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 as Business Analysis, Project Manager, 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 project management and consulting?

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 anyone 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!

Keeping Latinos Connected: Selymar Colon

By: Yadira Y. Caro

In the shifting news landscape, Univision’s news coverage continues gaining relevance. With a growing Hispanic population in the US and many watching from their own countries abroad, Univision’s journalistic team informs first, and second generation immigrants, and even those from later generations on stories relevant to issues in their region and the US. They also serve as advocates for the people.

Selymar Colon has been a driving force behind this continued growth in Univision telling the stories of the people while finding new ways to reach them. As VicePresident and Editor in Chief of News Digital, she has been a champion of digital integration since she started in Univision in 2006 after graduating college. She joined the news company as a field producer and continued rising through the ranks becoming a producer for Al Punto with Jorge Ramos. Her work has been awarded national and regional Emmys, named one of the Top 40 under 40 in latino Politics by Huffington Post and most recently, won along her team a World Press Photo Award.

In this interview, Selymar shared what drove her to journalism, the value of mentorship to advance professionally and how she stays informed.

Can you describe what you do?

I am a digital journalist in a newsroom where our main focus is the Hispanic Latino community in the United States. At Univision we have such a close relationship with our audience; that is extremely privileged. We cover the issues that matter to them, things that are happening in the United States that impact their lives, and headlines from the countries that would be of interest to them here as well. A big part of what we do is service journalism which is key to our audience to help them understand how the immigration system works in this country, how it impacts their lives. Obviously a big part of the audience is immigrant so this is information that it’s useful to them.

You studied journalism in your Bachelors (at Lynn University) and your Masters degree (at Florida International University). How did you know you wanted to be a journalist?

This is a little bit cliché, but the reality is I always wanted to give a voice to the voiceless. I was born and raised in Puerto Rico and I remember when hurricanes or major natural disasters would happen, the journalist felt kind of part of your family. They were the ones guiding you through the emergencies, through the news. I found that instant connection when I saw how much help they were bringing to the community and that’s what attracted me the most to the news: how can I be that guiding force, that guiding light in the community, how can we uplift voices that might not have anywhere to share their story, to get help. So that’s what interested me the most about the field of journalism.

Are there any misconceptions about what you do or about journalism?

Right now it is a difficult time for journalists all over the world. 2018 was one of the toughest and bloodiest years of journalism in the Americas. Mexico has become the bloodiest and most dangerous country to be a journalist. The rhetoric the President of the United States uses against journalists does not help either.

I think in any democracy, keeping a healthy press is extremely important. Also, its important for its citizens to make their own conclusions to what is happening in the country and the laws that are being enacted and may affect them. So I think in general, right now the time it’s difficult, but at the same time, it’s interesting because you’re seeing more journalistic work that is excelling, just going beyond to what we were doing before. Its gaining even more purpose. There are more people that are backing the good journalism that helps them conduct their daily lives and keep democracies alive.

Selymar Colon behind cameras with Al Punto host Jorge Ramos.

Since you started over a decade ago in journalism, what are significant changes that you’ve see on either the way you perform your job or overall in the trends in journalism?
We usually say a good journalist is a good journalist regardless of the times. I think technology has helped journalism and it’s the key that, like in any other industry, has made the biggest changes. In journalism in particular, technology had helped journalists gather and analyze better data and information to provide better reports. On the other hand, it has also allowed journalists tell their stories in various formats that reach bigger audiences that are further from them. Probably five years ago, ten years ago, people were used to their local newspaper, and now they read them on an app, they read them on their desktop, on their smart TV.

Technology has made a big change for consumers on how they consume news and for journalists in helping us gather better information and analyze it. Probably in some cases, you don’t have to go physically to a location to gather the data, you can create that data even from various sources, analyze it and include it in a story.

How is a regular day for you? Do you have to be constantly connected?

