Ramona
Glen, great to have you on the Manager Track podcast. I’m very much looking forward to this conversation.
Glen
Well, thank you for having me. Surprisingly to me, I wrote a book about foundation life, which I don’t know how much people know about, but so many people have wanted to talk about leadership and management and control.
Ramona
Well, let’s dive right in. What is it, or what happened in your life, that really sparked that interest and led you down that path?
Glen
So in the world that I work in, it’s a world of a great deal of capital, money, and power. People who have the ability to give away a lot of money, and they do it through tax-exempt structures, and people are out there looking for the money. So you have people that are trying to raise money for their causes.
Glen
And what I found, for years, I worked in training people who give away money. I trained them to give it as strategically as possible, and the way we trained them to do that was to give to things that they cared about most. We have an entire structure that we’ve built, a system around very wealthy people, encouraging them to do that.
Glen
And that is a wonderful thing. It’s great to be able to give to things you care about. But what comes with it is a desire to control everything around the money that you give. A lot of people in their regular day-to-day, when they give away money, they just write the check, right?
Glen
My wife and I give away some money every year. We just write the check, put our credit card number in, and away it goes. When you’re very wealthy, you might ask for a heck of a lot more. You might ask to be on the board of an organization. You might ask to control where the money goes. You might tell the leader of the organization, “I think I can do it better than you can, and I think you should do what I say.”
Glen
And that control has a real impact on how organizations work with communities. So I was training people to do it just that way. And when I eventually had the opportunity to run a foundation, and I run one now, the Stupski Foundation in the Bay Area in California, I implemented a lot of very controlling things. We started to get messages back saying, “You folks are very controlling, and we aren’t able to work the way we want to work, because you control the money.”
Glen
And it was painful to hear that. I really thought we were doing a good job, but it turned out we were doing a bad job. The organizations we supported, and even my own staff to some degree, felt very controlled by the way we had built the culture of the foundation. That was a turning point for me and for us.
Ramona
Oftentimes, when it comes to this scenario but also in the context of organizations and corporations, when a leader is controlling, they’re often doing it with the best intentions, saying, “I train people to do this, and I wanted to do this because I thought this creates the outcome we want.” Can you talk about the inner motive that drives those controls that other people perceive to be actually negative behaviors? What’s driving the person who’s controlling?
Glen
I think it’s kind of ironic, actually. We hire people, and we put people through many, many organizations, and I’ve certainly been on both sides of this, where we work really hard to get the best people to do these jobs. And at the same time, when we’re leaders of organizations or managing a team, we feel an obligation and a responsibility to make sure whatever we’re doing is going to be at the highest standard.
Glen
And for the most part, if you’ve achieved some kind of management position, I’m sure you’ve convinced yourself that you are the best at the job, and you have a responsibility to make sure all of this plays out the way you want it to play out. So the irony is that you bring together a team of highly talented people, and then you make them all do it your way.
Glen
Like you said, that’s not a badly intended thing. You’re trying to make sure you’re getting the best outcome you can as you understand it. But what I think makes for better leadership is recognizing that you may not be the best at everything. Maybe there’s something you’re really great at, which is just keeping a team together or setting the guardrails of the work. But if you’ve gone to all the trouble to put together an amazing team, then let that team be the team you want it to be.
Glen
So that comes with a lot of risk. If you personally believe you’re the best at it, there’s a huge risk to letting other people do it. But in my experience, the more you let other people do it, these great people you’ve hired, the payoff is much higher. And that applies not just to the workspace, but also who you bring in as contractors and otherwise. I think you really have to learn ways to give up control, because the payoff will likely be much higher.
Ramona
And to learn to give up control, how does one learn it?
Glen
That’s the risk part. We all define different features about how we behave in different ways. So my version of control may be your version of setting high standards. And what could be wrong with setting high standards? People generally aspire to that.
Glen
But the first thing that has to happen, and the first thing that happened for us, not only externally with the grantees we had at the foundation but also internally, we were taking surveys of the staff. The first way to find out if you’re being controlling or not is to ask people.
Glen
So first you need to be open to something that a lot of us struggle with, and that’s feedback. We love to talk about feedback. I know a lot of people like to say, “I have a growth mindset.” Typically, when someone says to me, “I have a growth mindset,” I already have red flags up, because they probably don’t. They’re telling themselves they do.
Glen
The one way to confirm whether you have a growth mindset is to go out to people and ask them. Whether you need to do it anonymously, or if you have the capacity to do it and they have the capacity to share the feedback, the first way to know whether you are controlling, or how your control is showing up, is people will tell you. I believe we’re all controlling to some degree. But how is your control showing up?
