Behind The Curtain: Anna D. Shapiro Speaks About Steppenwolf’s Executive Leadership Transition, Board Relationships, the Pandemic, and the Epidemic of Racism

It is no secret that Steppenwolf Theater Company is one of my artistic homes in Chicago. When the news came out about Brooke Flanagan’s appointment for Executive Director, and David Schmitz’s departure to OSF, I was excited and disappointed all at once. David deserves an excellent opportunity such as this, and Brooke seemed highly qualified for the job, but there had been no job search for the Executive Leadership position.

Once during my fellowship at Steppenwolf, Anna told me she saw my value to the institution, and to our field, in my ability ask the hard questions. With that in mind, I made a phone call, at first asking for a conversation, which became an interview. 

Rarely do our leaders seize an opportunity to tell the truth. When controversial decisions are made, I often ask arts leaders if they will sit down and speak to me about their decision-making process. They will always speak to me off the record, for my own education as an aspiring artistic leader. When it comes to going on the record? To date, every single leader has said no. Until now.

On May 27th, we spoke at length about not only Brooke’s transition, but her own transition into the position of Artistic Director, board relationships, racial inequity, the mysterious career “pipeline,” and police violence against Black people.  The world has already changed so much since then. I encourage you to read this in its totality. This is a rare offering of truth, and I hope it invites other leaders to be more transparent in their processes. My questions are in bold, all other responses are Anna’s unedited thoughts.

Regina: I think it would be most helpful to start with the timeline: When did you find out David was resigning? What was the immediate response from the board and organization in regards to how to handle it? 

Anna: Okay, so. I found out David had been offered the job – which was a different step than the actual taking of the job – I remember it well it was, I believe right before we were eating dinner at this great Japanese restaurant in Midtown before the second preview of The Minutes [February 27th]. 


Yeah. And he told me he had been offered the job. You know, it doesn’t surprise me! He is a young leader who is leading a successful campaign. In fact the way he started the conversation was by saying ‘remember when you told me I was going to get head hunted the moment this campaign was going well. You’re always torn in moments like that because I happen to really love David and I want what’s best for him. So there’s the personal and then there’s the professional. At that point though, to be completely honest, I wasn’t 100% sure he would take it. We had an enormous amount of concern he and I about him leaving during the campaign. As you know we’re in a building campaign raising over seventy million dollars for our new campus, and it’s pretty destabilizing to lose such an outward facing leader at that moment. 

I would argue there are a lot of theatres you couldn’t name the Executive Director of, right? But you can with David because he’s made a point of it and it’s been a very good thing for us. So I was very panicked as it set in over the next 36 hours – oh my God what if he takes this thing and it’s during the campaign? I reached out to our board chair Eric Lefkofsky and I said David is considering leaving. Eric is an entrepreneur of the highest order and is not easily shaken so it was like how do you fix it. I think that business people sometimes understand that we’re all replaceable in a way that we don’t, because we aren’t replaceable with each other, right? He was just wanting to move forward because he was concerned with losing an ED in the middle of a campaign! So we started, David, Eric and I started gaming out what the options were. There were a couple of options in this moment. At this point – and this lasted, literally Regina, 24 hours – all of the options involved a search.

So the initial motivation was to have a search. 

It didn’t enter David or my mind that we wouldn’t do a search. David was hired without a search and he didn’t want anyone to have to go through that.

He was hired internally, right?

Yes he was internal! So we asked ourselves, did we have anybody internal who could be interim? We didn’t feel we had that. Then, did we have anybody external that was good enough that they would leave where they were for a job they may not get? The other alternative in terms of the way the governance of all this goes, is that sometimes in an emergency the board steps in. I love our board dearly, but frankly that sounded horrifying to me. Really in the same way that –  I hate the homeschooling thing with my kids because it’s not the relationship I want to have? That’s how I feel about the board! I don’t want to have the relationship with them where they’re running us, and they don’t want to either. The board will do that when someone dies, I don’t want to be glib, it’s a necessary thing and God knows we have the people that could help us, but we all felt culturally that that felt gross. Then literally in twenty four hours from that conversation, COVID-19 went from a nuisance to a pandemic.

