Skip to content
March 21, 2019 · 16 min read

How to Lead a Meeting Engineers Love: Lessons from improv with Ushashi Chakraborty of Microsoft, Groupon, and Mode Analytics

A veteran of Microsoft, Groupon, and now Mode Analytics, Engineering Leader, Ushashi Chakraborty has gotten used to hearing the most abnormal feedback: “I love coming to your meetings!” 

She realized after some reflection that her extensive improv experience through Chicago’s famed Second City Conservatory, had instilled in her skills and habits that were just as useful for running engineering meetings as they were on stage. 

In this episode she recaps a presentation she made at the 2018 NY Nasdaq CTO Summit, entitled “Running Engineering Meetings Using Improv Skills.”

Ushashi Chakraborty

Director of Engineering for Backend Engineering at Mode Analytics

Ushashi Chakraborty is a Director of Engineering for Backend Engineering at Mode Analytics in San Francisco. She moved to California in October 2018 from Chicago where she worked in Groupon for 5 years as an Engineering Manager for Consumer Applications and before that as a Software Development Engineer in Test. She has also worked in Microsoft and Thomson Reuters. She holds a Masters degree in Computer Science from North Dakota State University.

Ushashi has been involved with theater since high school and, especially, with improv since 2015. She is a Second City Training Center, Chicago alumni and has performed improv, sketch and stand up across several small theaters in Chicago.

Read transcript

Ledge: Ushashi, it’s great to have you! This is so fun. Thank you for coming on our podcast.

Ushashi: Thank you so much, Ledge. I’m very happy to be here chatting with you.

Ledge: Could you give just a two- or three-minute background of yourself and your work before we dive in?

Ushashi: I’m currently director of engineering at Mode Analytics. It is a startup in the Bay Area. I recently moved from Chicago to San Francisco and, so far, I’m loving it.

Before Mode, I was at Groupon where I was an engineering manager for about five years; and then before that, I had worked at Microsoft as a software engineer for a few years.

At Mode, I’m currently looking at back-end engineering and I’m having a great time. It is a growing company and it’s, so far, been a phenomenal experience.

Ledge: Off-mic, you and talked about an experience that you have had in your past that, I think, is very interesting. You recently gave a talk at a CTO conference at Nasdaq.

Please go into that. This is going to be a lot of fun.

Ushashi: Absolutely! Thank you so much. About four and a half years back, I was going through a phase where it seemed like I was just working and then coming home and, perhaps, socializing with friends. That was my life.

I was thinking that I should pick up some sort of a hobby that I’m doing regularly; and I was looking into my high school years and saw that I had a lot of theater that I had done. So I wanted to go and do some theater but, at the same time, I did not have so much time on hand to learn scripts and things like that.

So a friend suggested that I could do improv. I was in Chicago and it has Second City so I went to that school and started taking up a few classes. And over the course of a few months, it became something very important and something that I started doing quite regularly.

And then, a year later, I had finished with the entire course and got eligible for auditioning for something called the “Conservatory” which is more like improv for actors. I got through that audition and went through another year of training ─ this time, a very strict training. We were doing a lot of writing. We were doing lots of shows. Finally, I graduated as a Conservatory graduate from Second City. After that, I had done three to four months of shows around various small theaters in Chicago.

Tying that back to engineering and my regular work, the last two years, I was getting a lot of great feedback particularly around the way I ran engineering meetings which is very interesting and odd because, usually, people would come and say things like, “You’re a good leader” or “I like reporting to you.” And, usually, you don’t hear feedback like “I love coming to your meetings.”

So I was a little bit taken aback when I would get that feedback regularly from peers, my directors, or managers.

I started looking into what had changed. And when I started looking into what changed, I started realizing that a lot of the things that were happening were habits that had formed by doing so much improv on stage.

And then, I started putting that together and understanding how I could coach others on the same so that they can do the same without going through that many years of improv.

Ledge: That’s fantastic. So what are those lessons? I’m sure you’ve distilled this out a little bit. Please tell the audience how they can do that.

Ushashi: Absolutely! To go into the lessons a little bit, I’ll give a little bit of understanding of improv or what happens when you’re on stage. For the listeners who do not know what improv is, improv is a form of theater where you go on stage and you will see a scene that is completely unscripted. It is based on suggestions that the audience is giving.

It might seem like something that has gone completely unrehearsed but there are still ways and training that go into it that makes a particular improv scene, perhaps, much better than another one. And what goes in is what actors are trying to do on stage that even if the scene or the topic is something that is completely unscripted and has just been heard of now and they’re trying to develop it on stage, they’re constantly trying to make sure that there is a story and there are relatable characters.

As the audience, when you see something on stage that has a story that you relate to, you’re going to like it more. So if you see two coworkers or two friends talking about daily stuff that you would talk to your friend about or you would talk to your coworker about, you’re suddenly like,

oh, yes, I can relate to this. And you are laughing.

So the key is story and with story comes characters and beats ─ characters being the people who are playing in the scene and beats being the progression. They’re also trying to make sure in the scene that they’re building and the scene is.

