144 The Story of an Improv Accountant
16 Nov 2023 · 30 min
Podcast episode '144 The Story of an Improv Accountant' (host Jason Staats, guest Jennifer Diamond). Jennifer describes leaving traditional CPA work, founding a local Portland accounting community (2011), starting improv in 2012, and now doing fractional CFO, coaching, and running improv workshops for accountants. The episode explains improv benefits (presence, active listening, burnout recovery), demonstrates a 'mind meld' warmup (including an accounting-themed advanced round), and discusses formats for team sessions (in-person preferred, virtual possible but harder). Sponsors mentioned: Live Flow, Forwardly, Copilot, Cloud Accountant Staffing.
Chapters
Okay.
If you've been hanging around for a while, you know, I did some improv this year.
It was fun. I don't do it anymore.
We need to talk about that because you know what? I found somebody who's a total pro at improv, and they're also an accounting geek like us. Is that. Can we say that? Is that a nice thing to say?
I think it's a term of endearment. Absolutely.
Okay.
Meet Jennifer Diamond.
She's here.
We're talking improv today.
Let's do it. Diamond, can you give us like the. The 32nd for people who haven't met you? Give us the 32nd life story. Ready to go.
Okay. So recovering CPA. I don't do taxes. I don't do audit anymore. I started my own practice in 2010 and currently doing fractional CFO and coaching work. I also learned lead a local accounting community in Portland, Oregon. Have founded that in 2011. So it's a labor of love and it's a really good group. I started doing improv in 2012 in secret, and then, yeah, the rest is history.
Okay, so you do a lot of things. Has anybody ever told you that?
Yes, I am very diffused and I get bored very easily, and I like to take on new challenges. So that's why I have so many different. I follow a lot of curiosity into my interests, and my interests change a lot. So.
Okay. Okay. So at some point in time, you were like, I'm an accountant, going about your whatever, and then you said, I'm going to do improv. Most people never do that.
What?
Like, why? Where did. How did that even start?
Right. So I had been working in a traditional CPA factory farm for about eight years, and so I was very burnt out and left. And I moved across the country and I spent about three months just sort of in an existential crisis, trying to figure out what I wanted to do because I had been going home crying every day. So I couldn't. I couldn't keep doing that.
Couldn't crack it and couldn't.
Yeah, just couldn't crack it. And. And in that time, I. I tried to do various different, like, recovery resets. So, like, I was so burnt out, I didn't even know what I wanted to do with all of my free time. And I was also struggling. Struggling just with my identity crisis of having free time because I'd always worked.
Yeah.
So I broke out my pro con list of moving across the country, and one of them was take a sketch writing class. A friend of mine did Sketch comedy in Atlanta. It was super fun. I was like, oh, this is great. You just memorize some script. That's awesome. I love movie lines. I could totally nail this. So I went to take.
I love movie lines.
Yeah, I can totally nail this. I'm great with memorization. Awesome. So I went to a local comedy club and tried to sign up for one of their sketch classes. They didn't have any at the time, but I had already committed to taking this class. And the only one else that was available was an improv class. And I was like, okay, well, I went to a taping of Whose Line Is It Anyway? That was kind of fun. This will be fun.
I got this.
I got this. It's fine. Totally different. Completely different. Yeah, I think I almost died. My first stage performance.
And to be clear, like your first onstage, like, actual onstage performance. That's after how many weeks of things?
Three.
Three. Oh, gosh.
Yeah. Oh, no, it was terrible. I literally almost perished on stage in front of a live audience. Yes.
Oh, wow. Okay. So for context, the thing I did was 10 weekly classes, and they stopped doing, like, the show on the 10th one because people wouldn't sign up because they were so afraid of it. But they checked you in after three.
So. Okay, so they had like a ten week session for intro to improv. Easy enough. And they had a student showcase that wasn't necessarily opt out. I'm sure if, you know, someone was going to have an anxiety attack, they could get a pass. But it was just sort of expected that everyone in class would participate in the student showcase and invite all their friends and family to fill that audience and ring up those bar tabs. Yeah, so. So, yeah, so that was sort of the. The expectation. But this theater also had an open jam every week, so they encouraged students to participate in the open jam. And somebody convinced me to put my name in. You know, another classmate, like, convinced me to put my name in, told me it would be fun. Said it'd be fun. Put your name in there. And so I did. And I got assigned to a team. And yeah, I thought. I thought I was going to die on stage, but it was. I survived and it was really fun. The student showcase, I almost died there too. But also, just like a little phoenix, I arose triumphant. And that was what, 10 years ago?
