Does your team health pass the vibe check?

In this Off the VPN episode, hosts Allison and Jasmine interview Sarah, a DevFinOps team lead at Jellyfish, to explore practical ways to build and maintain healthy engineering teams. The conversation covers authentic leadership, low‑effort rituals (dad jokes, sound effects, DJ intros) that foster psychological safety, and structured practices such as the "tree scale" sentiment survey and regular one‑on‑ones. A recurring "Choose Your Dysfunction" segment presents hypothetical team challenges (late delivery vs. misaligned fast delivery; senior non‑team‑player vs. no senior engineers; overly nice vs. constantly arguing) and elicits Sarah’s reasoning, highlighting trade‑offs between speed, alignment, mentorship, and conflict. The hosts also dissect a listener scenario about a junior engineer calling out a peer’s excessive overtime and rapid promotion, debating appropriate escalation and the dangers of rewarding overwork. Finally, they answer a listener’s request for light, casual mental‑health practices in meetings, emphasizing authenticity, sharing personal fatigue, informal check‑ins, and the "airing of grievances" exercise. Throughout, the tone is conversational, supportive, and occasionally humorous, with a clear focus on actionable tactics for engineering managers to nurture well‑being, alignment, and productivity.
Chapters
One thing that I really try to do is to just be authentic and be myself as much as possible. You know, you don't have to share everything in the world, but there are times when I'll come into a team meeting and be like, "Guys, I am so tired today. Like, I did not sleep." And everyone will like kind of laugh and whatever. You know, you start to build that dynamic where people feel comfortable sharing how they're feeling, even just before you try to do any kind of structured activity. So I think that's a big part of it as well.
You're listening to Off the VPN, the show where two work besties get real about working in tech.
Allison, what's up? How are you?
I'm doing phenomenal. Phenomenal.
How are you? I can't say phenomenal. I feel great, but phenomenal is pretty— I don't know. I don't know about phenomenal. I may have to review that. Let me get back to you on that answer.
Okay. It might have been a little strong. I'm not going to lie.
Strong start.
Probably should have went with I'm just doing pretty good.
No, I like the vocabulary usage. Yeah, that was good.
Well, today we have a very special guest who I'm super excited to introduce. Sarah is one of our amazing, should I say phenomenal team leads?
Yes, you absolutely should use phenomenal at Jellyfish.
And she has joined us here today on Off the VPN. We're going to talk about health, how you run teams that are doing good work, but also doing good mentally and in collaboration with one another. And Sarah runs an awesome team here at Jellyfish, so I'm super excited to dive into that topic. Sarah, do you have any words for us, for the Off the VPN listeners?
Oh, wow.
Oh my gosh.
I am so happy to be here. Yeah, thank you for having me.
Yeah, no, again, I want to thank— again, all of the things Allison is saying about Sarah, I super co-sign. I have had the pleasure of working with her when she was an IC here, and I was team lead at the time, and she was amazing, obviously still amazing. And just watching her kind of, you know, turn into a team lead and just kicking just complete butt. Just— we got to work together on several teams, and I've just always really enjoyed how Sarah has uh, led her team, which is why we're super excited about today's topic. Um, and I think Sarah, you have so many amazing, uh, things, fresh ideas when it comes to team health and how to lead a team and what are the different strategies that you can use to kind of uplift and keep your team motivated. So yeah, thank you again just for being here. Uh, I know Allison and I, when we were like, who's going to be our first guest? It was just like an immediate We already— we didn't even— it wasn't even a discussion. It was like, Sarah, it was like, absolutely, yes, Sarah.
Oh my gosh. Wow.
You're flattering me. So I couldn't have done it though without you guys. Of course, I feel like I've had so many different things that I've learned from both of you. You know, Jasmine, you've helped me grow so much in my leadership career and Allison, just like shared suffering and struggles together as team leads really has helped me a lot too.
So Yeah, no, I think we've all worked together in various, like, forms throughout, like, our years here, which is really, um, kind of cool. Sarah, why don't you, uh, tell us a little bit more about your role? Uh, what does your team do? What do you got? What do you even do on a day-to-day?
