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The Most Networked Man in the Arts
Episode 1

The Most Networked Man in the Arts

CI to Eye with Tom O'Connor

This episode is hosted by Erik Gensler.

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Erik and Tom talk about what makes healthy and happy organizations, what goes on in the bar at marketing conferences and how to create environments of trust where innovation can thrive.

Erik Gensler: Welcome to the first CI to Eye podcast. Thank you for being the guinea pig.

Tom O’Connor: Let’s hope it’s not the last.

Erik Gensler: For the folks who don’t know you, and I know that many do because you are one of the most friendly and networked people I’ve ever met in our industry.

Tom O’Connor: Isn’t that a nice to say ‘bigmouth?’

Erik Gensler: For the folks that don’t know you, can you give us just a quick professional bio?

Tom O’Connor: Sure. First of all, thanks for having me on. Happy to be here. I am currently a freelance marketing consultant, and I like to say I do all the unsexy parts of arts marketing consulting in terms of structural consulting, assessments, coaching, recruiting, all those kinds of things. I have been in the business for a little under 15 years, started my career in ticketing in Boston, where I’m from, loved Boston. I worked at the Huntington Theatre Company, which was my introduction to nonprofit theater, which is really where I’ve spent most of my career. For about 10 years before I started consulting, I was in Broadway nonprofits. I had a theater club, Roundabout Theatre Company, the latter of which I spent most of my time in New York at where I worked in marketing for about seven years.

Erik Gensler: That’s where we met.

Tom O’Connor: That is where we met. I believe we might have been one of the first CI clients. I was telling the story the other day that I remember the day you came into my office and said, “What do you think about the name Capacity Interactive?

Erik Gensler: Oh, really?

Tom O’Connor: I remember that.

Erik Gensler: A lot of people don’t know what Capacity Interactive means.

Tom O’Connor: Why don’t you tell us, Erik?

Erik Gensler: Thanks, Tom. It’s the capacity of the theater and trying to use digital tools to fill your theater’s capacity.

Tom O’Connor: That was really moving.

Erik Gensler: Thank you.

Tom O’Connor: Thank you.

Erik Gensler: Thank you. I have you to thank.

Tom O’Connor: This is a lot more…

Erik Gensler: A name for everyone new.

Tom O’Connor: This is a lot like our dinner conversation, only a little bit more restrained.

Erik Gensler: And I’m not drinking wine.

Tom O’Connor: Okay, maybe I should.

Erik Gensler: Interesting that you got your start in the box office, and I think that is an angle you see a lot of in marketing leadership, and I think it’s a really important thing to have the skill set, and it’s certainly an area where I don’t feel like I have a ton of expertise and I’m always, when I know that people have come from the box office side of things, that does give a real skill set around pricing and revenue management. Do you think that having that box office, or how has that box office experience helped you in your career as an arts marketer?

Tom O’Connor: Probably as a very egotistical statement, I always say I find my favorite marketers started in the box office, but for a number of reasons. One, for what you’re talking about, revenue management and all that, but also because marketers are again, this is all my opinion, fundamentally, students of human behavior and really understanding how demand works, how people interact, how people want to interact with the companies that they patronize, or give their patronage to. The box office are the ones that see that, the ushers in the front of house and all that, but I feel like the box office, in a lot of ways… This sounds corny, but a lot of ways, the windows to the customer for the company. They might very well be the only person that that customer ever interacts with who works for that theater or for that company. For me, that was a big formative part of my career and, also, from a purely practical standpoint, a lot of what I understood about marketing trends and sales trends and all of that kind of thing, I always say that I sort of climbed the data out of the box office into marketing because I understood the data, so I could understand the greater implications of marketing.

Erik Gensler: We’ve moved to a world that is so data-driven, and we talk about data so much as buzz words. I think that’s really been an evolution in the last, I’d say, 15 years along with the growth of digital and really the growth of using box office and CRM data to inform decisions. Do you think most theaters and arts organizations are… What is… Maybe a better question is, do you have an example of an institution that you’ve worked with or worked out that’s used that data well.

Tom O’Connor: I want to sort of back up for one second and talk about data and analytics and how it shapes marketing strategy and how I think it’s a broader topic than we often talk about. I should say that, in the consulting work that I do, I’m not tactically an analyst. I don’t necessarily get into the tables and rip apart numbers in that way, per se, but I’m a data-driven marketer who knows how to ask the right questions. I think that’s the piece that organizations are getting better at, so in thinking about what that could look like. For example, Roundabout was a great example of this, and they still are. In terms of having very powerful tools, I know that there’s no product placement here, but they use Tessitura, and they have very powerful tools in terms of the data that they aggregate. Perhaps in the earlier days, and I think this is true with many organizations that have powerful CRM tools, they have access to all the information, they have access to all the data, but they don’t necessarily formulate the questions in such a way that uses it well. You can have all the data in the world if you just want to sit there and stare at it and expect the answers to come to you. It’s not going to happen. You sort of have to build a culture around asking the right questions that are formulated in a way data can answer it.

Erik Gensler: It’s not a dashboard.

Tom O’Connor: Exactly.

Erik Gensler: It’s not getting a dashboard email to you. It’s a configuring… I always say market success in this modern-day world is very much driven by your infrastructure because that is what allows you to ask questions. It’s not only having the infrastructure. It’s making sure the infrastructure is implemented appropriately from your ticketing system to how you’re tracking your conversions and your digital advertising on your website, so that’s the first step. Then, I think there is this misconception that dashboards can just get emailed to you and answer your questions, but that’s really just one small piece of it. What you said, it’s really about asking the right questions of the right tools.