So do you like roller coasters?
I do, I do. Okay.
Yeah. Because I have a lot of questions, like, unrelated, like, why? And like, as an accountant, if something's going to hurt me or, like, seem deeply unpleasant, why not avoid it?
Well, Remember, I was in deep burnout, so I was already at fizzling low. Right. So anything just to reset the senses.
Yeah, sure.
That's what I was looking for.
Okay.
And I figured improv would be as. As removed and devoid of my accounting life as possible. It's the furthest I could get. I thought so. Yeah. So I just. I had committed to that class just like several other groupons. You know, I did hot yoga for all five sessions because I paid for the groupon. I hated it. You know.
Oh, gosh.
I'm getting my ROI right. I'm getting my full value.
Finish the food on your plate.
Yeah, absolutely. Doesn't matter how painful it is.
So why.
Why keep doing it like that? There's the whole question of why start? But also when that thing happens, like, there had to have been something sickly enjoyable about it. Like, why would you keep doing it?
It was each session. I mean, as you experience. Right. Each class, each two hour session is challenging in and of itself, but for those two hours at least, I mean, tell me what your experience was. Like, I did not think about anything else during that two hours at all, except what was happening in the moment throughout the entire session. Completely present, focused, maybe overthinking things a ton, but still very presently focused.
Yeah. In a way that, like, it's really hard to replicate. Like, just to be that locked into something.
Yeah. So it was like a moving meditation almost. So for someone trying to recover from burnout, it was very soothing to have two hours a week of silence.
Yeah.
From all of that noise.
Is there like a non performant version of this? Like, do you even necessarily need to get on stage to do this or just do the classes?
No, there's a non performant version. My good friend Jason did an improv class recently and he didn't perform at all.
I don't. That's. Yeah, we don't need to get into that. We're talking about you here.
But yeah, no, you don't have to perform. It's you. You can opt out. You can. You can participate to your comfort level completely.
And you did. You've done this for like over a decade or something? Long time.
Yes. I started in 2012.
Were you ever able to find a sketch writing class?
I did. I did take a sketch writing class. That was a challenge. Completely different. But the improv training did help. It was very applicable.
Gang.
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So we bumped into each other at Scaling New Heights last year when I was. Or was it this? No, it was earlier this year when I was in the throes of my brief little improv career there that didn't even end in a performance.
Not yet, not yet, not yet. We'll get you on stage.
But you what's fascinating to me is you are super into the notion of running sessions for accountants and I know you've done this a few times now. What does it look like to get a whole bunch of weirdo accountants into a space and like start doing improv exercises?
Yeah, it is chaotic. Like kindergarteners at a snack table. Right. Like just. But it's fun. It's like you experienced in your training sessions. There's a warmup period and then there are some group exercises. So what I bring to an audience, an accountant audience of folks that have never experienced improv before and might just think it's sketch or stand up, because all comedy is the same. We'll do a brief introduction of what improv is and the foundation of improv, which is the theory of yes. And which is pure agreement and then building on to what is gifted before you. So. And there are some other, you know, tenets in there, but what, what we'll do in, in a group format is we'll break into small groups of maybe six to eight people standing up in the room. So in a conference experience, it's like the only class you get to be out of your chair for the entire time, which is brilliant. So. And you get to be up and move around and switch through the groups. So you get to get, you get to know all the people in the class with you as you shift around in these different exercises. And the exercises are just warm up games. They're just, they're like playground games. They're games that, that teenagers can play and do. They're just very simple exercises. And we run through these exercises and groups and then we share what we observed. And people will say like, oh, I observed that when my mind wandered, I missed my cue and messed up the timing. Okay, how does that apply to a business setting? And they were like, well, sometimes when I'm talking to my clients, I get bored of what they're saying and my mind wanders and then I hear a question and I'm like, oh, I wasn't listening. Oops. I was like, okay, so how can we apply the lessons that we're learning in these improv warmups to increase our awareness and improve our active listening? How can we bring that back to our client conversations?