Regina: Okay let’s go back, so this 24 hour window of searching is when David still has the offer but hasn’t taken it yet?

Anna: No, I think at this point we’re getting closer and closer. 

[It was a total of 15 days from the second preview of The Minutes on Feb 27th, to Friday the 13th, the last day many theatre professionals in Chicago went to our offices or saw a play.] 

Eric and I realized which way the wind was blowing. So we’re trying to create the conditions for the best transition possible. When COVID hit… I feel badly saying this publicly but I think David would be okay with it because I think he understands it – I can’t share this story and not be truthful. I assumed David would stay. So I think I was also a little bit like, well now we’re in a fucking disaster, he can’t leave! And then it became clear for all of the reasons that are right and good that that was not going to be his decision, that he was going to go. But by then, every ED in the country is knee-deep in crisis, and nobody’s going to leave. In defense of David, he’d already been way down the path of this hire before COVID hit. 

Now, Regina, you’re in a sort of double-crisis. You’re in a situation that you’ve never been in before, that nobody’s ever been in before. You could maybe go poach someone from another place, but that’s not really okay, and that’s not a search either. At that point, Eric went to the Executive Committee and this is an important thing to understand: the Executive Committee on our board – and regionally this is pretty normal – hire and fire the Executive Director. In most theatres they hire and fire the Artistic Director as well, they just don’t do that at Steppenwolf. Martha did not hire David Schmitz. She approved David Schmitz. I think if she had not wanted David they wouldn’t have done it, but she did not hire David. She did not hire David Hawkinson. She did not hire Michael Genero. 

If you think about what the division of labor is classically, it’s one of the few if not the only organizational structures where there are two heads. The Executive Director (ED)and the Artistic Director (AD) they share that top spot. But each of those people needs to answer to somebody. The ED at Steppenwolf, and most places, answers to the board and in particular, to the Executive Committee of the Board. It’s about 20 people out of an 80 person board. So Eric went to them, and they contacted David and I, and they said our responsibility is the financial health and maintenance of the future of this theatre. We can go and get this person who knows our culture, literally knows our people, they knew it was important to David and I that whoever we thought about was ethically in line with our feelings. [Brooke Flanagan] has a track record of that, She shares our ethics, she shares our orientation. She is known to the funding community, to the Chicago community. 

Brooke and I worked together at Steppenwolf back in the day. When she left I was devastated and I said why are you leaving? She said I need to go out and get what I need to be a viable candidate to come back and run this place. That’s why she left. She was top of my list, she was top of David’s list, and she was top of their [Executive Committee] list. So they went to her, she’s been at Chicago Shakes for a long time, and they wanted her to have a future there. Steppenwolf she feels is her home.

We all felt that in this crisis, this is the person for us. 

I think Brooke would have rather won it in a search. Anybody worth their salt wants to win something in a search. You want to win it and you also want to learn if it’s the place for you.

Yes, it’s very important to interview the institution.

Exactly! That’s the process. But we were very lucky, I feel, in a bad situation, to be able to get Brooke. So, you know, David and I… we wanted a search. The timing was such that when OSF needed David couldn’t change, because now they were in crisis. He couldn’t stay longer so that we could do a search, because he’d made a commitment to a place that was now in the same crisis. 

Something I’ve been thinking about is, is it ever possible to leave a job like this at a good time? Truly, especially during a campaign.

That’s a good question. 

Even without the crisis I don’t know that ever there would have been a good time to leave this position, until the building was built maybe.

