Episode 291 features Scott Love in conversation with legal business development strategist Karen Kaplowitz on how lawyers can use charitable sponsorships to deepen client relationships and generate business in a way that feels authentic. Kaplowitz defines “charitable sponsorships” as the common scenario where a client invites a lawyer or law firm to support a charity through events such as dinners, honoree celebrations (often for a general counsel or senior executive), golf tournaments, or fundraising activities. While this can resemble other networking, she argues the charity context creates a stronger “expectation of interaction” and a closer bond because the client is personally invested. Done well, it is not simply writing a check; it is learning what the client and their company care about and showing up in meaningful ways that build trust and access in an increasingly competitive market where competitors are often being invited to the same opportunities.
Kaplowitz emphasizes that the biggest mistake firms make is treating charity involvement as a one-and-done transaction, which leads to wasted spend and missed relationship leverage. The value comes from being intentional: doing advance research on who will be there, coordinating internally to ensure the right lawyers attend, arriving early, engaging purposefully, and following up to convert introductions into ongoing relationships. She highlights high-impact approaches such as volunteering alongside clients (e.g., joining a client’s Thanksgiving service activity), helping a charity by mobilizing firm resources when a key client is being honored, and serving on boards where clients can see lawyers “in action” as problem-solvers. Her three recommended action steps are: (1) identify what charities your most important clients support, (2) plan specific ways to support the client and the charity (sponsorship, board service, volunteering, fundraising), and (3) execute with consistent follow-through as part of an organized relationship plan with clear activities and a budget.
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In this episode of The Rainmaking Podcast, Scott sits down with Karen Kaplowitz, a Lawdragon Global 100 Leader in Legal Strategy and Consulting, who is a master at helping law firms build client relationships through charity, and has personally raised over $20M in charity for a leading women’s civil rights organization.
Links:
https://www.legalmomentum.org/events/aiming-high-2026
https://www.newellis.com/PDFs/2010/May3-RightTimeRightGroup.pdf
https://www.newellis.com/PDFs/2011/April112011-CharityBegins.pdf
https://www.newellis.com/PDFs/2022/NewEllis-102422.pdf
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[00:00:10] - [Speaker 0]
You're listening to the Rainmaking Podcast. Hosted by high stakes headhunter, author, and professional speaker, Scott Love.
[00:00:23] - [Speaker 1]
You're listening to the Rainmaking Podcast, and my name is Scott Love. Have you ever come across one idea that revolutionized your business? Something that was so powerful, it made everything seem so much easier. Well, I've got an idea I'm going to share with you that will help you grow your book of business. This will change everything.
[00:00:41] - [Speaker 1]
And our guest today is Karen Kaplowitz. Now Karen consults to the legal industry, but our topic is perfect for anybody in professional services. And we'll get to the topic title in a second. But Karen is a LawDragon Global 100 leader in legal strategy and consulting. She's a master at helping law firms build client relationships through charity.
[00:01:03] - [Speaker 1]
Our topic title today is using charitable activities to reinforce important client relationships. We're gonna get into some really good strategies that I think are malleable and will help you connect with others that could lead to growing your book of business. As always, this show is sponsored by SharePoint Legal Insights, formerly known as Leopard Solutions, turning legal intelligence into opportunity, and also The Rainmaking Magazine. Don't lose business to competition. Read this publication and keep business development top of mind.
[00:01:35] - [Speaker 1]
Visit therainmakingmagazine.com today to chart your course to greater rainmaking success. One other thing, connect with Karen on our show notes. I put all of her contact information, even some other resources that will help you, even a link to an event that she talks about in our conversation today. And all of those I think will make a big difference for you. Anyways, thanks for listening to the show and here's my conversation with Karen Kaplowitz.
[00:02:04] - [Speaker 1]
Hey, this is Scott Love with the Brain Making Podcast. Our special guest today is Karen Kaplowitz. And today we're talking about getting more value from charitable sponsorships. Karen, thank you for joining me on the show.
[00:02:17] - [Speaker 2]
Thank you for having me Scott.
[00:02:18] - [Speaker 1]
Absolutely. This is great. I'm excited about this topic. We've never had anything like this in over two ninety, 300 episodes. So let's start with definitions.
[00:02:29] - [Speaker 1]
When you say charitable sponsorships, what does that mean exactly, Karen?
[00:02:34] - [Speaker 2]
So lawyers have a lot of opportunities to sponsor charitable activities that give them opportunities to connect to clients. So that's what we're talking about. We're talking about the typical situation in which a lawyer or a law firm is invited to participate in a charity by a client. That's the typical situation we're talking about.
