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improvisation skills

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Improvisation Skills

Improvisation skills in business sound counterintuitive. Afterall, there are strategic plans, goals, policies, procedures and other very carefully thought out activities. There doesn’t feel like much room for winging it. Yet today’s guest, Milo Shapiro, says using improvisation skills can actually make you a better business leader.

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What You’ll Discover About Improvisation Skills (highlights & transcript):

improvisation skills* Why improvisation skills can make you a better leader [01:53]

* How improvisation skill improve decision making [04:34]

* Why sharp listening skills are essential improvisational skills [05:26]

* How good improvisational skills can constructively advance business conversations [10:50]

* How improvisation skills create more awareness of team dynamics [13:08]

* And MUCH more.

Hanna Hasl-Kelchner: [00:00:00] Improvisation in business sounds counterintuitive. After all, that you’ve got strategic plans, goals, policies, procedures and other very carefully thought-out activities. There just doesn’t feel like there’s much room for winging it. Yet today’s guest says using improvisation skills can actually make you a better business leader.


Announcer: [00:00:25] This is Business Confidential Now with Hanna Hasl-Kelchner giving you the inside scoop on how to ignite more business success by doing the right things in the right way.


Hanna: [00:00:41] Welcome to Business Confidential Now, I’m your host, Hanna Hasl-Kelchner, and today’s guest is Milo Shapiro. Milo had an awakening right around the turn of the century in the year 2000, when, after 15 years of computer programing and systems analysis, he took a huge leap from the safety of that kind of work and that realm into the world of his passion, sharing the power and lessons of improvisation in the business world.


Hanna: [00:01:09] He had seen his improv classes over the previous 10 years and how the lessons were transferable into other areas of life, particularly into business. His training program TEAMprovising and his customized professional keynote has been praised by Kodak, Pfizer, Qualcomm, just to name a few businesses that are his clients. And Milo has also published three books, the latest being The Worst Days Make the Best Stories. These are true life tales with a lesson in each. It’s been called What Chicken Soup for the Soul might sounded like if Jerry Seinfeld had written it.


Hanna: [00:01:45] So fasten your seatbelts. We are in for a ride. Welcome to Business Confidential Now, Milo.


Milo Shapiro: [00:01:51] Thank you. Glad to be here.


Why Improvisation Skills That Can Make You a Better Leader


Hanna: [00:01:53] It’s wonderful to have you. Now, you know, improvisation is something we typically associate with comedians, yet most business decision makers don’t typically think of their business as a joke. What specific improvisation skills can help someone be a better business leader?


Milo: [00:02:10] We have great question right off the bat. I think when people think of improv, they are they are too quick to think of it in terms of comedy. And for sure, it’s a great form of comedy, which to me is far more fun because you just never know what’s going to happen. And it’s mixing of different people’s minds rather than just one. But keep in mind that the root of improvisation wasn’t to entertain.


Milo: [00:02:31] The idea of improvising is to be able to think of one’s feet, react quickly, find good solutions to things when they come up. That’s what life is. Life improvising is so through learning, but we don’t have any training ground for that. We’re thrown into the fire and usually we see everybody’s reaction and we see people panicking and that causes stress and others. So in learning how to have a mindset of when X, Y, Z happens, what is my reaction? What are the possible outcomes? Which ones are the better outcomes? Which ones are going to make people feel more comfortable and lead to better results? Choosing that better path is good improvising in the business place, but it’s kind of hard to learn that when you’re in the midst of it.


Milo: [00:03:14] So by taking in an improv class, one geared for business like the TEAMprovising program, we have a chance to practice good listening skills, building upon the ideas of others, non-verbal communication, creative problem solving, all things that you’re going to see in an improv show that’s for fun and for laughter.