Now, think about an engineering meeting. In an engineering meeting, what is something that every engineering meeting needs to have before you set up a meeting?

It is an agenda, right?

You are always going to have an agenda and every engineering meeting is going to have some attendees. So it’s quite like the beats and the characters from the improv or from the scene.

But, now, think of it in this way. You might have heard a lot of people say in terms of a story things like “I love listening to your story; it relates to me” or “I love listening to your talk ─ whatever you spoke about─ that was so relatable. It spoke to me.”

Have you ever heard anybody say something like “I love your agenda; it speaks to me”?

“Agenda” is an extremely technical word. It lacks heart where a story has heart and, hence, people relate to it.

I’m not asking you to go and change the word “agenda” with the word “story.” You can keep your agenda as “agenda” in the meeting but the key is “Can you treat your meeting as if you’re running a story and can you think of these attendees as characters and that means that every character has to play a role”?

Even if they’re silent characters, they’re still there in the scene for a reason. They’re either taking something out of it because they’re going to contribute to something later on ─ maybe to the story ─ or they’re in it because they’re contributing something directly.

And that is key. It’s also to understand how it ties to the bigger picture.

So, constantly, my idea is to run meetings in that fashion and, perhaps, in a certain way, it shows some heart; and, hence, people find it more relatable.

That would be the first concept here. I want to pause here for a quick second if you have any question before I move to the second.

Ledge: You’re reminding me sort of the Joseph Campbell and

The Hero of the Thousand Faces and the arc of the story and that everybody gets to be hero in their own way and that there’s only X number of story types.

I’m totally relating to this and I can see exactly where you’re going. I really want to hear about the character development because I can think of the engineering meetings that I’m in and there are definitely some character archetypes.

I wonder how you play that.

Ushashi: With the characters or the people in the meeting, again, I go back to thinking of it from the improv standpoint.

Once again, this disclaimer here: I had not understood that these habits that had developed were coming from improv until I paused and reflected. But now that I look back, I understand where it came from.

So with the character development, there is something very key that our improv directors or teachers would often tell us. Sometimes, we’d go up on stage and think it’s a great scene because the audience laughed. Every time the audience laughed, I thought it was a really good scene. And while that could be a good metric that you entertained the audience, that is not the only metric.

The bigger key factor is putting the spotlight on your co-actor and understanding what character they’re playing ─ reacting instead of acting.

So if they’re playing a certain character and they’re conversing with you in a certain way where they’re expecting you to be in relation with that character, then you would have to play that particular character that they’re expecting and respond in a certain way which means that, at all times, your entire focus in this is on this character’s words and what they are saying.

Now, a scene, perhaps, might not have two characters but three of four characters and they’re all speaking. Remember, it is unscripted so you could be talking over each other.

So it’s eye contact and making sure that it is your turn to speak. How will you know that in an unscripted scenario?

Once again, there are a lot of factors and a lot of understanding each other and knowing whether I should speak here and I’m expected to give this answer because this character expects me to and making it look organic.

Going back to a meeting, you’d see that, oftentimes, there are some people who are contributing more in the meeting; they’re the ones who are talking more. And there could be some people who are not doing that much.

If you were the person who is running the meeting, it is very key to understand, as I’ve said before, that every character should be there for a purpose.

So it’s fine if a person is not contributing as much because, perhaps, they’re learning more in this meeting and they’re taking it back. But make sure there is something for them to take back and find ways for them to incorporate their thoughts as well.

If they’re not contributing vocally about some ideas, is that because they are new and they’re learning about things and they are taking their time or is it because they’re too shy to speak up in the meeting?

If they’re too shy to speak up, you probably need to change your style a little bit so that they feel comfortable to contribute. Or another thing could be that they might not be so shy but they might be just thinking that their ideas do not have so much weight behind it; hence, they might think,

this is not the time contribute. Again, those things have to be understood.

At all times, I’m thinking of myself as a person who is on stage trying to understand these dynamics because the audience expects a scene that is scripted or that is organic and you’re really paying attention to everybody; and while you are making a scene and building a scene and having a story there and playing your character, being in your character, it is also a constant multitasking of which character is saying what and what they are doing, which is what I’m doing in a meeting as well.

That would be something that I would say for a character development and maintaining that.

Ledge: It makes me wonder how often you have an implicit storyline that you think or even want a meeting to come to. In fact, through that process, it’s not at all the same direction or it doesn’t end in the same place because of the other characters.

And I also wonder sort of as a leader and a manager that, sometimes, you have to have a certain objective outcome which means you override the script.

How do those things play out?

Ushashi: That’s a great segue to the third pillar that I lean on which, I’m sure, a lot of people have heard about and probably even practiced, which is “yes, and.”

Just pertaining to your question as to when, sometimes, you might have to override script, this is engineering world and this is an engineering meeting; and there will be times when you would have a different opinion than what is being discussed in the meeting or somebody else brings something up.

And that is only because, sometimes, you might have a meeting just because you’re going to discuss three or four different solutions, and then discuss tradeoffs and go.