[00:02:59] - [Speaker 1]
And what types of involvement is it? Is it events? Is it fundraising events? Is it golf tournaments? Is it dinners?
[00:03:07] - [Speaker 1]
What are some of the different types of events that you've seen?
[00:03:10] - [Speaker 2]
It can be any of those kinds of events. It can be any kind of a sponsorship. Typically clients invite their lawyers to support activities that they are active in. So it might be an event in which the client organization is active in the charity. It might be an event in which the charity is honoring a leader like the general counsel of a client organization.
[00:03:40] - [Speaker 2]
It might be a golf tournament, but it could be any kind of a sponsorship opportunity.
[00:03:47] - [Speaker 1]
Okay, that's great. And so what's the benefit? Why should somebody do this?
[00:03:51] - [Speaker 2]
Well, are tremendous opportunities for lawyers. Over the course of the twenty five years that I've spent coaching and working on strategy with law firm partners all over the country, I've seen just unbelievable opportunities for lawyers to take advantage of charitable sponsorships, but I've also seen an awful lot of money wasted. And that's why I suggested we talk about Okay,
[00:04:20] - [Speaker 1]
good, good. So how is this different than come to a trade association dinner, or I'm a member of the New York chapter of the Association for Corporate Growth. It's a good group. That's a worthy group. What's the difference between a charity involvement and some of your other traditional business networking or other groups?
[00:04:40] - [Speaker 2]
Well, in some ways they're similar. It's another networking opportunity. But the fact that there's a charity involved creates a special nexus. When a client is committed to a charity and extends an invitation to a lawyer or a law firm partner to participate in some way, there's a closer bond and more of an expectation that there will be interaction than there might be just meeting somebody at an association for corporate growth meeting.
[00:05:13] - [Speaker 1]
I like that. The expectation of interaction. And I like the way you mentioned it's a special nexus. And I think if we look at principles of relationship building, relationships are based on frequency of contact. When you work together on things, you're committed to a common goal.
[00:05:30] - [Speaker 1]
I've found one of the ways I can grow closer to a friend is to ask that friend for help with something. Can you help me with this? And, oh, they're pitching in. He or she is committed to helping me and I'm grateful. And we grow in our relationship.
[00:05:42] - [Speaker 1]
Is that kind of the same here, same thing here that you think happens within these types of organizations?
[00:05:48] - [Speaker 2]
Absolutely. So law firm clients have a lot of expectations around supporting their charitable activities too. I mean, that's something to take into account in creating a budget for your law firm for what you're going to need to spend to support a client relationship.
[00:06:10] - [Speaker 1]
And why do you think that is? Why do you think they're like that?
[00:06:13] - [Speaker 2]
Well, clients are very sophisticated. They know that they can look to their law firms and to the law firm partners who service them to support their activities because it goes with the territory.
[00:06:26] - [Speaker 1]
Right. Who usually gets involved in this on the client side? What are some examples that you could share with us?
[00:06:32] - [Speaker 2]
Well, typically the people who are involved on the client side are the clients who are doling out the work. So those are the people who are extending invitations to law firms. Whether they are the people who are themselves active in the charity or they are the people who are themselves being honored. They are the ones from home invitations are extended to law firms.
[00:07:00] - [Speaker 1]
Right. Do you think sometimes attorneys might feel, well, feel duplicitous, I feel disingenuous if I work with this charity just to get close to a client. Do you think that's something that people feel when do this?
[00:07:13] - [Speaker 2]
Not really. No. It's such a tremendous opportunity for lawyers and for law firms to bond with and collaborate with their clients. It's not just showing up at an event. It's learning about the organization.
[00:07:29] - [Speaker 2]
It's learning about the charity purpose. It's figuring out some other ways that they might be supportive of the organization other than just giving money.
[00:07:38] - [Speaker 1]
I see. Okay, good. So it's not just giving money, it's rolling up the sleeves and doing something. What have you seen attorneys have done? How have they gotten involved in organizations that you're talking about?
[00:07:49] - [Speaker 2]
Well, it's very important for lawyers to know what their clients care about and what their clients' companies care about and to look for opportunities to connect relating to charities. So, for example, if you know that you have a client who works for a homelessness organization and on Thanksgiving Day spends the day serving food to people who are homeless in their community, then one way a lawyer might participate is to offer to join forces or to organize a group of people from their law firm to go to the homeless organization and serve food on Thanksgiving Day.
