Skip to content
Follow Us

Get the best of Capacity Interactive delivered to your inbox.

This field is for validation purposes and should be left unchanged.
Leading an Organization with Empathy
Episode 39

Leading an Organization with Empathy

CI to Eye with Harold Wolpert

This episode is hosted by Erik Gensler.

0:00 / 0:00


Erik and Harold talk about demonstrating a healthy work/life balance as a leader, cultivating successful external partnerships, and how every patron touchpoint affects an organization's fundraising efforts.

Erik Gensler: Thank you so much for being here. I think you are one of the first people I met when I began my career working in arts administration. So let’s start with an easy question. What is the first theatrical show you remember seeing, and I’m curious if that was what inspired you to be in this business?

Harold Wolpert: When I was probably around 15 years old, my parents took me to New York to see “Torch Song Trilogy,” which was quite the experience. It was also fun because, afterwards, we waited by the stage door and I got meet to meet Estelle Getty-pre Golden Girls. That’s how old I am. I wasn’t aware of myself as being gay at that moment, but there’s no doubt that it had a big influence and, in that particular case, a very specific kind of play where it’s, Harvey Fierstein as someone who is happy or trying to find happiness so it made an impression on me. Years later, when I came out to my parents, I teased them, I said, “That’s why I’m gay, ’cause you took me to see Torch Song Trilogy,” so.

Erik Gensler: With Estelle Getty.

Harold Wolpert: Yeah, it’s with Estelle Getty (laughs). I said whoa.

Erik Gensler: Did you ever have a moment when you said, “I want to run a theater?” Was that a aspiration?

Harold Wolpert: I think I had a sense pretty early on. In fact, my brother-in-law, after one of my first jobs, and I was sort of being critical about my boss and why did they do this and why did they do that, my brother-in-law said, “I don’t think Harold’s going to be happy until he’s running the company (laughter).”

Erik Gensler: Leader or not.

Harold Wolpert: Yeah, exactly. I think I’ve always gravitated towards leadership positions. And, in fact, I’m doing an exercise right now, about core values and one of them is leadership, and, and the way it was defined was having influence over others, and I, and I liked that notion as opposed to suggesting authority or telling people or, or sort of dictatorial. That felt sort of natural and sort of aligned with how I think of what leadership is.

Erik Gensler: Let’s start with a number of factors of, of leadership, which is figuring out how to, one, work with people that may be different or have different points of view, and I know, throughout your career, we’ve talked over the years about labor negotiations, which is something I’ve never seen or experienced, but I know as a, theater manager, it’s something you probably spend a lot of time thinking about, and I’m curious, what are some of the things you’ve learned about, going into meetings where people have really different points of view, perhaps have very different outcomes that are very high stakes, but you still have to agree?

Harold Wolpert: The key thing is actually trying to figure out and see where the common ground might be. Sometimes it’s easier, sometimes it’s harder. As I’ve done it more and more over the years, I think there were times where I actually could sort of see where I thought we were going to end up by the end because I just knew enough about the issues, I knew enough about the other party. There were times where I would feel stuck in the middle. But it’s trying to realize that, somewhere in there, there was probably common ground. I guess, in a way, it’s a little, not to make it too grandiose, but the notion of a sculptor saying, “Oh, yeah, the sculpture is in there, I just chip away the rock or the stone.” If it’s partners that you’ve sat across the table with multiple times, you’ve built relationships, and viewing it. Well, in one sense it’s literally adversarial, but, as I just said, it’s partnering. You’re partnering towards, ideally, a mutually beneficial goal and, in some cases, if you step up to 30,000 feet, the union may say and we might say, “We want to ensure the success of the theater. Can we establish certain baseline principles or goals?” Now we have different tactics (laughs) about to get there. They might say a well-paid staff, union contingent is the key. I’ve seen instances around marketing and press and publicity, there’s been a shared understanding that, if we can bolster that, that’s to everyone’s mutual benefit, so finding those points. I also believe that a staff that is content with how they’re paid is not in opposition to management or the company. That’s, that is beneficial and, and I’ve often said at the table, “I generally will not argue with you about how much you’re worth. The question is what can we afford?”

Erik Gensler: Right. It’s reframing it.

Harold Wolpert: Yeah.