Yeah, I was, I was in graduate school. Not a big deal, but there was this guy there that ran an IT company and they like, had this whole improv group and then did all this training with a bunch of their members of their team. And he was so into yes and and was like, could not talk about anything else. And like how it transformed their sales process and this and that. I'm like, dude, this is weird. What in the world does this have to do with any work stuff? Because I think we think of like improv as you're going to have people that are going to go do improv who are like, oh, I'm Bunny, I'm going to go crush this. And those people can go do it and they're going to suck because everybody does in the beginning. And then you have people who are like, oh, I just kind of want to open my mind a bit and they're going to come and they're going to be really bad because like everybody is when they start. But it's so accessible.
Like they make it so easy and.
Maybe it depends on where you are.
But like it's also like so friendly. And like my class was like an.
Old lady, like a kid that was.
Like in college, like a middle aged.
Lady that worked for the state and had a bunch of kids. Like it was everything, like such a.
Diverse mix, which was really cool.
And everybody was kind of there for different reasons. But I was shocked at just like how accessible it was and loved that it fundamentally wasn't about being funny, it was just about being engaged. And like, sometimes funny will come out of that and like the weird specificity of what you get into. But like it was, it wasn't really about like, I'm gonna do this thing for hahas now. It was just about like, you can turn your brain off and you're gonna have to focus so hard on this that like it's kind of like cathartic.
Yeah, exactly, exactly. It's, it's, it's that meditative, present minded zone. Right? It's a magical experience. So it's, it can, I don't know, it's scary in the moment, but also it's a natural skill that everyone has. Like we all improvise all the time, every day anyways. Anytime you're talking with clients, you're improvising. Unless you're reading from a script. Jason.
Never done that in my life. It's honestly, it's kind of amazing. Like when I was doing that and we'd do a little warm up thing, I would come back and I would do with my kids and they're like so good at it and they would just say these stupid little hilarious things and that's kind of part of like we're like breaking our adult professional brains which are like very shackled and I don't know, just like trying to play the game, I guess, and not really engaging.
It's a lot of unlearning like taking the improv classes and going, like, face planting every week for two hours. It's. It's a lot of unlearning and unfiltering and unrestricting and knowing that everything you need, you already have.
For people who are listening to this, they're like, I'm kind of into this, let's say, like, for their team. They were like, what if I wanted to explore something like this with my team, what would you tell them?
Oh, I would say, you know, run, don't walk to your nearest improv theater in your area if you can, and organize some classes for your team. Or, you know, come to the next awesome accounting conference and sign up for my class. Or, you know, throw money at me and have me come fly to your office and lead a class. Yeah.
What I was going to ask, is there like a virtual version of it that really works? Or, like, does it just kind of break?
The virtual version is. It's not impossible. It's just very tough because in a virtual environment, it's tough to see who you're looking at, so it's tough to establish eye contact, which is a huge part of improv and scene work. And, you know, when you're a Brady bunch on a 2D screen versus people in a room taking space and moving around, it's more challenging.
Do you have, like, is there a version of this that we can do? Can we do, like, a really weird, uncomfortable version of this to hopefully get people more interested in it?
Yeah. Yes. And I have a great idea. Would you like to play a game?
Okay, let's play a game. Let's embarrass ourselves. Let me. I will embarrass myself. You're the pro. This is. I regret this.
