Life Is Improv! The Spectrum of Work and Play with Sarah Filman

We can play at work, and we can work at home. Work and play are on a spectrum as we practice showing up as our authentic selves in life and work. 

Our latest guest Sarah Filman is a pro at play, and her work reminds leaders to listen actively, build on contributions from our teams, and find the things that energize us in our work. If we really want our organizations to foster creativity and innovation, we have to create a culture and environment that allows for experiments, exploration, and most importantly: play! Build a metaphorical sandbox for your teams and let the rest unfold.

Credits: Raechel Sherwood for Original Score Composition.

YouTube Channel: Uncover The Human







Alex Cullimore: Hey, Christina. 

Cristina Amigoni: Hi. Friday.

Alex Cullimore: We are back again on a Friday, and we had a very good Friday conversation with Sarah Filman, who was just a wonderful coach and great perspectives and just very fun conversation. I don't even know what else to say. It was a blast.

Cristina Amigoni: It was. Yes. She brings the playfulness, not just in her coaching and in her job and in her business, but in conversations as well. So we'll see some of that in this one. 

Alex Cullimore: She has just great explanations for why it's important, how it can fit in, what it really means, and how this is what builds into life. I thought she had a wonderful explanation of bridging that professional personal gap that we'd like to try and create a wall around, where there's really so much flow between. But she describes it very well, and she has all kinds of great tips for how to expand and live a better life, really. Very fun conversation.

Cristina Amigoni: Yeah. Blurring the lines between personal and professional development. It’s not really one or the other. I'm sure there's all sorts of skills that we learn in one aspect and take into the other one.

Alex Cullimore: And how to put your fear in a sidecar. That was my other probably favorite analogy.

Cristina Amigoni: Yeah. Make sure it holds the tea and keeps it warm and then hands it over when you need that warm tea. 

Alex Cullimore: Please enjoy this conversation with Sarah Filman. 

Cristina Amigoni: Enjoy. 

Alex Cullimore: Welcome to Uncover the Human, where every conversation revolves around enhancing all the connections in our lives. 

Cristina Amigoni: Whether that's with our families, co-workers, or even ourselves. 

Alex Cullimore: When we can be our authentic selves, magic happens.

Cristina Amigoni: This is Christina Amigoni. 

Alex Cullimore: And this is Alex Cullimore. 

Cristina Amigoni: Let’s dive in. 

Alex Cullimore: Let’s dive in. 

Hosts: “Authenticity means freedom.” 

“Authenticity means going with your gut.”

“Authenticity is bringing 100% of yourself not just the parts you think people want to see, but all of you.”

“Being authentic means that you have integrity to yourself.”

“It's the way our intuition is whispering something deep-rooted and true.”

“Authenticity is when you truly know yourself. You remember and connect to who you were before others told you who you should be.”

“It's transparency, relatability, no frills, no makeup, just being.”

Alex Cullimore: Welcome back to this episode of Uncover the Human. We are here today, Christina and I, with our guest, Sarah Filman. Sarah, welcome to the podcast. 

Sarah Filman: Thank you so much for having me.

Cristina Amigoni: Welcome. 

Sarah Filman: I am so excited.

Alex Cullimore: Give us a little background on who you are. What do you do? What are you up to nowadays? What got you there?

Sarah Filman: Yeah. So I am a leadership coach, a playful facilitator, an improv comedian, cat mom, forest bather. I got here. My background is in product and people management in kind of the tech sphere. I got into this space because even though I was working on products, I found that I always was drawn to people and process. So pulling on those threads in my career and saying like, “That's what really lights me up,” is what brought me into this space. Then when I took my first improv class just about five years ago now, that just lit me up and helped me grow in a way that I had not seen before. So I love to weave in kind of playfulness improv into as much of my life and work as I can.

Alex Cullimore: That's awesome.

Cristina Amigoni: Yeah. That is awesome.

Alex Cullimore: I want to know about every single one of those bullet points, but the one that I can't really identify off the top my head is forest bather. What does that mean?

Sarah Filman: Yeah. So forest bathing originated in Japan, and it's like a meditative practice where unlike hiking, where it's like climb up a mountain. Forest bathing, you might only go half a mile, but you go very slowly. You've taken everything from your senses, what you're hearing, what you're seeing. So it's a very like meditative practice. But because for me, I love to move my body, and so while I do meditate, as well kind of like lying down or sitting, the movement and really just like the things that you can notice when you're walking around a forest really slowly. I've found snail eggs. I've found just the coolest mushrooms. It brings you into the present moment. So that is forest bathing.

Alex Cullimore: That is awesome. I like that a lot. 

Cristina Amigoni: That sounds awesome.

Alex Cullimore: I have to try that. 

Sarah Filman: Highly recommend. You don't need a lot of space. You don't need a huge forest trail. It can be quite small. 

Cristina Amigoni: Well, you probably have some good forests around you as well, too.

Sarah Filman: Yes. Being based in the Pacific Northwest, lots of trees, lots of ferns.

Cristina Amigoni: That’s awesome.

Alex Cullimore: I love the Pacific Northwest. I'm always jealous going out there of just how green everything gets to stay. In Colorado, we usually dry out. It's actually just surprising we have any greenery left this time of year.

Cristina Amigoni: Really? Yeah. So more – I think kind of California desert.

Alex Cullimore: Yes. 

Cristina Amigoni: Yeah.

Alex Cullimore: Our typical climate zone is called an arid tundra. So if that doesn't tell you what you need to know.

Sarah Filman: Yeah. The Pacific Northwest is, I think, a temperate rainforest.

Alex Cullimore: Somewhat different. 

Cristina Amigoni: I don't even think we have snails in Colorado. Do they exist? I don't think I've ever seen one.