Erik Gensler: Yeah. I’m going to talk more about leadership and who do you l-, look up to as, as leaders in either the arts field or, or beyond? Where do you look for leadership inspiration?

Harold Wolpert: I’ll just say (laughs) one just humorous thing. I somehow or other, on Twitter, stumbled across, what I thought was Warren Buffett’s Twitter feed, and I thought, wow, there are all these little inspirational things, “When you wake up in the morning, take a deep breath,” and this and that.

Erik Gensler: (laughs).

Harold Wolpert: It suddenly just kept, appearing on my feed more and more. It’s like I had no idea. I wouldn’t have thought Warren Buffett, and then I realized, on my way here, that’s WarrenBuffett99. It’s not (laughter), it’s not Warren Buffett. But I was like I had no idea he was so inspirational (laughter), but he’s not, not in that way, at least. There’s a lot of different people in my life and in my career and, in many ways, those two have come together, where people who have been in my career are now sort of in my broader life, my personal life. I think the common thread around the people who I look up to: What are the common qualities? I think integrity. I think passion for what people do. I think, generally speaking, these people work hard, are committed to what they’re doing, who set a good example, people who are mentors or teachers, either to me or to other people, people who collaborate or cooperate or sort of have an open spirit. If I looked outside of the field into the broader world, I think Harvey Milk, who was just incredibly courageous, had the courage of his convictions to act on what he believed, because I think it’s, it’s one thing to believe something very strongly, it’s another thing to do something about it and to, and to take action towards your beliefs. So what’s the expression? , do you talk the talk or walk the walk? And, and he did both and he was ahead of his time as well. That’s inspiring to me.

Erik Gensler: I think you put that spirit out there of openness and, it’s interesting how you talked about the personal and work worlds colliding. And I remember, when I first started working at TMG, who worked with Roundabout, you were just always wanting to go out to lunch and you invited me into the, the theater’s events because I was doing sponsorship consulting and you wanted me to be successful, and I felt like you were really just so open. And we’ve talked about this in the podcast before with, Bonnie Siegler, she’s actually speaking at Boot Camp as well, and she writes a book called “Dear Client: This Book Will Teach You How to Work With Creative People.” And, in the first chapter, she talks about, if you approach a vendor or a partner with suspicion or you’re questioning them and you’re, you’re not open, you’re not going to get their best work, and you’re the opposite of that.

Harold Wolpert: I have a problem with the phrase, “They work for me.” We work together. It is partnership. It doesn’t like you said, whether it’s a vendor or an employee or, at whatever quote-unquote level, we’re operating, that’s not how I see it. Having people who are theoretically on the outside of your company, who aren’t there day to day, but if they can be immersed as much as possible in what you do, it has a lot of benefits. If benefits them in terms of their growth and their interest, and then it comes back to the company. And I think treating the people who work at your ad agency or at your marketing agency or who, whoever it is as you would want to be treated, bringing them in, sometimes telling them maybe more than they want to know, but I think that’s helpful to me, having more context is helpful and more connection to the company and to the work, I think, is beneficial.

Erik Gensler: I think it’s certainly true here. The clients that are open with us and share and bring us in and maybe even tell us more, it just contextualizes it, and I have seen you demonstrate that with your press agents, with ad agencies, with everybody. And that whole, open, warm, inviting collaborative atmosphere, I think it produces much better work.

Harold Wolpert: I just had lunch today with our accountant, we talk throughout the year. We don’t just talk at the audit time.” It’s not high on their list to talk to their accountant. I think they will serve. This is a perfect example. They will serve us better if they know what’s happening, what’s going on with the company, if, they’re not hearing about something necessarily for the first time, they don’t hear it once a year. And that goes across a lot of different constituencies and a lot of different relationships.

Erik Gensler: And that takes a lot of work-

Harold Wolpert: Absolutely.

Erik Gensler: … emotional energy.

Harold Wolpert: It absolutely does, it would be sort of easier (laughs) to just not worry about that and not invest, but I think, on the other hand, making that investment up front saves a lot of time later.

Erik Gensler: You’ve worked in a number of theaters. I think of you as really involved with LORT, the League of Resident Theatres, in planning their conferences and being an active member of that organization. What do you think some of the major challenges facing theaters and theater leaders right now and as you just think of where the industry is in 2018?