Yes, it does come with the job to be almost all the time connected! I have push notifications from any and all major news organizations. There are some apps like Nozzle that do help you better see what’s trending, give you a sense of what people are sharing in your own network. So it’s through a combination of apps and social networks; and push notifications are key to stay connected at least on breaking news and announcements.

Do reach out, do find that mentor, and when you get that mentor, use their time smart and wisely. Know what you want to get of that relationship, and that’s going to help you tremendously in your career.

Selymar Colon

You’re leading a team of journalists. Is there any particular approach you have for management?
To communicate, to talk to people, to listen is really important. It’s something that even though if I keep a busy schedule, I try to do as much as I can to have one-on-ones, to listen to everybody in the meetings. Also I leave the journalism team some space if there are projects that they want to push forward. I think that’s really important because the day to day and the breaking news can consume you.

I think as a woman in this role, it’s also important to also leverage other female voices in the newsroom and not just the journalists. Also in the stories that we tell, and the voices we use as sources as well.

What advice do you have for women who either want to venture in technology or communications?

Get mentors, don’t be afraid to ask for mentorship. If you see someone that you might think ‘Oh my God, this person has such a big title and so much responsibility,’ the worst you can get from that person is a ‘No.’ Then you move on and you find someone else you want to talk to. Do reach out, do find that mentor, and when you get that mentor, use their time smart and wisely as well. Know what you want to get of that relationship, and that’s going to help you tremendously in your career.

Sometimes it’s good to also keep a balance of who those mentors are. There might be people that are directly in your industry of preference, but there could also be someone who is not in your industry, but its in a field or in a position that you might want to get to, or from an interest that you gain in some point in your career. It’s also good to hear from everyone, from other people what their experiences are. More often than not, I would say that people would be open to meet you, to talk to you on the phone and share with you their stories, share with you some of their experiences. After you have that information, use it for your benefit, take from that conversation what you think suits you the best and apply it.

Are there any two or three resources, either podcast books or anything that have helped you throughout your career?

I would say one thing besides the mentorship, is continued education. There are fields where continued education is mandatory, there are some where it’s not. Even if it’s not, we should always pursue continued education. I’ve taken some executive education courses, and I’m always looking for more of those because those are good places to continue to grow, to continue to learn. Attending conferences it’s also really important, and if you can’t go physically at least follow them and read about them on blogs.

All of the podcast I listen to have nothing to do with my field. I do like a lot How I Built This, because of the inspiration it provides. This goes hand in hand with the mentorship and learning from people that are probably in another industry. It helps learning from their career paths and how they made it. I listen to another one called Latina to Latina from Alicia Menendez. Its really good and empowering because I discover a lot of new voices of powerful and interesting Latinas in the United States; their stories are just magical. I do like another one called the Washington Post Retro Pod, which gives you 5 minute history snippets. I’m a little bit of a history buff.

In the morning, morning podcasts are really important of course. Up First from NPR and The Daily are my two go-to podcast every morning. For reading, The Nieman Lab is really good, it’s a website that gives you new things that are happening from most organizations.

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

Contact me!

Life Lessons from a War Virgin: Laura Westley

By: Yadira Y. Caro

War Virgin is not an archetypal war narrative of how protagonist vanquishes the enemy through a series of battles. Instead, Laura Westley describes her personal path as a military grad and recruit. The path covers her strict upbringing in Florida, attending the U.S West Point Military Academy, where she graduated in 2001, and her deployment to Iraq in 2003. She describes her day to day: the arduous and the redundant tasks, the restrictive discipline, the expected gender roles, the temptation and the harassment, all done with humor and candor. It also addresses life after the war and mental health challenges she confronted.

War Virgin was also a musical play, where Laura performs as singer and actor. These artistic endeavors helped Laura to raise awareness of the many struggles experienced by soldiers and veterans.

Aside from being an author and actor/singer, Laura has a seasoned IT career. She is currently a Technology Services Senior Manager at Johnson and Johnson. I asked Laura about her years in the military, her motivations to write War Virgin, and what she has learned along the way.

