243 - From Trials to Triumphs: Building Bridges in Philanthropy with Malcolm Macleod

Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Malcolm McLeod, welcome to Listening with Leaders. You are Uh, like me, a lawyer who went off on a very divergent path. And you also have a book which we'll talk about a little bit, and we can find more about you in the book at the website malcolmcleodauthor.com. And McLeod is spelled M-C-L-E-O-D.

Uh, M-A-C-L-E-O-D.

Yes, M-A-C-L-E-O-D. Sounds like a good Scottish.

Yes. Just come back from there, actually.

There you go. Let's start with a little bit about, we were chatting before we started recording. We both have similar careers. We were both trial lawyers. What got you out of being a trial lawyer and into where you ended up, which is philanthropy, which I find just fascinating.

I was a volunteer board member on a private foundation that was based in the US and I was practicing law in Nova Scotia in Canada. And I really liked this connection because I thought it was good for me to have an outside interest. And so I did that for several years, but kept taking on more responsibility. I had a family connection with the foundation, and so I was a board member. Then they asked me to serve on the executive committee, then the investment committee, and the investment committee was pretty busy at the time. They were building out the foundation's portfolio. And then other things. And finally I said, look, I've gotta stop this. Just too much time on this. And it gradually took over my life. The president asked me to take it over, and after some discussion, I thought that would be an interesting thing to do. And so I, I quit practicing law and went to, went to West Palm Beach to run this private foundation.

You went—

I did that for almost 20 years.

You moved from Nova Scotia all the way down to West Palm Beach?

I did.

So you spent—

I did.

You, you sound like me. 25 years as a trial lawyer and 20, almost 20 years running this family foundation in West Palm Beach. Wow.

Yeah.

And, and when did that stop?

I, it hasn't totally stopped. I transitioned from the CEO role and another person took over my place. And then I succeeded to the office of board chair. And so now I chair the board of this foundation and I chair the grant program committee as well. I serve on the investment committee, so I'm still pretty busy with the foundation, but it's no longer a full-time job. I'm no longer running it.

So you, you still commute from Nova Scotia down to West—

Yeah, but not very often. In today's world, we do most of our meetings this way.

That's right.

And So I go down, maybe make a special trip, maybe once a year. And we don't meet in, in Florida all the time. We meet where we have grantees and we have grantees in different parts of the United States and Canada. So we often meet somewhere else. And then I was in Palm Beach County for a long time. So I have a place down there. My wife and I go to escape the winter. And so I'm down there anyway for part of the time, but Most of the meetings that I attend and committee meetings and everything else are all by— are virtual.

Yeah. So you moved from being a trial lawyer to the CEO of a foundation.

Yes.

What were the skills that you didn't have as a lawyer that you needed to have as a CEO? And how did you gain those skills?

Well, that's a long story, but one of the things, when you're a lawyer, you react to things. A client brings you a problem, you try to make the problem go away, and if you can't, you have a trial and it goes away that way. And, uh, that's the total opposite of philanthropy. Uh, we don't react. We are, uh, trying to make things happen. We're trying to make change. We're trying to catalyze change. We're trying to I make things better. I help other people to make things better. If you're gonna sit around and wait for the phone to ring, it's just not gonna happen. You have to get out and do something. My first months in the office were very uncomfortable until I realized that I have to go out and immerse myself in the work, immerse myself in the organizations and the people that inhabit our areas of interest. Once I figured that out, at least it was a start. Um, the other thing I didn't know much about was grantmaking. I had served as a volunteer member of the board, but I had not been deeply involved in the grantmaking. I was there and approved things and agreed. And, but when I started to think deeply about grantmaking, I realized I didn't know the first thing about it. Anybody can distribute money. But it takes quite a bit of thought and planning to make a grant that will catalyze change. There's a huge difference. And you don't want to be a distributor of money. You want to be a catalyst for change. That took some time to learn. I bet.

And then you, how big was the foundation in terms of operations?

We had a lean staff, but foundation has an endowment of about $250 million. Has a grant budget of about $10 million annually. And that's, that's a nice chunk of grantmaking that requires some effort to make grants that are useful and, and that respond to a mission that we had carved out for ourselves.