Tom O’Connor: It’s really easy to think that you can sit and stare at something like a crystal ball, and it’s all of a sudden going to show it to you? Sadly, that’s not been my experience. I don’t think it’s been many people’s experience. There’s that great line my old coworker, Erin Koppel, always uses it. “When you don’t know where you’re going, any path will get you there,” that whole thing. I think it’s an Alice in Wonderland quote or something. That, I feel, is true for a lot of people in terms of the way they think about data. They don’t necessarily have the judgment to mix in with it, which helps you form the questions, which helps you interpret, which helps you decide what to do next.

Erik Gensler: Which also requires a certain skill set within your marketing department, which I think I’m starting to see a lot more organizations have but, historically, they’ve not, which is a data analyst. If I could design my perfect marketing department, it would definitely include someone, or multiple people just to analyze data because, as the marketing director, you can have all these questions, and you certainly don’t have time to dig into the data and answer them. I think that’s really just a trend we see a lot is doing so much with so many limited resources, and I always say strategy is how you allocate your limited time and resources. I feel like a lot of the challenge around using data to be successful. marketing just, again, goes back to the infrastructure of how you’ve built your department, who do you have there? You can be the smartest marketing director in the world but, if you don’t have someone to do your data analytics and you’ve not staffed that appropriately, you really can’t take advantage of these powerful tools. I think a lot of organizations think the answer is, “Oh, we’re just going to get Tessitura, and then we’re going to be in this great place but, if you get Tessitura and you’re using only 5% of its capabilities, there’s so much upside.

Tom O’Connor: I agree with everything you just said, and words like ‘infrastructure’ are words that I really lean on heavily when I talk about this kind of thing with clients and with potential clients. I should say, full disclosure, I did work at Tessitura. I should probably say that, though I do not anymore, though I have a very big fondness for them, but you bring that up as an example. Those kind of foundational tools are just that, foundational tools that you need to build upon. I also want to say, too, further to your point about having a data analyst on staff, I think this is something that’s true of both data, but also digital and also really a lot of areas within the marketing mix is that I think a lot of people think, “Okay, I have this data analyst,” or, “Okay, I have this digital marketing manager. It’s their job to do all of the things associated with that.” No. In my mind, they are the subject matter expert that helps permeate that thinking and that way of working across your entire team.

Erik Gensler: They’re the person who knows the most about it, probably, but everybody should be asking data-driven questions. Everybody should be thinking about, what are the digital implications of how we can make this happen? I understand there are a lot of functional operational reasons why that happens. Resources are limited, communication is strained because everybody’s doing way too much in a nonprofit. Whether you are a tiny nonprofit or a huge nonprofit, everybody’s doing too much. Bringing that person in as a subject matter expert, rather than being the person who has to carry the weight of the world on their shoulders…

Tom O’Connor: Ask all the questions.

Erik Gensler:… Ask all the questions, find all the answers, and take all the actions based on those answers. It’s like, “Okay, could you also hand me world peace while we’re at it?” That’s a little bit too much.

Tom O’Connor: I think, to that point, there’s also the, if you have that person, giving them the budget to bring in partners to do analysis. As a firm here, we just hired our first management consultant to do some analysis, and it was weird giving all this really confidential data to some people I didn’t know that well. What they came back with blew my mind. I see that a lot with digital. Like, what they came back with blew my mind. I see that a lot with digital as well, where some organizations have this mentality that we need to do it all in-house and to be perfectly frank, those are the ones that are doing digital the worst. Because-

Erik Gensler: They can’t keep up?

Tom O’Connor: They can’t. But they think they can and they think they are and, you know, I don’t say that directly to them but it is amazing because even-

Erik Gensler: Well, you just did.

Tom O’Connor: Right. Well, if they’re listening. You know, you look under the hood and then you’re like, “Oh my god they’ve been doing this in house for so long,” seemingly knowing, thinking they’re doing a great job, but like it is so complex. And so with your strategy of limited resources, even if you have someone say as your one digital person, digital now is email, it’s SCO, it’s SCM, it’s analytics, it’s your website, it’s social media posting, it’s writing the emails, producing the emails. Digital is not a job, digital is a channel-

Erik Gensler: It comes down to, sorry to interrupt you, it comes to what we always talk about, which is the difference between strategy and tactics.

Tom O’Connor: Right.

Erik Gensler: We get so focused on tactics and structuring around tactics and we forget that they’re part of a larger strategy. And I’m guilty of this, but it drives me crazy, I feel like people overuse the word strategy all the time. What is your Instagram strategy? What is your Twitter strategy? What’s your Pinterest strategy? It’s like well, overall what are you trying to do? And those are just the, Twitter is a tactic. It’s not a strategy.

Tom O’Connor: Yeah. Can I zoom out for one second, too, a little bit further, too, on the whole topic of outside perspective, because I think, I fully agree with you-

Erik Gensler: Not that the two of us are biased in any way-

Tom O’Connor: No, no-

Erik Gensler: In this conversation-

Tom O’Connor: No not at all. A consultant and the head of an agency. We have our own horses in the race, but we’ve both been in the field and-

Erik Gensler: And I always say-

Tom O’Connor: – both identified needs, exactly. We’re community members first, before I think either of us did what we do now. That’s the most self-serving thing I’ll say I guess. But,-

Erik Gensler: No, it’s not.

Tom O’Connor: We’ll get better. I would say that the, to zoom out from the concept of bringing in an outside person to look at your digital and outside person to look at your analytics or whatever, having an outside perspective, regardless of what resources it takes to do that, I think is a critical part of some of the more successful organizations that I see. And what that could mean is just getting out of your office, it means talking to your colleagues, it means investing in professional development for your staff to go to conferences and get some actual outside perspective. So often, the solution is to get a subject matter expert in there to help save you from yourself, but sometimes the solution is just for you to see how other people do it. For you to have that perspective and be a member of the community.

Erik Gensler: Yeah.

Tom O’Connor: Because I think we do have a tendency, and I’ve been guilty of this and you know most people have at certain points, to think that our problems are unique to us. And I’ve never met a single person doing anything whose problems are unique to them.