Alex Cullimore: Maybe a couple, but not much. It's too dry.

Sarah Filman: No snails, no slugs, no garden. What are your garden –

Cristina Amigoni: Endangered species.

Alex Cullimore: Mostly moles and rabbits. But I love the idea of forest bathing. It sounds like an in the moment practice, which is very much like improve, and I'd love to hear kind of what the tie in is and how you love to bring that into what you're doing now, leadership coaching.

Sarah Filman: Yeah. So I signed up for my first improv class because I was leading a team of about 16 folks, and I had great relationships one-on-one with all of them. But then we would show up to our weekly team meeting, and I was like a deer in headlights. My heart just palpitating, especially if I got asked a question that I didn't know the answer to right away because people want to know what's happening, what's our plan for this, what's my role, what are the responsibilities. People look to you as a manager to kind of have those instant answers. For me, it just sent a flood of panic through my body. So I signed up for improv to kind of get better at meeting the moment and answering questions in the moment and being more confident in the moment. I got that and so, so much more. Improv is really the process of listening to – It's fundamentally a team sport, I would say. So you're working with an ensemble of people to bring scenes and characters and ideas to life in the moment with no script. So you're making things up on the spot, but that doesn't mean that there aren't rules and mindsets that help you do that successfully. So it's not just like throw a bunch of people up on stage and say like go. There are skills that you develop to become a better improviser, one of which is really deep and active listening because that helps you pick up on everything that you're sensing and noticing from the other people on stage with you, and then build with it. So a lot of folks have maybe heard the concept of like yes and. So the yessing is listening and really saying, “Yes, I accept your reality. I hear what you're saying.” The and is how can I build with that. Through that, you build these scenes and characters that you never would have done by yourself. So that skill, it's a muscle. You can build it. You can practice it. Along the way, you are being silly and goofy. You are looking real foolish in front of peers. So it's this great training ground for building with mistakes, failing joyfully, all these things that in a professional workplace can feel really hard because everything feels so high stakes. In this space, even though the stakes are lower, those feelings still come up, the, “Oh, God. I don't know what to say,” or that kind of thing. But the more you do it, the more you can lean into it. So everything I just described, like active listening, building on other people's ideas, having each other's backs, and making each other look good, these are great skills for the stage to make people like laugh and chuckle. But they're also the skills that make great leaders, that make great teammates, that make great people in really any relationship because improv became such this incredible kind of personal development playground, personal and professional development. I don't really see much of a distinction when it comes to certain things. But because it just became such a great playground, I was like, “This is incredible. I am growing more. I'm just growing an incredible amount. I feel myself transforming.” So that was happening. Then I also knew about this coaching skill set as well, and there's just so much overlap, being curious, building because it's not just applying a happy go lucky mindset. You can build with anger. You can build with confusion. So it's really just accepting the reality and building with that. So that is why it felt so powerful for me to pull into my work as a manager, my work as a coach, my relationship with my partner to really pull that in. It's not only productive, but it's just fun. It's just fun, and I think adults, we don't have enough fun. We don't rest enough, all of those things. So the state of mind when you're in a place of play just unlocks incredible things.

Cristina Amigoni: That's awesome. Yeah. As you were describing the improv piece, I was like, “Wait. That's exactly like coaching. It's the deep listening. It's really understanding, acknowledging, and validating yes and. Then building as a team and not building just one way as in like, “I have all the information. Let me give it to you.” It's more about, “Let's build from that. Let's understand everybody's reality and then build from that.”

Sarah Filman: Absolutely. It sounds a little meta, but like life is improv.

Cristina Amigoni:Yeah. Life is improv. 

Sarah Filman: Right? We're living our lives without scripts. There are kind of scripts that we're operating on in terms of like the habits and the people that we think we are and our identities. But we are always at choice to actually change those if we can raise our awareness to them. So things that seem like they are fixed and must be a certain way, they're really not, right? If you start to like pull up those stakes and say like, “This doesn't have to be this way. We can make a new choice.”

Cristina Amigoni: Leadership is improv. Because as a leader, if you're out there and you're not walking in with your script, regardless of what's happening, you're actually constantly listening, constantly building, constantly saying, “Yes, and let's figure this out.” It really decreases the resistance. It decreases all those things that could make it so much harder if you walk in with this is the way this needs to be done, whether it's a project, team meeting, whatever it is. Let go of that and walk in with an improv/coach mindset of, yes, I may have the answer, and I may not have the answers, and both are okay. Let me help the team get to the answers because I probably don't even understand the problem. Maybe the team doesn't even understand the problem. So you're jumping to answers for something you don't even understand if you don't have that open mindset.

Sarah Filman: Absolutely. That openness to see what could be built. I think, especially the majority of my career has been in product management, and there are a lot of people come to you with questions of like when is this going to be done. So your job is to try to predict accurately and control. To control the situation and the outcome, it can feel like a big risk as a leader to come in and say, “I'm actually not trying to control the outcome here. There are some guardrails. I have a mindset that I'm going into this.” But releasing that control can be so scary, so scary.

Alex Cullimore: It seems improv and leadership, you would walk in with the idea of maybe you have your own idea. At which point, the other person enters the scene, and it's something entirely different like, well, now we're on this, where we've had to do this many times. That's a great skill to get more comfortable with that because it's going to happen a lot. 

Sarah Filman: It’s going to happen a lot. I was in a scene once where somebody stepped on stage and went, “Oh, my God, a meat eater. They said meteor. I heard meat eater. So it took the scene to like, “Oh, my God. There's somebody that eats meat. Let's be scared,” when they were like imagining a scene that was like a meteor that was going to crash into us. But the yes ending is like we are now running away from a vicious meat eater. That person had meant like, “No, I meant a meteor.” It just would have been less fun. We took it to the fun place, and that person yes anded it, and we had a fun scene about veganism. 