So my team is a financial workflows team. It's called DevFinOps, uh, here at Jellyfish. And day-to-day, I'm really, like, working on things like planning, what kind of deliverables we're going to have and really just helping to organize the work as well as a lot of Zoom meetings to just coordinate different aspects of the team, different people, making sure that people know what they're working on. So yeah, a lot to do with delivery.
How do you keep that fun for your team? We'll get into this a little bit more later, but just if you have like a quick, cuz that sounds very like, you know, business, which it is, but how do you keep that daily, you know, sort of like planning and coordination. You mentioned a lot of Zoom meetings, which I know for a lot of people can become tiresome. Like, how do you keep that fun?
Yeah, I think part of it is just making sure that people feel autonomous and able to express their opinion, just very involved. But I also try to add goofy bits, like I'll make really dumb dad jokes. Or during planning lately, every time we complete something, I play a different sound effect. So I think one time it was the Taco Bell bong for everything that we finished, and that was really fun. I think people will get a good laugh out of that. So just try to spice it up and keep people on their toes.
I love that.
I love that. And is that reminding you of Allison? Like our team? Do you want to tell the story?
I was just going to say that we have one of those. Our very own Jasmine used to play like DJ sounds, like, like in the daily standups. It must have been like 9:30 in the morning. Like, no one was ready for it, but she would just like come in hot with these like DJ noises that no one was expecting.
Wait, but I have, I have context. Like, I asked like, hey y'all, like, I feel like we should start Monday planning when we do our boardwalk with something exciting. Like, what do you guys think? And it was like crickets. And I'm like, what, do you want me to just make like a like a DJ intro? And they're like, sure. And they thought I wouldn't do it. So I did. And it was a custom. Our team name was Hydra, and I literally made it with the Echo. I put the thing and I played the sound. It'd be like, time for the Hydra Boardwalk. And it would just be— yeah, no one stopped me. We still laugh about it today. So I really value those goofy bits. Taco Bell sound is fire, though. That sounds like a good day.
Okay, we're gonna shift gears here a little. We're gonna do a new segment with you, Sarah, so we'll see how this goes.
So the new segment we call Choose Your Dysfunction. So I'm gonna give you two options, and so if you were gonna pick a team that you were gonna lead or manage or whatever, which team would you prefer to take? Uh, and you can say a little bit about why and like what would you even do as first steps? With this team. Sound good?
Yeah, sounds good. I'm excited.
So choose your dysfunction, a team that always delivers late or a team that builds things super fast, but they're not really aligned with the business or what the users need.
Ooh, well, I would probably say the team that's delivering late because we definitely had a little bit of that before. And I think it's, I know the playbook of like what kinds of things you can do to speed that up. I think that's a bit easier to fix than changing people's mindset about how the business works. That definitely takes a lot more education and effort.
That's a really good point.
That's a very good point.
Is that, is that where you're swinging, Allison, or which, which way do you think you would've picked?
I was swinging that way, but I wanna try and think about like the other case a little. If your team is working basically on the wrong thing, but they're delivering efficiently, like How do you, how do you bridge that gap? Like, how do you actually align them? Is that harder than like the mechanical, like, here's how we can deliver faster? I don't know. It's a really interesting question. But to your point, Sarah, like if you already kind of have those mechanics of like, like what does it mean to deliver late? It's so subjective, I think sometimes. So if you have those mechanics down of like, no, no, no. If we just like move this over here and optimize here, We can do anything, but I, I do feel like that alignment piece is something that you could potentially fix. But if you have devs on your team who are unwilling to sort of change their mind, which is, which is like maybe kind of what you were getting at, then like, yeah, there's no shot at sort of fixing that. Like if they're like, no, no, no, I firmly believe that like we need to turn the app pink. And like, they're like really adamant that that's what the users need. Like there's no reasoning with that, I guess. So yeah, that's a tough one. Yeah.
Speeding up delivery, I feel like is a lot more like check a bunch of checkboxes until you hit the right thing. Whereas, you know, teaching somebody to think differently takes a lot more like effort and it's very subjective, like the way that you can do it right, quote unquote.