Erik Gensler: Right. That’s a great point. It’s a really great point. And I mean I found the exposure, when you go to conferences, even if what someone is presenting is not exactly what you need, being away from the office and having that space for your brain to just, I’ve been reading this book “The Power of Habit” and after you do something a number of times it actually switches to a different part of your brain so you work on autopilot-

Tom O’Connor: Mm-hmm. Go pathways.

Erik Gensler: Yeah. When you go to a different city or you go to a different room and you spend time talking about similar subject matter, but even if it’s a little different you’re seeing a new perspective, often for me, sparks these crazy ideas that may not even be related to what the persons talking about, but triggers a different way of thinking. And then you come back with a long list of things that do it better but I think that community of colleagues, and you brought up professional development, you know, as someone who produces a conference Digital Marketing Boot Camp, we hear a lot from people like, “Okay I have a choice, we have the budget for me to go to one conference a year or two conferences a year,” and then we also do this Digital Marketing Benchmark Study and we ask “What is your biggest challenge to being successful in digital marketing?” And one of the answers that comes back a lot is lack of internal knowledge.

Tom O’Connor: Mm-hmm.

Erik Gensler: And so these things have drawn me to the conclusion that as an industry I think, this is not statistically significant, but like I think we’re really under-investing in professional development and I think that’s ultimately gonna hurt us in the long run if it hasn’t already.

Tom O’Connor: I think it’s one of those “you get what you pay for moments.” You know, it’s one of things where if you don’t invest in your team and you don’t invest in your people growing and evolving, nothing that you do is going to grow and evolve either. And I think it comes down to a lot of, I think a lot of the things that we see from colleagues or clients or whatever is that people get it in their heads that there’s a way to do things and that thing doesn’t change. And everything changes constantly. Especially for marketers, never mind the art forms. But especially for marketers there’s a different tactic coming along every day that’s gonna achieve the same end result that we’ve been trying to achieve all along so that maybe perhaps the goal doesn’t change, maybe the strategy overall doesn’t change, but the tactic we use to do it is always changing. And when we say we’re not investing in professional development or we’re not investing in sending people off to get some perspective elsewhere, what we’re really saying is we don’t really believe that that’s true. In my opinion. Again, this is totally biased because I think, fundamentally, consultants and outside perspective is fundamentally there to create space for thinking. I think that a lot of the time people think of consulting, whenever I talk to people that do informational interviews or talk to people about what it is to be a consultant, I think a lot of people think it means you sort of swoop in, you write a report, you drop it on somebody’s desk and say wouldn’t this be great? And walk away. And sometimes in the worst case scenarios, that is what happens, but in a lot of cases you’re going in to create space for them to have conversations around things they don’t inherently make time for. And so that’s sort of another form of what you’re talking about with going to conferences and getting your head out of the day-to-day. Which is so crucial.

Erik Gensler: Yeah. My boyfriend’s dad runs a business and he hires a lot of consultants, but he says, “That consultant, you’ll pay him to look at your watch and tell you what time it is.”

Tom O’Connor: Yeah.

Erik Gensler: He is like-

Tom O’Connor: Well we’ve all had projects like that, too. I mean it is sort of like it takes two to tango. I think that there’s a, there are organizations that know how to use consultants really well and there are organizations that you go in there and you find that everything that you would recommend is there and they don’t trust their people enough to actually implement those things.

Erik Gensler: I hear that all the time. It is just like people will come up to us and say I’ve, they’ll hear me speak at a conference, and they’ll come up and they’ll say, “I’ve been saying this for years, but I need you to say it. So I need you to put it into reports so I can present to my board or my executive director,” and it’s like there’s a lot of skepticism from people internally, which is disappointing because often times, I mean look I think intellectually, I think things can change when you look at the time frames and if we look at the last 20 years as a time frame, it’s been the fastest and most dramatic time of change in marketing. And I know that that’s only going to continue. And so people who have been doing this for a really long time or may have even started before that pace really picked up, their world view is challenged. Its super difficult, I mean change is hard period. But then being faced with fundamentally having to rethink how your institution communicates is a huge lift, especially for someone who is not born in, or didn’t grow up with a computer, didn’t grow up in the digital age.

Tom O’Connor: It all comes down to trust in that as leaders of organizations, but even as heads of marketing. We have to trust that the people we brought on board to be subject matter experts are going to keep up, we’re going to invest in them keeping up, and they’re going to advance us ’cause we can’t as, and I’m saying we from the perspective of when I was a department head, we can’t be across everything, keeping up with everything. It’s impossible.

Erik Gensler: Yeah.

Tom O’Connor: And so this fallacy, or sort of, you know, misconception that executives at any level can be the ones to advance organizations at every level is impossible. We have to instill some kind of trust and create that culture that actually advances us and again saves us from ourselves, which is probably one of my favorite expressions so I’ll try not to use it a hundred times. But, I think it’s a key one.

Erik Gensler: A couple years ago you spoke at our Digital Marketing Boot Camp and in your presentation you said, “Culture eats strategy for breakfast.” Can you remind me what that means?