Cristina Amigoni: That's a great example.

Alex Cullimore: That's a hilarious example. Yeah. That's great. 

Cristina Amigoni: But I would venture to say like in a leadership position, how many things that come to you or how many things that happen in a day of a leader are actually planned and scripted when we wake up in the morning. I would say, I don't know, maybe 5% if we're lucky. On most days, it's 100% of what actually happens that day. You had no idea what's going to happen the way it happened.

Sarah Filman: Absolutely. 

Alex Cullimore: And you consider the coaching angle of it. It's a co-creation moment, like somebody stepped in. There was just a misunderstanding of what the original word was. But you're co-creating now the world in which people are afraid of meat eaters, which – Great. That’s where we're at now, right? That's coaching, and maybe that's what needed to be talked about. Maybe that's just what this – Listen deeply enough because this is where we're at now. Let's talk about that.

Sarah Filman: Yeah. Well, and maybe a difference where I've noticed that coaching and improv maybe deviate is that there's kind of this loose rule in improv of don't ask questions. What that means is don't put all the – Don't make your partner put in all the effort to have the answers to things. So if they come on stage, you're like, “Where are we going?” They're like, “We're going to the park.” “Why are we going to the park?” We're going to the park, so we can go forest bathing.” If you keep asking your partner questions in that way, you're not sharing that – It’s not a burden, but you’re not sharing the opportunity to create something both. So in that case, it'd be like they'd say, “We're going to the park,” And you might say, “Oh, wonderful, I've been meaning to try forest bathing.” Then you can go from there. Whereas I feel like in coaching, that lens of curiosity is huge, where it's like when you say meat eater, what does that mean to you? Then the person could say, “Oh, I didn't say meat eater. I said meteor.” Then you've kind of clarified, and then you can move forward with their intention. So in coaching, there's a lot more of the kind of powerful questions than there would be on an improv stage.

Alex Cullimore: I suppose that's true of leadership, too. If you come in and say performance review, and somebody is saying something else, you still probably want to go back to performance reviews. Probably is what originally you’re supposed to talk about. 

Sarah Filman: Yeah. But if you say performance review, and somebody expresses a lot of fear and anticipation, that's an opportunity to meet that moment, where it's at and say, “Oh, yeah. I noticed you're having a reaction to this. What are your past experiences with performance reviews? What are your thoughts here?” So it's really this constant invitation to dig in. One of the improv mindsets is everything is a gift. So every whether it's a complaint, emotion, idea, it's a gift that can be worked with. 

Alex Cullimore: There’s one thing you said earlier about that you don't really see a distinction anymore between personal and professional development. I think people are probably tired of hearing Christina and I talk about that, but what does that mean to you, and how does that 

Sarah Filman: Yeah. So my – I spend a lot of time talking to people about like work and play and saying like these two things do not need to be siloed. We can play at work, and we can dissolve that divide between those two things. So I think similar to like what is professional and what is not, what is that line? If I learn how to relate better to someone, to communicate better with someone in my life, and I'm able to take that into the workplace and relate better to someone and communicate better with them. I am me. We are moving through the world in different spaces and contexts. Who defines what work is? If you're volunteering, that's work. If you're doing work in the home, that's work. We make these distinctions. To me, it's more of a spectrum. It's more what is this environment asking of me? What do I want to put into this environment in this context? So I've just found that every way that I've worked on my own personal development has yielded so many benefits in the workplace because I spend a lot of my life in the workplace. My antennae go up any time there's kind of like a, “Oh, this or that,” or any kind of you can do this here but not here because I think everything's so much more nuanced and complex than that. That's where my mind goes. I think with professional development, there are certainly certain skills-based trainings that may only make sense in the context of your workplace. But I think, especially when it comes to leadership development and developing your communication, collaboration, I see no distinction in that realm of development.

Cristina Amigoni: Yeah. Shockingly enough, I think we would agree with that.

Alex Cullimore: I think that is well explained. I like that a lot. That's a good explanation for what the changes are and the fact that there is always nuance in those. I also love the image of somebody who comes up with some new skill and a personal life and then goes to work. I’m like, “Well, I can’t apply that here.” 

Sarah Filman: Right. I know. 

Alex Cullimore: Sure, it would help. But I learned that in life, so I can't do that here. 

Sarah Filman: So people really do make the distinction I think with life and work, with play and work. I don't think it serves us. 

Cristina Amigoni: Yeah. I'm not quite sure where this work stuff became not part of life. It was kind of like separated from – It’s not part of the day. It's not part of the week. It's not part of your humaneness and your human experience. It's this secondary planet that you just get it, put your suit on, jump to it, leave everything else behind because you're now a different creature. I wonder when that started happening in the workplace, that expectation.

Sarah Filman: Yeah. I like that image of just literally like rocketing off into space and you're just – It is a completely different universe, as though especially now, we're not just like walking to our dining rooms and hitting Join Meeting, right? Like literally, my life is – My piles are just in every nook and corner, nook and cranny around here. So I'm blasting off to nowhere right now.

Cristina Amigoni: It's the meta experience now. It's like, “Okay, we're in metaverse,” as part of our work and our work suit. We're now green instead of our natural colors. We have antennas or whatever it is expected to be non-human for the next few hours.

Alex Cullimore: I particularly like your angle of pulling play into this as well because it's like I love the companies like to tout that they are innovators, and they like people who are going to go take a risk or whatever. Then it's rarely reflected in actions. It's usually like, “Oh. Well, that person made mistakes.” Well, are they making mistakes or are they trying? Are they brainstorming? Are they doing something creative? Then we demand creativity, and we demand innovation, and we're like, “But you can't play.” Don't let your mind wander. You have to be somehow full bore creative eight hours a day in what is a very linear path. Is that how creativity works? So this happens? 

