What does it take to be an elite rainmaker?

We asked the best in the business

When Perry Dellelce graduated from law school, at the University of Ottawa in 1990, he landed an articling position at one of the top firms on Bay Street. He hoped that this highly competitive placement would be a launching pad to a great legal career. But when his articling term ended, he was the only member of his cohort who wasn’t offered a job as an associate. “When you’re the only one out of 18 that doesn’t get hired back,” he says, “it can be very difficult to get an interview.”

Nonetheless, Dellelce was determined to work on Bay Street. “I certainly didn’t understand what it meant to work as a securities lawyer,” he says, “but I had always been interested in the stock market.” He decided, ultimately, to co-found a brand-new firm: Wildeboer Dellelce LLP.

In short order, the firm established a clear identity. “We knew from the outset that we wanted to do business law, and that transformed into corporate finance and transactional work,” says Dellelce. “We also wanted to be less bureaucratic than the larger firms. We wanted to be entrepreneurial and really understand our clients’ businesses.”

Before he could achieve any of those lofty goals, however, Dellelce had a more pressing priority: to continue finding new clients. “When many of my colleagues from law school began practising, they were able to focus on understanding statutes and caselaw,” he says. “My job was about meeting payroll, so I was focused on business development by necessity.”

Luckily, Dellelce was a natural rainmaker. Today, Wildeboer Dellelce is one of Bay Street’s leading corporate law firms, with more than three dozen lawyers in its ranks. That growth is the direct result of the firm’s track record for delivering topnotch legal advice and its business-development acumen.

In the legal profession, rainmakers are at the top of the hierarchy. If you have a proven ability to land new clients, you’re almost certain to take home the most money during compensation season. Not only that, you will become a prime target for poachers and recruiters, who will incessantly try to bribe you away from your current workplace. This culture is fuelled, in large part, by a pervasive belief that there is a limited supply of natural-born rainmakers who can dominate the cocktail-party circuit and bedazzle the business world with a hypnotic charm.

But this is a vast oversimplification. If you examine how Dellelce amassed a client roster, for instance, he didn’t rely on an innate superpower. In fact, there’s no reason that other lawyers cannot — with enough hard work — emulate his playbook.

Illustration of a suited man running on rain clouds

“The key component to my success over 27 years is meeting contacts, gaining contacts and staying in touch with them,” says Dellelce. He doesn’t expect to leave each meeting with a new paying customer; his objective is to maintain relationships with people who might, one day, call him for advice. And because he can’t predict which connection might turn into a client, he casts a wide net: “I meet with all sorts of contacts I’ve made over the years, at social and charitable events, as well as colleagues.”

In his view, the most junior members in the profession possess their own powerful networks. “If I had one piece of advice for any young lawyer wanting to hone their client-development skills, they should, from the very beginning, keep in touch with any contacts that have the potential to be clients,” he says. That includes connections they’ve made through their undergraduate degree, law school and extracurricular activities, as well as not-for-profit and philanthropic work. Those relationships should not be left to wither and die. “You can’t go through a 10- or 15-year career and see that your buddy becomes general counsel of a corporation and then call them up and ask them for legal work. You’ve got to be there all along.”

Is it possible, though, to cram so many meetings into a busy work schedule? “You do a coffee in the morning, a lunch and a coffee or two in the afternoon,” says Dellelce. “That’s three or four a day. If you’ve got eight hours of billable work, and you’ve got three hours of meetings that are one hour each, that’s 11 hours a day. Get used to it. But trust me: if you follow that formula, you’ll have a million-dollar book of business inside of two years.”

Dellelce, for his part, might take upwards of 1,000 non-client meetings over the course of a year. In his experience, rainmaking is a numbers game, and that’s the sort of volume that is required to initiate and develop business.

The best rainmakers, to be sure, must have a relentless dedication to meeting new contacts. But that doesn’t mean they’re all high-energy socialites. Consider the career path of Joyce Bernasek, one of the top rainmakers at Osler, Hoskin & Harcourt LLP. Once she made partner, in the firm’s financial-services group, she felt the expectation to bring in business. To help Bernasek develop her skills in this department, Osler sent her to a rainmaking conference for women, which she considers a turning point in her career. “The takeaway from that, for me, was that you may not see yourself as a rainmaker per se, but you can become a rainmaker,” she recalls. “I think it’s generalized that rainmakers have to be extroverts. The sort of person who walks around at a party, shakes hands with 50 people, gets a bunch of cards and is quite loud.”

Bernasek is partial to quick daytime meetings with potential clients, but she fosters those connections in a way that aligns with her personality. “I’m an excellent listener,” she says. “And I care. I care about my clients’ business. I care about their success. And I want to be a part of that.”

Illustration of woman working at a desk with rain clouds above

Though Bernasek does attend the occasional networking function, she is hyper-strategic about how to take advantage of these opportunities. “I have three young kids and an investment-banker husband, so our schedules don’t really permit much nighttime activity,” she says. “So I don’t go to parties cold. I research who’s going to be there, identify who I want to meet and I go and meet them.” (Bernasek is aware that her clients often have young families, so she is also sensitive to their busy schedules.)

The savviest rainmakers know that it’s not enough to solely drum up new business. They also pay close attention to their current client base. “If you really want to know who the best rainmakers are in a law firm, ask the clients,” says Jordan Furlong, an Ottawa-based legal consultant. “The client will say, ‘When I’m in trouble, I call her.’ And what makes them call that particular lawyer? Clients will tell you that the lawyer ‘gets’ their business, their strategy and their concerns. There’s a sense of advocacy and reliability.”

Georges Dubé, a partner at McMillan LLP, stresses that a lawyer can generate plenty of additional work — and, in turn, revenue — simply by offering sterling advice to existing clients. When clients like a particular lawyer’s work, they become repeat customers. “I think people get enamoured by lawyers who attract new work,” says Dubé. “But if you look at most firms, it’s 80 percent current clients and 20 percent new clients. You get most of your work from existing clients and relationships.”

Bernasek is in regular contact with her lineup of clients. “Every week, I’m in touch with 15 to 20 people on a continual basis,” she says. “It’s a repetitive and consistent system.” This keeps her top of mind, but it also allows her to anticipate the unique needs of each client. “If I work on one thing for an existing client and I see something else that might be of interest to them, I reach out. That’s increased even more as the COVID-19 situation has evolved. It’s doubly important to stay in touch with clients right now and let them know we’re here to help them.”

The road map to rainmaking might be clear, but it takes practice to navigate it like a master. Young lawyers need time to establish a routine that lets them meet contacts throughout the day and, at the same time, learn how to practise law. And though extroversion is not a necessity, it takes skill to intuitively present oneself — at a coffee, lunch or networking event — in a way that projects confidence.

Dellelce, for his part, doesn’t expect his associates to have an instant aptitude for client development. “We have a ton of client events that we tell our students and associates to attend,” he says. “We do that on a regular basis, so our young lawyers can mingle with senior clients and market themselves by osmosis.” The firm also instructs associates in their first and second years to focus on developing their skills and legal expertise. Only by third year are they encouraged to up their rainmaking game.

Emily Lee, a co-founder of ALT Recruitment Partners, has found that associates are showing an increased willingness to learn the secrets of rainmaking. “Associates are discovering that it’s an important skill to develop,” she says. “Especially now that partnership is more elusive than it has been in the past. Being able to build up business and bring in clients is being requested of associates a lot earlier.”

To Dellelce, there is one final ingredient to rainmaking success: persistence. “Like any salesperson,” he says, “you have to call and call again and call again — and then call again.”

This story is from our Summer 2020 Issue.

Illustrations by Jenn Liv.