[00:08:35] - [Speaker 1]
Yeah, that's great.
[00:08:35] - [Speaker 2]
That would be an
[00:08:36] - [Speaker 1]
example. That's good.
[00:08:37] - [Speaker 2]
Another example might be to serve on a board. If you know that your client is passionate about a particular charity organization, let's say it's a veterans organization, whatever the nature of the charity is, there are opportunities to serve on the board. And those are tremendous opportunities because lawyers have so much to give in the course of board service. Because what are lawyers essentially? We are problem solvers.
[00:09:09] - [Speaker 2]
So when we serve on boards of directors, of charities or other organizations, our clients get to see us in action solving problems that might be relevant to some future work opportunities.
[00:09:23] - [Speaker 1]
So let me kind of take what we've talked about so far. Getting involved in charitable sponsorships is a really good thing to do to get close to clients, existing clients, and even prospective clients. Ways they can do that is to roll up the sleeves, get involved doing work, sitting on boards. Is there anything else that you think outside of those two areas, what are some other ways they can get involved in charitable sponsorships? What about getting involved in raising funds or opening up their network as a resource to help out charitable organizations.
[00:09:56] - [Speaker 1]
What do you think about those ideas, Karen?
[00:09:58] - [Speaker 2]
Oh, I think that's a terrific idea. Well, the most important thing is if a client approaches you as a law firm partner and says, I am being honored at an event for a charity that I care about in a month or two, do not ignore the invitation. The first thing to do is to get mobilized immediately in your law firm to support your client. An invitation from a client is an invitation to take action. So that's the first thing I would recommend to lawyers who are interested in supporting their clients and building their client relationships.
[00:10:41] - [Speaker 2]
So the question is, if it's an important client relationship, what do you do? You take action. You go to your law firm if you don't have your own budget and funds available and you say, this is the strategic opportunity that we have. Our client is being honored. It's an opportunity for us to support the client, to meet other people in the client's organization, to introduce the client to other people in our law firm.
[00:11:11] - [Speaker 2]
And there's a great strategic value to us. We need to participate in a meaningful way.
[00:11:18] - [Speaker 1]
That's great. So this is something that's important enough to reach out to your chief marketing officer, reach out to other partners that might be affiliated or even on the periphery of that group and get them involved. I see this as a way of growing closer to clients. I actually had a conversation with somebody recently that business has gotten hyper competitive. Even if you've got a good client relationship, there's 10 other people right behind you trying to get in and get work from that client.
[00:11:48] - [Speaker 1]
And I think by getting involved in things that they care about, that alignment of shared interest working together, that's a way they can insulate that client relationship from anybody else getting in there. What do you think about that?
[00:12:02] - [Speaker 2]
Well, it's a super competitive environment. I mean, you have to expect that if you are being invited to attend an event, for example, at which your client's being honored or the company is being honored, that they are also going to all of your competitors. And the question's going to be who is going to step up first and who is going to step up most generously? So competitive even in the context of supporting these events.
[00:12:34] - [Speaker 1]
Right. Do you think there's been an increase in attorneys getting involved in charitable sponsorships since COVID? Do you think over the last five years it's something that lawyers see as this is a good business development opportunity? Or is it just something that hasn't been on their radar?
[00:12:51] - [Speaker 2]
I think that COVID slowed down some of this activity because people didn't physically go to events as much. You know, for an organization I support and for whom I organize an annual fundraising event every year, during COVID, we had virtual events. They were very different kinds of situations. And this type of relationship building is an in person event. And it's special.
[00:13:21] - [Speaker 1]
That's great.
[00:13:21] - [Speaker 2]
So there's more activity now that COVID is not as critical a threat.
[00:13:27] - [Speaker 1]
Right. And tell me about what you've done. How have you been able to do what you're talking about to really build relationships within the legal community, Karen?
[00:13:36] - [Speaker 2]
Well, for me personally, I've had the opportunity over the last twenty five years of supporting a women's civil rights organization called Legal Momentum by creating an event honoring very powerful women and men business leaders who support the organization's mission of protecting the economic and physical security of women and girls.
[00:14:03] - [Speaker 1]
And
[00:14:04] - [Speaker 2]
to do that, I've tapped this understanding I have of the dynamic between law firms and their clients. So we go to powerful business leaders, general counsels, senior executives, and we invite them to be honored by the organization and to reach out to their business partners. Who are their business partners? Their law firms, their accounting firms, their public relations firms, and invite them to support the organization at this event. And that's been a very successful venture.