Tom O’Connor: First of all, I wish that was my line, but just to say that’s a Peter Drucker quote, the management consultant. May he rest in peace. But, that’s all about, I think, it’s part of the fundamental question, or part of the fundamental idea we were talking about before when it comes to our role as third party either consultants or agencies, we deliver strategies, and we make recommendations, and we bring them into the cultures that we’re working with at our client’s organizations. The cultures need to be positioned in such a way, need to be built in such a way, need to be essentially ecosystems that can then incorporate those strategies. So, we can think our way into the most brilliant strategy there is, but if we’re not in a place where we have the built in trust, but if we’re not in a place where we have the built-in trust, if we’re not in a place that can adapt to change, if we’re not in a place that is really in the business of innovating, and I know that’s a big word, but if we’re not in a place that adapts to new things, then any strategy in the world is just going to prop up a desk. It’s not going to actually do anything. I think we’ve all seen it. It’s not always a bad thing, that a strategy doesn’t get implemented, because fundamentally we’ve all come up with bad strategy before, too. But in terms of the ability for a culture to assess and prioritize and then implement, that’s a lot bigger than just having the idea, and I think that that’s the piece that we often forget. Obviously we spend a lot of time at marketing conferences, gladly so. We talk a lot at marketing conferences about strategy. We don’t really talk about culture beyond throwaway lines like the one that I mentioned. We talk about it as a sort of assumed baseline of how we can all succeed as organizations, but in actuality, I wish that the split was more like 30 percent that and 70 percent marketing strategy, because in actuality, and we always talk about this, any marketing director that has staff and that is part of a mid to large-size organization has to be part practitioner and part politician, and there’s so much that goes into actually making those things being strategy actually successful. That is so much more than the idea. It’s about the people you’re interacting with. It’s about your resource realities. It’s about where the funding’s coming from. All of these things are not just throwaway things on the side that we can pretend are oh, well, the idea’s good enough. All those things will fall into place. Not really how it works. So, that’s sort of what that gets back to.

Erik Gensler: Yeah. It’s about creating an environment that is open to change and embraces change, that is productive, where everyone is bought into the mission and working towards the furthering of the mission and not towards their individual goals, necessarily.

Tom O’Connor: I agree, and no one is off the hook. That’s the thing that I always want to get across to people, is that it’s really easy for people to sit, junior level people, mid-level people, senior level people, and point to the other levels and say, “Well, they’re the reason why this can’t happen.” Every single person at every level has an opportunity. We’re getting into me just pontificating here. This is not what I’m brought in to tell organizations per se, but I think it’s a common thing that I hear and a common thing that I see, well, oh, it would be great if I could do this, but so and so won’t let me.

Erik Gensler: My board won’t let me-

Tom O’Connor: Exactly.

Erik Gensler:… or my executive director won’t do this, or my marketing director, or I don’t have the junior staff to implement this.

Tom O’Connor: Exactly.

Erik Gensler: Or the money, or the time.

Tom O’Connor: And that may very well be true. I’m by no means discounting resource realities. They make things hard and make things really difficult, but I think that it’s perhaps a little naïve to think that we can’t impact and influence our own small world of what we do, and if we can’t, if there’s absolutely no way, why are you in that job? That’s a question that I wish more people asked themselves. If you cannot get any wiggle room, and you can’t get anything done that you want to do, is that really the best job for you?

Erik Gensler: That’s a great question. That’s a great question.

Tom O’Connor: I’m not trying to be flippant. I’m not trying to belittle anyone’s challenges, but I think it’s something that we need to be realistic about.

Erik Gensler: Absolutely. Talking about culture and you come with strategies, but to that quote, culture eats strategy for breakfast, my version of that is from Elaine Stritch’s, may she rest in peace, one woman show-

Tom O’Connor: Now we get into the good part.

Erik Gensler:… where she comes out on the stage and she says, “It’s like the old prostitute said. It’s not the work, it’s the stares.” Right?

Tom O’Connor: Mm-hmm (affirmative).

Erik Gensler: The work.

Tom O’Connor: Thank God you said it first.

Erik Gensler: The work is often the easy stuff, it’s all of the stuff surrounding the work that stops it from getting done. Here at Capacity, with digital marketing, we have got to a point where we know how to run very successful campaigns, like a social campaign or a display campaign, but if you have an organization that doesn’t have a culture for innovation, or that our client-side team is constantly having to fight or isn’t responsive or isn’t engaged or isn’t excited about the work, it hasn’t laid the pathway to support it, they’re just not going to have as good a results as an organization that is communicating well internally, that is passionate about innovation, that has support from the leadership level of whatever they’re doing. So, the work can be the same, almost, but you’re going to have different results if you don’t have the culture to support the work because it’s only going to go as far as the culture allows it.

Tom O’Connor: Just to add onto that, I think we should probably grab on to the I-word for a second, innovation. I don’t know why I place that emphasis that way, like Ricky Ricardo, innovation. In terms of what we mean when we say that, I want to wrestle that word back from technologists at every possibility, because I think that so often when we talk about innovation, it’s around technology. It’s around what tools and products we’re developing to solve certain business challenges, but we innovate at every level of the organization. We innovate at every level, whether it’s tactics, whether it’s strategy, whether it’s goals. I talked about this in my Boot Camp presentation, I think, in the same one you referenced earlier, that I think too often, when we think about innovation, we think about, oh, we don’t have the money to spend on technology products. That’s not what it means. Innovation is a fancy word for change to meet the evolving business need. That’s it. And that could be in a person’s mindset. That could be in a person’s way of working. That could be in a tool you use. That could be in your strategy, but it could be any of those things. We can’t be hamstrung by thinking about it as something that takes cash.

Erik Gensler: Right. Well, I often think the word technology is often misused as well, where I often get asked to speak at conferences about technology. I’m not an expert in technology. I’m an expert in digital marketing, which is using technologies to communicate, but technology is such a broad word that can mean so many different things.