What made you go to West Point?

I kind of joke when people ask me that, ‘Do you have a leather couch for me to lay on and talk about my daddy issues?’ (laughs) I think a lot of it could have stemmed from the fact that my father really wanted a son and he got two daughters. I was the first born and I felt like his love wasn’t unconditional. Whenever I would do something that was more perceived as masculine, whether it was excel in sports or do something more traditionally masculine, I just felt like I got more positive affirmation from him.

I remember when he was reading from U.S. News and World Report an excerpt about West Point and I just liked the way he was trying to paint the picture ‘imagine you doing that Laura.’ So I think at a deep level I thought I’d be more accepted and loved. Other reason I think is because it seemed like the ultimate challenge. I used to be all about doing the absolute most difficult things in life. I’m definitely not that way anymore (laughs).

” I wanted to tell a true story, I wanted to write the book that I wish I would have read before going to West Point, before going to war. “

Laura Westley

What was one of the greatest challenges you had there?

I think the hardest part is sleep deprivation. There were definitely some academic geniuses there, but I felt like the people that did the best overall were able to survive on such little sleep. To me that would be the absolute number one struggle: it’s just not having enough hours in the day to get everything done and then also get a good night sleep.

You spent your time in Iraq. How long were you there for?
I was deployed for seven months: I deployed in January 2003, in Kuwait in the middle of a desert, in a camp made up with tents and porta potties. I was there for two months and then I was a part of the Invasion. I went in March 21, 2003, and then came home in August.

Scenes of War Virgin: The Show

From your experience there, how much did your expectation differ from what was going on there?
I could not believe that we were at war. It was really surreal. I think my top expectation would have been preparedness and to take war more seriously. We didn’t train sufficiently, the gear that we had wasn’t sufficient. Even the way that we were making plans and the way information was disseminated just seemed like a big joke to me.


I remember wanting to go practice the range on my weapon more and my supervisor being like ‘No, you need to work on the spreadsheet for me,’ and me getting into a fight with him since he just would not let me go. I remember that was the first time I publicly cried, because I was seriously worried about needing potentially to use my weapon, not being skilled enough at it, and dying because he wanted me to work on some spreadsheet. We just didn’t seem to take it very seriously, and at the same time, it’s like most of the people, especially the leadership, conveyed that they could not wait to go to war. They were glorifying it, but they weren’t taking the right measures to properly prepare for it.

You detail a lot of your experiences in your book War Virgin. What made you want to write that book?

I wanted to tell a true story, I wanted to write the book that I wish I would have read before going to West Point, before going to war. I feel like now with technology and social media, and now that some people have put books out there, I see the real authentic stories are more accessible, but they didn’t really exist before. I got so sick of every military story being written by some male who’s this stereotypical hero charging off the platoon and winning victory. I feel like that’s actually only a tiny percentage of who serves.

I feel like my experiences, as absurd as they were, might actually be more common than those other experiences, like the boredom that I talk about, and the lack of preparedness, or how you’re confused during war and information’s not being passed along and you don’t know what the hell is going on. Another really common theme, I think, is the feeling of wondering whether or not you’re actually being a productive member of the military, if you actually should be there and questioning your role instead of just being like, the stereotypical ‘I served my country. I fought for your freedom.’

How was the reception to the book? Were you surprised in any way?
I was prepared to receive more backlash. Now when something gets posted on social media, I don’t comment. I was trained by a Washington Post editor, because I remember publishing my first op-ed back in 2012, I read comments and laughed and had a good time with it, but he was like, ‘don’t engage.’ Since then, I think trolling has become much, much worse.

But the feedback that I was aware of was overwhelmingly positive. I thought that there would be more negative ramifications. I definitely took measures to make sure that I changed names (in the book); I didn’t want anybody to get in trouble. So I was actually surprised that there wasn’t more backlash. It was overwhelmingly positive.

“I feel like it’s my responsibility to help them find the right resources to make sure that they’re happy, that they’re enjoying what they do, that they feel like they have a good future ahead and that they are nurturing their talent.”