[00:14:43] - [Speaker 2]
I've been fortunate to have the opportunity to help them raise more than $20,000,000 over the last twenty five years. And it's based on this understanding of the dynamic between clients and their law firms as it relates to charity.
[00:15:02] - [Speaker 1]
That's great. Are there any pitfalls that somebody should watch out for? Let's say they hear what you're talking about. They say, I think I want to be more proactive in this. Are there any pitfalls or danger areas or things they need to watch out for as they start taking action in this way?
[00:15:18] - [Speaker 2]
Well, it's like anything else in building relationships with clients. It isn't a one and done opportunity. So if a client invites you to support a charity, showing up for a dinner on one occasion isn't going to be the end of the job. The job is relationship building. So the opportunity is being organized to take advantage of each of these opportunities along the way.
[00:15:50] - [Speaker 2]
So, if you've been trying to meet other people in a law department, for example, and a client invites you to a charity event, whether it's a golf tournament or a dinner or whatever it is, that might be an opportunity for you to say, is so and so who you've been trying to introduce me to going to be at that event? And maybe the answer will be yes, maybe the answer will be no, but you have to be organized to take advantage of the opportunity. And then, you know, it's not one and done. You don't just show up at the event, meet somebody, and that's the beginning of a new pipeline of business. It's just the beginning of the pipeline of business.
[00:16:35] - [Speaker 2]
It's the beginning of an opportunity to build a relationship, to make a plan to get together another time.
[00:16:41] - [Speaker 1]
That's great.
[00:16:42] - [Speaker 2]
For example.
[00:16:42] - [Speaker 1]
And I liked what you said before also about board level involvement. When do you think an attorney should consider things like that? Could an associate do it? Somebody that's on the cusp of becoming a partner? When they're a partner, absolutely they need to get in front of people like that.
[00:16:58] - [Speaker 1]
But when do you think is the ideal time someone should really look at getting deeply involved in charitable organizations, especially as a board member?
[00:17:06] - [Speaker 2]
I think that there are opportunities for lawyers from day one to be involved in charitable organizations on boards, whether they are law related charities or other kinds of charities. There's no age limit. In fact, if we think back on our own careers, I'm sure that both of us did a lot of charitable activities and organizations as very young lawyers. And you don't have to wait to become a partner. You might have to wait to become a partner to control money from your law firm as a contribution to an organization, that might flow more readily to a partner level person than to an associate.
[00:17:51] - [Speaker 2]
But I encourage lawyers at a very young age to get active and to get involved.
[00:17:59] - [Speaker 1]
So why do you think this works so well? If somebody's at a charitable event, what's the psychology behind this? How is this able to help pave the way for them to get more business? And do you think, cause I always wonder, would it be, am I questioning my motive to go to this terrible event because I really care about getting business? Those things like that.
[00:18:20] - [Speaker 1]
How do you think people should manage that? And what's some of the psychology behind this working so well Karen?
[00:18:26] - [Speaker 2]
Well, it only works if people put in the homework to do the research they need to do in advance. They need to know who they're meeting. They need to arrive at events early. They need to have been coordinated with other people in their organization to meet the people they want to meet, to sit at a table next to the people they want to talk to and to engage with them. I mean, nothing happens just because you show up.
[00:18:57] - [Speaker 2]
You need to engage with people at these kinds of events, just like at any other kind of business networking opportunity.
[00:19:06] - [Speaker 1]
Let me go back to the board level involvement, which I think is a pretty good idea. I've seen that in a lot of partner bios that I read in my recruiting business. I'll read, I'll see people that are involved in certain sort of charities. Do you think that clients and client prospects give weight to a partner's involvement in charitable activities when they're looking to give business to people? What do you think about that?
[00:19:28] - [Speaker 2]
Well, being involved in charities can be very educational for a lawyer. For example, if you represent pharmaceutical companies and you're involved in a charity that serves a population of patients whose drugs or medical devices are used by the pharma or medical device company, that makes you maybe more qualified to be a lawyer doing work on behalf of a pharmaceutical company. If you're a tax lawyer and you are on the board of a company and you help them solve a tax problem, people can see that you are smart and effective and might call you when they have their own tax problem. That's the way it works. So, are people impressed?
[00:20:20] - [Speaker 2]
I don't know that people are impressed just seeing it on a resume. I think people are more impressed seeing you in action in person.
[00:20:28] - [Speaker 1]
That's a good point. So where should someone go from here if they want to get involved in this? Maybe could you share a story with me of somebody you've coached that you've worked with in your business development coaching, someone where you help them get involved, you advise them to get involved in charities and charitable sponsorships, things like that.