Glen
Now, if you resist the feedback, if you find yourself getting on the defensive, “That’s not what I intended. That’s not what I meant to do. You misunderstand the context.” If you find yourself saying those things when you’re getting feedback, you have work to do. You need to reflect. You need to take a step back. You need to ask yourself, are you really trying to grow, or are you really just trying to dig in and be what you want to be? Which, for someone on the other side, might be experiencing a great deal of control and dominance in the workspace.
Ramona
I do this type of work with leaders all the time, because it’s such a deeply ingrained sense of control in us, and especially the more career success we have, the harder it is to tame that. It takes real effort, and often goes through coaching or through feedback, like you just said, and really being able to be open-minded, because often we experience some setback or hardship that makes us say, “Okay, let me entertain the idea of doing it differently going forward.”
Ramona
Now, I’m going to play the devil’s advocate here, because every so often I get this objection: “Well, I hear what you say, and yet if you look at the most successful leaders out there, Steve Jobs, Elon Musk, you name it, they’re highly controlling. They’re the people who will dig in and tell people exactly what to do or not to do, and are very direct with what they want and don’t want.” So how is that possible?
Glen
Well, I think there are degrees to this. I have had the benefit, being in the Bay Area, of crossing paths with people at Pixar and other places. My sense of the people that worked with Steve Jobs, not to go overboard on his story, is that he did give a lot of room for people to be creative agents in the organization.
Glen
He did have a strong vision. Having a strong vision is different than being an aggressively controlling manager. So if you have people that have worked at Apple or Pixar, any one of these subsidiaries of Apple who’ve worked with Steve, they might say, “This guy has no idea what he’s talking about.” But from the lore that I understand: strong vision, high standards for the organization, but a wide range of creative liberation to the staff.
Glen
They were able to build products, designs, innovations, that all had to stack up to what his vision was for a product. And that was kind of what I was getting at with guardrails. To the degree that you can have a strong vision and drive the organization in a particular direction, but give the freedom to the team you’ve built to do the work, to design, to test, to fail, I think that’s what you’re going for.
Glen
I still lead a structure. I lead a foundation. There is a set of principles and a mission and a vision we have for the work of this foundation, and I have a course that I am taking us on. But I also give as wide a latitude as possible underneath that vision for the team to do their work. We do a tremendous amount of work in communities of color.
Glen
In my growing up, I didn’t grow up in a community of color. I didn’t grow up in a community that was marginalized in many ways by society’s rules and norms and laws. We have a lot of people who did, who work at the foundation. It would just be completely insane for me to turn to them and tell them, “Here’s how you should be making your grants in that community.” I brought them in because they can help the foundation meet the vision we have for our organization. I’m going to make sure that they’re continuing to work on that vision. But I’m going to get out of the way when they do their work.
Glen
It’s not just a linear thing. It’s a constant. You’re really talking about everything here. You’re talking about structure, you’re talking about culture, and in many ways you’re talking about how people’s own self-interests play out inside a space. So you’re talking about all the dynamics of behavior. As a leader, in both dynamics, manager and leader, you need to be really cognizant of how all of that is playing out, and how you’re giving up control appropriately so that people can do their work effectively.
Ramona
I like how you distinguish this: control of the how we’re doing things versus the vision. That’s really clear. Now, on the point of we’re all being controlling to a degree, one thing that stood out to me as you were talking about this: how someone responds is a big indicator. When I see people who are resisting feedback, or don’t like when someone is giving specific suggestions or advice to them, that resistance is also control. So while we’re telling the other person that they’re controlling, we’re being controlling ourselves by resisting it. It’s just a good mirror, sometimes, through that reflection of, why are we resisting this in the first place?
Glen
And let’s think about the implications of that. If you’re dealing with someone on a team that has a team, and they are resistant to having a conversation about their own feedback, imagine what their team is experiencing. You probably don’t have eyes on that every day. But if they are resisting your feedback as a boss, as a supervisor, as a leader of the organization, you can be sure that the people working for them are in a very dominated state.
Ramona
What are some of the biases, the behavioral biases that you call out, or other red flags or indicators that there’s an issue around control?
Glen
Well, again, the book is called “Control: Why Big Giving Falls Short.” So I’m very focused on my sector, which is people giving away money. What’s interesting in this conversation, and how it applies to the work that I do, is that you brought up Elon Musk and Steve Jobs, and all of these folks have private foundations that they’ve given money to.
