185 Jessica Eastman Stewart: How to Bring More Joy and Ease to Your Team

Speaker A: Foreign. Hey, everybody, and welcome to Learning from Smart People. I am your host, Rob Oliver, and I appreciate you being with me today. Our smart person today is Jessica Eastman Stewart. She is the founder of the Joyfully Managed Team. She is a former nonprofit executive who now helps leaders of teams lead with more ease and joy. She is on Instagram, and she has a weekly email that includes five tips for life and work that you can sign up for. And I will put the links to all of those things in the show notes so that you don't miss them. In the meantime, Jessica, welcome to the podcast.

Speaker B: Thank you so much for having me. I'm really pleased to be here.

Speaker A: Absolutely. So let's start here. Tell me a little bit about your backstory. How did you start? How did you go from being a nonprofit person to being in business, helping people with joy? Like, what's the journey?

Speaker B: Yeah, Well, I actually started my career as a classroom teacher, and then, um, saw that there were policies and practices in the school systems, um, at the state level and the district level that weren't serving kids or teachers or families. And so, um, joined a group of folks and helped start a nonprofit policy, uh, education policy advocacy organization, and then spent a little more than a decade doing that as my professional work. It was an incredible opportunity, and we got to do a lot of impactful work. Um, and I learned a lot about starting an organization and leading teams. And so about a year ago, I branched out on my own, and now I get to support folks to create the kind of teams they want to lead and the kind of teams they want to be on. And I love talking about everything from team culture to productivity and time management and all of those things. It is a joy.

Speaker A: Okay, so let's talk about this. What's, um, the difference between the team that you want to manage and the team that you get sometimes? Like, is there a difference? Is that a fair question?

Speaker B: I think it's. I mean, it's a fair question. It's not an easy question sometimes, you know, as a team, you get to hire your own people and design, you know, the roles that you need on your team and the work you're going to get to do in the world. And that can be an incredible thing. I've gotten to do that. I've also had the situation where I needed to step in and lead on a team that somebody else had hired and kind of designed. Um, and they both come with their challenges and their beauty. Um, uh, so I would say both of them can be the kind of team you want to be on and the kind of team you want to get to lead. Um, but it just takes a lot of intention in order to make that true.

Speaker A: Okay. I would imagine that they both come with their own complexity. And here's why. When I am assembling a team, I am generally tempted to create a team that has more players on it that look a lot like me and people that think the way that I do. And when you are given a team that is already in place, sometimes you have a diversity of, uh, viewpoints and it feels like there's some tension in there because of that. Can you comment on those two scenarios?

Speaker B: Yes. Oh my goodness. There is such. There is definitely that tendency to want to find people that quote, unquote, feel like a good fit for the team, which sometimes can be folks who are thinking and acting and looking a lot like us, you know, and that bias is totally real. It's something to protect against. Because the best teams, and the research is actually pretty clear, the best teams are actually diverse teams who think differently, who look differently, who come from different racial and class and identity, uh, backgrounds. And so, um, yes, building a team that you want, building that carefully requires a lot of self reflection. What's the kind of person that I am, what strengths am I bringing to the table and what differences do I need to surround myself with? And sometimes that's pretty straightforward and easy. You know, I've heard plenty of leaders say, you know, I am great at the, you know, uh, the public leadership or the strategy, but I'm a hot mess and I really need people around me who are highly organized and can, you know, bring that structure to the team. You know, so sometimes people are incredibly aware of it. There's often a lot of that subconscious, you know, realizing, wow, I actually need somebody who pushes back on my tendency to A, B or C, you know, and that can be uncomfortable. But it's so important if you want to have that high performing team.

Speaker A: Okay, where would you say the balance is when you're creating a team? Between making sure that you are self aware, but also that you have the end, um, goals of what the team is going to accomplish in view as you put the team together. Like, where's the balance between those?