But I think it depends though, right? Like I think to your point, like I didn't think about it that way of like, If people are building the wrong things and they think they're building the right things, that's a very different stage than like they're building thinking it, you know, like if they are unmovable, right? Like, no, no, no, I feel like the thing I'm building is right, then yeah, that's probably a lot harder problem. But also delivering late, again, it depends. Like, is it because there's unfocused, to which you talk about playbooks? Like, are we delivering, trying to deliver too many things? Or is it because I have a bunch of engineers who maybe need some like Skill work, right? Which would be a much— I wouldn't pick that one, right? Maybe that might be a little bit harder. Cause I definitely lean towards the business alignment part. Like I feel like that's somewhere that, and again, it's choose your dysfunction for me. Like definitely the deliver late, I have the playbooks there, but I feel like the alignment one is really interesting because it'd be challenging in the regards of like, well, where is this info coming from? How can I best align them to the business? So I definitely think you're right that I think it's easier to figure out the delivering late part. But for me, I'd probably choose the other one because I find that way more interesting. I have a bunch of people going super fast. The impact could be crazy if I could align them, like the impact would just be larger.
Yeah. You're just like, move a little over here and then—
Yeah. If you just—
Yeah.
If you go over there.
Yeah.
Right. But alignment's super important. You could be going as fast as you want, but if it's in the wrong direction, it doesn't matter. All right. I got another one. You ready?
Yeah.
Okay. So choose your dysfunction. A team that has a senior dev that isn't a team player, or a team with no senior engineers on the team?
I think it's a team with no senior engineers. I really find it satisfying to coach people and help them grow. And I think when people are more junior, they're more excited and willing to, you know, try different things and learn. Sometimes when there's like a very senior person, I think they're a little bit more stuck in their ways and their routine, and it's for a good reason usually, you know, it's something that they've learned from past experience, but it also means that they might be less open to different approaches.
Allison? Yeah, this is another tough one. I, I feel like I would go for the senior dev but who's not a team player.
Same.
I think, I think it's because, I don't know, you can't— everybody has different skill sets, right? And so I think I would value someone who is senior and who can share their seniority and their knowledge technically, even if they maybe don't wanna like, you know, play Zoom games on in meetings, or if they don't really wanna like hang out with the rest of the team. I think one thing to consider is like, what does it mean to not be a team player? Like if they're like outright rude to the rest of the team, like, okay, that's, I would maybe draw some lines there. But I think that that becomes like a, you know, like a manager's problem really to work with that senior dev on like, you know, helping them interface with the team a bit better. But I still think like having that seniority would be generally speaking, like very helpful if not for like, hey, that's what not to do when you become a senior dev. Don't like be mean to your teammates like that. You know what I mean? And I think there's still value even beyond the, the technical bits. But it definitely depends on what that not team player piece actually looks like in a day to day. Like, if they're hostile, okay, absolutely not worth it. But if it's just like, yeah, I don't really want to play your games on Zoom or whatever, I feel like we can live with that. Yeah, I'm leaning there. Jasmine, what about you?
Yeah, I think you guys both raised good points, and I'm kind of divided. I do think it depends on what needs to be done and the type of work, right? I definitely don't shy away from like a, I know we've talked about this in a previous episode, like a prickly senior engineer. I find like that to be, you know, what does a team player mean? Like I agree if it's an activity thing to your point, which I think is how you interpreted it, Allison, I literally don't care. Like I'm always like, no, I don't wanna go to this event or whatever. I'm fully encouraging people to do like what? Gives, you know, provides them, gives them energy, right? And so, but I do think the absence of a senior leader or of senior engineer puts a lot of onus on you as a lead to mentor, and it will be harder, like, to kind of get other tasks done. But that being said, it's not impo— like, either are not impossible. I do think I would, If I had to choose one, I would choose the former. I would definitely choose the senior engineer because I would, it's a lot easier to kind of figure out how to take their, um, experience and like target it in ways that work with the team and finding out how to like navigate where their boundaries are or like try to figure out how to get them to work better with the team. In my head, that actually is just like a part of team dynamics, right? Of like, How do people operate? Is this person a little more independent? Are they easier able to— and then there's obviously like hard lines of like, to your point, are they being rude? Are they like not listening to others? Those are things like, as a manager, like you just need to like shift out. And in general with engineers, a lot of engineers are like that, right? Like they, they think their way is the best way and you know, whatever. So I would pick the senior engineer because I do think experience is like, I would definitely want that experience to flow out to other engineers and also teach the junior engineers how to. Work with a senior engineer who might be, you know, a little bit like, oh my God, you don't know how to use that terminal command. You know, or like this PR is bad. Like I'd rather them to get that experience if I had to pick one of the two, but I think either are workable.