I have to say that I think that David would be the first person to say this isn’t a great time. He’s not in denial this wasn’t well-timed in relation to the campaign, but people leave during campaigns all the time. It’s just that David is a real face of that campaign so that’s something that’s hard for all of us. I do also wanna say, it points up. You know we had a big ensemble meeting yesterday and we were talking through everything, and one of the things a company member said that was really generous and loving was: what do we all do all the time? We say we’re going to do a play and then something comes up where we can make more money and we do it. And we see it as a bigger opportunity for our family and we’re all always negotiating that. We have to extend that same latitude to the administrators in our business as well. It’s not fair to say well, the artists get to move based on what their opportunities are. Everybody has limited opportunities. Everybody has aspirations, and challenges in their life they wouldn’t choose. We have to be more gracious about it and not see it as being abandoned or as something we wouldn’t do, it’s just not fair. So I think that we all got stuck in a problem that was bigger than anything we understood and we had to do what we needed to do.

That makes a lot of sense to me, because I think a lot about when you’re allowed to leave the table, right? As an Artistic leader and an Executive leader there’s not a lot of mobility. I was talking to an Executive Director friend about this even before this happened specifically asking: what if you wanted to leave this job? What would that look like and where would you have to go to make that make sense? I know David has been at Steppenwolf for a very long time and is a leader who loves to be challenged and grow. When I saw this opportunity it made sense because how many places can you go after a 70 million dollar campaign that is challenging and also fulfills your values? That is rare.

I think that’s right, that’s a very compassionate view that you have. In an artistic practice, your barometer has to be internal. Because everyone’s always got something to say. About what you do, what you don’t do, why you did the thing you did. Everybody’s got something to say about what you make! Some people think you are the greatest thing, some people think you stink and can’t even believe you get to do your job, and most people don’t even care. So those are the three categories. In everything you have to have a moral barometer around what you did and why you did it, and be able to check in with yourself. That doesn’t mean you can’t get checked by the external world, you should, but that’s only of value if it’s in a dialectic with a journey you’re on genuinely. What I mean by that is– if you’re checking someone who doesn’t give a shit, Regina, it’s a waste of time to be checking them. They don’t care, they don’t have the values you have, they’re not aspiring to the same thing. So you’re shouting down a well. That aside, you have to decide as the people that are the future of the American Theatre, which is your generation and people like you, who are you gonna engage with in this conversation and have it be valuable, and who is a waste of fucking time? 

That’s so real. Yes. [ I was a little stunned by this realness. Still am.]


I want to loop back to make sure I understand something, it sounds like there was a desire for a search, the idea was approached, it seemed like it maybe started or you were asked to pool candidates?

We were just making lists. For a second. For a second.

That’s how it would usually start though, right? Everybody makes their lists..

It differs, I’ve never done one at this level, I’ve done it at the university level. At that point we were pretty clear about what we needed before the pandemic. We’re in a campaign where you need somebody with serious development chops. You need somebody who’s got a public face, and you need somebody who is local. I will be totally honest and say I’m not 100% sure had we done a search, how viable a person from outside the city would have been? I would have loved to have been in the conversations, holy mackerel I would have loved it, but again… Let’s have an abstract conversation: in a crisis when [your company] has a tendency to grab people in the pipeline, you’re not able to make the positive impact on that pipeline that you want to do. You can’t do that. You have to identify that there is systemic racism and sexism in our business in terms of administration. Everywhere, but we’re talking about administration. We all know that. Anyone who doesn’t know that is blind or a liar. So what you have to do is create [career] tracks. What happens in a crisis is you have to go to the people in your “rolodex.” If you live in a – if your world is informed by systemic racism, the rolodex has got a very particular set of people in it, does that make sense? 


Right? So it starts to, unfortunately, reinforce the problem.

Wow. So, I wonder – I’m curious about this comment about the rolodex and the pipeline. It seems there are two pipelines almost because I feel like my way of getting into the pipeline has been by being in people’s rolodexes and trying to crack open that as well. I’m wondering how we can start to integrate those things more.