How do you think that, how do you, tell me how you think being a trial lawyer for 22 years was advantageous to learning philanthropy.

Communication is very important in philanthropy and being a trial lawyer, that's what you gotta do is communicate. And also learning and analysis is very important in trial work. In a trial, basically you learn somebody's story and then you analyze it, see how it can work in a legal context, and then you teach it to somebody and you try to persuade them at the same time. And there's a lot of that in, in philanthropy, you have to learn the story of people. You have to learn if you're interested. We were interested, for instance, in Indigenous people. I had a lot to learn, so I had to basically go to communities, go to reservations, go to people and say, tell me what's, what are the issues here? What do you need? How could we help? And that was a lot to learn. My training as a lawyer helped me in that, I think, because I was pretty used to going to people and saying, help me understand this.

As you look back on your 20 or so years as a CEO of the foundation, what strikes you as being one of the, the best or most impactful types of work that your foundation was able to do?

Oh gosh. We, we created an MBA for American Indian entrepreneurship. And that was a huge program on We say we created it, we didn't really create it. We came up with the idea, actually it was one of our grantees, a tribal college that said this would be a big help and we conceptualized it. We went to different universities, we found a university that would do it. We made a grant to them to allow them to build the curriculum. We, we paid for the first few cohorts of students to come and That's just a fantastic program. It's still going. It's the only one of its kind in the country. It has produced almost 100 graduates. It's at Gonzaga University. And Gonzaga University has an MBA in the top 25% in the country. And this MBA is just as— it's the same thing. They, they need to have the same entrance requirements. They have to fulfill the same course requirements. It's not an easy thing at all. It's very rigorous. And there's about 100 graduates of that program now, almost 100. And they are a network of Indigenous business leaders and nonprofit leaders in the country. And they, it's fabulous. Wow. They've done wonderful things. One of them sits on our board now and heads up the largest scholarship provider, Native Forward, in the country. It's, so that is one program that I'm really very proud of, and it's in its 25th year now.

Wow.

And another, we've done some other ones that have been excellent. There's an organization called Eye to Eye, which is in another one of our areas of people with disabilities. And we, they are mentors and advocates for people with learning disabilities. And they were just a little fledgling organization. They operated out of, out of the founder's apartment. And didn't have a board, didn't have staff, didn't really have a program to speak of. And we spent some time with them, made the first big grant that they ever received. And now they're huge. They've got a, a presence in most parts of the country. And the chief executive officer has written a book and been very well received. And it's just a great program. We're very proud of that grant too. And there are a number of other tribal colleges. We have a tribal college program. For Indigenous students studying business. And that program has been going on for almost 30 years now, and literally thousands of people have gone through, and they're doing great things on their reservations, great things off the reservation. But they're— what's— it's been a good, a good thing for us. And the people we've met, people that have actually done that work, the teachers, the college presidents. They're just fabulous people and I will always remember them.

Wow. So you've written a book about how to do philanthropy. Tell us a little bit about that.

Yes. When I started, you asked me about the learning curve and most people come to philanthropy from other work. They have a business or something and they go to a foundation or they do something else. And when I made the transition, I said, okay, this is what I'm gonna do now. I really was ill-equipped for it. I did not have the skills and it's not all intuitive, like a lot of running a law firm or a business, or it's intuitive. It makes sense. But philanthropy is something that most of us don't have a lot of experience with. And so a lot of the lessons I had to learn were unique to philanthropy and So I did what other professionals might do. I looked for a precedent. Who's done this before? There must be something I can read, something I can use, something I can copy. And the field is very idiosyncratic. There are not a— there aren't any precedents. It's not the way it works. It's very individualistic. And so I thought, I'll go and get training. And there's not much training. There was none when I started. You go to conferences, but they would not have continuing education. We would go to a conference in law, as you well know, and there would be continuing education to be mandatory. You'd have to take it. But in this, there just wasn't any. So I thought if I had to learn by trial and error, I had to learn by talking to people, by— I thought if I ever get a chance to write a book, I'm gonna write the book that I needed when I started. And so I did. When I wanted to write it while I was running the foundation, there just wasn't time. But when I retired from the CEO position in 2020, I sat down and wrote this book. Wow.

Yeah. During the pandemic, what a good time to write a book.