Milo: [00:03:34] But applying those skills in the real world every time the phone rings and it’s someone calling that I don’t expect, I am improvising. I don’t have a script ready for what I’m going to say when that phone rings. That’s improvising. And how well you handle it can affect whether someone wants to work with you, whether you’re going to close a sale, whether the person is going to if it’s not a sales environment, a coworker, whether they’re going to feel like they can rely on you, that’s improv.


Hanna: [00:03:58] Well, that’s an interesting way to look at it. And what you’re saying certainly makes a lot of sense. I’d like to unpack that a little bit with you. OK, and maybe this is delving into this TEAMprovising program that you have. And I don’t want you to give away all your secrets. That’s not the point here.


Hanna: [00:04:19] But if somebody is open to this, realizing that, hey, this might make me a better decision maker, but at the same time, they may feel like, oh, improvisation is like going off the rails. We don’t really want that, do we?


Milo: [00:04:34] No


How Improvisation Skills Improve Decision Making


Hanna: [00:04:34] So let’s talk about the listening skills and building on other people’s ideas, because I know in some of the meetings that I’ve attended when I was in corporate, it was really easy for an idea to just get shot down. Nope. Sorry. Next. Is kind of how it went. And I don’t think that’s the kind of . . .


Milo: [00:04:53] And you’re the one who put that idea out there. That is not a good feeling. And often the company missed out on something because it wasn’t fleshed out.


Hanna: [00:05:00] That’s right.


Milo: [00:05:00] Before making a choice, a good choice, maybe it was the wrong idea, but how about hearing it through and seeing it in the context of other things and asking appropriate questions before helping that person maybe realize that their idea wasn’t a good idea? If they realize it, they’re going to have less hurt feelings. And maybe the reality is maybe a piece of that could be implemented, but not the whole thing. And we wouldn’t have gotten to that without delving.


Why Listen Skills Are Essential Improvisation Skills


Hanna: [00:05:26] Exactly. So let’s talk about listening skills and how we can improve, because from the research that I’ve seen, we don’t listen all that well. We jump to conclusions and listen just so that we can know when to enter. React and tell the other person to shut up.


Milo: [00:05:44] So would you say I was reading my email? I meant . . .


Hanna: [00:05:48] Touché


Milo: [00:05:51] Yeah, it’s really rough. We have this feeling that we’ve got to shove 14 hours into 8 hours, and the only way to do that is to multi-process. And one of the easiest ways to accomplish that, not successfully, but to accomplish that is to listen less. So we are we’re looking at our phones and we’re looking at other things while we’re listening, especially now. I don’t know how far out in advance people will hear this this cast. But at this point in time, our lives pretty much revolve around Zoom and its compatriots and other types of things. And it’s really easy to look like you’re listening.


Milo: [00:06:24] And the downside, besides to the person listening, the downsides of the speaker is not having a sense of did I connect or not? If you’re in a meeting room table and someone is on their phone scrolling through it, you know they’re not connecting. But if they’re looking fairly close to their camera because they could be looking at you on the screen, you can’t tell. Other people don’t tend to look into the camera when they’re listening. Look at you on the screen. You can’t tell if someone is paying attention or not. So it hurts on both sides.


Hanna: [00:06:52] Yeah, definitely, and especially if you have a Zoom call where somebody is not using the video, only the audio.


Milo: [00:06:58] Oh, I haven’t even encountered that, but that could certainly happen.


Hanna: [00:07:00] Yeah, yeah, exactly. Because they are doing something else. They need to be in attendance. But that’s about all. They’re not necessarily planning to participate and they certainly don’t want to be seen. So, yeah, very, very interesting. How can we improve our listening skills?


Milo: [00:07:20] The first step is to want to. People have to have an awareness that that’s something going on, because if you ask people if they’re good listeners, they will say yes. And if you ask them if other people around them are good listeners, they will say no. It’s kind of like everybody thinks they’re slightly above average, you know, and whatever you ask them. So you have to have a first mindset of maybe this is an area, even maybe this is an area that I could improve on, and making a conscious choice to say I’m going to do things that good listeners do.