If I use you as an example, I’ve been at Steppenwolf for five years. We have amazing apprentices and interns that move through, and they’re all amazing. But some of them stick to you. You are that for me. You’re in my rolodex. But the reason you’re in my rolodex is because opportunities were created for you and conversation loops weren’t closed. When you can’t do a search your conversation loop is closed. When you don’t do a search your conversation loop is closed. I would be very surprised if in doing a search Brooke wouldn’t have been the Executive Director. I think she’d be pretty hard to beat. I feel blessed beyond words that she is the Executive Director.  My shoulders have dropped, I am reinvigorated. If you’re my generation the fact that she’s a woman is incredibly moving, incredibly moving. BUT… or I should say AND because these things can live together at the same time, [it’s] not great for the organization that we didn’t have a search [for the position]. Not great for us spiritually, not great for us emotionally, and a missed opportunity for a lot of different reasons. I think Brooke would give me an amen on that.

Thank you for saying that, because that is it. Both things can exist.

They do, they do exist right now. I was saying to Ian [Barford] that I’m living such a binary moment because half of me is in anguish about the loss of that conversation, and the other half of me is in the deepest relief about who my partner is going to be.

What are you most excited about when it comes to working with Brooke? 

Here’s the thing about Brooke. She’s an incredible listener. She is so curious about other people’s stories. She’s always had this thing when you’re talking to her where she’s looking at you and you can tell she’s not waiting to talk. She’s taking you in and she’s thinking. Out of that warmth there’s an unbelievably sharp and efficient mind. Look, I have to be honest with you: I think that’s the result of being a woman in management. I think she has had to find a way to keep her heart and her integrity but manage situations where, for most of her life, she’s a small blonde woman – a small blonde white woman. There were some negotiations, certainly, in her arc up. If I were to ask her what were those she would say oh Anna. She doesn’t need to talk about those things, because that would feel to her like an excuse. She would never allow this conversation. She wouldn’t. Because she looks and she sees where the real inequities are and she doesn’t waste her time. I also love that on all of her board and committee work outside the theater, she works on the behalf of the lives of artists. Which of course because I’m a wife and mother, I like to think it’s because she’s a partner and a mother. I like to ascribe those things, but it’s not because of that. She was like that before she was a partner and a mother. She is a person who is tireless in her commitment to this city. She’s a civic leader, it’s why everybody knows her. There’s nothing of the politician in her, so she’s that great combo.

I’ve been thinking a lot about: what is an executive leader’s art? That’s a different interview perhaps, but I’ve been thinking that civic leadership is the Executive leader’s art. We don’t have to conflate the two as much, you don’t have to also be good at the rehearsal room. 

[Laughs] I think your guys’ model is going to be a lot different than ours. I cannot wait to be talking to you from my retirement home about what a great job you guys are doing at reshaping these models. 

[laughs] Well, you know, that ‘reshaping’ is something I’m really passionate about! Now, you went through your own hiring process as an Artistic Director, how is the board involved in that? Conversely, how was the ensemble involved in your hiring versus Brooke’s?

The board was not involved at all in my hire. I imagine that if they had a problem with it I wouldn’t have heard about it, because they had to continue working with me. Martha basically said Anna’s the next Artistic Director after a negotiation with some members of the ensemble. So, I would argue we don’t have a really great process for electing an artistic director. Because we don’t know how to really do that in a way that’s healthy and not about power struggles or something. We’re still trying to figure that out. We’re looking to have a wider conversation about when those shifts happen. Part of that is because we’ve never had a succession plan. I don’t think its a mystery that I’m dying for a succession plan, I have a list of things I want to do before I go, and one of them is to create a sequence for succession that feels really healthy, exciting and good. Do we have that now? No. In terms of David’s hire the ensemble had nothing to do with it, because there are no ensemble members on the executive committee of the board.. 

But they have seats on the board itself?