Speaker B: Yeah, I mean, I would say that the balance is you've got to have a team that works well together. Right. So a team that has like an incredibly high amount of tension is not going to be effective together. And at the same time, if everybody is always agreeing on everything, you're unlikely to be doing work in the world that actually matters and is impactful, you know, um, or is different in a way that is valuable. So I think the balance is somewhere in the middle. I honestly think that for, for folks who are struggling with this, um, and trying to find that balance, some sort of great executive coaching can be really valuable to help them figure out where are the potential blind spots that I've got so that somebody can kind of support you, but in a way that doesn't just, um, is helping you to uncover like m. You have a tendency to, for example, avoid conflict. And this might be how that's showing up in your leadership and how you're building and coaching your team, or you have a tendency to want to be really liked by your team. And that can be really beautiful in some ways because you might be able to build a safe team culture, but it also might be a place, uh, where you're not actually giving folks the real feedback they need to do their jobs well.

Speaker A: Okay, talk to me about this because you are talking about a joyfully managed team. And when you use the word joy, what does that word mean to you?

Speaker B: Yeah, I think I have an instinct that joy might be the whole point of life. What else are we here to do other than get to live joyful lives? And honestly, that is why I got into education as a career, to start my career, um, because joy is not as accessible to all of us as it should be. It's not evenly distributed. You know, not all of us have the same access to the choices that allow us to design lives that are joyful. Um, and I wanted everybody to have access to that. And I think that, you know, getting a great education is one of the ways that you can be able to make those choices in life. And so, um, I, I want to create a world where everybody's got as much ease and joy as is possible. And I acknowledge that it's not the same for all of us and that, you know, just life happens, you know, to us. Right. But I want folks to be able to plan for their joy because you get more when you plan for it. Um, and to create system structures, routines, and, um, teams on purpose that allow everybody to have joy at work and at home and in life.

Speaker A: Okay, you brought up the concept of systems and everything, but before I get there, I've got to quick story that I've got to share, and that is there's a legend, and I don't know if it's true or not, about, um, John Lennon when he was a. He was a child, allegedly his Mother told him that, you know, that the whole point of life is to be happy. And so he went to school, and they asked him, like, what do you want to be when you grow up? And he said, I want to be happy. And so the. Apparently the teacher brought him in and sat him down and said, listen, I don't think you understood the question. And then tried to help him understand what the question was. And legendarily, at the end of it, he said, actually, I understood the question. I just don't think you understand life. So, uh, who knows if that's a true story or not, But I think that seems to kind of fit in with what you're talking about. Is that resonating with you?

Speaker B: Yes, it really does. And I think, as, you know, as I'm a parent and as I raise my kids, that's what I want for them. I want them to be happy, you know, And I could go more in depth into what that means, but honestly, at the end of the day, that's the foundation of everything. I want my kids to get to have a happy life. And I, you know, if I went one step further, it would be. And that they are helping other people have a happy life, you know, um, and that could look so many different ways, but at the end of the day, I don't really care what they choose to do for money, you know, Um, I want them to be happy. And so probably we live in a capitalist society. They're probably going to need to have a job that creates some sort of money for them in order to be happy. But really, at the end of the day, if they get themselves to a place where they're happy and they're creating happiness for others, I will feel like I have absolutely hit a home run as a parent.

Speaker A: Excellent. I, uh, love the fact that what you're talking about is not just them being happy, but them creating an environment of happiness around them and creating happiness for other people. I love it. All right, so let's go back to what you said earlier. You're talking about systems and team function. Let's talk about this, because it sounds to me, and I'm biased, and I'll admit this, it sounds to me like the opposite of joy and is creating systems. Okay, so how do you put those two together?

Speaker B: Yes, I think that actually systems create space for ease in life and for joy. And I mean, I will. I understand. And I'm not surprised to hear you say that they sound like opposites, but I believe they actually enable each other. Um, and so I have just learned over the years that folks who take the time to create the systems they need to do the work they want to do in life and at work are able to find more peace, more joy, and more effectiveness in what they try to do because they've created systems that actually allow things to happen without everything being a total hot mess and with things being really, really intentional and planned.

Speaker A: Okay, so talk to me about the process of, uh, creating systems. What do you mean by that and how does that work?