Milo: [00:07:50] So I’m going to take notes. Even if I don’t keep them even. I can’t tell you how many meetings, I immediately throw the notes away afterwards on Zoom because I don’t need them. But having taken those notes while the person was talking, put me in a position of saying I definitely caught that and I probably asked better questions, which is part two, based on having written down certain keywords that the person said.


Milo: [00:08:12] The other side of my business is I’m a public speaking coach. So a lot of the time I’m taking notes while the person is talking to ask questions. And if there was anything really great we came up with in that I might send it to the client. So they have a record of it. But typically I delete that Word document afterwards. It was for my use in being a better listener and in giving better feedback to the person after their program or after they were explaining what their goals were to me in doing the program.


Milo: [00:08:37] So having that first, the idea of it. Second, asking good questions, summarizing backward the active listening at the end of a conversation saying, “so what I hear you saying” just to make sure I’m leaving this conversation right, is that in the business place we want to make sure we are providing good service. Listen to that about whatever the person was saying.


Milo: [00:08:58] And there’s just something so comforting about the other person getting to say, “yes, that’s just what I was trying to get across.” I had . . . I went back when I was in the corporate world because I was there for 15 years before I ventured off into what I do now. I had one client just so infuriating because I would explain something. And all I wanted all I wanted was for John to say, “got it? Or Yes, that’s what I meant.” Because I would be paraphrasing his long-winded answers to say so.


Milo: [00:09:25] You’re saying you want me to move that date to the top left side of the screen, I think was just a yes or no. Just say yes or no. So I know I got it. And it was so difficult to just . . . because he wasn’t clear and he wasn’t allowing me to establish I have clarity. And for him, you would think he would go, “yes, Milo, that’s just what I want. Thank you for summarizing it.” It was it was a challenge to be working with John.


Hanna: [00:09:51] Yeah, I can understand. There are some people that just keep circling around and around instead of being more direct, but summarizing or paraphrasing to concur that I understand you correctly. Am I getting it? Did I get it right? Also gives them an opportunity to clarify and.


Milo: [00:10:10] Yes.


Hanna: [00:10:10] So that its relationship building at the same time


Milo: [00:10:14] Because I wasn’t trying to show off that I got it. I just didn’t want to go and preprogrammed his thing and have him go that’s not what I want. If I’m wrong. Great. Good thing I asked. And with most people you’re not going to have the John reaction, you’re going to get just what you said you’re going to get. That’s just what I meant. Or not quite. You’re on the right track. But what I really meant was and that’s a good thing.


Milo: [00:10:33] So the fact in improv is that good listening skills are critical. And in playing the game, I don’t want to say that there aren’t games about it. In playing the games, succeeding and entertaining and feeling good and feeling like something happened, a lot of that comes from good listening.


How Good Improvisation Skills Can Constructively Advance Business Conversations


Milo: [00:10:50] I got to give you a super over the top easy example, but you can imagine it’s got more depth if you and I are in a scene together and then you leave and your name was Dolores in the scene. And then I pretend I’m opening a letter and I go, Dolores, come quick. And you’ve forgotten your Dolores. You’re standing in the wings watching. I’m in trouble. I needed you to be a good listener so that you could respond. That’s a very obvious example, but hopefully you wouldn’t have forgotten something that obvious. But the little details of improv can make or break how well things go.


Milo: [00:11:22] Another big thing that’s huge, and it’s just kind of relates to something you were saying earlier with shooting down each other’s ideas, is there’s a typical reaction with beginners in improv to want to be interesting by negating you say. “What a beautiful day.” And I say, no, it’s not. It’s raining. Well, I’ve just made it harder on you because you established it was a beautiful day. Why don’t we both know what the weather is if we both came from outside? So it’s learning how to do. You may have heard this term before. How to “yes and.” How to build. Yes. And since it’s such a beautiful day, we ought to go on a picnic. Now the scene has direction.