Sarah Filman: Yeah. The mind wandering. Forest bathing is fantastic for mind wandering and making those connections between things that you wouldn't otherwise think. But, yeah, I totally agree. There's this capital I innovation and like we innovate here. Yeah. If you don't create those sandboxes to play, you're not creating the conditions, the culture, the environment for people to actually be creative. The word play ends up resonating differently with different people. A lot of times, I ended up substituting the phrase, like how can we experiment with that? Especially I think in maybe like the tech sphere, where people are – There's more of a leaning towards kind of like logical, analytical parts of the brain. It's like, “Okay, then let's tap into that. What kind of experiment? How do we want to experiment with this?” Because I think experiments help you stay detached from the outcome. If an experiment “fails,” I think we've been like trained since we started our little Bunsen burner experiments in school to say like that's still data. That's information that's valuable, even if it wasn't what you expected.

Cristina Amigoni: I really liked that distinction and that use of the wording. It's interesting, though, especially in the tech world, and having been in it and worked in it for quite a while, it's back to that kind of like strange dichotomy of the seriousness, where if you use a word like play, there could be misunderstanding, resistance, whatever, lack of connection, whatever it may be. At the same time, not to generalize, but a lot of people that are tech-oriented are the ones that are into Star Wars, Star Treks, Minions, all those things that are related to play. 

Sarah Filman: Video games. 

Alex Cullimore: Video games, exactly. Like the playing is actually part of what they do in probably their daily life in one way or the other, whether it's having a little Star Wars figurine or playing video games or building on Minecraft with their kids. Again, it's back to that like, “Oh, but now your work.” Yes and – What’s the point? Da, da, da, da. 

Sarah Filman: Yeah. The thing that came up for me when you were talking was we are making broad generalizations here. But I think there's something useful in I identify as an introvert. I think that a lot of folks that gravitate into the tech space identify that way. So I think that there's a distinction between I really struggle in open-ended social situations. I do not know what to say. I feel weird and awkward. It's hard for me in that sense. But play in games, what I love about them is that there's enough structure and some guardrails and kind of challenges set up, and there are some rules and some guidelines. Then within that, you get to play. So that combination of structure meets openness, it's very similar to coaching, right? Coaching has a structure, even though there's lots of openness, and great games and playfulness do as well. If you just stick a bunch of people in a room and say, “Okay. Well, go play,” people are going to shut down because just to say go – It's like a blank piece of paper. There's not enough guidance there on how to engage. So I think one of the – When I'm facilitating with teams, it's kind of meeting people where they're at and saying, “Okay, what amount of structure would be helpful for you to engage?” We're not going to – I mean, people, especially when they hear the word improv, think that they're going to like have to do scenes in front of each other, and it's like, “Wow, that's a huge leap. How about we have a conversation, where the last letter of the last word that you say becomes the first letter of the first word that I say?” Let's see what happens. Let's just add one little rule on top have a normal conversation and just notice what happens, and incredible things happen. So it's really this tiptoeing in. I don't know if it's introvert. I just know that for me that structure provides an amazing way to engage, and the level of connection I'm able to have with people far exceeds what I'm able to do in just like an open-ended social situation.

Alex Cullimore: Basically a great point that open-endedness, and this comes up with leadership too. When people feel like it's too open-ended or they don't even know what they're supposed to be doing, then it slows everything down. For the same reason that you can't just like put people in a room and say go play. You put one piece of structure, one little thing. Like, “Everybody, there's one block in the room. Go play.” That’s like, is it a competition? Is everybody using that block? Is that what you just play catch with? I mean, there's tons of different things from there, but even just that one tiny little seed is enough to help grow something or at least anchor something so that you can go grow off of. It gives you some kind of constraint to say, “Okay. Well, we can go from here.”

Sarah Filman: Yeah, the growing. I just imagined like that lattice or a trellis, right? You can grow and bloom in all these beautiful ways, but you've got something to hold on to. I think I agree. As a leader, rather than trying to control the outcome, trying to instead put the right trellis in place, the right structure in place, and then saying, “Here's your anchor. Here's the block in the middle of the room. We can play with lots of different metaphors here.” But like focusing more on process than outcomes, focusing more on what are the practices that need to be in place, what are the behaviors that we want to be seeing that align to our cultural values. Then you get to blossom into whatever vibrant, whatever, but you've got this thing to hang on to.

Alex Cullimore: Yeah. That was – I love the thought on process as well. I think we just recently – Somebody shared with us a quote from – I think it was Winston Churchill, and I'm going to butcher it. But it was something along the lines of we plan our buildings, and eventually our buildings become the structures of our lives. We kind of plan these structures, but then those structures that we put in place dictate how we can interact and behave. So the process is very much the same way. We try and plan these processes. Eventually, our processes become us if we don't get diligent with that and curious about what's working and not. Those become the structures that are leading us down the wrong path and are not enabling the – You want to get towards an outcome. Sure. But how are you actually getting there? Those processes are super important and reevaluating that constantly. It is the trellis.