Speaker B: Yeah, so I'll give a specific example. So one of the systems that I really love for teams and for my business, um, and even in homes, is the idea of a Polish week. And week might be a misnomer because this doesn't need to take a week. And sometimes it can. It can be really effective. But when I was leading teams, we would take time, twice a year to, uh, and we would say, this is our Polish week. We had to put it on the calendar pretty far in advance in order to make space. But during that Polish week, we wouldn't have meetings. Folks could work when they want to work, how they want to work. But we had clear expectations of during this week, we're going to clean up, we're going to polish up our systems and routines at work, and we're going to make. We're going to clear the decks, essentially, so that every other week that follows is way more effective because we've taken time to kind of clean up, polish up those systems and routines at work.

Speaker A: Okay, So I live in Pittsburgh and we, um, have Polish weeks all the time, except there's a slightly different pronunciation and it's Polish week.

Speaker B: I know, okay.

Speaker A: But the other thing is Pittsburgh, we speak our own language. Okay. We have words that we've invented. And, uh, you know, for example, the U plural here in Pittsburgh is Jens. But there is a concept that in Pittsburgh, we talk about the fact that you need to read up. Okay. And read up is some kind of contraction of readying and tidying. Uh, and so what you're doing is when companies coming over, you have to read up before they get there, which you're preparing for them to come. And it sounds to me like what you're talking about is reading up for the future, um, where you're getting prepared to tie up all the loose ends from what's been going on in the past and be ready to, to kind of start, hit the ground running when next Monday comes. How does that sound to you?

Speaker B: Yes, that Redding up sounds like a really good way to describe, uh, Polish Week for folks from your part of the world. I love that. Um, yes, and it's, you know, Polish Week looks different for everybody. And I actually have, like, a sample checklist that some folks have found some value in. But honestly, here's some examples. And not all of these will apply to everybody, but I feel like describing what you might do during a Polish Week could be really helpful. When I was leading my most recent team, um, here's the kind of stuff we would do during Polish Week. We would spend some time in our email inbox unsubscribing from stuff we don't want anymore. We would update our Internet browser bookmarks so the systems that the documents, the resources we need to get to most frequently were bookmarked. And that random article that we bookmarked seven months ago that we already read or we didn't read or we don't care about anymore is deleted. So it's not in our visual field anymore, blocking things up. We would clean up the desktop of our computer with all those files and logos and other things that we have still hanging out there that we don't need. We get rid of them and organize the ones we want to keep. We would put birthdays of our team on our calendar so we could be joyful teammates and say happy birthday to folks. You know, we would update our calendar and call the question on, do we need that Thursday afternoon meeting anymore? Does it have to be an hour? We call those questions, clean that up. We start to say, you know what? I've learned that after every board of directors meetings, you know, I really need some time to follow up from that. So let me make sure that I don't go from that meeting straight into another meeting. Let me go to every board of directors meetings and just put an hour and a half block afterwards. You know, I've also learned that before our all staff gathering, I really need the whole day beforehand to get ready because, you know, I just need to. I'm the person in charge of that. And I've got all these loose ends I've always got to do. So let me just go ahead and do that. We say, you know what? I've been having a no meeting Friday, and, and that's great. And now I actually want to see about no meeting Wednesdays too. So we revisit that. Um, we brain dump all the, you know, I've been needing to call that doctor. Let me just get that done. You know, get that out of my head. I've been needing to, you know, clean up my desk why do I even store my hole punch on my desk? I use that thing once a quarter, you know, and we just clean things up and just freshen things up and get things really ready. We update the data, we pull the reports, we reflect all of that stuff that makes your work better. Updating the software that you keep clicking snooze on because it just makes things so much faster. But you gotta create the space to do this.

Speaker A: Okay. You, um, have hit on a couple of nerves with me and I'm apparently going to. I don't know if I'm going to. I'll just say this. I'm going to have at least a polished hour once we're done here. Because it's so true. I have accumulated bookmarks in my computer from a couple previous jobs and from a couple previous computers. And I think that there are things that are in there duplicate, triplicate sometimes. And uh, trying to find them, I actually, I've given up on visually finding them. I have to go do a search for them in my bookmarks. And the other thing is I have tabs on my computer that are open for things that I wanted to look at and ah, I'm pretty sure they've been open for several months. And so I need to go through and clear out those things. Thank you very much for inspiring me and reminding me like, hey, you know what? Sometimes in order to be more productive, you have to take some time to be. You, uh, have to take some downtime in which you're not being productive. And can you, can you help me put that in better words? Because it sounds like I'm, um, sounds like I'm saying it's a great idea to not be productive. But that's not quite the case, is it?

