The Improv Analyst: Kupe Kupersmith

By: Yadira Y. Caro

Business Analysis and Project Management are not concepts that make us think of comedy – at least not often. For Kupe Kupersmith, these terms are associated, if you want to be better at your BA or PM job that is. As a keynote speaker and coach, he uses his “improv advantage” to teach better methods of collaboration. He knows all of these fields well: aside from working for over two decades as a BA and PM, he was also an improv artist for many years.

In his quest to help make people “more awesome” as he describes on his website, Kupe also co-wrote the book Business Analysis for Dummies, alongside his former colleagues at B2T training. Aside from his training and speaking engagements, he is also a consultant helping organizations in collaboration and strategy.

In this interview, Kupe talks in depth about his “improv advantage” and shares some details about his career.

Did you start at first in the career path of Business Analysis or Project Management, or were you first an improv artist?

I didn’t know what I wanted to do going into college, so my dad’s like, “You like math, you might as well become an accountant.” I wasn’t really excited about it, but I didn’t know what else I wanted to do. So I graduated, thought I should use my accounting degree, became an accountant for an organization and failed the CPA exam miserably. I decided, “This is not for me, it’s not what I want do,” but I still didn’t know what I wanted to focus on. I had this creative itch: I actually tried stand-up, didn’t do that well in it, but then auditioned for an improv troop. They brought me on, trained me, and then I performed in Atlanta for about 10 years. Within those 10 years, that’s when I transitioned.

I was a subject matter expert for financial applications at Turner Broadcasting and I was working with project teams. At the time, we were going from Excel docs and Access databases to an ERP system. I was on the business side helping the IT project team. I really enjoyed working on projects so as there were openings, I kind of slid over into a BA position as being a subject matter expert in Financial Applications. So then I did business analysis, project management and kind of stayed in that space.

How did you realize that you could combine your improv skills with the project management and consulting skills?

In 2006, I decided to join a training company, B2T Training, that focused solely on Business Analysis training. Our goal was to try to help people get better in this role. I thought, “Why did people wanted me on their teams? Why did I enjoy being part of a team and help out?” Then I thought, “Wow, there’s all these improv skills that I’ve learned on stage that made me a better collaborator, that have made me a better team player. They’ve allowed me to be more empathetic.” I started to figure out, “I don’t perform on stage anymore, but how can I bring these skills to the people that we’re trying to train?”

What is a key skill that you have taken from improv that people could apply?

There’s a concept in improv that there’s no denying. Since there are no scripts, in improv you get ideas from the audience and you start acting out a scene. The actors on stage don’t have scripts to go back and forth with, so you can’t deny when somebody says something. If I’m like, “Yadira, let’s go play baseball” and you responded with, “No, I don’t want to,” that would kind of kill the whole scene, it would be boring, right? So if I say, “Let’s go for a run,” and you’re like, “Yeah, give me a second. I got to put on my shoes and yeah, let’s go,” you keep the scene moving forward.

Kupe Kupersmith during a speaking engagament.

How does that translate? One of the games we play to work on this is called “yes and.” The concept is that when somebody is having a conversation with you, you never deny. This happens all the time in the stuff that we’re doing. When we’re brainstorming with people on solutions, people typically will get frustrated, or somebody will have some idea and they’re like, “That’s a crazy idea, that’s stupid, let’s not work on it.” So try to have this “yes and” mentality in the office.

When I do this at keynote presentations and workshops, I have people play this game: I give them a topic, people pair up, then one person will start with a sentence and then the next person will be like, “Yes, and… ” and add to the conversation. I get them in the mode of going back and forth saying, “Yes, and… ” and adding on to what the previous person is saying. In those examples, you can get crazy: for example, you’re going to build a vacation home on the Moon, so have a conversation about that. People start building pools on the moon and they’re coming up with all these crazy things.

In real life, we have real constraints: we have budget constraints, we have time constraints, so we can’t do everything. But if somebody has an idea, you can’t just deny that idea. To them, it’s real. To the person, their idea is not crazy. They wouldn’t have said it unless they thought it had some merit, right? So it’s really putting it back on you that you don’t understand yet enough about that idea.

Listening is the other (skill). In improv we don’t have scripts so if I’m not listening completely to the other actors and what they’re doing and saying, then I might respond with something that has nothing to do with what they said. That’s the same thing with our conversations. If you’re interviewing me and your mind is elsewhere, you’re just hearing me talk and then you just follow up with another question, I’m going to be like, “Uh, did she even listened to what I was saying?”

As a Business Analyst and Project Manager, we’re facilitating constantly. If we’re not focusing on what’s happening in the room, really listening, paying attention, and adapting our style to how we communicate with others, then we’re not going to be as effective.