Yeah. It was a good time to write it.

Can't do anything else. So what is it, as you look back on this long career you've had, what do you think it's, what's unique about you as a person that you were able to bring to the table that made all of this work?

I don't know. I spent my whole, uh, time in philanthropy telling myself that I wasn't special and, uh, disagreeing with anybody who wanted to make me feel that way. Because in philanthropy, unlike law, in philanthropy there's a power imbalance between the grantor, the philanthropist, and the grantee. Because the grantor has the money to grant and the grantee needs the money. And, um, uh, Philanthropist doesn't have to make a grant, doesn't have to do anything. Uh, can just be idle and arbitrary and everything else. And the grantee really needs the money. And so that is something you got to overcome to have an honest relationship. We can't just have a relationship where you're nice to me because you need money. We have to have an honest relationship where you can tell me honestly what you're doing, what your mission is, what your aspirations are, how you're gonna do it, what your problems are, what you're afraid of. I need to know these things if we're gonna do business. And we have to somehow try to deal with this power imbalance. And one of the ways is for me not to think that I'm special or that I'm gifted and that I'm in this position because I'm such a great guy. That's not it at all. I'm in this position because I'm in this position. That's just where I am. And if you're doing the work, uh, that serves the mission of the Foundation and your own mission, you're probably the good one in the pair. You're probably the gifted one. You're prob— you're certainly the one that knows more. And I never allowed myself and never allowed anyone else to, uh, tell me that I was special or there was, that I was unique or anything like that. The work was special, but I always thought I was an ordinary guy. I cling to that, by the way.

Good for you. So that suggests two, two things that come out of all that are unique. One, humility, and two, the importance of listening.

Yes. Listening is, it's everything. Look, in philanthropy, and you've made a big thing about listening in your work, right? I think listening is one of the great skills and of anything you need to listen. Everybody needs to listen.

And what's interesting to me is that we're never taught how to listen. We're ordered to listen as children. We're ordered to listen as students, but we're never taught how to listen so the other person feels heard. And I think that's where the big gap is. In fact, I think that if we really truly knew how to listen in the way that I teach, we would not have the kinds of problems we have in our society today. We, we— people might not agree, which is fine, but they wouldn't be at each other's throats either, because really what's going on here is situation where people simply want to be heard and respected. Yes, that's all it is. And when you have two sides that all they— each side wants is to be heard and respected, then it becomes a fight to be right and no one gets heard and the fight just gets more intense. And that's what we're— that's what we're seeing here. Um, but, and I think that humility is a, a really powerful way underrated attribute of leadership that we all read the headlines of some of these multi-bazillion billionaires, right? I won't name any names, but we all know who I'm talking about. Humility is just the farthest thing from them. And they are not people that engender inspiration. They're not people that you really want to follow and maybe not even admire very much. And I would think that in a, especially in a position as you're talking about, the power imbalance between the grantor and the grantee, that being humble allows people in the grantee position to feel safe. And because you're listening to them and you're humble, they're willing to open up to you and then you can get to the truth and make a determination. How may I best serve you?

Yes, that's absolutely right. I write in a in my book about humility, and it sounds so basic, and it is basic, but it's very important. And certainly with, in dealing with grantees, there are ways that you can act out your humility. It's not just a question of hearing them. That's very important, but you do need to make them feel safe. And there are ways of doing that. For instance, multi-year grants, letting them define the agenda. It's their agenda. You're investing in their work. They're the ones doing the work. So they're the teachers, we're the students. And so I'm not saying that you just have to agree with what every potential grantee or nonprofit says. No, I'm not saying that at all. You have to be very diligent and analytical. In choosing the nonprofits you're gonna work with. And they have to fit your mission. They have to be good at what they're doing. They have to be so many things. But once you've made that choice, that's, I would argue, 90% of your work. Once you've made that choice, say, okay, I'm gonna work with you, Doug. I'm gonna work with your organization. Then, then the relationship changes and we become the, the student saying, okay, how can we help? This mission that we both share? How can we move this forward? What do you think? And you might say, I think we do X or Y, or I need money for a new accounting system because right now I'm not able to, whatever. And I'm listening. I trust you.