Milo: [00:11:57] We don’t do a lot of scene work in early improv stuff, but it’s easier to explain things with scenes than games if you’re not that familiar. So we’re on the same path with a “yes and.”


Milo: [00:12:08] Another thing that people do “is, yes, I got that.” And then they try it. They say “yes, but” and they don’t even know that. They say it was positive. I said yes, but you use “but” instead of “and.” You might as well have said no at that point, because now you’ve given a mixed message, which is worse than negating. So we start to pick up on it.


Milo: [00:12:25] One time. it’s only happened once, I heard someone in a beginner’s class, an improvising, a corporate class, doing scene building with me; someone said “yes and but” and went on and everyone laughed. He said, “Why are you laughing?” And we said, you just said “yes and but.” He said, no, I didn’t. And everyone said, yes, you did.


Milo: [00:12:40] It’s just an awareness. We don’t even know we’re doing it. So the more people do improv . . . TEAMprovising is a wonderful for a day out for a corporate group. But what I found was people who took improv classes with me every week, showing up, were saying I am just different at work and people are reacting differently to me at work. And I’m noticing when I’m stepping on people, I’m noticing that other people are stepping on each other. I didn’t have an awareness. You don’t know what you don’t know. And improv wakes you up when these things are happening.


How Improvisation Skills Create Awareness of Team Dynamics


Hanna: [00:13:08] Couldn’t it also be interpreted that through improv classes, that it’s developing team building skills?


Milo: [00:13:16] That’s why I call it TEAMprovising . . .


Hanna: [00:13:18] Well, it’s . . .


Milo: [00:13:19] because using improv . . .


Hanna: [00:13:21] It’s for the team.


Milo: [00:13:22] Yeah, absolutely for the team.


Hanna: [00:13:23] But still . . .


Milo: [00:13:24] Team building once upon a time in the late 90s started getting a bad reputation and people were rolling their eyes at it and with good reason because anyone who had a group of something fun to do suddenly saw corporate dollars and said, we do team building. Go karts. That’s team building. Well, you have a good time together. There’s something to be said. Absolutely. For simply having a good time together, going out for a meal, doing something fun. But the next day, what you’re going to apply to go karts, to teamwork is probably pretty minimal.


Milo: [00:13:54] Whereas with the improv stuff time and again, I’ve heard from people, I’m still hearing the message of what went on in that meeting, in that room together in my head or so and so has been very different since taking the improvising course. I think something’s flipped the trigger there, and I can sometimes be the cause of that.


Milo: [00:14:11] If I can say to you in a case where we’ll take it back to the earlier example, the it’s a beautiful day out when he says that and he says, no, it’s raining, I can go. You know what? You’re . . . you kind of negated . . . . give it a try again, but this time agree. “Yes and we should go play football.” How did that go? Oh, we had a much better scene after I agreed to play football, so I’m helping that person see it. That’s why I like small improvising groups where I can give that feedback.


Milo: [00:14:41] When people call me up and say we have 200 people for a team building event, I can’t give them that kind of one on one. And that makes a difference to be able to really point out those little differences. I’m not lecturing. I’m not making a person feel better. I’m helping them do better in the game so that they feel better about the same work that they do or the game that they’re playing.


Using Improvisation Skills to Advance the Five Cs of Teamwork


Hanna: [00:14:57] Fair enough. Now, I think somewhere in your writing, you talk about the five Cs of team work. What are they?


Milo: [00:15:08] Oh, a quiz to see if I can get the all five yes. Did I learned one thing along the way? Yeah. You’re better off with five different letters than the five C’s of because then you have to remember them all. But I think I can do it as the communication, cooperation, commitment, creativity and creativity, cooperation, communication, community and commitment. I think I got the five there. I think I did. I’m going to double check. I did. OK, good. I should have had that in front of me, but we were just in a conversational mode, so I didn’t have notes in front of. That’s fine.