Yeah, the mentorship component is definitely a really good point. I think though, one thing I found with the junior engineers that have been on my teams in the past is that sometimes they come up with like the best and most unique ideas and giving them the space to do that without a senior engineer being like, hey, like this is the type of stuff you would do. If that's the way that they're rigid, it doesn't allow and give as much room for those new ideas. So sometimes it also is good.
But Sarah, when they're stuck on that great idea, who's gonna help them? That's very true. That's the thing I'm thinking about. 'Cause I agree, like I love leveraging, like pushing junior engineers. I think they have the most creative, they have so much value to bring. And they don't know it because they're new, right? I completely agree with that. But also when they're stuck, it's going to be me. I have to help them unstuck. And I'm like, man, I don't know. I, you know, especially if you're not coding every day, uh, when you're managing or something, it's just, it'll just shift your role. But, um, yeah, I, I like your, your point of view. Choose your dysfunction. We'll all choose our own. Okay. I have one more. Okay. So would you rather, uh, choose your dysfunction. So would you ever rather team who's too nice to each other, just, just super nice to each other, or they always argue?
That one's tough. I think that there's definitely value in, like, I've heard people say this, being kind but not nice. So that's like in the long run, you know, you're doing something that's better and for the greater good, better for that person growing, that sort of thing. So there is like a valid point there for, you know, sometimes arguing can be constructive. But I think that that would stress me out too much day to day, honestly, with constant arguing. I'd probably pick the nicer team.
I was thinking the exact same thing. Like, if I'm being purely selfish, we're being nice all the time. You know what I mean? Like, I don't want to go to work every day and deal with that. But I think because I like to think of myself as not a purely selfish person, I think I would probably rather us like argue all the time and like work through why we're doing that. Even if it means at the end of the day, like, we gotta split this team up. We're just not gonna make it. You know, I'd rather us like kind of say what needs to be said respectfully, of course. Again, assuming this is like healthy arguing or debate around, you know, like technical pieces or how you approach work or. Something as simple as how the team should function, like how many meetings should we have? Like, I would rather us like air all that out than like be very nice to each other's faces, but secretly like, you know, hate working together or hate showing up to work or whatever it is. Because I think that long-lasting impact in like 6 months or 1 year, like what's that gonna be like? So I feel like we'd have to just push through all the fighting.
I think though there's also ways to coach out of the, like, being too nice to each other, preventing growth. Like, you can do exercises where people are thinking independently and then you bring everything together. And then it's kind of like maybe a bit more on you as the lead to guide that conversation and make sure productive discussions are happening. But I think that's easier to do than it is to like say, hey, take it down a notch, like be a little more self-aware because I think sometimes That's just something that people don't click as much with.
Mm. I think that's like a really good point. Like the impact can be much higher possibly if there's like too much arguing, like people getting spinning off or whatever versus being nice. But to Allison's point, like that brewing part is not good either. Right. So, and sometimes, I don't know, I've had, I've definitely dealt with either like folks arguing or folks being like way too nice and I'm like, you're never making a decision. Like we're, we're not gonna get anywhere. I feel like this is the hardest one.
Um, yeah.