Harold Wolpert: I think we’re at a real turning point. There are more and more leaders, some of whom are founders, some of whom are close to being founders of their organizations, who have been, leading the companies for a very long time, and that presents a huge challenge. the companies and the leaders are so clearly aligned that it may be difficult to distinguish one from the other. That’s true externally. It has a lot of implications internally for, for staff, for board, in terms of, a lot of the burden and responsibility for leading the company has fallen onto those very capable shoulders, and now we’re in a moment where that responsibility needs to be spread across more people. And I should add that there are plenty of people, especially workers and staff in the theaters across the country, who are beyond ready and capable to, to take that on. They’ve been chomping at the bit. So that challenge of a field that is really maturing and companies that are becoming more institutional and are suddenly not startups.

Erik Gensler: We’re entering a whole new phase and a new generation and, what it means for employees and what they expect and want and maybe not, looking to or wanting to work really long hours for not a lot of pay, and the disconnect between maybe a different generation, “Well, that’s what we did. That’s how you have to do it.” And that, that has to be grappled with and that requires attention. So you’re back from, a couple weeks off, which I know is something you’ve done every summer since I’ve, I’ve known you and I’ve always really admired your focus on work-life balance for yourself. And I think, a lot of people are afraid to demonstrate that, this idea that working harder and nose to the grindstone, is something to be admired. And I’m just curious about your point of view around this and how you’ve always just been so, “No, it’s August and I’m taking my time off and I’ll be in P-town (laughs).

Harold Wolpert: On the one hand, fortunate that I’m able to do that, and I’m aware of that. I, also know that I need that. I know, it’s not entirely, but, the theater is, is a lot sort of fall, beginning of the fall season, so at Signature, we’re going to have a particularly busy fall and I know that I need. I know myself and I know that I need to, to recharge myself. I know I need that downtime, and it’s fluctuated from year to year how, how much I’ve totally disconnected and how much I’ve stayed connected. Trying to take that time, trying to whether disconnecting or not, just to refresh myself, and to have that carry through as long as possible. And I practice what I preach, so when staff who work with me go away, I won’t, I won’t contact them. I won’t send them an email. I won’t call them, I’ve told them, if you need me, contact me. Be judicious,” if you’re the boss, that’s what, how it works, but, trying to respect people and encourage people to take their time as well. it’s a, I think, sort of uniquely that American/Protestant work ethic, that I think is admirable, but I know myself and I know what I need to, to keep going and to make sure I can be there, for other people. It’s pretty crucial for me.

Erik Gensler: I think it’s super important. I try to demonstrate and I think more leaders can demonstrate because it’s just not the go, go, go mentality can, crash and burn.

Harold Wolpert: What they say on an airplane, right before you take off, “Please, put your mask on yourself before you put it on someone else who might need assistance.” So, I mean, it’s not quite analogous, but the notion of you’ve got to take care of yourself if you’re going to be running a company and be responsible for a lot of other people. I’m doing this leadership self-renewal seminar four times this year with the Shannon Institute outside of Minneapolis, actually in Saint Paul exactly. the concept there is people in the not-for-profits and the helping fields, you need to take care of yourself so you can do a better job for yourself and for the people who are counting on you. If you, if you’re burnt out, if you’re fried, that’s not going to help your institution at all if you can’t deliver your best self.

Erik Gensler: What else have you learned at the Shannon Institute?

Harold Wolpert: We’re doing an exploration in core values at the moment. It’s really fascinating to dig in and, and think about things that you might not otherwise, take the time to think about those, and what are your core values, and, try them on and see if what you say are your core values match up with what, you do, the leader of the, of, the seminar told a great story. He said, ” I used to think that one of my core values was honesty, and then my wife came into the room after she had bought, a new dress, and she tried it on,” he said, “and then she said, ‘How does it look?'” And he said, “And then I decided my core value was caring (laughter).” I was like, “That’s great (laughs).”

Erik Gensler: Right. Well, it’s like what you said about Harvey Milk-

Harold Wolpert: Yes.

Erik Gensler: … he practiced what he preached. Yeah.

Harold Wolpert: Exactly, exactly.

Erik Gensler: We talk a lot here at Capacity about, giving or receiving feedback, and I’m curious, what is one of the hardest pieces of professional feedback you’ve ever received and how did it change you?