Glen
The interesting thing about them is that they are, as you pointed out, exceptionally successful as economic capitalists in our society. They’ve run businesses to extraordinary levels. And we as a society assume that they can easily take that into the social sector. That if you’re Bill Gates and you’ve been successful at selling operating systems on computers, then naturally you can get rid of malaria.
Glen
If you kind of laugh at that comment, it’s true that we believe that. But it’s also an irrational thing that we’ve set up here, that just because you can build a great company doesn’t mean you can solve a social problem. But we believe they can, and that’s the system we’ve built. So one of the things that I think is interesting is that they bring their ability to run a for-profit company into the nonprofit sector. It’s an example of where somebody might be misassigned to a job, and what happens when that person comes into a role that they really weren’t built for.
Glen
What you tend to see is that a lot of these wealthy people who run foundations, or sit on the boards of foundations that they put themselves into (they don’t need to be there, there’s no requirement for them to be on these boards), they put their name on them, so they assume “I should be the chair of it.” They tend to be very frustrated in these roles because it’s not easy.
Glen
It’s one thing to build an amazing car. I have one of Musk’s cars. I love it. I think it’s one of the greatest cars ever. But do I want him trying to figure out US international foreign aid? Well, he tried to figure that out. What did he do? He got rid of it. So now we’re struggling globally because we’re no longer engaged from a foreign assistance standpoint. He looked at it as a vertical within his company that is not performing the way he wants it to, and eliminated it. He was in the wrong role for the work he was doing. And what happens when people get into the wrong roles and bring that bias in? They can make some pretty poor decisions.
Glen
I don’t want to get into a debate about foreign assistance, but I will say, was Elon Musk the guy to decide that? Probably not. Is Bill Gates the right guy to figure out malaria? I don’t know. So what kind of bias comes out when they show up? That’s the control that really concerns me.
Ramona
Which I think is such an interesting topic. If you look at this a little bit more closely, even if you stay with philanthropy and don’t make it a one-on-one match of how it shows up in organizations: it’s an idea, an identity. Those philanthropists come in with this identity, and then they apply that same identity, and therefore the behaviors that reinforce the identity.
Ramona
Even if someone is not a controlling leader, even if they would say, “No, actually, I am going to delegate work, and I am able to step back, and I hire people who know better than me, and I’ll let them run it.” But then they go into this organization where now they feel like, “Wait, I probably don’t know anything, and so I need to be more involved. In my company, I kind of have an understanding of what good and bad looks like. With this foundation, I actually don’t know.” Can you tell us more about what this looks like from the inside, and how to detect the behaviors, and then how to shift?
Glen
That’s a nightmare. I have this in my book. As a CEO of a foundation, I’m in the sisterhood and brotherhood of people that lead these foundations, and I’m lucky. I get to have incredible conversations with incredibly talented people, many of whom are deeply frustrated when they run these foundations under people like we were just talking about.
Glen
I talk about this in the book. There was a tech leader, very well-known, who decided he wanted the organization to get into racial justice work. So he hired a leader right out of the community that they were really focused on. This leader had a whole bunch of ideas that came right out of community solutions, organizations that had been working in a very scarce environment but getting good results.
Glen
He wanted to implement all this, and the chair of the board, the person who made the initial donation to the foundation, this tech leader, was very frustrated with what this person was doing, because it didn’t come off like an innovation or an entrepreneurial endeavor. His brand, the tech leader in this case, his brand was associated with being an entrepreneur and an innovator.
Glen
So he let go of that leader. It was more important to him that the perception of the foundation was innovation and entrepreneurial outcomes, not actually solutions that are proven on the ground that were not his or not the foundation’s. That’s a dynamic that goes on all across the sector.
Glen
You said it very well: identity is a huge driver. Brand is a huge driver. And these people want everything they do associated with whatever their identity is. Doesn’t mean it’s going to have impact, and I would argue it has less impact. If you don’t let the people on the ground do the work they know best, I think you’re going to fail.
Glen
Chances are, the wealthier you are (this is obviously not universal), the lower the proximity to the communities you care about or your team might care about. You are not experienced in the life and the challenges and the successes of those communities. You’re probably going to come at it with what you know best. And if you are not in the right role, or you don’t have the right vision for this, you most likely are going to fail.
Glen
I do think that you can see that dynamic outside of philanthropy. You can see it in a lot of places where people get jobs for reasons that may not be about their qualifications, maybe someone they know, maybe someone they’re born to, and they end up running a company, and they run it into the ground.