Speaker B: Yeah, no, I know what you mean. It can feel like you're not doing what work. If you were to take a whole day or a whole week to say, you know what, I'm just going to polish things up. It can feel like you're not actually getting stuff done. I totally understand that. And that's the reality in some ways. And so the best way to find the space for this is to plan for an advance. Um, if you want to plan a whole day to polish up systems, you're going to have to look a couple weeks out at least and get it on your calendar, you know, especially if you want to create space for your whole team to be able to do this, you've got to look ahead. Um, and then you've got to create some accountability. If it's going to be hard for you to take that time. You're going to have to figure out, like, do I need external accountability? Am I the kind of person that is only going to do if somebody else expect me to do it? Then you might need to say, what about my Polish work is the kind of thing that somebody else could be depending on? And let me let them know to expect that, you know, like, hey, I'm gonna recreate the plan for our week during this time. Or I'm going to, you know, clean up our shared Google Drive and let somebody know to expect that from you if you need that external accountability. But if you can create that space and you some, maybe you need to, you know, take some of this habit science and like, pair it with something you want to do. So the only time I get to watch my favorite Netflix show is also while I am cleaning up my desk or while I am organizing my files. Pair with something you want to do, because creating space, it will make everything faster. Specifically to your tabs and your bookmarks. Some people had this with their email where they're like, I'm going to get back to that email from October 2019. It's really still in there, my inbox. I'm going to get to it one of these days. Sometimes you just need to declare bankruptcy. On your tabs, on your browser bookmarks, or on your email. You just say, you know what, we're just going to start from scratch and delete everything. Uh, or say, for email, I'm going to archive everything that is from a month ago or more. And there are ways to search your email for that. You can Google them. I lead a workshop on getting your email under control, and I show people how to do it. Because sometimes you just think, I'm going to get to it. And you've got 9,000 emails in your inbox, or 114 tabs open, or 355 browser bookmarks. And sometimes you just need to say, you know what? I'm going to either delete all of it and just assume that if it's important, it will come back, or I'm going to pick a date and say anything that happened before this week or before this month. I can just say that, you know what, I just got to clear the deck. I'm going to archive it so maybe I can find it later if I really need it. But it's not going to be my inbox, it's not going to be my bookmarks. It's not going to be open because your computer Needs to get restarted every once in a while. Maybe that needs to be on the Polish week is restart the computer.

Speaker A: Right. Okay. Um, I'm feeling very, very, uh, vulnerable right now. And I will tell you, I literally have one window that has 290 tabs open in it.

Speaker B: I think that's the tab champion. I don't think I've heard that much. I love it. Congratulations. Here's your trophy.

Speaker A: Thank you very much.

Speaker B: Now you can get rid of all of them.

Speaker A: Right? Well, I've got it. You know what? I don't have room on my desk for the trophy because I need to clean that up, too. So we'll just. Okay. Um, let me. I want to go back to this concept of joy that we were talking about, and joy when it comes to leadership. Joy. When it comes to a team, does joy come from activity? Does joy come from a culture? Like, what is the way in which a team leader can really develop joy amongst the people on the team? Or let me ask, uh, this. Is it a matter of creating a joyful team, or is it a matter of finding joy in your own leadership?