If somebody has an idea, you can’t just deny that idea. To them, it’s real. To the person, their idea is not crazy. They wouldn’t have said it unless they thought it had some merit.

Kupe Kupersmith

What is another key skill that would be good for either a Project Manager or a Business Analyst?

Curiosity is probably number one, especially in the BA profession where we’re trying to uncover what the real need is and how can we solve it. If you really don’t understand, don’t just take a note and say, “The customer wants a blue button over here.” Tell me what is that blue button going to help us with. How does that get us to our end game?

Being empathetic is the next one. I talk about empathy by comparing it to sympathy. Sympathy is kind of understanding or feeling for someone. It’s like, “Oh yeah, I see your job is really tough. I understand that. We’re going to try to help you.” I think we become sympathetic when we have one-on-one interviews or group interviews where we’re just talking to people. But empathy is about feeling with the person. You actually know what it is they’re going through.

I think especially in the BA profession, we have to be doing the work of our stakeholders or our customers to really understand what they’re going through to come up with good solutions. Being with them, observing, doing the work with them, to really understand what’s happening.

I joke a lot of times that I think people are liars. If you’re just interviewing someone, they’re going to lie to you. If I ask somebody, “What are the steps to do your laundry?,” someone will say, “You get the dirty clothes, put them in the washing machine, put soap in, turn the washing machine on and we’re done.” So I would ask, “Well, where do you get the clothes? Do they automatically just appear in a pile somewhere or do you have to go room to room to get them? How many trips are you taking to get the clothes from all these rooms? Do you sort the laundry that you put in? Does everything goes in? I didn’t hear you say you actually closed the lid? Do you just throw the clothes and put soap in and turn it on. So the lid is open and water is splashing all over?” You don’t know if those gaps are missing.

We have to be doing the work of our stakeholders or our customers to really understand what they’re going through to come up with good solutions.

Earlier in my career, people would say, “wow, you really get us.” I think that’s what as project professionals, we’re trying to go for with our customers: being empathetic because you’re in there with them, you’re doing the work.

The ability to build relationships (is another skill). Everybody talks about what tools and techniques to use. “Do I draw a context diagram? Do I write a user story? Teach me how to write user stories. I need help using JIRA.” To me, that’s table stakes. I could teach you that tomorrow. (Focus on) how are you getting the information. Are you getting the information from the right people?

If we have a good relationship, communication is going to be easy. It doesn’t matter what tool is used: we can do requirements over chat if we had to, because we have such a good relationship and we know each other. If you have a good relationship, the communication, the conversations are going be deeper, people are going to open up more. I think both Project Managers and BAs need to focus on building real relationships with the people they work with.

Cover of the book Kupe Kupersmith co-wrote.

In term of terms of books, resources or podcasts, what are your recommendations?
There’s a number of books by Patrick Lencioni. I recommend all of his stuff. He really has good things to say around team work. Daniel Pink has a book called To Sell Is Human that I recommend. There’s another book called Drive that I recommend as well. More specific to some of the stuff that we do, there’s a book I recently read called Outcomes over Outputs by Joshua Seiden. I am reading now An Elegant Puzzle, Systems of Engineering Management by Will Larson, because I’m working on this agile transformation or how the organization is delivering work. He’s got some good ideas.

The podcasts that I listen to have nothing specifically to do with our profession: I listen to TED Radio Hour, Freakonomics Radio and Revisionist History by Malcolm Gladwell. I think there’s some interesting things that apply to what we do.

My take on podcasts and books is that as professionals, if we’re trying to improve stuff, read as much as you can and pull out different concepts that make sense, that feel good to you, that feel good for your organization. Don’t look for something that’s the silver bullet and the best practice. I think that there’s a best practice in a particular context. Your context is going to be different than what this person’s context was when they wrote it.

Since you are an improv artist, who are your favorite improv artists or comedians?
I think overall my favorite is Robin Williams. He was a stand-up comedian, an improviser, and he was just unbelievable. Growing up what got me interested in comedy was probably Chris Rock, Eddie Murphy, and Jerry Seinfeld. Ellen Degeneres too. I think why someone like Ellen and Jerry Seinfeld are so funny is because they can take everyday moments that you and I do every single day, twist them around and somehow make them hilarious.

At an early age for me what got me into comedy was probably The Carol Burnett Show. It was sketch comedy but they improvised a lot too. They would be cracking themselves up on stage, so they’re trying to hold back their laughter. It was just so good.

Do you have questions, feedback or suggestions of people to interview? Contact me!

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