Making It Rain: Practical Tips from Those Who Do – An Interview with Kara Baysinger

Kara Baysinger is a partner in the Corporate & Financial Services Department and a member of the firm’s Insurance Transactional and Regulatory Practice Group with Willkie Farr & Gallagher LLP. 

Top Three Tips to be a Successful Rainmaker 

  • It starts with doing excellent work. It is essential to do a great job with every client and matter, no matter how small. The best new clients are current clients.
  • Be hyper-responsive. Many clients complain about how other lawyers don’t return calls or respond in other ways. Make sure no one can ever say this about you.
  • It’s all about relationships and face-to-face meetings. Outside counsel solve big problems. Clients trust big problems to people they trust personally. You can do excellent work and be hyper-responsive but relationships are key. My biggest clients are led by people I am very close to. That’s why face-to-face meetings with clients or prospective clients is my top marketing activity and the one I would choose above all others, now and in the future. A face-to-face encounter is where I hear about what they worry about, not what I think they worry about, and it allows us to build the relationship so that I worry about the things they worry about, freeing them to do their work. Law has become a much more competitive field since I began. RFPs and panel interviews to compete for work are much more common. This is both a risk and an opportunity. Having a strong relationship provides a true competitive edge.

My Marketing Activities

Marketing is a big part of my practice. I spend about 15-20% of my time devoted to client relationship management and marketing. Here are some tips for making marketing a frequent and useful part of my practice:

  • Make business development a daily activity. I do business development every day. Consistency and regularity are an important part of business development. You don’t need to spend two hours a day on marketing (which can be hard to find), but 30 minutes at the end of the day or between meetings in small snippets of time can deliver important results over time. You don’t have to call 10 people, but you can call one, or you can send an email to a client to catch up or forward an article of interest. You can send an update on the firm or your activities, or perhaps forward an article in a trade publication. I generally have a half-hour timeslot at the end of the day devoted to business development.
  • Create a system to facilitate daily business development. I create a set of daily to-do lists that run about three weeks in advance. I have two columns: Client Matters and Business Development/Marketing. I also put personal items to tackle on the list, at the bottom. Having a detailed list in advance makes it easy to use small amounts of time, such as when I am awaiting a client call or waiting for my kids or for a flight.
  • Prioritize relationships. While I do a couple of speeches a year and write occasional articles, send emails, forward trade articles of interest, etc., the majority of my business development is focused on relationship management. For example, during a recent business trip to New York, in addition to my meetings on client business matters, I spent a significant portion of the two days there meeting face-to-face with clients, some for a meal or coffee, one for a substantive presentation to her team, and another for a walk and talk.

I’m not much for attending events together like sports or arts events. I prefer to have meals with clients, so we can really talk, and I like to involve their team and my team so we can build broader relationships.

The pandemic has presented some challenges to my top priority of face-to-face meetings, but like everyone else, I have had to adjust. I have done plenty of Zoom wine dates with many clients during the pandemic, as well as check-in zoom calls and even full-blown pitches. However, I have started to return to face-to-face meetings.

For example, I recently went on a business trip to Chicago but doubled the time I spent there so I could meet with other clients. I orchestrated a “Women You Should Know” dinner for a couple of female GC clients, I hosted another dinner for a client and his direct reports, and I went for a long walk with another client, in between both of our meetings and his evening commute home.

Follow the Three Times Rule

Although my major focus is on relationship-building and management, I do try to give a couple of speeches a year. It’s important to provide up-to-date content and to speak to audiences who can buy your services, but my key tip for giving speeches comes from Sara Holtz, who shared this tip with me early in my career: only speak when you can repurpose the content. My rule is to repurpose three times. This content doesn’t have to be used the exact same way the three times. Rather, it can be incorporated into a blog post, an article, another speech, or a CLE for clients. I did with a presentation just before the pandemic and offered it as CLE that is (easily) tailored to a number of clients. You want to make the most of speeches or articles and the time investment in preparing them.

Look for Partnerships

I’m fortunate to work for a firm that has a deep bench of talented people in my practice area and others, and a strong culture that encourages collaboration across practices. Many people don’t have that situation, so my advice is to seek partnerships with people in other firms. Focus on what clients need and get that for them, one way or another. I just recently referred work that posed a conflict for me in my firm, to a trusted partner in another firm, and I received a referral of some work in my space from a former colleague who moved to a firm that doesn’t have insurance specialists.

War Stories about Unexpected Clients

An example of an unexpected client came early in my role as outside counsel. I spent the first 10 years of my career as in-house counsel. My first client was a competitor who I had worked with in some lobbying matters, and who knew my area of expertise. He asked me to help him as outside counsel when he was confronted with an issue that he suspected I had worked on when I was in-house. We ended up working together, he as inside and me as outside advisor, for years.

Another more recent example comes from a merger and acquisition. I was representing Client A, who was being acquired by Client B. We had a transaction with its usual substantive roller coaster of negotiations and issues, including a difficult regulator from whom the buyer needed approvals for the transaction. In leading the transaction for my client through that deal, our work included strategy and action to help resolve the regulatory issues for Client B. Usually my work would end when Client A was acquired by B, but Client B asked me to stay on with the surviving company to help them navigate post-closing issues and to help them develop a regulatory strategy for that regulator and others for their business generally.

Future Marketing Focus

My plan to prioritize client relationships and face-to-face meetings won’t change, but my favorite thing is to do more to integrate my team and the firm into solving problems for and developing broader relationships with clients. I’m blessed to work with amazing lawyers, some of whom have practiced with me their whole careers, or at least for many years, and with a new (to me!) firm that is absolutely best of breed for insurance company work. I am super invested in making sure that my teammates have robust and satisfying practices, and that our clients see a deep bench of talent with me, my team, and my firm.

About the Author

Rachelle J. Canter is the founder and principal of RJC Associates, which provides executive coaching and training to lawyers, law firms, and other professional organizations. Contact her at

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