Oh, I don't know. I want to say argue, but I'm kind of— Sarah's convincing me of the other side. I don't know. I, I, I can't. I'm having a struggle. I'm struggling to decide on one. Yeah, I picked too nice because I feel like that I'm— I— but this is more of like a me thing. I think that I really relate to that kind of gut instinct, which is to kind of like hold yourself back or not know how to give constructive feedback or not know how to receive it. And so for me, I think that I can speak from a very like authentic place. And so that actually would probably be an easier muscle for me to flex. I could do either, you know, but I do think that that's like an easier muscle. So if I was picking the easier one, it would that, because I agree, like if people are, are always arguing or something, they probably just don't have something aligning them. And sometimes it just, it's a lot of strong personalities is what, uh, argument, people arguing all the time. So, but I don't know, both, both kind of suck. I want to mix. I want to mix, but I think, yeah, I'll pick nice because it'll make my day to day like a little smoother, but it's also hard because then if you're trying to get someone's like idea and they're not giving it to you and you're like trying to dig. But I, I guess I have to choose my dysfunction. I'll go with nice. So as we're talking about, you know, there's different things to think about with, in terms of team health, um, there's different types of dysfunctions that you could choose on a team, or, you know, there's just, there's always gonna be something up. Um, so I have a story for you that talks about some shifty team health things, like what's going on and how do people actually deal with it, uh, within the team. Am I the asshole for calling out a coworker for working outside of work hours to get ahead? This new guy joined our company a year ago as a junior software engineer. However, he recently got promoted to senior software engineer, something that usually takes people 5 years to do in our company. Management is always praising him and telling all of us what a great worker he is, but I've noticed that this guy is logged into his work laptop almost until 8:00 PM on weekdays and pretty much most weekends as well. First of all, can never be me. Like, what? 8:00 PM on weekends? What? Like, maybe if there's like an incident, but like willingly, willingly they're, they're working hard. All right. He's been doing twice the amount of work most of our senior devs do every sprint, and everyone thinks he's a genius, but it's mostly because he's giving the company a lot of free work outside of paid hours. There's some well-deserved people on my team who are passed over for his promotion because of him. And I think this guy is just setting a bad precedent in our company. We were all having lunch to celebrate his position, and once again, some of the business analysts and management were fawning over him. And I jokingly said, well, if I worked 80 hours a week, maybe I could get a promotion too. At this guy's lunch, promotion lunch, it's like, Well, yeah, I would too if I was working all these hours. That's crazy. Uh, nuts. A colleague pulled me over and said that that was rude and uncalled for. Was I— was I an asshole? Was it asshole-ish? Uh, I'm not jealous. I'm a senior dev too, and I make good money, so this doesn't affect me. I just don't want this to be a norm going forward.
I feel like this is very much time and place. That was a really rough time to bring that up. You know, I'd probably say bring it up to your manager rather than at the lunch celebrating the guy who made the achievement.
No, I don't think so. Like, that is so— what would you guys do if you were in this meeting and someone said that? What do you think your response would be?
Wait, was it a meeting or was it a lunch?
No, it was a lunch.
Oh, okay.
Well, who am I?
Am I a bystander? Am I the person who just got promoted?
I don't know. Like, what do you like? I'd be like, wow, that's crazy. I love that someone pulled him over and told him that that wasn't okay. That was a good sign of, of standing up and sticking up. Greet, not a good time. Imagine being the person who got promoted. I'd be like, yo, what?
That's what I was just thinking. Like, what would I do if I was that person? And someone said that to me.
Yeah, that would be so uncomfortable.
I'd be like, wow, that's crazy. And then I'd collect my check. Like, it's, it's clearly not the junior. Let's, let's start with like, the junior engineer is not at fault here, right? Like, mm-hmm. Even if they're working all of these hours, which again, I'm like joking, like they're making the, the decision, an active effort to kind of like get these deliverables done and push themselves, like. Somewhere along the line, someone is not noticing this, right? Like they're, or they're not like talking to this guy and being like, hey, maybe you shouldn't be working all of these hours, right? And then a junior dev, like who's working twice as much and doing as much as, I think he said twice the amount of a senior software engineer. That's crazy. I can't tell if this person is actually senior or not, or if is it just like, I feel like even if I had a junior engineer doing double the work and they're, they're, they're working 80 hours a week and they're doing as much as a senior engineer, like I don't, I, that doesn't necessarily mean they're senior at all. Right. And so I don't know if those are the characteristics, if it's just by purely an output standpoint, it doesn't necessarily mean they're a junior. I mean, they're, they're not a senior engineer, right?
Yeah, that's true. I mean, I also think one other thing up for debate is the, like, why do you know what this person's doing on weekends and at night? Why?
What are you looking at their timestamps for?
Yeah.