Sarah Filman: Yes. The how is so important. One thing that I've picked up from being in tech is kind of sprint planning and sprint retrospective. So sprints are these like containers to do work like, “Okay. For the next two weeks, here's what we're going to do. Let's not try to plan the next six months or a year. Let's just plan the next two weeks.” The end of a sprint is a retrospective where you're asking what worked. What should we keep doing? What should we stop doing? What should we change? I think to keep the building analogy, it's like you're only ever kind of putting up tents, and we can take down tents and change tents. It's like you're never putting anything too solid, but you can keep running with the things that feel like they're working. But making space to ask those questions of what is working and what is not working I feel like doesn't happen enough. That concept can happen. Coaching is great at that, too. Coaching is kind of like a bunch of a big retrospective. What did you learn? What do you want to put into practice? What do you want to change? I just love that the process that that's the trellis. That's what you anchor on to is like I know that I can – It’s safe to try this thing because I trust myself to check in later and change course if it's not. I think one of the reasons that people in the workplace especially struggle with change, I mean, for a lot of reasons. But when somebody says we're going to do this thing, you're imagining that you're going to have to do it forevermore, and what if you hate it? What if it doesn't work for you? What if it stifles you and suffocates you, and you're not innovative and creative? So all those things, and then you get that resistance. But if at the outset, as a leader, you can say, “Here's this thing that we're going to try for four weeks. Here's how we're going to check in on it at the end of four weeks. Here's how your voice is going to matter and be input into that.” I've just seen that tension melt away from people when they know that there's an opportunity to change things if it's not working.

Cristina Amigoni: That’s a huge piece because of that kind of tendency that Alex mentioned earlier, which is like we're in an innovative company. But make one decision and follow it all the way through. Don't change course. Don't make mistakes. It's like, “Well, that's not quite going to work. Even if you're not an innovative company, you can call yourself a rigid company, and it's still not going to work. It's just not how anything really works in life or in business. So having that openness, that conversation of we're trying this, and you will be asked. We want to hear from you afterwards about how it went. It takes a lot of practice. It takes a lot of muscles to be able to be on the receiving end of that feedback and have the courage and the vulnerability to say, “I want feedback, and not just positive. It's the stop, start, continue feedback. So bring it on, and I will work with my coach.” On the other hand, when I take it personally, and I lose my confidence after that feedback, but that doesn't mean that I'm going to not go solicit it. 

Sarah Filman: Absolutely. That leadership development, that personal development of the leader themselves to be able to receive feedback and do that detachment and say, “Okay, this experiment failed.” Not I failed. Not I am a poor leader or an incapable or incompetent leader. But this experiment didn't work. The conditions weren't right. The whatever wasn't right. It's not even then that the leader has to go off in a hole and fix it. So back to that, yes and. It’s like tell me what went wrong. Tell me what ideas you have. There's just such brilliance in your team because they were the ones that actually experienced the process. So I think sometimes we can get in that mindset of like, “Well, okay. I accept that it's broken. Okay. But I have to go fix it. I am solely responsible for fixing it.” That just doesn't have to be the case, and actually leads to less buy in on whatever the next iteration of it is. So it's like there's an opportunity there for that co-creation.

Alex Cullimore: I think that’s very well said, and I think that we put ourselves in like cements in both directions, we believe. If you said, “I love the tension melting piece,” like you remind people this isn't like a permanent. I'm not – That's why I think about cement. I'm not pouring cement around this, and we're all stuck here now. This is how we do it, and best of luck moving in the future. We want that relief of not thinking that it's permanent, and yet we can't give it to ourselves. Then we want the relief of not being the only person that's responsible for this ourselves. So this way, this play mindset and getting into coaching and getting into that, I loved what you said that coaching is a large retrospective. It's like your own retrospective on life. Getting into that allows that flexibility, and it's very hard to get to that space where you can allow that. We have a lot of systems saying you do it right, or you're not doing it, and it's hard to allow that flexibility, even though like you said, that's exactly what melts the tension, just to be able to try the first thing. It’s just saying, “By the way, we're not going to be stuck to this. This is an attempt at what we think will improve the future.” It’s much easier every time you do those retrospectives and start to figure out what did move the needle. What did we like about this? What other parts of the situation contributed? How can we replicate that or not? 

Sarah Filman: Yeah. That permission piece is huge. I totally agree that it's one thing to say, “I know I don't have to do this on my own.” It's another thing to actually ask for help or ask for support. Yeah. You pointed to the systems, the overall culture of what we think needs to be true and what success is and what productivity is. Those things live deep in us. I think that's why coaching can help because it can bring that to the surface again and say, “Yes, this might be something that feels deeply ingrained.” But that does not – But you have the choice to have your actions aligned to something different. You are at choice. As hard as it might be, as guilty as you might feel, as foolish as you might feel, do you want to take this action anyway because it aligns to how you want to be a leader in this world, want to be a person in the world? If the answer's yes, and you kind of like do it anyway, it doesn't mean that those feelings are just going to evaporate. But over time, I think you can build that muscle and see the results.

Alex Cullimore: I like that you said that the feelings don't evaporate. It reminds me of a lot of the quotes on like courage. It's not that you move without fear. It's that you move with the fear. The feelings are there. The worries are going to be there. It's how you react to that and whether you let that stop you that's going to determine what happens next, not whether you have the feeling. It'll be there. It will come back. 

Sarah Filman: I had the false belief, I guess, that once I'm not scared, then I'll do the thing. Once I get over this feeling, then I'll be ready. I think that's just such a great reminder that it can be a companion on the side. It can ride in the side car of whatever you're doing. But once you get rooted in, “These are my values. I really believe this. I really – This is how I want this team to work. This is – I believe in this culture. I believe in this organization and what we're trying to do,” like that rooting and grounding in that can help that fear stay in the sidecar, rather than like taking the driver's seat and like pumping on the brakes.

Alex Cullimore: I love that sidecar image so much. It makes me think of your fear as this dog with big flapping years and goggles, sitting in this little like motorcycle sidecar.

Cristina Amigoni: That's a better image than I had. I just had like you're sitting there and holding my tea, while I go through something. Like, “Okay, break. I can MIT for a second. Okay, I'm good. Stay there. Hold the drink.”