Tom O’Connor: Yeah, I think that’s also a great thing to chew on a little bit, is as modern marketers, and I consider myself a marketing generalist, I know enough to be dangerous about most of the areas of marketing so that I can be across all of it and guide it and give recommendations in it. I would never call myself a technologist. I would never call myself an expert in a lot of the areas in marketing, because nobody can be, because they’re very nuanced areas of an operation or a strategy that people spend their whole careers perfecting and mastering. So, I think the expectation that any one marketer is going to be an expert in all of those things is unsustainable, technology being one that is particularly unsustainable. We can understand our piece of it and how we need to use it and how we can keep up as much as possible, but we have to set reasonable expectations for ourselves of what we can do. Key example to this, I’ve had moments in my career where I’ve stopped and thought, okay, wouldn’t it be great if, for example… and this was several years ago, so perhaps this is a dated example, but thinking about how to connect CRM data to digital advertising and how to bridge that chasm, and I would sit there and bang my head against the desk and say, “How can we do this based on what we have?” And then I would go and read AdWeek and I would read about companies with billions of dollars to spend who have the same problem. So, that makes me stop and go, “Okay. Well, I’ve got some outside perspective now. Perhaps I’ll move on to something else, or perhaps I’ll think about some other intellectual challenge that is within my world that I can actually tackle.” So, that’s another piece that sort of combines the idea of both considering outside perspective, looking bigger than your one organization, but also then setting your priorities of what you’re trying to keep up with accordingly.

Erik Gensler: Yeah, and you asked a really good question a few years ago and we’re really starting to see that manifest, with the ability now to upload CRM data into various digital platforms and target people so you create a list in, say, Tessitura, and upload it to Facebook and target people accordingly. We’re also building up a product here internally at Capacity that’s going to really bridge that gap in a profound way to access CRM data and use that to understand unique individual user behavior on a website and then be able to use that data to do all sorts of really targeted digital things. More on that soon.

Tom O’Connor: Can I say, too, just real quick on that, when we’re talking about CRM data and we’re talking about the things we have already. I think, especially when we’re talking about technology, and especially when we’re talking about what people are trying to chase after, we talk about the term big data, and we talk about it as if it’s something that is crucial to what we need to advance our businesses and I feel like we have not even come close to harnessing the data we have.

Erik Gensler: Right.

Tom O’Connor: Like we are not even close, and so hold your horses on big data. That’s just sort of my feeling. Once you can crawl, then you can run, but I feel like that’s a-

Erik Gensler: Or you can walk first.

Tom O’Connor: Exactly. I guess there’s something in the middle. But people talk about marketing automation, and they talk about all these things, and they’re not even necessarily leveraging what they have.

Erik Gensler: Right, right. If you’re not doing that CRM targeting and Facebook, don’t worry about the next big data thing. A lot of this conversation stems back to human resources and just the day-to-day of running a marketing department. I had a short stint at New York City Opera where I was in a marketing leadership role. I just remember the day to day was so filled with meetings. I’d love for you to talk about your experience as the marketing director, around about what those days look like and how you were able to carve time to innovate or to be thoughtful and strategic about things when pulled in so many directions. Just walk me through a typical day and what that looked like or a typical week.

Tom O’Connor: Let me first start by saying that as with anything this is an ideal that some days are done better than others. I think it comes down to a lot of things. You bring up the meeting point. You bring up the being pulled in many directions point. Structure has so much to do with how effective you can be. I think we underestimate or we underemphasize that aspect of things. Again, this is perhaps something that is more geared toward large organizations like the ones like the ones I’ve worked at, but if you have so many direct reports, and you actually are doing a good job of cultivating those direct reports, you cannot possibly have time to do your job effectively on other levels. There’s also the point of knowing when you need to be in the room and when you don’t. I think that there is a certain element. I don’t know if it comes from ego. I don’t know if it comes from control. I don’t know if it comes, again, from a lack of trust, but I think that there are so many situations where there’s… This is such a nerdy way to put this, but there’s no mechanical advantage to the way I work with an employee. For example, if I have an employee that I’ve hired to do these 10 things, and they need me to sign off on every single step of the way on all those 10 things, what is the advantage of having that person do that? I think that I need to be able to turn one gear and have four gears turn. That’s the kind of thing. I don’t mean to belittle people down to machines because they’re not. There’s so much more to it than that, and we need to treat people like humans, which I think is another piece that we could talk about for an hour and a half. That, I think, is the key element, but there’s no escaping. At certain size of organizations and with certain revenue goals and with certain realities of time of year there’s no escaping the fact that you might spend seven of your eight hours of the day in meetings when you’re in a certain role. Then the only way to navigate that and the only way to be successful in that is, again, to have the right people who know and raise the right information to you at the right time and be very clear in both directions. It’s a lofty way of saying it, I guess. I have never been one who enjoys when people brag about how busy they are. I’ve never been one who likes to play the game of who has the hardest job and all that. I think that, fundamentally, if you cannot return an email within three weeks because you’re just so insane at your job every day, I think that’s not something to be proud of.

Erik Gensler: No, you’re prioritizing.

Tom O’Connor: I think that’s really not something to brag about. I think some people think about that as a statement of their worth. I think that it just is speaking to an operational flaw.

Erik Gensler: Absolutely. I just recently read a book by this guy, Karl Sakas. He’s a consultant for digital marketing firms. He said that one of the hardest things as people transition to roles of leadership is managing a team and being a leader, it’s not about your… Your success is bringing out the success in the people that report to you. When you step into that leadership role your day evolves from and has different varying degrees of this, but it goes from having your lists of tasks to complete to 30- to 60-minute blocks of helping other people complete their tasks. Once you recognize that, and you recognize that leadership is about helping your team achieve their goals, it totally shifts the equation.

Tom O’Connor: Absolutely. That dovetails with what I was saying before about our jobs being half practitioner, half politician. Politician is perhaps the wrong word, but I do think that we underestimate or undervalue the amount of time we should be spending helping people set goals and actually having real conversations about whether they’re achieving them or not and why. That is really the root of what we were talking about before when it comes to the number of direct reports you have and all of that. It’s one thing to think that everybody that reports to you, your job is to make sure they’re fulfilling their tasks. That’s not my idea of what it means to be somebody’s boss or somebody’s leader. It’s cultivating them. It’s setting goals with them and watching them succeed and giving them the tools to do that. Whenever anybody, and this is going to sound like bullshit, frankly, but it’s not. Whenever anybody asks me my proudest moments of my career, it’s watching employees who didn’t necessarily think they could do something, do something. That to me, I’m just as interested in leadership as I am in marketing. For me, that’s the most rewarding thing. It’s great when the house is full, obviously. It’s great when you successfully hit your revenue goals, obviously. That’s what we’re here to do. That’s the expectation. To me, the proudest moments are the human moments.

