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Law Practice Today

December 2023

Making it Rain: Bridget O'Toole, Esq.

Rachel Clar and Bridget Ann O'Toole


  • An interview with the managing partner of a boutique law firm in western New York.
  • Bridget sees authenticity as critical to her success as an attorney, including in winning new business.
  • Staying active in her community and forming relationships with no expectation of a return also has been a winning formula.
Making it Rain: Bridget O'Toole, Esq.

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What are the top three tips that would you give to a lawyer who wants to be a successful rainmaker today?

  1. Polonius' advice to Laertes “To thy own self be true” Act 1, Scene 3 of Hamlet; it is used ubiquitously but it is still sage advice. If you pretend to be someone you’re not, people will pick up on it and won’t trust you.
  2. Know what you bring to the table.
  3. Give freely of yourself without an expectation of.

What is (or was) different, either about you, or your firm, or anything else, that has allowed or enabled you to become a successful rainmaker?

I’m not afraid to ask for an opportunity, and I see opportunities where others might not. For example, I moved my practice from a city to a rural community in 2023 to better align with my authentic self. This shocked and alarmed some of my colleagues but it has proven to be the right decision ten times over. Also, I’m active in my local community as a volunteer, so that also brings in referral sources from unconventional backgrounds. Even though I consider myself an introvert, I really enjoy building relationships, which is the heart of rainmaking. I believe there’s power in doing what you love - and I love helping people take an active role in their communities. I find that clients, just like a customer in any industry, strongly prefer to work with people that they know, like and trust.

Describe your typical marketing year:

How much time do you devote to marketing? 

I consider so much of what I do to have a “marketing” component; in a sense, everything I put out into the world is marketing.

What types of activities are you engaged in?

I volunteer with many community organizations, participating in the local and statewide bar associations. For example, I am vice president of our local historical society, chair of a local committee for a political party, and chair of the Rochester, New York chapter of the Albany Law School Alumni Association. I am also passionate about the environment so I organize a local Lake Ontario coastal cleanup event every year in conjunction with the Great Lakes CleanUP.

What type of support do you have from your firm? 

I own my firm, so whatever I ask of my team.

If you could only engage in one type of marketing activity (e.g., speaking, writing, networking, meetings, participation in bar associations or other trade association) for the next 12 months:

What one activity would you choose? 

My favorite activity, hands down, is relationship building. I have a deeply ingrained mentality of being a “giver,” and as such, I am always trying to give people value above and beyond what they directly ask for. 

What would that activity look like? 

I especially enjoy grabbing lunch with a client or peer where the interaction is not transactional, but rather, rooted in generosity - ideally it is mutual, but I’m not a scorekeeper. Phone calls, emails, lunches, activities with people I like without a tit-for-tat expectation

Why would you choose only that one? 

I genuinely care about helping people to succeed; I want them to have the very best of whatever I can make available.. 

If you could only choose one more activity, what would it be and why? 

To me, a really enjoyable way to build relationships is in working side by side with others on a common activity or towards a common goal or project.

“War Stories”

How did you get your most unexpected client?

A key account found me through a random Google search; and when we connected, we quickly built a very positive working relationship. The particular matter that they were calling me about was best handled in partnership with another firm, for political reasons, but the new client was impressed with my decision-making when we had to navigate that, and they ended up asking me to represent them - exclusively - elsewhere throughout the state. When I first spoke to this client, we were able to identify shared values, as well as shared contacts - that makes it so much easier to establish credibility. But the “referral source” - a search engine, and the result of getting a statewide book of business - that was not expected nor typical. Again, flexibility, generosity and openness are essential tools in my rainmaking toolkit.

How do you get in front of clients/get asked to respond to RFPs?

Typically direct referrals.

How do you “close the sale” once you are in front/in contact with a client?

These days, I am my authentic self everywhere I go - I believe that is something that maturing gives us. If I sense it is not a good fit, I will give a good referral to someone who I think is better aligned with the client. I don’t refer bad clients and I don’t refer bad attorneys.

What obstacles have you overcome to build your book of business? How did you overcome them?

I stopped trying to be someone I wasn’t, who I thought clients wanted me to be. I have identified my core values and I use them as guideposts for every major decision I need to make. I am an opportunist, and I’m flexible - I consider it necessary to thrive in the business world., I believe that any planning must be able to adapt to new opportunities or circumstances.

Knowing what you know now, if you were starting over as a lawyer today, what would you do differently?

One thing that has helped me make some key business decisions for my firm has been my participation in a peer-to-peer mastermind, where I am in a regular conversation with other women who own their own law firms. We share advice, feedback, and discuss our growth strategies. But that was not available to me when I was just starting out, and right or wrong, I had to learn certain lessons the hard way, by myself.

How has the world of marketing legal services changed over the last 3-5 years?

In my world, it hasn’t. If you’re in a more direct-to-consumer field there are a lot of opportunities in the digital sphere, but that isn’t my focus.

What, if anything, do you plan to do differently with respect to marketing your services next year or in the future?

I see my firm’s website needing an update, as we continue to expand, and I’m anticipating growing my team. Presuming that happens, I see myself introducing that new attorney or attorneys into my existing network, and mentoring that individual how to grow their own network, too. It’s a pleasure to mentor my team to use the same “techniques” I use; relationship building is not just good for business - it works because it feels good to connect with people. I also learn from my team, and imagine that they will identify new marketing opportunities or “strategies” to grow the firm as we continue to scale.