Speaker B: That's a great question. I think it's both. Um, I think that joy can't come from outside, so we can't depend on a team to bring us our own joy. And at the same time, joy can be planned for in a group setting. So I would say one thing the research is deeply clear about is that appreciation matters at work. And I think that's one place that joy comes. Folks have different kind of appreciation languages. Some people really like to be. Words really matter. Some people, it's like little gifts to show that they were being thought of, you know? Um, so it can be different things and look differently. But Gallup has done research, you know, of, like, literally millions of people, and the most engaged employees will answer positively to the question. I have been appreciated at work in the last seven days. So appreciation also needs to be frequent, more frequent than people think. They're like, I said thank you to Joe in July, so Joe, it should be appreciated. And it's like, well, you know, that July was a while ago. Um, Joe actually needs to be appreciated this week. Um, and so I think, uh, appreciation really matters, and that's a great way to bring in joy. And, I mean, people can use systems to support them, Right? So if that's not your strong suit, then set a reminder on your phone, send yourself an email, and snooze it, and then snooze it every Friday and say, that email reminds me that I need to appreciate folks on my team. And. And that can be a text, it can be a slack message, it can be an email, it could be a quick phone call, it could be a handwritten note. Um, it could be a Starbucks gift card just to say, hey, great job this week. Um, and the more specific, the better. Right. So if you can plan ahead for it, too, like, oh, you know what? Uh, Jamal is leading our budget work, and I anticipate that he's going to get that annual budget approved by the end of June. So let me make a note that at the end of June, I'm going to send him a bottle of wine to say thanks so much for your work on that. Uh, that was a big lift and you did a really great job. And you specifically got us to a place that was better than last year in A, B and C wiz. Um, I think appreciation is a big one for bringing joy to a team.

Speaker A: Okay. And how much importance is there on whether it's a symbolic appreciation or whether it's a tangible appreciation? And here's. I'll give you an example. Okay. I was working for a nonprofit, and we had one of the ladies who was there who just did a phenomenal job at what she did. And I felt like she was underappreciated. Um, I wasn't her supervisor. I was just a coworker. And so I actually. I went on ebay and I bought a bunch of million dollar bills, and I wrote her a little note, and it said, like, we're at a nonprofit. You don't get. You don't get paid what you deserve, and you don't get the appreciation you deserve. But I want to let you know what I think you're worth. And so, um, I did it, and I was embarrassed to death because she actually took the letter and the million dollar bill and taped it up on her door because it meant that much to her. Okay. And it's completely symbolic. You can't spend it. You can't anything. But can you talk about, uh. And we're almost out of time with this, but can you talk about the difference between getting something that is symbolic in nature versus something that is tangible in nature?

Speaker B: Yeah. Well, I love that story. It shows how much appreciation matters. And I think, honestly, it really depends on the person. And actually, um, there's a book called Languages of Appreciation. It's actually connected to the. The, like, love languages that a lot of folks have heard of, right. That we different. We receive and give love in different ways. The same is true of Appreciation, there's actually a quiz folks can take a little book they can read. I've done that with my teams and I've done some trainings with some other teams these days to help them figure out what is everybody's different language of appreciation. And it's not that everybody can't appreciate different types of appreciation. Some people love gifts. Some people just want to be given like a really kind note and words. Some people, um, you know, they want time with their manager and if they're not getting time, they feel really underappreciated, like if their check ins are always getting canceled. Right. Some folks really want people to appreciate them by, by helping them out, you know, seeing like they are busy and they want to be appreciated by saying, hey, uh, can I, is there anything I can take off your plate, you know, let me help you out with something or can I take that, that you know, little task off and do those calls for you so you can extra. You can really supercharge appreciation and joy and your team by getting clear about what matters most to everybody and what their style is. Um, but honestly, even the smallest thing of saying, we're going to put five minutes, the beginning of every weekly team meeting and this is a space for folks to appreciate each other. That is a very easy, simple thing. And folks can just say, you know, I want to say appreciation to Daisy because last week she just really did an incredible job creating that graphic and turning it into a video and, and people loved it. We got lots of great feedback on that. Right. And you can have your team do it for each other. It doesn't have to all come from the leader of a team, but there are little ways. And then if you really want to take it to the next level, you can use a resource like that book the Language of Appreciation at Work and really dive deep into your team. But honestly, whatever you do is going to add value, especially if you're not already intentionally bringing that appreciation into the team.

Speaker A: Very cool. Uh, a practical suggestion and I appreciate that. Listen, Jessica, it's been wonderful. Um, if people want to learn more about you, learn more about what you're doing, what's the best way to do that?