I'm like, that just feels like you're, I don't know, over-investigating this person. Like, why are you online at 8:00 PM to know they're online at 8:00 PM? Like, you know what I mean? Right. I just feel like I'm questioning a lot of the assumptions that this person has about the junior dev. Yes. Especially also, like, I think it's more common these days for people to have a bit more flexibility in their schedules so that, you know, maybe this person is like taking an extra hour at lunch to walk their dog and then they're working until 8 PM as a result. Like, I feel like there's a lot of room for possibility here that doesn't even necessarily mean that this person is actually working like way, way more hours outside of traditional work hours, like they could be doing that for a good reason and they're still actually maybe pulling like 40 hours a week. You know what I mean?
That's a very good point. Sarah, you think that this is like a bad precedent?
I mean, I think if people are trying to get ahead and they're succeeding in it, you can reward that. I, I will say though, like you said, I don't know that he's actually like necessarily senior in the sense of like the way he's thinking, the way he's acting. It might just be based on output, which then I think fundamentally the promotion ladder here is just busted up.
So, yeah, completely agree. I mean, I love to know like what type of things this person's working on. Like, I don't hate the gr— I'm not a hater on the grind, but I think like whoever promoted him needs to think about like, like to the, to, to this person's point, I do think they made like a valid point, like You'll only get promoted not based off of like your efficiency. Like as a senior engineer, I expect you to make the same for the same amount of junior developer hours. The senior developer hours, they're going to just output more like per just FTE, right? It's gonna, they're just gonna do more and be able to handle more complex problems, right? And so that's like what would signify like a promotion. And by doing this, I do think they make a valid point that like Assuming, making the assumption that the only reason why they're promoted is because they're working 80 hours a week. Yeah. Then what, what are you saying about how do you get promoted if there are people who are quote unquote more eligible dealing with complex problems and they're setting boundaries and only working 40 hours a week and that person was chosen over them, that does set a bad precedent. And so I would be wondering even prior to this promotion, why isn't someone, if I had, and Sarah, you can, you can back me up on this cuz you've worked with me, but like if I had an IC who clocking in way too many hours, I'd be like, you need to slow down. I'd be like, please take off. I'm like, this isn't even a question. I'm like, literally choose the 3 days that you're taking off because this is crazy. Like, this isn't— we're not even having this discussion. You need, you need to PTO. Like, that's nuts. I get it, sometimes you work more hours than others. I'm definitely guilty of that, but you've got to balance out work, otherwise you're going to burn out. Like, this is a marathon. This guy can't work 80 hours a week for the rest of his life. It's kind of a scam. Like, you're scamming people, you know what I mean?
40, bro.
Like, why are we doing 80?
Yeah, this person's gonna burn out, and they are just like really setting themselves up for failure, man, because there's no way you can keep doing this for the rest of your life, right? So like, you gotta think like about the long-term thing happening here, right? So whoever is managing this person, if they were not— maybe they don't know, but if they did know and they're encouraging it they, they need to reevaluate. Like, this is not a healthy way to run a team or to run or to manage someone or to allow someone to work this way. That's assuming that's a, there's a lot of assumptions baked into that statement.
I know.
Yeah.
You definitely have called that out before. I definitely remember you saying, hey, you need to take some PTO. So definitely could vouch for you there. I think if the person had brought it up in the right setting of like, hey, I'm concerned about this person. To that person's manager or to their own manager. That would've been a much more appropriate way to handle it. And then, you know, it's not really your, your job to tell other people how to work or what to do, but you know, manager can help them with that instead.
Was there a verdict?
Yeah, I was just about to ask that. What's the verdict? Is this guy an asshole?
I think so.
Yeah. I think so too.
I think that wasn't okay. Like this junior engineer, it's not their fault. There were a lot of options that he could have brought it up prior to this. This just wasn't appropriate. Like man's is just trying to celebrate all of the hard work that they did, whether or not they should have gotten that promotion. They didn't, they didn't give themselves the promotion. He's not the one to be mad at. Right.
All right.