This episode is sponsored in part by Copilot. Okay, gang, circle around. Bring it in. It is change management season for most accounting firms. You're going through some hard tech decisions. Honestly, it is spooky and, like, high stakes and really hard to decide because there's a bunch of solutions out there, Frankly, a lot of good solutions. But it is high stakes because if we go, like, switch all this stuff, how are we going to ever unwind that? What if we don't like it? Or if we go put this thing in front of a bunch of clients? What if they all revolt or we don't end up liking that? And the more stuff we're changing, the more risk there is inherent in that. And I actually think this is a solid argument for Copilot who is only tackling the client portal problem. And if you've watched much of my stuff, you know how adamant I am about the value of client requests, about clients being able to self service in a portal to come get a tax return or a month and close or so they don't have to email you for that stuff because it's 2023 and you should have a website where people can get that stuff. But if you're stuck on changing, I don't know too much at once, or the notion of chucking all your stuff into this all in one tool where it's like, well what if I like the workflow better over here in the portal over there? I actually think this is a solid argument for Copilot. All they're doing is trying to give you the most flexible client portal experience out there. You can embed stuff from external services. They got a bunch of their own built in goodies, but they are really wanting to build a platform, not like a super opinionated portal so you can customize it to be whatever you need. So that sounds good to you? Check out Copilot at the link in the show Notes this episode is sponsored in part by the fine folks at Cloud Accountant Staffing. Do you hire accountants? Bless your little heart. Not the best part of the job in my opinion. Not something I ever enjoyed. Well listen, you can build your accounting dream team with talented offshore accountants in the Philippines that work 100% full time for your firm. Their accountants aren't freelancing or contracting for multiple firms. They're a whole yours. They work exclusively for you and are incentivized to stay with you and your team long term. They're not going to get swiped. Cloud account staffing is 100% dedicated to the accounting industry and founded by a former accounting firm owner that understands your business, knows your pain points. They had to hire some accountants and they said you know what, we're going to build our own pipeline in the Philippines, going to pull in some super talented people and then open that up to other firms. Basically that's the story. I've been talking about a lot about staffing, building more resilient staffing pipelines for your firms. I had staff in the Philippines like totally red pilled me to like oh geez. Like we need to globalize the way.
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Check these folks out link in the show description cloud accountantstaffing.com okay, so this.
Is a warmup that's good for two people that doesn't require a shared physical space called mind meld. Okay so the goal is for us to say the same word or phrase at the same time.
Finish each other sandwiches kind of thing.
But at the same time.
Completely synchronized on zoom. This will totally work.
Totally work. Yeah. Never tried this before. It'll be totally fine.
Okay.
Or it'll crash and burn. It'll be super fun. Okay. So the goal is for us to say the same word or phrase at the same time.
Okay.
We'll attempt this by success through failure, essentially. So we're going to just guess at any two words and then see what they have in common and guess that word.
Okay.
At the same time.
Okay.
And try to get closer to the same word so it's like a two sided word association at the same time.
As simple as that. No, I've done this lots of times. Yeah, you've got it.
You've got it. You've done this with your kids, Probably.
Yeah.
So to start, I'll. I'll say one, you say two, and then at the same time, we'll say one, two, three, word. And then whatever word we come up with can be any word you want.
Okay.
Or if you want to make it challenging, I'll have a. I can. I'll pocket that.
We'll.
We'll. We'll keep it simple. You go with any word, and then if you feel like you want a challenge, I can add a challenge.
Yeah, we'll see.
Yay. You ready?
I'm ready.
Okay.
One, two, one, two, three. Car.
Sailboat. What'd you say?
Car.
Car.
Very nice. I said sailboat. So.
Car.
Sailboat.
So then we do the killing thing again and then try to say another word that's the same.
Yeah, we'll try to say it. We'll try to say the same word. Now that we know car and sailboat, what might we say that comes to our minds?
Okay.
For car and sailboat.
Okay.
Okay. Ready?
One, two. One, two, two, three.
Three.
Duck boat.
Luxury.
Close.
Luxury. Duck boat.
Isn't it supposed to be something between.
A car and a boat?
It could. It's something that your mind associates by melding those two things together.
Okay, I went the wrong direction there. Do we now have to somehow marry Luxury and duck boat.
That's right.
Got it.
Luxury and duck boat.
Okay.
Okay.
One, two, one. One, two, three.
Limousine.
Vacation. Ooh. Vacation. Limousine. Okay. Okay, ready?
One, two, one. One thousand two, three.
Airplane.
Bachelor party. You said airplane.
I don't know that we're getting any closer.
We might not. If we. If we can't get it soon, we can wipe it and start over.
I feel like we're almost there. Okay, I'm ready.
One, two, one. One, two, three.
Vegas Warmer. Yeah. You want to keep going?
Yeah, I feel like we're almost there. Okay. One.
Two, One. One, two, three.
Three.
Conference wedding.
I didn't know you were gonna go so deep. All right, that's a. That's a wipe.