Harold Wolpert: I was a camp counselor for many years. I was paid, so it was professional.

Erik Gensler: (laughs).

Harold Wolpert: I was probably around 18 or 19, maybe 20, and, the director. I looked up to him. I was very close to him. he singled me out at a staff meeting in front of everyone else and it was about not, kowtowing to the children, not trying to get them to like you, but instead sort of standing your ground and setting an example and being tough. And the irony of it was, it wasn’t really about me. I was in a situation where my co-counselor did that and, as a, as, at, at the age that I was, you sort of want people to like you I was the bad cop, he was the good cop, the director singled me out in front of the whole staff as sort of this example. That’s not the way to do it. My recollection was he yelled at me. It was very upsetting at the time. It clearly left, a big impression on me, in a calmer moment, we had a conversation and he, he didn’t say explicitly, but he said, “I said it to you. I, I knew who I was choosing. I thought you were strong enough to hear that message and I said it because I want you to remember, do not try to be liked by people. going down that road is a bad road to go down ’cause you will not be liked by everyone.” keep doing what you’re doing. Go along the path that you’re going. Those children will remember you for a longer time than the one, than the, the counselor who’s trying to be liked.” So respect, and, staying to your core and to your beliefs, it was a difficult way and, and sort of a hard lesson to learn, but I, I think back on it often.

Erik Gensler: Do you come across moments in your career now where that you’re taking the path of not being liked, but ultimately being respected in the long run?

Harold Wolpert: I think one of the things that I feel good about myself is that I think I’ve found a way to thread that needle, not trying to be liked, but because of my style, because of my approach, that the respect and the like sort of come hand in hand, that I can have a way I fired someone once and, at the end of the session, they hugged me (laughs). So I think, I think there are many times in which there’s a way in which I can speak to people, my demeanor that, again, has their respect, but also, that people sort of have a certain kind of affection, because straddling that, that fine line

Erik Gensler: I read recently that, if there’s not conflict at your job, you’re just not doing it right. Like everyone’s going to have differing opinions and by having everyone agree, you’re not going to progress and so you have to be the voice of dissent.

Harold Wolpert: There are absolutely times where you’re going to say things that people aren’t going to like to hear. I’ve done it, as we said, at the negotiating table. I’ve done it to staff. There have been lots of instances where one group of people thinks one thing, one group of think another. You’re not going to make everyone happy all the time. It is commonly said, but I think it’s true, and you can’t run from that.

Erik Gensler: Yeah.

Harold Wolpert: Yeah.

Erik Gensler: So one constant in working in the arts and having a leadership position, even if you’re not born to be a fundraiser, you’re involved in fundraising. And I know in your last role at Roundabout, the way it was structured, you were not directly in charge of fundraising, but, of course, there’s a fundraising piece of it. Curious what your role in fundraising is now at Signature and if there’s anything that you’ve learned about fundraising that may be useful or novel to the podcast listeners.

Harold Wolpert: Sure. I think a couple things in a not-for-profit theater, whether people know it or not in the way every single person who is involved on the staff, on the board, is a fundraiser, is a relationship builder, is an ambassador for the theater. I think fundraising is often misunderstood. A lot of people, I hear them say, “I’m not a good fundraiser. I don’t like raising money.” And then when you walk them through and talk, “Well, you did this and did that. Well, that’s fundraising.” People equate fundraising with asking for money, and there are so many component parts of fundraising. Fundraising can be, an usher in a theater helping someone to their seat, answering a question, a smile on their face. That is a piece of fundraising. People have a good experience, that can play a part that leads to the moment when someone’s being asked for a gift. If you think about a moment where you have a bad experience (laughs) and how, maybe you’re asked for money and you say, “No. No, thank you. No, I’m not. I wasn’t treated well.” So it’s all and it’s all a part of the piece and, again, looking at fundraising as a series of pieces, like a series of components, not just the “Will you give us money?” So in terms of Signature, I’d said early on, right around the time I was hired, I said I’ll be spending 120% of my time on fundraising. It’s just, the nature of running a company, this day and age, I think, as an executive, where often, we can make the biggest difference is putting our time and energy, not to say that our fundraising team isn’t totally capable and talented, they are, but having, the, one of the heads of the theater deeply involved, in terms of, I don’t know if, new or, or novel, a lot of people have been doing it longer than I have. I think it, relationship building. Focusing on fundamentals, thanking people, it’s surprising to me that the small things, when they’re not executed properly, the impact they can have. sometimes when they’re done well, it’s not noticed. But when they’re not done well, it is noticed. So it’s really critical and just focusing on basic building blocks and, reminding everyone and making everyone aware that you’re all part of the fundraising team. We had a full staff meeting at Signature not too long ago and we had staff, a staff members stand up and say, ” What? I don’t really understand exactly what the development department does.” And I think, if it’s true that everyone is a fundraiser, then the development team needs to help everyone to do that, to make them aware and to support them and know how they fit into the picture, whether it’s board or house staff.