Milo: [00:15:42] And when I do it in class, I always have it in front of me just to make sure. And as we’re doing the exercises, I will say afterwards. OK, so in that last game, which of the five Cs do you think we hit? Because I don’t want to do any games that don’t hit one of those. And some people might play that game with a cooperation game and other people might say, well, it was kind of a community game, like, you’re both right. There’s no one answer to it and with any game. But we want to be playing with those five to make sure that there’s value in the game.


Milo: [00:16:07] The nature of improvising is that I can vary it. So one of the questions I always ask the manager before we do the day is on a scale of zero to 10 where zero is, I don’t care if they have fun at all. It’s only about what they learn out of this. And ten is I don’t care if they learn a darn thing. This is just for them. They have fun together. What number would feel right for your group? And five of the most typical number I get, but I’ve gotten ten. This is a reward for them. So then I can throw in some games that are really a lot of fun, but there isn’t much to learn. And if I hear two, which thankfully is the smallest number I ever heard, I need to think someone wanted the people to have no fun. But someone said not, two. This group really, really needs to improve. And it’s nice that they have fun. . . but. So then I made sure every game, clearly there was a clear goal to learn from each game. And it’s nice to have that that ability, the vary it.

How Practicing Improvisation Skills Offers a Safe Space to Fail in Order to Succeed


Hanna: [00:16:55] Now I know in one of your speeches, you get the audience playing improv games in their seats or in an online breakout rooms called We Got to Fail to Succeed. Tell me more about that.


Milo: [00:17:09] Sure. So I was doing the TEAMprovising program for a couple of years and people kept saying to me, it’s great that you do this with ten to twenty-five people and can give us individual feedback. But Milo, this stuff is really powerful. You’ve got to do it like in a room like, like two or three hundred, like a motivational speaker. And I said, I don’t know how that could possibly work as a motivational speaker. And I commented on that to someone at an improv festival. And he laughed. He said, you have no idea who you’re talking to, do you?


Milo: [00:17:35] I said, I know you’re playing for the Las Vegas team. He goes I’m also the president of the Las Vegas chapter of National Speakers Association. And these people in your audience are absolutely right. You can do this in the keynote form you just don’t know how. You need to get involved with the National Speakers Association. And I’d done Toastmasters, but that was about improving my own speaking. It wasn’t about how do you build a speech for a large audience like that.


Milo: [00:17:59] So I got involved and discovered that a lot of event planners were craving a speaker who could get the audience doing and interacting and playing and not just watching the speaker for the full hour. So I developed a speech called We’ve Got to Fail to Succeed, meaning that if you succeed all the time, chances are you’re not pushing your borders very far and not growing very much. But if you’re willing to fail along the way, see what you learn and build from that. You get better and better and better. And I share stories from history and business and my life.


Milo: [00:18:30] We’re taking a chance, taking one’s lumps, learning from and building from there got us to a place we wouldn’t have been otherwise. And then I tie that back to improv. Improvisers who play it safe rarely get very good, but improvisers who are willing to fail and laugh at themselves and see what they did wrong tend to grow faster. And then I say, I see you all nodding. That’s making sense. Do you want to turn to the person next to you now? We’re going to try it. And I pull out a couple of games that we can explain very quickly because we don’t have much time in an hour that they can play with the person next to them. There’s no stage fright because they’re only playing with the person next to them. And I get them playing the game.


Milo: [00:19:06] And then I run around the audience and eavesdrop a little bit. And then I go back and talk about the kinds of things I notice in pairs. Can’t give the personal attention that I can in TEAMprovising. But beginners tend to make similar mistakes anyway. So I’ll say, how many of you have this happen in your pair? And 90 percent of the audience will raise their hand. So we get to talk about what they learned through the game. We get to play two or three games, depending on how long the keynote is. Really wakes up a conference. But more than that, it’s great that people go I didn’t realize how safe I was playing it even after you said everything that you said in the first part of the speech. And so you woke me up to that with the games.


