Women in Dealmaking: A Chat with Jesslyn Maurier, Partner at Bennett Jones LLP in Toronto

In this interview series, we profile trailblazing women working in M&A, private capital, finance, and business law who are driving deals. We highlight their experiences and achievements, and share their insights on what the industry can do to ensure that we see more women on deal teams and at the dealmaking table.

What one quality do you think is most critical to succeed as a legal advisor in the dealmaking world? 

The most important part of my job is understanding people’s motivations and goals. That’s the crucial first step (though it gets refined throughout the deal process)—drawing out the motivations of my client and of the other side.

Knowing the parties’ real objectives is important for understanding the context and determining the optimal shape and details of the deal. This helps to solve impasses—knowing what to give on and what to stay firm on. In negotiations, it helps you shape your asks in a way the other side will agree to.

In your experience, what’s the number one reason that deals go bad?

Parties sometimes have unrealistic expectations about the deal terms that can be achieved.

My job as a lawyer is to try to shape the deal terms to accommodate my client’s expectations, and sell that to the other side. Sometimes it means trying to adjust my client’s expectations by offering them a different perspective. But at the end of the day, it’s the client’s call.

I’ve had difficult deals close and then have watched clients struggle afterwards. There are times when it’s better not to force things. Sometimes the parties have expectations that are so fundamentally mismatched, the deal just isn’t going to work.

What do you find the most rewarding about the work you do?

Closing a successful deal for a client feels like I solved a puzzle. It’s extremely satisfying to translate what my client wants into the legal structure and terms of a deal.

A deal can sometimes start as a nebulous concept. When I help shape that into a legal and business reality that benefits my client, it’s very rewarding, professionally and intellectually.

What do you think the legal landscape for dealmaking will look like in 10 years?

Human judgment and human relationships will remain the same. Parties will still have to look each other in the eye and mutually extend their trust for deals to be done.

I’m sure technology will continue to get more sophisticated and will be increasingly used to assist lawyers, investors and others involved in dealmaking to make better decisions and work more efficiently. Knowledge management and technology infrastructure can promote collaboration, increase productivity and drive efficiencies for clients. Artificial intelligence and machine-learning will continue to improve productivity and cost efficiencies on large, document-intensive deals.

While legal judgment may become better informed through technology, the people aspect that’s at the core of deals won’t change. We will still need to understand why people do what they do and what motivates them.

Did you have a mentor or role model that encouraged you to become a lawyer?

I was a “lawyer” at 12 years old. That’s when I started to practice the art of negotiation—with my father. If I wanted to do something, or got into trouble, my dad and I would sit down and I would make my case to him. I saw the power of persuasive argument and that’s where my journey down the road of law began.

And I’ve always loved words, and getting them to do what I want them to do. Elegantly articulating an intricate concept. I majored in English literature in undergrad and always have at least one book on the go. My shelves are piled high with books I intend to read, eventually. I am curious about everything. My love of language, persuasive argument and learning made law a calling for me.

What unique challenges do women face in law and deal making? What scares women away from the legal profession?

I don’t think women are scared away from the legal profession. The stats tell us that the issue is more about retention of women than needing to encourage women to enter the profession.

In every year since 2014, there have been more women lawyers than male lawyers licensed in Ontario. In age groups up to 49 years old, there are more female than male lawyers in the province. And for many years there have been more women than men entering and graduating from Canadian law schools.

The real challenge today is preventing attrition, though I’m not sure there’s a simple solution.

What are the biggest barriers to gender parity?

A monolithic approach to people’s working lives is a major barrier. Work is becoming ever more demanding and families (not just women) need to structure around it – and vice-versa.

But there are steps law firms and companies can take. One is having longer timelines and no ‘up-or-out’ approach to partnership to accommodate maternity leaves. Parental leave can be made gender neutral so it’s not just a matter for women.

It’s helpful to recognize that ‘face time’ in the office is less necessary than before. Technology can allow people to work remotely or on a more variable schedule and get their work done while also meeting other obligations.

Caring for families shouldn’t (and doesn’t) always fall disproportionately on women. It’s not only about children, either. Many people provide care for elderly parents and have other external obligations. People need to figure out the balance that works best for them and their family. As all varieties of those work/life balance configurations appear, law firms and companies will evolve to realize it’s not a women’s issue but a people issue. Along the way, gender will become less of an issue.

Does your firm have initiatives in place to encourage gender parity and diversity?

Yes. We were one of the original signatories to the Law Firm Diversity and Inclusion Network, a group of Canadian law firms who work together to promote diversity and a culture of inclusion in our firms and the legal profession.

We also sponsor many organizations that celebrate and support diversity, such as the Women’s Executive Network (WXN) annual awards gala and Young Women in Law, and host events for our female clients. A recent panel in our Toronto office featured an extraordinary group of women officers who are redefining leadership in the Canadian Armed Forces.

Internally, we have a diversity policy and strategy, hold seminars and workshops for our female lawyers on the unique issues they face, and host events to foster mentoring relationships among our female lawyers. We consistently send female associates to the intensive Business Leadership for Women Lawyers program offered by the Rotman MBA School. On a day to day basis, we try to meaningfully embrace diversity (both visible or less visible) through practising mutual openness to all different kinds of people and their ideas – that’s true diversity and inclusion.

How is more female representation changing your industry? What positive changes have you seen since you started in your career?

Having more women in leadership positions makes it more normal. This shifts people’s thinking and creates new expectations and standards. It’s becoming increasingly uncommon to think about a dealmaking team without women in prominent roles.

It is encouraging to see the growing acceptance of a difference of perspectives and ways of doing things. It’s something we need in the legal and business worlds, and we are seeing more of it.

I think change comes both through deliberate and mandated changes, and also through attitudinal and cultural transformations. Each reinforces the other in a positive feedback loop, and I think that is happening at many levels in the legal field and throughout society.

Are there encouraging signs that make you hopeful for the future?

One promising sign is that clients are expecting and demanding more diversity from their law firms. Some proposals require a firm to describe the diversity of the lawyers that would work on a deal, including statistics. More clients want the mosaic of their workforce or customer base reflected in their outside law firms.

What advice would you give the next generation of women preparing for a career in M&A, private capital or finance?

Stick to your values and have confidence in who you are. Have an influence on the culture around you and work to make it fit you. You really need to create your own path and not simply conform. But change does not always have to be loud and dramatic—meaningful change can happen quietly.

Don’t be discouraged if change is taking longer than you’d hoped. Change can sometimes be slow and incremental, but it is happening.

Jesslyn G. Maurier
Jesslyn G. Maurier

Jesslyn Maurier is a partner at Bennett Jones LLP. She represents clients in a wide range of corporate and commercial matters including acting for both companies and investors in debt and equity financings, private M&A and asset sale transactions, and commercial transactions. She acts for technology companies throughout their entire life cycle, from start-up to exit, which includes providing advice on corporate development, shareholder arrangements, and corporate reorganizations.

A major aspect of Jesslyn’s practice involves advising companies and directors on corporate governance and director protection matters, and she frequently acts for independent committees of directors in connection with public and private M&A transactions and other strategic matters. She is the lead author of several chapters of Directors’ Duties in Canada, 6th Ed.

Jesslyn has practiced law for going on 15 years, all at Bennett Jones. She is the mother of three children, aged 11, 8 and 4.

To learn more about Jesslyn and Bennett Jones’ private equity practice and the driving factors behind PE investment decisions, see www.bennettjones.com and the firm’s recent study Due North: U.S. Private Equity Sets Sights on Canada.


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