Speaker B: Yeah. So people can get on my email list. I send an email every Friday with just tips for more joy and ease in life called the Friday five, which is my favorite thing. Uh, they can find me@jessica eastmanstewart.com um, and if you go to jessicansmanstuart.com freebies there's like a Polish week checklist. If you want to, you know, that you can actually edit and make it your own. There's also 12 pages of meeting icebreaker questions, because I think those can bring joy to a meeting and kind of getting people into asking fun questions of each other, um, and connecting as human beings. Um, I'm on, uh, instagram @joyfully managedteam with kind of daily leadership team tips and productivity. And I'm also on LinkedIn if folks are there. Jessica Eastmithstuart. And I try to share the best things I'm finding and thinking about, uh, work and leadership, uh, there every day.

Speaker A: Cool. And I will put those links in the show notes so that people can connect with you. And that's awesome. Hey, Jessica, thank you so much. Um, it is now time for three questions to establish your humanity. Are you ready for this, my friend?

Speaker B: I mean, as ready as I'll ever be.

Speaker A: Okay. Um, do you know if you are related or even distantly related to anyone who is famous? Are there any famous Eastmans or Stewarts back in the, um. Back in the line.

Speaker B: That is so interesting. Honestly, I don't think so. You know, my grandfather's name is John Glenn, but not the famous one.

Speaker A: Okay.

Speaker B: Um, and then maybe there's a connection to Eastman Kodak, you know, maybe. I'm, um, not totally sure. I haven't figured that out, but now you're kind of making me want to go look into that. Um, but my parents would always say when people needed to spell their name, like Eastman, like Kodak. So maybe the Kodak company somehow.

Speaker A: There you go. That works. Okay, um, this one, um, is an overrated. Underrated question. The Star wars franchise. Overrated. Underrated. As far as quality of movies.

Speaker B: Mmm. Maybe I'm. I'm a Star wars fan myself. Not like the biggest Star wars fan, but, like, I'm a fan and think that everybody should watch it, you know? So I guess I would. But it's also. It is pretty. I think it's appropriately rated.

Speaker A: Okay.

Speaker B: You know, like, I am, um, Like, I like Star Wars. It's great. And, uh, it deserves its fame, but I'm not gonna say that it deserves, like, twice as much fame.

Speaker A: Okay. That's fair. Okay. If joy was a food, what food would bring joy to Jessica Eastman Stewart?

Speaker B: Uh, Chef Boyardee M. Uh, canned spaghetti and meatballs. Really, it is my favorite, um, comfort food. I eat it for lunch at least one day a week. Sometimes up to three, three or four days a week. And it makes. It's a little embarrassing, but I've started to Just embrace it. Because I feel like a child. I strongly believe that it is. I mean, like, one time we got grocery delivery, and they accidentally brought us, like, 10 cans of SpaghettiOs. And I was like, who eats SpaghettiOs? This is gross. Like, what am I, a child? And my husband was like, uh, just because they brought you the wrong brand of canned spaghetti. Spaghetti. I don't know if you can just. Hey, this one's ridiculous. Uh, but I was like, this doesn't taste good at all. But Chef Boyardee spaghetti and meatballs is delicious, and it deserves to be eaten multiple times a week. So, uh, it brings a lot of joy, and it reminds me of my childhood, and I love it.

Speaker A: Okay.

Speaker B: And I'm not sorry.

Speaker A: No, no apologies necessary. You are in a judgment free zone here. I will tell you quite honestly, I understand where you're coming from. My wife was raised no canned products. Like, really, like, canned soup? Not really canned spaghetti. No, that I was raised on Chef Boyardee and Campbell's soup. Like, that was when it was lunchtime. There was going to be a can opener, and it was opening some form of deliciousness. And ever since I've been married, my wife's like, yeah, no, no, nobody. Nobody needs to eat that. Nobody should eat that. And, um, every now and then, there's a little piece of me. It's like, you know, that. That wouldn't be a bad thing to eat. It would take me back to a fun and happy place. Listen, Jessica, thank you so much for being here. I appreciate you answering my questions. I appreciate talking to you. Uh, what you've brought is proof that you are indeed a smart person to all my listeners. I will remind you that when you stop learning, you stop living. Have a great day, everybody.

Speaker B: Sam m.