Yes, now, I do want to make it really clear that had the Executive Committee come to me with Brooke and I’d hated Brooke, she would not be the Executive Director. We have a really healthy relationship with them. It’s also why – there was this moment where, I said to David, I feel like I’m caught between my beliefs and my responsibilities. One of the reasons Steppenwolf is going to be okay, during this and forever is because of the way those people have managed this theatre. The EDs they’ve hired are the reason we’re okay right now while other theatres really could close. When those people are looking at you and saying – this is what you have to do? That’s the moment. 

I love hearing about what the framework is about when the board steps in. It’s a big question, and they stepped in in a gentle way here. At least having worked in several organizations in the past where the board has stepped in in an intense way, seeing the trust that you have with them is great.

These guys are amazing. They are so non-interventionist. Our board members have a deep relationship to the theatre emotionally. I would say that most of them are at the point now where they’re like we want to make sure Steppenwolf is here for our children and grandchildren. If you asked them why they were on the board that’s what they would say. Look, they have weird things in the for profit world where they’ll go well you should just do this! and David and I would burst out laughing and go we can’t do that! They always listen to that. It’s mostly cultural, and we have great laughs about it. We bring, I think, a sort of humanist position to them, and they bring a reality to us. I could not have gotten through this without them. Their leadership is extraordinary, and their support’s incredible. I trust them. Deeply trust them.

This is amazing. Sorry. I’m in awe of this amazing board relationship if you couldn’t tell. Let’s take a moment here because I think that what is interesting about this, is that your relationship to the board seems highly functional. I think this is something a lot of people don’t see as a possibility. It’s fortunate!

Really?! Is that true? 

Yes! Because I’m sitting here, and I’m surprised that I’m surprised! This is coming from someone who knows your board and the type of people they are, so if I’m shocked I’m sure other people will be.

I can’t imagine – well I’ll never run another theatre but Steppenwolf so it won’t happen but – Regina, my favorite thing about this job is them. I’ve learned so much from them. I’ve also learned about ambiguity from them. I have literally sat across from someone, more than one person on the board, whose politics are abhorrent to me. And yet, they give millions of dollars to the arts. They don’t believe life is worth living without it. This is critical for me, as an artist, to be in conversation with. I feel like I have been confused about who the enemy is.

I would be very curious about where you now seat that. Where, if anywhere, is there an enemy?

I think that there is evil in the world afoot in who is running our country. I don’t think it’s a coincidence that there’s – I mean, Regina we know each other well enough for you to know that I think everything boils down to race, you know? I am boring in my repetition of that, because I’ve learned so much in the last few years and – I just thought oh my God America equals racism. It’s not a coincidence exactly where we are in the time of this pandemic, the rhetoric of our President and the people that represent him and the fact that it is, again, open season on Black men. Open fucking season on Black men.

And we’re all inside.

And we’re all inside! And yet still. It’s sickening, it’s sickening, it’s sickening. And so these lines that need to be drawn between the evil, and the less informed, is a distinction that I need to hold onto. I think interacting with a board that is like our board, that is filled with all different kinds of people, I have learned that there is nuance here. But I don’t want that to be confused with me thinking there isn’t evil in the world because I think there is. I just think I thought it was other places that I don’t think it is anymore. Somebody having an opinion that’s different than yours, but a belief in your art-making, is a really interesting spot to learn in.

I keep thinking about, and this is a larger question, but my thought right now is: who do they choose to patron? 

Who do they choose to what, dear?

To patron. As a board I think they can listen to you in a different way, maybe than if I were to go to a board meeting – no, a board dinner or social event – and talk about race. What if I were able to talk about race in a way that is less charged because I’m in the company of people who are like me, or who at least think that I’m like them? I’d be able to have that conversation in a different way. There’s something about being invited – not even invited, but at that table – where you can speak their language. I wonder what effect that has on our pipeline conversation. 