So it is quite obvious that in such meetings, you would not be saying “yes” all the time.

Let us just hold that thought for one second and, first, understand the crux of “yes, and” because it took me a long time to really understand “yes, and.”

I was aware of it even before I did improv and it seemed like if somebody said something and you said “yes” to it and agreed to it and kept going on from there, that would be it.

But it became kind of difficult as I started doing it on stage because, at the crux of “yes, and” is not just the “yes”; it is the “and” as well which means the “building.”

A quick demo would be something like if I say a line like “It is such a warm, bright summer day today.” And the other character is responding to it with “Yes, it is.”

The scene wouldn’t move forward if that person just stopped with “Yes, it is” because now the first character has to think of something else to say as well. And on the stage where you don’t have a script and people are watching you, that might become a little too nerve-racking.

So both the characters need to. So if one character is saying something like “Wow, it is such a nice, bright summer day today,” the other character says, “Yes, indeed, it is. And summer days like this remind me of childhood, of grandmas.”

Suddenly, there’s a lot to explore because, now, on the top of bright summer day, the other character has now incorporated the concept of nostalgia which means, perhaps, they could be siblings or maybe cousins and they could talk about the summers that they have spent at Grandma’s and the story becomes relatable because a lot of us would relate to that story.

Coming back again to that engineering meeting, focusing on the “and,” if somebody said something you’re saying “yes” to it and then you’re building on that, with building on that, I’d take it as contribution. So I’d take this “and” as a contribution.

Now, going back to the times when you have different opinions, in meetings we often talk about a concept called “disagree and commit.” It’s like all right even if we have disagreed, we’ll commit and we’ll just move forward to that.

But even in my own career, I’ve seen a lot of times when it’s very hard to do that because you are so attached to your original idea that after committing, you’re still going back and thinking,

I still think that that particular idea is better.

In such situations, I rely on that “and” which is contribution. Even if it were somebody else’s idea that I’m not originally on board with, once a commitment has been made, I try to contribute to that idea.

Doing an active contribution, I have suddenly put a stake; and by putting a stake, now, I would want to make this a success even if it were something that I probably disagreed with initially.

So I view “yes, and” as a commitment plus a contribution ─ it’s a totality of the two concepts ─ and take it from there.

And that is why I’ve had an easier time with committing to anything even if I was not a hundred percent on board with because, now, it is the entire team’s idea.

Ledge: It strikes me that micromanagers would not survive long in your organization.

Ushashi: Oh, well! Yes. Even with that, there are ways to kind of understand where that micromanaging is coming from and there are ways to play with that. But, yes, this entire that I’m talking about is dependent a lot on situational leadership and in understanding how that particular person or the person you’re working with would be comfortable.

Ledge: Absolutely! You have a lot of fast trust going on there. I imagine that your onboarding goes quickly. There’s an indoctrination into the way that the organization starts to work; and unless everybody learns these tools one way or another, you’re going to have the “no, but” people instead of the “yes, and.”

I also imagine there’s an attrition there that as the organization grows and gets better, you don’t get a lot of chance to be the stick in the mud. Obviously, you bring people along and you try to make it work.

My guess is that things evolve and, sometimes, an organization accelerates fast the “no, but” folks and they wind up somewhere else.

Ushashi: Yes. Such situations could happen. And there’s also coaching that is happening on the side, too. It’s very important to understand even the people who are “no-butting” as to where that is coming from.

Again, going up on stage, there could be people who are really “no-butting.” A good example is I would think that I was a very supportive actor but there were times that my director made me realize that I was no “no-butting” all the time.

For example, if I go up on stage and the co-actor says a line of dialogue, statement like, “I think I’m really stupid” and then because, by personality, I am the supportive person, I’d say, “No, you’re not. You’re just an amazing person.”

And then, the director would say, “Cut that because you just no-butted your co-actor.”

“What am I supposed to say, ‘Yes, you are a stupid person’?”

Then, the director would say, “No. You can say something like, ‘Yes, aren’t we all?’” You are saying “yes” but, at the same time, you are not making this person look bad. Saying “yes” is important because this person just put a concept out there.

Going back to the “no-but” people in the organization at work, I would really work with them on the side and try to understand, firstly, if they realize what the “no-but” is doing or if that they’re “no-butting” because they might not be aware of that.

You’d actually be surprised how many people with the right coaching understand and want to help the team and want to do things that would work.

I think there are very few people who would be like, “No, I’m still going to do it because I want to be the jerk.” Those people wouldn’t, perhaps, survive in the ark.

But most people would be coachable and would be able to do the right thing.

Ledge: I love that. Those are great insights. I can already think of some times that I do it. I’m going to be reevaluating my “yes, and’s.” I try very hard.

It’s wonderful spending time with you. Thank you so much for these insights. This is a lot of fun and we look forward to sharing it with the audience.

Ushashi: Thank you so much. I’m happy to share them and it was great talking to you as well. Ledge, thank you so much for having me on this podcast.