[00:20:45] - [Speaker 2]
Sure. Well, every year I encourage all of my clients to identify charities that their clients are interested in or involved in. That is one of the jobs I give people in figuring out where to go in building client relationships to understand what their own clients are interested in. So, for example, if you and I were working together, I'd be very interested to know about your commitment to the work of Protect Our Defenders. I'd be very interested to know what you've done because that's an organization that I would be interested in knowing more about since it serves victims of sexual abuse and harassment.
[00:21:38] - [Speaker 2]
So I would question you just the way I would question any client about what you do with the organization, how you could be more engaged with the organization, and how you might introduce that organization to other people in your network. That would be the kind of interaction I would see.
[00:21:58] - [Speaker 1]
And from what I've done in that group, like you mentioned, when I go to the events, you're in, you're in. I wouldn't say you've been vetted because they're not looking to vet people, but you automatically have greater levels of trust because you're in the organization, you're doing work. They see that you're helping out, you're pitching in, you're actively involved. So I think that in itself gives people privilege in terms of getting closer to clients, client prospects, just because you're working together. That shared interest, that shared motivation working together on something I think makes a huge difference.
[00:22:34] - [Speaker 1]
Agreed. Agreed. So if we could look at, let's say three action steps. If we were going to look at a partner that says, wanna do more of this, I wanna have some sort of a system or ideas or recommendations. If we could look at it in terms of three action steps, Karen, that you'd recommend a partner do to get more involved and get more value from charitable sponsorships, what would those three action steps be?
[00:23:01] - [Speaker 2]
The three action steps would be to first of all, understand what each of their important clients' charitable activities are. That's number one. The number one activity is focus on what your clients' interests are. Know what their charities are in advance. Number two is plan how you can benefit the client or the client's charity.
[00:23:31] - [Speaker 2]
Is that some kind of a sponsorship? Is it board service? Is it some other kind of activity? And the third thing, the third activity would be to follow through. You know, whatever you do in this arena is not a one and done.
[00:23:49] - [Speaker 2]
It's an organized activity with a plan of action, with a budget, with activities, and with follow through. So those would be the action steps I would like.
[00:24:01] - [Speaker 1]
That's great. Well, Karen, thank you for sharing this idea with us. I think this is an important area that for many partners is overlooked for many, anybody in professional services, business development. This is the first time we've ever had this topic on our show and we've had a lot of shows. So I appreciate you bringing this to me and suggesting this.
[00:24:20] - [Speaker 1]
And I know everybody listening here got some good value from that. And it's such a simple idea, but something that's overlooked and there's opportunities here where you can serve, you can make a difference in a certain charity and benefit through the relationships that follow from that. So tell us about what you do, your offerings that you have. What would you like our listeners to know about you, Karen?
[00:24:39] - [Speaker 2]
So my work for over twenty five years has been coaching law firm partners in law firms all over the country on business development strategy. So that's what I do. I work with partners who are motivated to be rainmakers in developing a plan of action. That's always the first step, Making sure that they have a business plan and a business strategy in place and then supporting them as they implement that strategy. And I do that both in person when people are either close by or in cities that I'm visiting, like New York, Chicago, or Los Angeles, or remotely on Zoom.
[00:25:24] - [Speaker 2]
And I'm delighted to work with partners all over the country who are active and interested in building their client base.
[00:25:35] - [Speaker 1]
That's great. Thank you for sharing that. And thank you for being a guest on the show. We're going to put all of your contact information on the show notes. So everybody listening, go to the show notes and you'll be able to connect with Karen directly.
[00:25:47] - [Speaker 2]
Thank you. And there are also going to be materials. I've written a lot on this subject of getting more value from charitable activities. And I will share those citations with you and my publication.
[00:26:01] - [Speaker 1]
That's great. Karen, thank you so much for sharing this insightful idea. And I'd love to have you back on the show in the future.
[00:26:08] - [Speaker 2]
Thank you, Scott. I appreciate it. And I appreciate the fact that you have initiated the Rainmaking Podcast. How wonderful that you serve rainmakers in the legal community.
[00:26:20] - [Speaker 1]
Thank you so much, Karen.
[00:26:24] - [Speaker 0]
Thank you for listening to the rainmaking podcast. For more information about our recruiting services for international law firms, visit our website at attorneysearchgroup.com. To inquire about having Scott speak at your next convention, conference, sales meeting, or executive retreat, visit the rainmakingpodcast.com.