Okay, so are we gonna go to the advanced mode now? Since we nailed that.
Since we nailed that. That was great.
Okay, so give yourself a hand. Is it supposed to be like, okay, these two words make me think of this thing next?
Yes.
Okay.
Like, it's a word association of those two things. Not necessarily. Like, if these two things had a baby, what would it be called?
Right? Like a duck boat.
Like a duck boat. I mean, that was brilliant. I loved that direction.
If we were doing this in person, how would it be different than doing it on zoom with latency, talking back and forth.
There would be a lot of physical mirroring to help with timing. So a lot of deep eye contact. A lot of physical mirroring, like body language, and then a lot of dancing and celebration when we got closer to the word.
You could see the duck boat in my eye before I said it, right? It would be easier.
Absolutely. Yeah. You get it.
Are we landing the plane there? Is that where. Is that as good as it gets?
Do you want the advanced round?
Oh, oh, sure. No, let's do the harder one.
Okay. So the advanced round. I've never tried this before. It could totally crash and burn. But that's the fun of it, is to do a mind meld, but only use accounting terms.
Oh, now we're speaking my language.
The language of business.
Okay, let's do it.
Okay.
One, two, One, two, three.
Sadness.
Ledger. What was yours?
Sadness.
Too soon.
Too soon. We're almost there. We almost got it.
Okay.
One, two, One, two, three.
Ten.
Key.
Reconciliation.
Okay.
Reconciliation. Ten key.
Okay.
One, two, one. One, two, three.
T Account.
Bookkeeping.
Okay, we're getting there. Okay.
One T Account.
Two, one. One, two, three.
Financial statement.
Sell Excel financial statement. Just out of ten things I can't say. Okay, ready?
1, 2, 1. 1, 2, 3, 3.
QuickBooks.
I didn't receive it.
Dang it. I didn't receive.
Anytime I ever gave clients financial statements, they're like, oh, no, I didn't receive it.
Do you actually play this game with people?
And it works.
Like I said, I've never tried an accounting restricted one before.
This would be super fun in, like, a speed dating format. Like, when you're. You're, like, hopping around to different people. This Would be super fun. I'm not sure that today we brought anybody any closer to considering improv.
Awesome.
That's not true. Do you do this stuff? Like, if somebody's like, hey, can you come make my team feel uncomfortable for an hour? Is that something that you do over zoom?
Oh, yes. With. Oh, over zoom.
Yeah.
To do team exercises over zoom for a, a group.
Yeah.
Maybe we just have this kind of.
Discomfort over zoom for multiple people.
We might have just put the nail in that coffin.
I mean, it's a, it's a worthy challenge. I haven't developed that yet.
Definitely.
I do the in person ones.
What does that look like? Like if you actually go out to somebody's place, like, what is that?
So we'll either, we'll decide like ahead of time what their goals are for a team building experience. We'll talk about any kind of struggles they might be having within their team and various different pain points that have emerged and sort of assess their team size and pull in any additional instructors if we need to, to get a good ratio. And then we design warmup exercises and group exercises specifically tailored to address those pain points. And then we do a lot of breakdown and discussion within those teams. And so it's a, it's a lot of the lessons are cultivated from within those experiences.
Man, this would be so rad on like an, an off site or like an annual. Like if you got a remote team, like an annual when you get everybody together kind of thing, that would be so cool.
Yeah, I would, I would love to do retreats and stuff. Willing to travel.
Diamond, how do people find you? Are you on the socials? Are you on LinkedIn? Where do you exist in the universe?
I am on Twitter at Jenn Diamond. I am on LinkedIn at Jennifer diamond also.
D Y M O N D Y.
M O n D yes.
And we're about to go have the time of our lives at QuickBooks Connect.
Yes, it's going to be a big party and I can't wait to meet Ryan Reynolds with you.
Oh, in your dreams.
Yes.
Diamond, super been out of shape that I get to do the meet and greet and she's still fighting people for access to that.
I still have a chance.
This is going to air the day after qvc, I think. So hopefully we got a few folks who meet you there and are able to hang before they hear this. But diamond, thank you very much for coming and doing this.
Yeah, thank you, Jason. This was fun.
That's it for today. See you all tomorrow.
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