Sarah Filman: Is it doing something useful?

Cristina Amigoni: What I experienced is – Yeah. 

Alex Cullimore: Yeah. That’s really nice. I’m here to keep that warm. Hold it for you.

Cristina Amigoni: I know. I know you're there, and you're needed. Good. You can hold the tea.

Sarah Filman: Speaking of fear, a lot of people shy away from like their first improv class or bringing in improv because it's uncomfortable. I was talking with a friend recently, and we were detangling comfort versus safety. So, yes, doing something silly in front of your peers might be deeply uncomfortable, really awkward. But are you safe? Have the conditions been created to create a safe environment? I think one of the things that improv encourages is like having each other's back, creating that environment where you feel like you keep that because we're constantly sitting in situations that are uncomfortable, and that's not a bad thing. But so many of us are so uncomfortable with discomfort that that becomes a reason as well to not step in.

Alex Cullimore: I think that’s a fantastic distinction, that comfort or safety, and something – I don't think I put those two together in my head before, but that is perfect distinction. Creating a culture of safety is not the same thing as creating a culture of comfort.

Sarah Filman: Yeah. But I do think I've been in spaces or led meetings where people say, “I'm uncomfortable. Therefore, I am unsafe.” So they kind of escalate that. Detangling those can be really helpful because sitting in that discomfort together is how you have hard conversations. I mean, not everything is playful. There are hard conversations. Conflicts are real. Differences in opinion, like those are uncomfortable to navigate. Culture clashes, identity, folks have different identities coming together and trying to work together on something. It can be deeply uncomfortable. It may not feel that the way we think of like play and light, but play can help us get more practiced at being uncomfortable, and then take that into the workplace and say, “Okay. This feeling here, I'm not in harm's way. I just feel uncomfortable.”

Cristina Amigoni: Yeah. I think that's huge. Learning the distinction of that feeling is maybe we tend to call it fear in both situation. But is it fear because of safety, lack of safety? Or is it fear because it's something new? It's fear of embarrassment. It's fear of not knowing what to say. It's fear of maybe failing. So it's a different distinction. It's a necessary place to be when the goal is to grow. The goal is to be somebody else and do things differently and change our behaviors because growth doesn't happen in comfort zone. Growth happens when we are uncomfortable.

Sarah Filman: Absolutely. And it may actually be the case that it's not safe. I don't know like psychological safety in the workplace. It may be more than just discomfort. If you do not feel like there's openness to your ideas, if you fear being ridiculed or shamed for the half-cooked ideas that you want to share, if it's not a place where your ideas will be welcome, then, absolutely, those feelings of discomfort may be pointing to something that truly does not feel safe to be to put yourself into.

Alex Cullimore: That's a really good point, and that's why language ends up being so important in our own ability to navigate our internal language. This is like the entire concept of Brene Brown’s Atlas of the Heart, like giving you the language to navigate the feelings, rather than the three that people tend to come up with, the happy, sad, and –

Sarah Filman: Angry. Yeah.

Alex Cullimore: Yeah. It's a whole book on like all the different versions. There are times where you're uncomfortable because it is unsafe. So knowing that difference, knowing what that means to you and how you'd like to approach it is huge. Knowing that for other people is even bigger as a leader, like trying to figure out how do I create this for other people when – Did they fall off the cliff of safety? Did I create something that was uncomfortable? Am I missing something here? How do you approach that with curiosity again and not go back and be like, “I have to fix this,” as much as, “Okay, I need to figure out how to open this space, how to get this into a larger vision.” I love that distinction because that internal language is incredibly important. I'm curious for both of you guys. So you guys are both coaches. I'm going through the coaching training currently. Have you found yourselves like that when you do introspective work, meditation, journaling, anything, do you find yourself labeling your thoughts? You’re like, “Wait. Oh, nope. This one’s an assumption.” I'm now in my own like, “Oh, I just watched through this. Yeah, I can see now I'm not defining that word or like what does that actually mean to me?” I find myself more and more doing that now. I'm curious what you guys experience are.

Sarah Filman: Yes, yes, yes. 100%. I think it’s – Sometimes, I wish I could take a break from my own self-coaching because it's constant. Oh, yeah. I am using this word a lot. What does that mean to me? What assumptions am I making? What beliefs am I holding here? What is the block that I'm feeling? I mean, yeah, all those tools that we use externally we can use internally. I'm not kidding when I say I sometimes wish I could take a break from it, and I think that that is a thing that’s like the forest bathing or swimming or whatever other activity, just because once your mind opens up to, “Oh, these are my thoughts. These are my feelings. These are the beliefs I'm holding. I'm at choice.” Once you realize that everything's at choice, sometimes I wish for the autopilot days again because then you just – That kind of like everything's happening to me, and this is the way it has to be. Once you realize that this is not the way it has to be, it can feel incredibly overwhelming. I think that overwhelm, for me, is one of my, I would say, go to stress responses is just this is too much. I'm just overwhelmed. I know how many choices I have here. I know that there's a bunch of different actions I could take. It's hard for me to focus and find the one that aligns. So, yes. So I would say, Alex, get used to that.

Cristina Amigoni: Yeah. I would definitely 100% agree with needing the break from the self-coaching, needing the break from the constant looping soundtrack of Britney Spears’ Oops!...I Did It Again. I was like, “And there it is. Okay. That was an interpretation. That was an assumption. That was a limiting belief.” Or even things like I picked up some practices when I started a coaching journey three years ago, four years ago, where I write down the three things I'm grateful for every single day. Sometimes, I have to go back because I skip a few days. So I go back and kind of reflect, do the retro on my week so that I still don't break the streak. I started noticing that I use the same words. I’m like, “Why am I always grateful for health and safety,” which means I feel like it's not there. It's not automatic. It's something that I have to acknowledge because I actually don't feel safe. So when I do, it stands out. So then I start evaluating what are my life choices? What choices do I have in this situation to improve my just autopilot baseline safety so that I'm not constantly seeing it as, “Oh, so great. Nothing happened today, and I felt safe.”? Why am I always expecting something to happen? What about the environment, the condition that’s causing that?