Hanna: [00:19:40] Well, let’s talk about some of those common mistakes, because this is where improvisation could help and make someone a better leader. So what are the common things that you come across?


Milo: [00:19:52] In the Games what I find is that people are so determined to win the game and to succeed in the game that they forget to play within the game. There’s one game that I get to and this is sort of the big aha after the game. But I don’t know if your audience will be in my audience so I can say this, I explain the rules and I tell them it’s too long to go back to how you play the game right now, but I try to tell them to try to do this game without making these mistakes. And they will go so slowly with their partner. It’s like they’ll look at every word before they say it to not make the mistake that I tell them to watch out for that they can barely get a sentence out.


Milo: [00:20:31] And then I’ll ask afterwards, how many of you made no mistakes? And they’ll proudly raise their hand and I’ll say, great. And are you talking like this? And they all laugh at themselves because they realize I just told them they had to take chances if they wanted to succeed. And they played it totally safe. And then I give a surprise to the person who made the most mistakes, because I said I never said there was any penalty for making more mistakes than anyone else. I just try not to. That’s the game.


Milo: [00:20:59] And engineers just it’s a new world for them to be to be allowed to make mistakes. But what happens is when we start allowing for that and we start recognizing that it’s going to happen to all of us it can change the workplace. How different is it when five people gather around the water cooler and say, “oh, did you hear what happened to Joan the other day” when one of says “eww Joan” and then “oh, hi, Joan.” Poor Joan, poor Joan, poor Joan versus going someone going up to Joan and saying, hey, I know that Friday didn’t go so great in the sales meeting, but you were so rushed to get that presentation together, you did the best you could under that circumstance. I just wanted to say the next one will go better and we’re all behind you.


Milo: [00:21:37] How different is Joan’s work environment when someone comes up and says that? And how much safer is it going to feel for someone else to make a mistake knowing they back Joan that day? So that’s the kind of mindset to change. And for someone to say, you’re right, I made a mistake, but, boy, did I learn from it. And I feel way more prepared now for the next time I needed to make those mistakes, to just be open about that and to be the team that supports that. That makes such a difference.


How Improvisation Skills Can Change Your Mindset Around Risk


Hanna: [00:22:03] So it sounds like a large part of improvisation is getting a change in mindset, more of a growth mindset.


Milo: [00:22:15] Yeah, it is a mindset. I call it the improv mindset. In fact, it’s funny to use that word. It’s the ability to say what is, how can I add to that next? What’s the next piece I add to that? Not down the way I. . . . I understand the point of goals. I understand the idea of long-term vision. But if you don’t marry that with a certain amount of what should come next, you can strap yourself to your goals.


Milo: [00:22:43] I remember at my last job how frustrating it was every month that they wanted me to come up with my goals for the next month because my main job was to handle crises when they came up in IT. How could I possibly know what they were? And I had coworkers who said to me, well, what you do is you don’t report some of the things you plan to actually do so that when you don’t get to them, you can just put them into the next month. But you can. . . . I was like, oh, my goodness, how hard are we working to pretend we all have 100 percent goals? It doesn’t make sense.


Milo: [00:23:16] So to be able to say what is right now, what should I do from here? If I answered the phone and said to people, when people ask me if I could do something, there are times the answer is that’s not something I’ve done before and therefore it would be a dead end.


Milo: [00:23:31] But to look at what they said and say, I don’t do anything exactly like that, but here’s something I do not frequently and may be going a little beyond that in the direction you want is closer to what you want than that I’ve done before. And maybe it’s better than what you actually were asking me for, because I’ll meet these other goals, too.


Milo: [00:23:50] So in the end, I’m proposing something to them that they didn’t even know could exceed their expectations. And I’m not promising something I couldn’t do. I have to start from a place of I heard what you wanted. What can I add to that? So that it’s a possibility. If  I hadn’t, I would have missed on a number of corporate gigs leading Simon Says. You may not even seen that on my website. And it’s not a major thing that I do. But somebody came to me and said, I need someone who can lead 300 people in fifteen minutes in, Simon Says. And of all the people I have in my phone bank, you’re the only one I thought maybe he could do that.