Ramona
So if you’re imagining being that leader that was hired in the community, the first interview that they had with the tech leader: what would you advise someone to bring up in a conversation early on, to either assess if this is truly the job they want to take, or to create some kind of alignment or a contract? I don’t mean a legal contract, but an agreement about how this is going to go. Because I’m recalling like five conversations with clients right now where the initial understanding and why they were hired seemed right, but then within weeks they realized what they said they wanted is not actually what they seem to want, behavior-wise.
Glen
Those are such excellent questions. I’ll do my best with that, because I haven’t thought about it that much. I have to set the context: I’m coming at this from a social foundation setting. I’m not talking about a for-profit environment, and there are differences. So I’ll do my best and play out what I know.
Glen
Look, first of all, running a foundation is an incredible privilege in many ways. We are doing social sector work, we’re paid very well. We have incredible access to amazing people, some famous, some not so famous, but still totally amazing. It’s a job people want. So I don’t know how many people are going to listen to the advice I’m giving right here.
Glen
But if you’re talking with someone who is considering you to run their foundation, I think I would want to know off the bat what they know about the communities they want to help. How much experience have they had with those communities? How many people do they know in those communities? How many times have they been to those places? What work have they already done there? And I would bet, in most occasions, it’s going to be not much. So then if the answer is not much, the next question has to be: what kind of latitude are you going to give me to lead this organization?
Glen
I will tell you, having been in several interviews for foundation jobs, people are not afraid to tell you what they think about their own leadership. I worked with a really dynamic woman. Her name is Joyce Stupski. She passed away in 2021, but we worked together for six years. She gave me a very strong sense of who she was. Whether she intended that or not, she definitely did make it clear to me. I would not be running the investment side of the foundation. She would handle the whole portfolio. I would just handle the grants.
Glen
Well, I would never stand for that again. Now, she wasn’t wrong to want to do that. It’s very typical of a foundation that the wealthy family members want to manage the money inside the foundation. But there’s so much damage that’s done, in my opinion, when they do it, that if I were running one, I would never stand for it today.
Glen
But she was very clear. So right there, looking back in retrospect, there’s an aspect of this organization that she was going to control, and I needed to be comfortable with that. I was never going to be in a place where I would control that money. And by the way, it’s the way most foundations operate. That meant she would be controlling 95 percent of the assets in the foundation, and my job would be to handle 5 percent every year. That’s a pretty controlling setup.
Glen
So I’d want to know: what’s your experience with the community? Joyce, by the way, was a school teacher in the very communities where we worked, so she had a good experience with the communities, and I admired and valued that. She was far more liberal about letting the team do the work than other governing structures I’ve seen. But she was very controlling when it came to the portfolio. She was very controlling about how we looked and spoke, what we said, and how we communicated. She felt she was really strong in those areas.
Glen
And guess what? She told me all of that in the interview. So the guy I am today would not have taken that job back when. But it took the experience to have it. I don’t know, for people that are hearing this right now: these jobs are so exciting to get into. You might hear a lot of things you’re going to put red flags up about, but I would imagine you’re probably going to still take the job unless you have the experience to say no.
Ramona
Well, I do see this when people elevate in their careers, that at some point this kind of evaluation just becomes incredibly important, just as important as in the earlier years. So there’s definitely a clear parallel. Thank you so much for elaborating on this. So as a quick wrap up, tell us how people can learn more about you and the work that you do.
Glen
Well, yesterday, I was honored. I was one of 100 people who were selected by Time Magazine as the most influential in philanthropy. So if you go on Time Magazine, Philanthropy 100, you can see my work and the work of 99 other very dynamic people, and people you probably will recognize right away.
Glen
The foundation is called the Stupski Foundation. We are at stupski.org. We are a private foundation, so we give out money. We don’t actually raise money. And I recently put out this book, “Control: Why Big Giving Falls Short.” I really appreciate, Ramona, the questions you’re asking, because the book, while very intended to talk about some of what we were just getting into with donors and wealthy individuals, you will pick up some of these ideas around control, how it shows up, and how we could all benefit from stepping back and letting go.
Glen
We actually have a Slack channel inside the foundation called “Letting Go,” and I challenge people all the time to try to identify where they’re being controlling. And when they do, and they figure out how to let go, I have them post on Slack, and we celebrate people being able to let go. I hope more people will consider doing it. I think it would make for much healthier corporate and foundation structures.
Ramona
Yeah, what a great practice. Thank you so much, Glen, for joining us on the Manager Track podcast. We will include all those links in the show notes, and wish you all the best and lots of success with what you do.
Ramona (outro)
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