Alex Cullimore: That is a great explanation and validating from both of you. I appreciate that, and thank you for sharing that. More and more, it feels like that there's that old quote about like, I don't remember which president said it, the Oval Office is oval because there's no corners to hide in, and it feels more and more like that. You’re just like, “Yeah, okay. Even when you want to sit, and you want to be frustrated, and you want to go hide in your cave, and you turn away like, I see myself doing this, and you can't unsee that, even when you want to go back to the autopilot days. I think that's a great metaphor for it. Even when I really would like just to rage a little bit, I know what I'm doing here, and I know that's not what's happening. It's like this dragging yourself back to the, yeah, I do know better than this. I know the limiting beliefs here. It's interesting, and I love the concept of things like forest bathing and challenging that like, “Okay, what do I want to change about my environment? What do I want to change about doing this?” This is giving you good information, even when you don't want to have to face it as information.

Cristina Amigoni: Yeah. One of the things that I learned past my coaching certifications, it took me a long time, at least longer than the coaching training part, was to accept that I'm still human. So, yes, I have coached training. Yes, I live in an oval office now. The cave is oval, so there's nowhere to hide. Yes, I know better. Yes, I can recognize it pretty fast. That doesn't mean that the expectations for me, for myself, is to always be perfect. That perfectionist of just because I know better, yeah, I'm still going to make mistakes, and that's okay. I'm still going to fall. It's still going to happen. I'm still going to make assumptions and interpretations and judgments and all of the things that we can recognize right away. What I can do is recognize it and then choose what I want to do about it next time.

Sarah Filman: Yeah, and making sure that it's so natural and normal for us to walk around feeling like, “I've still got to get it right. I'm the coach now. I've got to get it right. I've got to be the absolute epitome of aligning to my values.” That's a lot of pressure. It's a lot of pressure, and it's not realistic. You might be more conscious of making choices aligned to your values. But, yeah, Christina, to your point of adding the pressure that you can't have that sidecar of fear or the sidecar of perfectionism. Like we've all got our sidecars, Maybe there's a double sidecar. But, Alex, you were talking. One of the quotes I was thinking of is, “Everywhere I go, damn, there I am.” 

Alex Cullimore: Wherever you go, there you are. 

Sarah Filman: Yeah. And one of the things, when I think about doing kind of like improv activities or playful activities and why I think it can be so helpful is the stress responses that you have or the perfectionism that creeps up, that shows up even when the stakes are very low in a play-based setting. So it can be a great place to bring awareness to the fact that those things are happening. So I've gotten into situations with people, where we're playing, and I can tell they're thinking really hard. I'm like, “Why aren't you saying the first thing that came to your mind?” It’s because they're like, “Oh, I didn't think that first thing was good enough.” Where else in your life do you feel like the things that you think of aren't good enough? Where else are you hesitating or holding back from sharing because you think your idea wasn't good enough? There's always a place because everywhere you go, damn, there you are. 

Cristina Amigoni: There’s a sidecar still there. Pick your passenger, but the sidecar is still there. Yeah. It's really fascinating. Another piece that I'm curious about very quickly, Sarah, is what are some other examples where you integrate the improv into playfulness, into coaching, leadership coaching?

Sarah Filman: So one of the things that I use a lot in my work are these play personalities. Play researchers have identified these eight different play personalities that align with how we like to play, and a lot of these were formed when we were children. So there's the joker who finds humor in life's weirdnesses and quirks. There's the kinesthetic who plays through moving the body, the explorer who loves to discover new places, and people and things that competitor plays to win. The director loves to be in charge. The collector gathers the best objects and experiences. I think at six. The artist and creator plays by making and creating, and the storyteller builds worlds and stories. So most people identify with at least a couple of those that really stand out and say like, “Ah, that's the way I love to play.” So for me, like the kinesthetic, the dancer, the moonwalking through the woods, like I think through movement. So one of the ways that I pull play into coaching is having people identify what is your play personality because what are the ways – Say you're a storyteller. Maybe you've only thought of that outside of work. You do creative writing, or you love to read. If that's how you love to play, where is that showing up in your work? Are there opportunities for it to be showing up more? If you're someone who loves to discover new people and places, what are the opportunities for that to show up? It's a really great way for people to identify where they get their energy and identify like where in your leadership, where at work could that show up more. It might not feel like capital P Play to you. It will probably feel deeply aligned. It will feel like flow. It will feel energizing to you. It won't feel burdensome when you can tap into those things. So for me, like that kinesthetic, thinking through moving, it's no wonder, given that's how I like to play, that if I'm sitting – If I want to be creative, and I open up my laptop and just have a blank document, my mind goes blank. But if I go take a walk, seated with the idea of something, suddenly I'm brimming with ideas. So those are great ways to identify. People want to feel productive, feel impactful. So it's like how do you align those things with how you feel in flow, how you like to play. Then sometimes, in coaching, we literally play something. So once I know kind of the play personalities, I have a whole inventory of little activities and things that we could play together to kind of get in that spirit, in that head and body and heart space, and then move on. So a lot of coaches, when you're settling into a session, offer to do like a breathing or centering activity. I will ask my clients, would you like to do one, both, or none of the above? Would you like to kind of do a breathing centering exercise? Would you like to play a quick game? Do both or none? I think the folks that find themselves resonating with my approach are like, “Let's play a bit.” It takes a couple of minutes, just like a breathing exercise was, and it's just the energy shift that people experience. In just a few minutes of that, it's connective. It's creative. It's really incredible.