Erik Gensler: That’s right. My friend who has a very senior role at Google, was there very early in the founding of Google…

Tom O’Connor: That little place?

Erik Gensler: Yeah. It’s nice work, if you can get it. He told me about what management meant to him. He said it’s about hiring the right people. If you hire the right people, you need to give occasional praise and occasional, what he said, is corrections. I don’t like that word, but I would say feedback.

Tom O’Connor: Smart, constructive feedback.

Erik Gensler: Right. Smart people want feedback. Smart people want to get better. If you hire the right people, it’s not about making sure they’re doing a task. It’s about working together to cultivate the vision for that role, and then being a mentor, and being a coach and being a supporter to help those people evolve in that role. This is not easy. It’s something that I am really working on. Also, the recognition when you turn to a leadership role or become a manager, that is your work. Management and leadership are things that you actively have to work on, and that’s not natural. If you built your career being task oriented and being to get projects done, and then you find yourself in a role where you’re now leading a large group of people, you have to acknowledge that change. It’s something I’m really working on.

Tom O’Connor: My very dear friend who you also know, Wendy Hutton, has this great expression that she says: “They can do the tasks, but can they do the job?” The job is bigger than the tasks. I don’t know where she got it from, so I’ll let her correct the record, if that’s not something she created. I think that it speaks to what you’re talking about. There’s a certain level of, I think, emotional maturity and emotional development that comes of being a good leader too, not so much just receiving the feedback as an employee but being a good leader who has that sort of open dialogue and has that ability to be genuinely interested in watching people succeed and helping them succeed, but letting them own that.

Erik Gensler: Right, which goes back to your earlier point about culture where it’s like if you’re hiring people, having some sort of cultural framework in which you’ve defined what does our organization stand for, culturally? Then that should inform everything that goes into the work of that organization because the work is going to change, but the culture will always be there. If you don’t have a firm understanding of what your culture is, you’re hiring with no guard rails. Having a culture where you know, our environment is one where we are incredibly all committed to this mission or whatever your culture is, then it’s easy to narrow down the people you’re hiring who believe in that mission. Then you can look more specific at the tasks. As Wendy’s quote, it’s you can do the job, but can you… or you can do the tasks.

Tom O’Connor: You can do the tasks, but can you do the job?

Erik Gensler: Right. Then the job is more about that cultural piece.

Tom O’Connor: Absolutely. It’s about your relation to others because I think we don’t really talk about that enough especially when you’re in an institution. Whether you’re large or small, so much of it is about human interaction. So much of it is about how you work with other people. It has nothing to do with your specific area. This could mean a lot of different things. Often when we talk about “silo-ing,” quote, unquote, we’re talking about the divide between marketing and development. We’re talking about the side between administration or artistic. We’re talking about all those things. I think that every person can often be a silo. Everybody is learning things as they go. Everybody is succeeding and failing and learning something as they go about their day to day work. Our emotional connections to one another, and our ability to be open with one another, and our ability to get into the messier parts of all this is what actually makes us better. This is something I wish we talked about so much more. And as individuals, but this is more my personal interest, not so much my consulting work. But that’s something I wish we’d talked about more as both people and professionals, but also as a field. And I don’t mean that we have like sharing hour and marketing conferences where we all emote. That’s not what I’m saying. What I mean is…

Erik Gensler: That happens though.

Tom O’Connor: Though that happens at the bar. What I mean is that I wish that we would have sort of slightly more vulnerable conversations about failure. And slightly more vulnerable conversations about real challenges. And not everybody put together a power point of the one thing that went right this year. Because I think that that’s what we do a lot. I’ve been guilty of it too. And I think that we could learn a lot more if we had frank conversations about the five things that didn’t work, instead of just the 10 things that did.

Erik Gensler: When we look at the feedback from our Boot Camp, that’s almost every year we hear that from at least one person. Because we ask what are other topics you want…

Tom O’Connor: It’s probably me.

Erik Gensler: That say, I want people talking about things that didn’t work.

Tom O’Connor: Because that breaks down so many barriers of people.

Erik Gensler: Totally.

Tom O’Connor: And it brings out… I come at this from a somewhat biased standpoint because that’s the reason why I feel like I’ve been in this business is because of the community in this business. And what I’ve been able to glean from colleagues. And what I’ve been able to learn from others, good or bad. And mainly that has come from individual interactions. We talked about in the beginning, I have a big mouth and I talk to a lot of people, but it’s for a specific reason. A, I love people, but B, I like to know people’s stories. I like to know what… Not just their personal stories, which are to me very important too, and why they’re doing this, but what they’ve encountered in their day-to-day. What they’ve really experienced because everybody can learn from that.

Erik Gensler: Yeah, talking about people, if you’re comfortable, who are some of the people who you think are doing this work really well, or that you follow for inspiration or that you admire and why?

Tom O’Connor: You’re talking about arts marketers?

Erik Gensler: It could be arts marketers, it could be anyone. Who do you look to for inspiration?

Tom O’Connor: Well this is such a cop out answer and I apologize but it’s true. There’s a reason why I like to keep a lot of people in my orbit, because I think every person, every arts marketer that I know has an aspect of what they do that they do well. And there’s no one of us that does every single one of them well.

Erik Gensler: Sure.