I think that’s a good question. If you look at a board in a building campaign, joining the board means being able to give a giant gift, right? If you are able to give a giant gift it means you have a lot of money. If you live in the United States of America who can usually give a lot of money? The syllogism just plays itself out, we always get back to the problem of systemic racism. It’s not insurmountable. It’s something we are working on, actively. We all see it. There’s no one on the board going what are you talking about? There’s a lot of women on this board! We don’t have that kind of archaic conversation going on. It’s ongoing, it’s active, it’s aware and we’re all invested in what’s wrong with this picture.

Everyone says diversify your board as though it is a simple thing to do. It’s not simple because – I mean we know there are Black people with money in Chicago, we know that —

Totally! But why would they join a board that doesn’t make the art that they care about? What’s the point in that?

And [a board] that is largely homogenous!

That’s totally right! And that’s one of the reasons why our board is starting to get more diverse. It’s not a mystery! It’s just not a mystery. It’s – oh I can see myself, this is a place that’s invested in my stories. And we’re invested in those stories not to get ourselves board members. We’re invested in those stories because we live in Chicago, that’s our community we want to speak to all of Chicago. It’s not rocket science, but you know, we’re a historically white institution and you hear me say this all the time – we never defend ourselves. 

One of our company members said to me: how do I defend that there was no search? I was like defend it?! There’s nothing to defend, nor should we. Here’s the situation. They realized, oh right, we may not have been able to do the best thing that we wanted to do. That happened to us. And we came out with an incredible leader. As I said you get to have a discussion about the disappointment of not being able to do a search, and the loss of those conversations, and have them not have anything to do with Brooke.

I have a question that comes from talking to a colleague whose Executive Director search was a year and a half, and I just realized how long a search would have been. I just thought of the timeline of a thorough search. Leelai [Leelai Demoz, associate Artistic Director]’s search was months, right?

Leelai’s was long. We could have expedited it. But we couldn’t have expedited it in COVID. I mean, we had nothing. 

I think the question that comes up is why couldn’t you do a Zoom search?

You can second guess it, and you may even be right. What’s important is we hear it, and I agree that it should have gone a different way, for everybody. 

The thing that I thought, and perhaps this is a leading question, but there’s something emotionally aggressive about saying ‘let’s launch a year long search right now, also not be able to manage the things [an Executive Director]  was supposed to manage, while also trying to manage a pandemic, and our lives?’

Oh are you kidding me? You basically just recited Eric Lefkofsky’s position. He was like Anna, what do you think is about to happen? This is BAD. And he’s right. Because I have been working nonstop. So has every department head. Working Nonstop. We do scenarios everyday like we’re freaking General Macarthur. We. Are. In. Triage.

Our ability to make this [work] happen so quickly is why we’re at the front of virtual programming in the country. It’s why we were able to make sure that our artistic programming and the representation that is so important to us is maintained, that we continue to put our energy into voices of artists of every stripe. And we’re doing that. That’s not to make up for this other thing. It’s just that that thing happened. But, we are able to go forward.

Going forward is something that I’m thinking about too, because in a week I’m going to TCG to do this panel about hiring practices that’s really informed by the COVID situation. How does one even do a search right now? I know this was accelerated because someone is leaving, but if this were to happen again, how do we conduct a search at this moment?

Really I – I have no freaking idea. Schmitz loves to say this thing, we were building the plane while we’re flying in it? But in this case our plane was plummeting towards earth. So I have no idea if there’s anything to be learned in terms of process. What I do think has always pointed up in our business is, if you want a bigger rolodex diversify your board. The bummer is that Steppenwolf really wants to be at the front of changing those things I’m not asking for sympathy. As I said, I am in a moment where two things exist at once. I think we have the right ED, in fact I know we do. I can’t hedge my feelings about her, I just can’t. She’s incredible. And a beautiful human being to be leading this organization. A perfect evolution from David I’m thrilled. And I wish the process were different. 

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