Milo: [00:24:27] And I said, When’s the event? She said, It’s in three months. I said, by then I will be able to lead 300 people in Simon Says. And I took my improv skills and watched videos on Simon Says and found groups to practice with and knocked it out of the ballpark. We got it down to a winner in fifteen minutes.


Milo: [00:24:44] So it’s about being willing to say, “what could we do,” even if it isn’t exactly what we thought we were going to do? And we have to also be willing, sometimes this is so hard for some people to hear, we need to be able to implement with a B minus because that means you met your deadline. It meant they gave you an opportunity to say this is all we could do with the resources we had in this time and just say we’ll continue to improve or we’ll do better next time, but to not be stopped in their tracks by the fact that you didn’t get the A plus. And that’s hard for some people. It’s hard for me, but it’s a good lesson to have.


How Applying Improvisation Skills Keeps You Moving Forward


Hanna: [00:25:19] Well, a lot of people would like perfection, but that’s not the real world we live in. And as one person told me, sometimes you just have to stumble forward, but at least you’re moving forward. You’re building on something you’re learning in the process, like, OK, maybe that didn’t work quite as well as we had hoped. What else we can do? You know, what are our choices here? What are the options? The improv is a healthy way to do some brainstorming.


Milo: [00:25:47] It’s a safe place to do it. So if you give yourself permission to be safe, because the reality is you’ve very little to lose in that game where I said I have people count how many times they make a mistake at one of the things I point out to them. Afterwards I say to them now, I told you to count on your fingers every time you made the mistake, when you had to go from one to two. What was the implication of that tomorrow? What will that matter? It’s not going on your performance review. You’re not going to be paid any less. Nobody thought of you. It was literally lifting a finger. And yet how resistant were some of you to do that simply because you knew it was acknowledging making a mistake when the penalty was virtually nothing? So make that mistake.


Milo: [00:26:23] I love that phrase used, by the way, if you don’t mind me stealing, stumbling forward, I love that because it means making progress. Right. There’s a term that I like to use. I like to say direction, not perfection.


Milo: [00:26:32] If we’re in the right direction, we’re going to be closer and closer to our goal. And that’s really all we could expect of ourselves. Because perfection is a curse. If we stumble into it once in a while, high five. But setting perfection as a goal is just setting yourself for a very difficult life. And who would want to work with someone like that? It’s draining on everyone around them, especially if you’re the manager.


Hanna: [00:26:55] Yes, it’s exhausting, to put it mildly. And it creates a real fear-based environment where people are afraid to. Oh, my God, what did that look mean? Oh, they stared at me. Oh, I got an email. I don’t know if I want to open it.


Hanna: [00:27:11] All of those types of things, the anxiety is insane. The stress level is nuts. So I can see where. Yeah, like you said, you need to have a safe environment. And I need to ask you one question, though. In the teams that you’ve worked with, have you come across fear-based environments where the teams aren’t getting along and maybe somebody thinks, oh, this will make them play nice, so help them play nice? And there’s just a tension in the air that you can kind of cut with a knife?


Milo: [00:27:41] Yeah, I have. I’ve gotten anywhere from that to this is clearly a reward for these people because they already get along great. But that’s the easier one to talk about. Let’s go back to the first one you were referencing.


How Improvisation Skills Can Help Defuse Dysfunctional Teams


Milo: [00:27:53] There was one, in fact, where the guy said to me afterwards, I didn’t want to tell you how bad this group was because afraid you’d turn it down, I wouldn’t have turned it down. But it actually would’ve been useful information going in. But actually, it was good that I didn’t know in that case because I treated them like they were all going to get along. And the games brought out this good in all of them. That I didn’t know really that until he told me later how dysfunctional the group actually was.