Tom O’Connor: I can think of off the top of my head of 10 people that are people that I would turn to, to ask about a specific topic. So that sounds like a cop out answer, but it’s genuine. To me, I tend to look outside of the arts a lot too, because I think we do tend to be in a bubble. And I don’t mean looking from an arts to Google, or looking at tech companies or things like that. I mean truly looking at psychology, looking at human behavior, looking at understanding why human beings make the decisions they make. And not just in the sort of behavioral economics and all that kind of stuff, but literally just emotional reactions to things and why people do what they do. So in that regard going back to what we were talking about before, in terms of the benefits of having open dialogue. I know that you and I are both big fans of Brené Brown. People like her who encourage this kind of vulnerability and encourage talking. For those who don’t know, Brené Brown is a great author and she does a wonderful ted talk, and she’s a shame and vulnerability researcher. Why not talk about shame, we’ve come this far? But no, thinking about the opportunities for growth that come from that, that kind of thing to me is just as important to my development as a professional as…

Erik Gensler: I think it’s more important.

Tom O’Connor: More important than studying a marketing textbook. I’ve never read a marketing textbook.

Erik Gensler: Right.

Tom O’Connor: And for me, my career has been very practical. I’ve not been somebody who’s been steeped in theory. I’ve come at this from a very practical standpoint of loving people, loving numbers and loving the art. And so I’ve put all of that together and it seems to work. But a lot of the inspiration for how we can deal better and learn better together and do all these things together come from that kind of thinking I think.

Erik Gensler: Yeah I think that that’s so true. And I feel like my evolution as a professional has really just been working on my own self-awareness and ability to be mindful. And what that means is the ability of how you communicate with your peers and how you accept feedback. How you deal with challenges. Because the people that are really successful and I think are truly the most evolved, are the people that really do have that level of self-awareness. And that takes years to cultivate. And it takes a lot of work on yourself and a lot of acknowledgement, and it’s super interpersonal. And you’re right, bringing the personal to work is always a tricky balance of… And I think in order to be an effective leader, you have to have that level of care and that level of connection with the people that are on your team. And I think in corporate America, that may be harder, but because we work in the arts there is that A, shared love of mission and shared love of the art form, which I think bringing two and two together I also think the kind of people that are drawn to working in the arts are a certain kind of person. Not to generalize, but that sort of allows for this more focus on interpersonal development or getting close to your colleagues in a way that perhaps wouldn’t happen in like an investment bank for example.

Tom O’Connor: Absolutely, and as arts professionals, we are in a business of expression. We’re in a business of humanity. We’re in a business of connection. To assume that that’s only going to live on one side of the in the language of theater is I think to our detriment. I’m not saying that there should be a wailing in every office and we should all sit around emoting all day. That’s not what I’m trying to say. I’m just trying to say that the open and encouraged dialogue of what we bring to the table and what interests us and why we do what we do, I think is often skipped over.

Erik Gensler: Yeah. What did you love the most about working in an arts organization? And on the other side of that, what was the most frustrating aspect of working in a non-profit arts organization?

Tom O’Connor: Let’s see, I would say the best part of it is by far the familial aspect. The idea of working together on something… Having spent my career in theater, which is such a collaborative art form from top to bottom, having that sort of all hands on deck familial kind of feeling, it was fantastic. And those are the relationships I’ve held onto forever. It’s also frankly just good to be the client, let’s just be honest. But in terms of the frustrating part, I think it comes back to… And I’m not bad mouthing this at all, it’s because I think it’s a reality, but the resistance that is born of the layers of stakeholder. So for example, thinking about not just what’s the best… What we were talking about before, not just what’s the best marketing strategy, but how does that relate to what’s happening in fundraising? How does that relate to what’s happening with the board? How does that relate to the larger brand of the organization? How does that relate to the work on stage? How does that relate to the artists? All those pieces, and those are what makes it amazing. And those are what makes it happen. So I’m not belittling any of that.

Erik Gensler: It makes it super challenging.

Tom O’Connor: But it makes it very challenging. And so it’s by no means meant to say that those things are bad. But it is a big challenge, which is why I think we under value and under appreciate the amount of work it takes to make all this happen. Just like it takes magic for all the pieces of a theatrical production to come together and work. It’s the same thing on the administrative side.

Erik Gensler: Right.

Tom O’Connor: I think there’s no difference.

Erik Gensler: And you can see parallels of I’ve heard really great directors are actually just really good at casting. It’s the same thing of an organization. Really successful organizations are probably really good at hiring. Being really clear about what their culture and mission is, and bringing the right people on the boat. Same with an amazing theatrical production because you have all the right people cast, and there’s leadership to that too, where the director and the choreographer if it’s a musical. But there’s parallels on the stage and off for sure.

Tom O’Connor: Yeah and so it’s fitting that where the greatest frustration is, is where perhaps the greatest return and reward can be. It’s like there’s no possibility without uncertainty. And there’s probably no growth without frustration.

Erik Gensler: Oh there’s definitely no growth without frustration. And that as a leader myself, I always used to get really uncomfortable when my team would get frustrated or my team would get super stressed out or I would ask them to do a presentation in addition to all the work they have. Or they would have a separate project that was sort of outside of the scope of what they do on a day to day basis, and it was super stressful. And, they would be anxious, and there was tons of work. But, always on the other side of that is growth, and so now, when I see people going through these challenging moments and they do have a lot on their plate. And, the stakes are really high. And, they’re stress out. I know it’s all about time frame, and if you just step back, in three months, they will be so much better for it, and they will be so much stronger at their job. And, they will be so much more willing and able to take on the next super challenging thing. That’s the difference between an elite athlete and a really strong athlete is the ability to endure pain. It’s really like, if you’re going to take something to the next level, you have to be able to endure discomfort.

Tom O’Connor: And yeah, and to what are we, when we’re thinking about organizations, when we’re thinking about in your case an agency, are we adding a level of pressure on top of that process? Is an organization adding a level of fear of failure that is on top of people trying to slog through a really challenging situation? So, that, to me is often a very interesting thing that perhaps makes that process even more stifling. Is this person operating in a system-

Erik Gensler: Of fear. It’s-

Tom O’Connor: Where they’re working out of fear? So that, the task a hand is actually only 50% of what is in their mind. The other 50% is, “Is this going to mean my job?” Not that there shouldn’t accountability, how complicated is that equation?