The whole, this whole concept from a, just from a mindset shift is so different from what you need to be in a courtroom. Fake humility in a courtroom can be okay, but no one ever accused me of being humble when I was a trial lawyer. It took me doing many other things to learn the truth of what you're talking about. How did you— how do you make— I made the shift. I mean, it was slowly. I think I really learned humility when I started the Prison of Peace Project. I was going into maximum security prisons training lifers how to stop prison violence. That opened my eyes, and that really shifted me. Was there anything dramatic that happened to you that got you out of the trial lawyer mode into, into a more normal mode?

No, I would have to say that it— this, like I said, this gradually took over my life, and I found that I would rather be doing this than doing the other. And I was, I caught myself one day thinking how I could delay this case that I had.

Oh.

And I thought, that's not good. I'm not doing this.

Right.

And so that's when I realized I had to get out.

You have the final realization. I had that sort of the same thing happening. I was sitting, standing in a courtroom cross-examining somebody one day in the late '90s. The thought came in, what the heck am I doing in here? So that kind of a moment. You can relate to that.

Yeah.

So you've had this long career. You're now the chair of the board. It sounds to me like you're gonna continue working with the foundation as long as you can, as long as you get joy from it, as long as your health permits it.

And, well, um, term limits, age limits rather. Oh. And so I'm gonna be probably there for another couple years and then I'm gone.

Okay.

But that was one of the things that I, championed, I thought was a good thing. So I don't plan to hang on there and be an old fossil. That's for sure. They've, I've made my mark on the organization for better or for worse. And there will be a transition and be a new gang in town and good for them. They're doing great work. I'm really proud to be on the board and I'll be proud to leave them too.

It's, yeah, I know. I can feel that. I, I'm the chair of a board, the board of trustees of our local law school, and I've been doing that for 25 years. Get to that point where the dean and I are gonna move, move off and let the new leaders come in. It's an interesting, yeah. So you got your book out there. Are you doing any consulting work?

Are people calling you and saying, I am, I'm doing, I consult and I speak. Oh, good. People will ask me to come and speak and I will, and I'll talk about governance or I'll talk about grantmaking or whatever. There's, quite a number of investing. There are quite a number of topics that I, that you really need to be a good, have a good knowledge of if you're gonna, if you're gonna run a foundation, either as a trustee or as a, as a CEO. And I frequently talk to boards. And so yeah, that's my new thing and I enjoy that. I enjoy meeting people and I do love to, to teach.

Yep.

So, and I have some other volunteer activities that I like, so I'm actually, as busy now as I ever was.

Wow. And you're able to split your time between Nova Scotia and, and Florida. Yep.

I spend most of my time in actually in New Brunswick and Nova Scotia. We have a house in New Brunswick and St. Andrews, and we also a summer place in Nova Scotia where I grew up. And then, and then we have a place in Florida, so we just follow the geese around.

Good for you.

Yeah.

One more question, Malcolm, I'll let you go. What's one thing about yourself that we would never know about unless you revealed it to us?

Oh gosh, what's the one thing that you would never know about?

No, you wouldn't know that I'm a jazz violinist unless I told you.

You're a jazz violinist?

I am.

My son's a jazz musician. He's a musician? Yes. Well, good for you. Let's That is talent. No, I'm the opposite.

A lot of practice. But what about you? Something like—

played hockey until I was 50. You probably wouldn't know that. I was never a great hockey player, but I enjoyed it. And I'm pretty, pretty ordinary. There's not a heck of a lot to—

playing hockey until you're 50, it says something.

I still play tennis. You'd know that though, if you were anywhere around.

Playing hockey until you're 50 tells me how tough you are.

There were tougher guys.

Yeah, I'm sure there were, but that's pretty impressive. Malcolm, it's been a really great conversation. Thank you so much for taking time out of your day to speak with me.

Doug, thank you. Thanks for having me on this. I've enjoyed it and I've enjoyed finding out about you. And so thank you.

You're welcome. Take care.

Yeah.

Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media, just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up, ratings, and Your likes and views go a long way to help promote the show and mean a lot to me and my team. Want to know more? Go to my website, DougNoll.com, or follow me on LinkedIn, Facebook, and Instagram. That's @DouglasEnoll. Thanks for listening, and we'll see you on the next show.