Milo: [00:28:17] But there are other times when I could feel it. There was a group I . . . how can I allude to the industry? The industry is people who I’ll just say they serve the Navy in some sense. But it wasn’t the Navy. And there was some clear tension between some of the people and some of the groups. And, you know, we’re not going to fix that in a day. But creating an environment where people can play and chuckle with each other and have that sense, it’s a good thing. It’s healing.


Milo: [00:28:48] One woman called me up about her group, I can say, with a governmental group, and she said, I’m just going to be honest with you. We are doing this because if I make up a name because of Thelma, we are literally doing this entire thing because no one can stand to work with her. She’s good at her job. She’s not going anywhere. We don’t have any ground to fire her. But nobody can work with her.


Milo: [00:29:10] And I said, good, that’s really good for me to know. So I purposely paired up different people with Thelma all the time. I usually don’t plan out the pairings, but I was conscious of doing it in this case and Thelma never knew we’d have that conversation. And I tended to hover. I don’t think she picked up on it because it seemed random to whoever Thelma was paired with as I was wandering around getting everybody’s attention.


Milo: [00:29:31] But Thelma and other person got more of my attention and it helped because when Thelma would cut people off, I’d point it out and in a loving and supportive way, a different way, try that. And she would. And I was rooting for her. Yeah, that would better. How did that feel? How did that feel receiving it? Great! See how you two do. And Thelma, with my guidance, started having more fun and better interactions with people. And at the end of the day, Thelma was like, like, you know, as people were drifting out, she was like in the middle of the group. She’s like “bye everyone see you tomorrow.”


Milo: [00:29:59] And after she left, all of a sudden, everyone left was like, oh, my gosh, I had a conversation with Thelma. Thelma smiled. Thelma laughed. I have . . . supported my idea. And, you know, I would like to believe that carried over into the office. The boss gave me a really nice letter where she said it happened. Hopefully you can see it in the long run. Like anything, it needs reinforcement, but doesn’t really have to be for me, just reinforcement from coworkers thanking her, saying, I enjoyed working with you today, that kind of support. You know, you start a ball rolling, you got to keep pushing a little bit.


Hanna: [00:30:29] Wonderful. Well, this has been great. Milo, thank you for sharing your tips. And I could definitely see how improvisation can help add some skills to our leadership toolkit. It’s a way to engage a team, to grow, to learn from each other, to get to know each other as people, because I think sometimes we put on these masks in the office of, you know, do you know who I am? And I have my title and this is my responsibility. And you do this, this, this. And people get carried away. And it’s a way to connect.


Hanna: [00:31:01] If you’d like to contact Milo to learn more about improvisation skills and his programs, you can find that information in the show notes at And if you found today’s program helpful, tell a friend and leave a positive review on your podcast app or at


Hanna: [00:31:23] You’ve been listening to Business Confidential Now with Hanna Hasl-Kelchner. Have a great day and an even better tomorrow. Thank you.

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Guest: Milo Shapiro

Milo ShapiroMilo Shapiro had an awakening right at the turn of the century, in the year 2000. After 15 years of computer programming and system analysis, he took a huge leap from the safety of that realm into the world of his passion: sharing the power and lessons of improvisation in the business world. He had seen in his improv classes over the previous ten years how the lessons were transferable into other areas of life, particularly into the business world.

His training program, “TEAMprovising” and when he does his customized “IMPROVfessionals”  keynote he uses ten improv games to prove ten points on sales, management, teamwork, or other business topics.  Kodak, Pfizer, and Qualcomm are some of the clients who have praised his creative methods.

Milo is also a published author of 3 books, the latest being “The Worst Days Make The BEST Stories!” True life tales with a lesson in each. It’s been called “what ‘Chicken Soup for the Soul’ might have sounded like if Jerry Seinfeld had written it.” 

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Contact Milo and connect with him on LinkedIn and Facebook.

Also check out Milo’s quarterly ezine.

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