Cristina Amigoni: That's really fascinating. 

Alex Cullimore: I like that a lot. 

Cristina Amigoni: Examples. Yeah. I like that a lot. Now, I'm wondering which play person I am. A few of them definitely stood out to me, so I have to look into it a little bit more, spend some time reflecting. Maybe there's one of the personalities that person has to spend time and reflect.

Alex Cullimore: I think the one most immediate example for us, Christina, at least as a duo, is probably end of the week on Fridays, we're usually just like mentally flattened. So we will include in a lot of the presentations we're putting together and the decks and whatever activities are, we often end up with a series of gifts related to whatever's happening. So that's one of our go to. This has become – We’re slap happy now. It usually ends up – We end up like keeping it, and it ends up being one of the more popular relatable pieces of what we get to present the next week. That's I think one of the most fun ones we get to do. But that's an aside. I know that labels one of the areas, but it is definitely one that we have found a lot of joy in and has been a good way to connect with people.

Sarah Filman: So it's probably the Joker. I feel like gifts are really good at like – The memeable ones, like they are – The reason we love them is that they're just relatable. They're pointing out something funny. It's a facial expression we all make but with a clever, witty text on there. So maybe it's that.

Alex Cullimore: Yeah. It’s very disarming.

Cristina Amigoni: The Joker does make sense. Yeah. Because I also – The other thing that we do, and we tried to do a lot, and we'll know when we have a right fit with the client as well, is when there's a lot of joking in any meeting. So clearly, the meeting is going to have some serious conversations. It's going to have some hard conversations and a lot of the times because we're dealing with change. But at the beginning, like we always try to start the meeting in a light way. So what's the joke of the moment? Is it Alex's 10 cats or something that happened with me with my kids or something that happened with somebody else in their life? What's that joking thing? One of the elements that I always look for in the trusting relationship between us and the clients is as soon as we get to the point where there's banter back and forth, we've broken down the wall. Now, there's trust established because we know that on both sides, people are not taking it personally. Hopefully, people are not taking it personally. It’s always a test of waters. But if you can have banter, be on the receiving end of banter, like the client is feeling like they can joke about us, and we can also joke about them, then that's a good element for pretty much any interaction that we look for.

Sarah Filman: Humor and laughter can be so connective, so connective, and can absolutely be built in that space really effectively. I feel like humor is a catalyst for building trust at a speed that I have not found anything else that builds trust faster. Did you say that Alex has 10 cats?

Alex Cullimore: Currently, there are 10 cats in my house. Yes. 

Sarah Filman: Oh, my goodness. 

Alex Cullimore: We foster.

Sarah Filman: Alex. 

Alex Cullimore: So there’s – We currently have a couple schools of kittens going through right now. 

Sarah Filman: Speraking directly to my heart.

Alex Cullimore: I guess only one visited during this call. So that's rising honestly. With that, Sarah, thank you so much for all of your time. We only have a couple of questions to wrap up here, and the first one being the larger one and the more ambiguous. But what does authenticity mean to you?

Sarah Filman: Authenticity, to me, means your actions align with your values and beliefs, the true values and beliefs that you hold that are stripped of the shoulds, stripped of the have tos, stripped of the fear, yeah, and your actions aligning to those things.

Alex Cullimore: I like that. 

Sarah Filman: I like that a lot. Yeah. 

Cristina Amigoni: So where can people find you and play with you?

Sarah Filman: Oh, yes. Let’s play. So people can find me at So Playful Perspectives is my business, where you can find out more about leadership coaching and team development facilitation. I'm in the social media sphere. I'm most on LinkedIn. You can find me there and a little bit of Instagram. Instagram is more where I go to kind of share my doodles and jokes and things like that. So it's a little more of my creative playground on there. But, yeah, I would love to connect with anybody that this resonated with and who wants to play and work and dissolve the divide between the two. So I would love to connect.

Cristina Amigoni: Well, thank you so much.

Alex Cullimore: I think I’m speaking for Christina and I, and I want to say, we would absolutely send anybody your way. So if you need to talk, if you know us, go ahead and send it to us, and we'll send it out. But thank you so much there. This has truly been a blast, really fun to share this space with you, and thank you for all of your perspective. It's very refreshing and really well-thought-out, and I appreciate it.

Sarah Filman: Thank you both so much. This was incredibly fun and, dare I say, playful.

Cristina Amigoni: Always. 

Sarah Filman: Thank you. 

Cristina Amigoni: Thank you and thank you for listening. 

Cristina Amigoni: Thank you for listening to Uncover the Human, a Siamo podcast. 

Alex Cullimore: Special thanks to our podcast operations wizard, Jake Lara; and our score creator, Rachel Sherwood. 

Cristina Amigoni: If you have enjoyed this episode, please share, review and subscribe. You can find our episodes wherever you listen to podcasts. 

Alex Cullimore: We would love to hear from you with feedback, topic ideas or questions. You can reach us at, or at our website,, LinkedIn, Instagram or Facebook. We Are Siamo is spelled W-E A-R-E S-I-A-M-O.

Cristina Amigoni: Until next time, listen to yourself, listen to others, and always uncover the human.

Sarah FilmanProfile Photo

Sarah Filman

Leadership coach & facilitator creating playful possibilities ACC, CPC

Sarah Filman is a leadership coach, team development facilitator, and improv performer. She is the founder of Playful Perspectives, with a mission to help leaders and their teams connect, create, and thrive by dissolving the work/play divide.