Laura Westley

How was your transition into the corporate world?

It was interesting because I fantasized about War Virgin allowing me to become a full time author or performer speaker. That was a very far fetched fantasy, especially for being financially practical (laughs). I kind of beat myself up for a little bit thinking ‘Okay, if I have to go back into the corporate world, I failed at War Virgin.’ But then I realized I had this professional IT career before this and I was building it. I did take time away once the book was being published and once I went on tour. But I had to go back to that.

I also wondered, ‘what can I go back to doing?’ I want to make sure that whatever I do is in alignment with my values, that I don’t compromise who I am. When I go back to the corporate world, I don’t want to have to be shut up and not expressive. I also was wondering, ‘Does having War Virgin out there will impact me getting a job?’

I spoke to a fellow West Pointer who was interested in hiring me for this associate vice president position. I just had the feeling that we were not a good match and I said ‘I want you to read War Virgin and then come back.’ He had concerns, but he was very conservative. Interestingly, he also has a sister who went to war and went to West Point and he’s like ‘I didn’t even know what it was like for women.’ It just wasn’t going to be a good match.

What ended up happening is I got a good (referral) in for my current job by someone who knew me because of War Virgin. She was from the first class of women who graduated from West Point. And so its ironic that War Virgin actually helped me get the job that I have now, which is a really good corporate job.

How do you describe what you’re doing right now?

I lead a new software development department at Johnson and Johnson. I take care of software developers, software testers and project managers, trying to make us a really valid force to be reckoned with.

Really, everybody else, they’re the doers. I joke that they do the real work around here and it’s my job to take care of them. So I actually tell them that they’re all my bosses. My job is just to whatever obstacles might be in their way, let them be able to fully focus on what they need to do, even if that is something beyond the work environment, even if there is something that they may be struggling with at home. I feel like it’s my responsibility to help them find the right resources to make sure that they’re happy, that they’re enjoying what they do, that they feel like they have a good future ahead and that they are nurturing their talent.

Are there any resources that you recommend that have helped you throughout your career?

When I wanted to learn how to be a better storyteller in my writing, it was almost like an academic pursuit for me. All I had known was academic writing and so I did take a comedy writing class. It was helpful for me to understand that if you’re going to write a book to be consumed, you can’t write in this high brow or dry academic (tone), you have to write as a story teller. In order to be a better storyteller I took a comedy writing class, and I joined a story-telling competition group in Massachusetts. One of my favorite books is called The New York Regional Mormon Singles Halloween Dance by Elna Baker and it was hilarious. Before she wrote her memoir, she did stand up comedy and so she perfected the art of story-telling orally and that translated to the page. That got me thinking and got me into doing the live story telling. Then it eventually evolved into the show.

There were definitely some people that came into my life that helped me to know more about storytelling. I was taking it all in, and working with theater professionals. Now I am really obsessed with an author named Jo Piazza. She has a podcast called Committed and my favorite book of hers is called Charlotte Walsh Likes to Win.

I’m trying to think of books about IT career and I know that there’s a lot out there. But I find that I’m running into the same frustration that I did with military books with respect to how boring they could be, or how masculine they can be. I feel like there’s a lot of books written by super successful women like a billionaire CEO, or COO, but it seems like those are the books that get published, by these very privileged highly educated, multibillionaire white women. I would love for there to be books that are written by more normal women. Why can’t I read a book by a mid level manager? Those are the kinds of jobs that are more popular than the super crazy executive positions. I’m probably going to have to write the book that I want to read with respective to navigating a corporate environment, especially in a traditionally male-dominated environment.


If there is anything in the future, I want to collaborate with other women.

Would you recommend any women to join either the military or go into West Point?

It’s hard because when I think about it, I get a little knot in my stomach like ‘it’s going to be brutal.’ But I don’t want to say, ’No, don’t do this’ because sometimes that’s just your calling in life.

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