Erik Gensler: And, the thing I said before about the difference between an elite athlete and someone who’s really good came from Tim Ferriss, who is a podcaster that I love, and one of the things he also brought up in a recent podcast that you just made me reminded of was a quote from Oprah, who says-

Tom O’Connor: It’s all fun and games until we get to Oprah.

Erik Gensler: But she said, and I’m paraphrasing, I’m paraphrasing his paraphrase, which was like, “the two dominant emotions in all, everything can be boiled down to these two emotions, joy and fear.” And so, is this emotion that you’re having driven by joy, or is it driven by fear. And if you think about that when you’re confronted with lots of things throughout your day, if you’re driven by fear, asking yourself why? And then if you’re in a culture of fear, so I think organizations are, if you have to boil it down, ask yourself, is my organization driven by joy or is my organization driven by fear? And if it’s driven by fear, see what you can do to impact that, or then do what you say, which is, find something driven by joy.

Tom O’Connor: And, it’s about finding out what level that really comes from because if comes from the top, that’s very different than it coming from the middle or even from a lateral place. Eyes wide open here. We know that we can’t always impact how everybody works from every level, but we can impact how we work.

Erik Gensler: That goes back to another thing I’ve thought about, and you see this a lot with organization where, and I’ve experienced it. I’ve worked in a number of organizations for-profit and nonprofit where organizations often, I’ve seen it with clients too, organizations often know that there are a few people that are particularly like challenging to work with. But, most organizations don’t deal with it. They’d rather just sit and work around this person than either work with them to change that behavior, confront them head on, or figure that that person’s not the right fit for the organization and gracefully part ways with them and make space for an organization of joy.

Tom O’Connor: And, I think that it’s very easy for this to sound like pie in the sky thinking, an organization of joy, because I agree with you fully, and I think that there’s, in the context of an organizational culture, I think it’s also a culture of respect. I’d put it with joy because there’s obviously not going to be joy 24/7 in any organization, but is it a place where people respect and aim for that kind of-

Erik Gensler: I’m just quoting Oprah.

Tom O’Connor: I know. I don’t mean to dis Oprah at all. I’m just trying to bring us to a place of thinking back to realistically working within an organization, what that would look like. Not just beating the idea, but what it would actually look like because I think it would be very easy to have everybody listening to this say, “I do not work in a place of joy.” It would be very easy to say that. I’m going to restate that.

Erik Gensler: That’s fair. No. I think that’s totally fair.

Tom O’Connor: But, I am going to restate it just to say that I do think, and this comes to another point that I have to remind myself often, so this is by no means meant to sound like a criticism of anybody else, but I think that perfectionism kills. I think that there is an idea that something is either 100% of zero. And so, when talk about, whether we’re talking about a culture of joy, whether we’re talking about innovation, whether we’re talking about strategy, and failure, and all of these things, we have this underlying theme of perfectionism being unsustainable and unrealistic. And so, taking that out of the equation is probably an important part of the conversation.

Erik Gensler: It’s all a continuum. There’s a continuum between joy and fear, but I can think of in my head of organizations that we work with, but I can just tell that they come from a culture of joy because the people are collaborative. The people are happy. The people are joyful. They’re appreciative. They’re great partners. And, I can also tell the organizations that are working for one of fear because I hear, “Oh, I have to prove this to my ED, or I have to go get the board to, they don’t believe me and I have to prove that this was worth it.” Of course, everything is absolutely on a continuum, but I think generally swayed to one side or another. And not to get political, because you and I can do an hour and a half on that easily, but look at the current change in leadership where we went from a culture of joy to a culture of fear. I think that often comes from the top of an organization.

Tom O’Connor: In that case, and again, we won’t spend too much time on this because we could very easily.

Erik Gensler: And, we do, often.

Tom O’Connor: That in a lot of ways is about messaging and motivation, the style of motivating people toward what you want, and that is universal anywhere.

Erik Gensler: This is the last question. This is your CI to Eye moment. If you can broadcast to the executive directors, leadership teams, and boards of, say, 500 arts organizations, what advice would you provide in order to help them improve their business or day-to-day.

Tom O’Connor: I don’t know. I think if I have to say one thing, it would be, hearkening back to some of the other things I’ve talked about, which is about trust. Do you trust the people that you have in your organization to carry out the vision that you set forward? And, if not, why? And, if not, is that your fault of theirs? And, I guess that’s probably a bigger, it’s not a silver bullet of how to solve your problems, but I think that’s fundamentally so many of the situations that we encounter on the day-to-day come down to that central question. How empowered are people to really impact their organization and make change? And, are they actually treated and thought of as experts in their area? So, I guess that would be, again, a lofty idea, but it would be, to me, it’s a central idea, something that runs through literally every single project I work on.

Erik Gensler: That’s a great answer. Well, thank you so much. It was really fun talking to you.

Tom O’Connor: This is a lot of fun, and I don’t think I swore once.

Erik Gensler: That’s amazing.

Tom O’Connor: That’s like a personal triumph.

Erik Genlser: Thanks, Tom.

Tom O’Connor: Did I do once? Okay. Let the record show that I was just signaled that I did swear once.

Erik Genlser: Okay, good. We’ll keep it in for authenticity.

About Our Guests
Tom O'Connor
Tom O'Connor
President, Tom O'Connor Consulting Group

Tom O’Connor is the President of Tom O’Connor Consulting Group, providing arts and culture organizations with strategic leadership toward organizational health. TOCG offers a mix of organizational development, marketing strategy, executive search, and coaching services. Tom is also on the faculty of the Yale Theater Management program and a licensed social worker.

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