Erik Gensler: I love that. Everything you do is fundraising. Every touchpoint a person has is ultimately leading to the potential ask.

Harold Wolpert: Absolutely.

Erik Gensler: What’s something you’ve learned in the last year or so that’s been profound in how you work or think?

Harold Wolpert: I had some time off between Roundabout and Signature and I spent some time just, not doing much and then I was doing a lot of consulting, and I think what was driven home to me is always possible it doesn’t matter how old, but even at the point in my life that I am, it’s possible to change. It’s possible to do things differently. It’s possible to change your outlook. It’s possible to change yourself. My father actually used to say, “People don’t age, they intensify,” which I think is true.

Erik Gensler: (laughs).

Harold Wolpert: I think it is possible. I think you can change yourself. I mean, as long as we have free will, if, if we say, I want to go in a different direction. I want to do this. I want to do that. All things being equal, I think you can, you can put your mind to something and, and, and you don’t have to feel that you’re stuck or that things are sort of established in a certain way.

Erik Gensler: So we’ve come to your CI to Eye moment, which is the final question, and the question is, if you can broadcast to executive directors, leadership teams, staff and board of a thousand arts organizations, what advice would you provide to them to help them improve their businesses?

Harold Wolpert: I would say that, we’re producing art. we’re not producing widgets, a play ends, maybe people will take home their program, maybe they buy a t-shirt, but they’re not really taking anything tangible home what audiences see, whether it’s in a muse or on stage or, at the ballet, is accumulation of effort, and communication. We always have to remind ourselves that it is a business that is very much based around people. Is it, is it the only business? No, but, it’s people standing up on a stage in front of an audience of people looking at them. So that interaction, and focused on each individual and focused on what we’re, what we do collectively as people is critical. It’s not about hard skills. It’s not even about soft skills. It’s just being mindful. That is our capital. We rely on the creativity. We rely on the energy. We rely on the innovation, the energy of people. We have to nurture that in this field. it’s hard and you’re not going to be paid a lot and, you’re going to work a long time and we have to elevate and value the people in our companies and continue to, do that. That’s critical.

Erik Gensler: Right. Thank you so much.

Harold Wolpert: Thank you.

About Our Guests
Harold Wolpert
Harold Wolpert
Executive Director, Signature Theatre

Harold Wolpert is the Executive Director of Signature Theatre, an Off-Broadway theater in New York City. He transitioned to Signature after serving as the Managing Director at Roundabout Theatre Company for 11 years.

Read more

Related Episodes

Transformational Leadership
EP 125
Apr 02, 2024
Transformational Leadership

Holding the artistic reins of an organization is no easy feat—especially when that organization has been around for generations and has a deep-rooted legacy. As a leader, how do you honor the rich history of your institution while effectively steering it into the future?

As New York City Ballet celebrates its 75th anniversary season, Artistic Director Jonathan Stafford reflects on the Company’s continued evolution, how they’ve adapted to this new digital era, and the unique challenges of leading such a storied cultural entity.

Words of Inspiration To Power 2024
EP 121
Jan 30, 2024
Words of Inspiration To Power 2024

In 2023, we spoke with remarkable thought leaders both within and beyond the realm of the arts. They all answered the same question: “If you could broadcast one message to executive directors, leadership teams, staff, and boards of thousands of arts organizations, what would it be?”

We call this their “CI to Eye moment,” and in this special episode, Dan revisits these key insights to offer encouragement and perspective for the year ahead.

Don’t Miss an episode

Don’t Miss an episode

Subscribe to CI to Eye and have your insight and motivation delivered on demand.