers feel insecure about their abilities at the outset of their careers. So, I would like to share some of the lessons that I learned in those early days which may be helpful to new lawyers.

Early on, I would find myself in meetings with sophisticated business clients discussing complex matters (or at least they seemed pretty complex to me considering my lack of experience.) There were many times that I did not understand what was being said, and I had no idea whether asking a question would make me look very smart or very stupid. I quickly figured out that I had to risk asking questions and looking stupid, because it was much better to take that risk than to take the risk of proceeding with the work without understanding the instructions and then looking stupid after spending many wasted hours doing the work incorrectly.

Forcing myself to always ask questions when I did not understand what was going on in a meeting produced the following results:

1.     About 85% of the time, no one at the meeting thought that my question was stupid, or if they did, they were polite enough not to say so;

 2.     At least 15% of the time I felt like an idiot when it became clear that my question was way off-base. However, I soon learned to accept that the embarrassment was simply the cost of my inexperience;

 3.     Many times, the ensuing discussion would make it clear that someone else at the meeting also had not understood what was being said and was happy that I had spoken up; and

 4.     As I realized that most of my questions were valid, my confidence slowly improved.

I would also often find myself going up against more senior lawyers. On one occasion in my first year of practice, I attended a meeting with opposing counsel. I was representing a business owner who was going to transfer three corporations, each of which operated an active business, to a holding company which he would own and finance. Opposing counsel represented the person who was going to operate the businesses, obtain options to acquire an equity stake in the holding company subject to meeting performance standards, and take responsibility for acquiring additional businesses. 

Those of you who are familiar with the golden rule of business (‘the one who has the gold makes the rules’) will recognize that my client was in the power position. 

For some reason that I cannot remember, neither counsel knew who the other counsel was going to be prior to the meeting. When I arrived at the meeting, it turned out that opposing counsel was a senior associate at the firm that had rejected me just months earlier and had quite probably recommended that I not be hired back. He looked at me with apparent shock and exclaimed, “you?” 

“Yes,” I said, and carried on.

Experiences like this gave me little time to think about the disadvantage that I had because of my lack of experience. What I did learn was that if I prepared like crazy by reading as much material as I could get my hands on concerning the area of law that I was working on, I could make up somewhat for my lack of experience. Before I knew it, I was in the thick of things and, as I held my own, my confidence grew.

I also learned that more experienced lawyers would try to take advantage of my inexperience.  It was not uncommon for them to profess that, ‘things are always done this way,’ or that they ‘had never seen a person in their client’s position agree to what our side was proposing.’ I learned to see that sort of thing for what it was, and to call ‘bullshit’ when necessary.

The most outlandish experience that I had with a lawyer trying to take advantage of my inexperience occurred a few years later, although that was also a case of a big firm lawyer representing a big client thinking that she could put something over on me because of how important she thought that she and her client were. 

In that case my clients were small business owners who were selling their business to a large institutional client represented by this other lawyer. We were at the closing meeting at the big purchaser’s lawyer’s office and were negotiating the opinion letter that I was to give. With a perfectly straight face and in front of my clients, this big firm lawyer took the position that I should be providing an opinion that all of the representations and warranties given by my client in the share purchase agreement were true.  This was an absolutely ridiculous position to take, but she insisted that it was a perfectly reasonable and completely standard request, which vendor’s lawyers always agreed to, and tried to make my clients think that I was the one putting the transaction at risk. Of course, my clients had no idea whether or not her position had any merit.

I kept my cool and called back to the office and asked an associate to find an article written by anyone at a large downtown firm, but ideally by someone at this lawyer’s firm, saying that this was ridiculous. Luckily for me, my associate located an article written by the partner to whom this lawyer reported which said exactly what I wanted it to say. I told my associate to copy the first page of the article, circling the name of the author, followed by the relevant pages of the article and to fax it to me at the meeting care of the purchaser`s lawyer (email not having been invented yet.)

Later in the meeting I told the vendor`s counsel that I was expecting the fax and she went to retrieve it. I counted on her looking at it before she gave it to me. She returned to the meeting room and handed it to me. When I said that I was now ready to discuss the opinion letter issue, she simply dropped the request.

From this situation, I learned to beware of slimy lawyers. There may not be many of them, but there are some of them, and you can find them at all sorts and sizes of firms.

I also learned that you have to trust your instincts.  A few years into my practice, I attended a meeting to assist a senior real estate lawyer at our firm representing a municipality which was proposing to enter into a development agreement with a private real estate developer. Although I was a corporate lawyer, I also did commercial leasing and the transaction was being structured as a ground lease, so I had a role to play. 

All of the other lawyers in the meeting on both sides were senior real estate lawyers. At one point someone proposed a restructuring of the arrangements. As a corporate lawyer I had some hesitation to speak up about a problem that I saw with the proposal, but I plunged ahead and asked whether the proposal would constitute a breach of the Planning Act. There was dead silence from all of the real estate lawyers, followed by an acknowledgment that the proposal had a fundamental flaw.

Since I was effectively the co-head of the corporate department in a 14-lawyer firm from the day that I started practicing law, it should come as no surprise that I became a supervising lawyer early in my career. In fact, I hired my first ‘junior’ at the beginning of my third year of practice. As you can imagine, at that time I did not have a lot of the skills that a young lawyer would look for in a supervisor or mentor. (I have not spoken to this lawyer in about 37 years. I expect that I owe him an apology.) 

 Having since supervised and mentored many lawyers over the years (and maybe learned a few things along the way) I now offer the following suggestions to young lawyers:

Seek Guidance from Those Who Might Know

For some reason that I have never understood, when articling students have a question, they tend to ask equally clueless articling students for input instead of asking a lawyer who may be able to help them. When first year lawyers have a question, they usually ask other first year lawyers, or perhaps even a second-year lawyer, instead of asking more senior lawyers. And so it goes.

 When you have a problem, never hesitate to ask the most senior lawyer who is willing to help you.  It saves a great deal of time to address your questions to people who actually know the answers.

Do Your Homework

Before asking any question of any senior lawyer, do everything that you can to find the answer yourself. The first question that a good supervising lawyer will ask you when you ask them a question will be, “what do you think the answer is?”  

 If you can answer that question by outlining the steps that you have taken to find the answer and your tentative conclusions (which should, if your question relates to a point of law, include reviewing any relevant statutes, regulations, and caselaw and not, as one student once offered, a ‘google search’) the senior lawyer will be impressed and will usually be willing to provide you with an answer. If you have not bothered to look for the answer yourself before asking for help, the senior lawyer may simply write you off in his or her mind. And be warned, there are many lawyers (and I regret to have to admit that I used to be one of them) who will form an early impression of you that is then hard to change.

Don’t Let Your Ego Get in the Way

I once hired a junior lawyer who had good qualifications on paper and experience at an excellent firm. Unfortunately, he was so hell bent on proving to anyone who would listen how smart he was that he was incapable of learning anything. Don’t be that person.

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Your first few years as a lawyer will have their challenges. Believe in yourself. Work hard. Be open to learning. It will all work out. I went from “has no confidence” at the end of my articles to “Murray, there is such a thing as having too much confidence” (spoken by the Managing Partner of my firm) 10 years later, to being the Managing Partner of my firm a few years after that.