So to close things off here, let's do a little advice segment. So I have A post here from an EM, an engineering manager, asking how to promote mental health or wellbeing during weekly team meetings. So I'll read the full post, but we can get into like how we would all maybe think about those things. Engineering manager here running multiple teams of a total of 30+ folks who all report to me. Specifically, we have a pretty close-knit team of 8 people that have worked together closely for years. Our team meetings are light and pretty casual. We do give the usual 5-second take care of your mental health thing and some links to well-being activities, which is perfectly fine, but it does seem like just lip service at times. Just wondering if anyone here does anything during team meetings that helps well-being or mental health. Light, optional, not awkward, casual. Then they gave an edit: we have an average of 40 minutes of meetings a day. I actively try to reduce them. Some of us are hybrid, some of us come into the office with optional, with an optional, like enforced policy, that sort of thing. So yeah, I think they're really looking for like light casual tips for keeping some of those work meetings, I guess, more centered around wellbeing and like promoting, like, is everybody doing okay here? Types of things. So what thoughts do we have? Sarah, Jasmine and I have both seen you do a ton of fun things with your team, so I really wanna hear you talk about those things.
Oh yeah.
Well, I think to, even before you do any of those things, you really just need to build a good foundation, right? Like making the environment safe and comfortable for people to like really enjoy those activities and to feel a sort of bond, right? So one thing that I really try to do is to just be authentic and be myself as much as possible. You know, you don't have to share everything in the world, But there are times when I'll come into a team meeting and be like, guys, I am so tired today. Like, I did not sleep. And everyone will like kind of laugh or whatever and it's fine, jokey jokes. But at the same time, then other people might be like, hey, like, I'm kind of tired too. Yeah. Oh, had a rough night. And you know, you start to build that dynamic where people feel comfortable sharing how they're feeling even just before you try to do any kind of structured activity. So I think that's a big part of it as well.
I love that. So you set the example, basically. Yeah.
Yeah, exactly.
Yeah. And you know, not everyone's gonna open up in like quite that way, so maybe there's other avenues as well. Like if you have a one-on-one with the person, trying to start with some more casual conversation and eventually kind of build up to it and maybe even ask leading questions that don't necessarily like directly ask it, but maybe make some hints. Or a lot of times I'll start out one-on-ones with a very open question of like, How you feeling? Or how you doing? And like, just let them take it from there. Or like, how was your week? Really just as open-ended as possible to see where they take it.
Yeah, you're not showing up immediately like in your, in your suit and tie, like, all right, let's get down to business, you know, tell me about this thing you're working on. You have to build a relationship first. Yeah, definitely.
Yeah, yeah. I love the idea of like, as a leader, like having first Being authentic is such a game changer for how you are, like your relationship with your team and how your team is seeing you. And I love the point that you make about like sharing like the ugly stuff, you know, like I'm not, I'm not, I'm not the first person to tell everybody my business, but I do think by showing imperfection and showing like where you're at helps other people feel more comfortable with their imperfection. That being said, there's also different dynamics, especially this person, they're manager of multiple teams, right? So you're the quote unquote boss, right? And so there's like an aspect that you can't really shake, right? Like there's going to be, I remember when I first became a manager and I went from knowing everybody to then the second, it was like the second I was a manager, they were like, I was like, hey, can we talk? And they're like, is there something wrong? And I'm like, oh, oh, I'm realizing there's going to always be that thing. So for my advice for that is like trying to make as much effort as you can to see the human side, but also like showing what you're willing to do for someone. Like I'm maybe a little bit like of a pushy, I think, and like not a negative pushy in a positive way, but like, hey, you seem like this isn't the— is that right? Like what can I do for— or I give them options of things that you can do. But yeah, I think to your point, like being authentic, sharing. I know Allison and I, our old team we had, we used to do an airing of grievances and that was like one of the first things we did when I was team leading at the time, which is a little bit different than managing. But, uh, just going around and saying something negative. It, it could be like a stupid negative to like, I don't know if you remember Allison, anything funny, but like, uh, I don't know, like, oh, I got my socks wet walking.
Talked about laundry every week.
I did. I always talked about laundry and it's a very like scoped way to share something that doesn't feel crazy, but it, it felt like comfortable where I think you can have like an environment of like overly positive or overly negative. Right. So I think like continuing to have a positive, like leadership style and kind of like moving things forward, but still making room for people are human. Like not everything is gonna be sunshine and rainbows and like, you don't wanna like accidentally like stifle people how they're feeling, right? So I think really active listening, being authentic, sharing your imperfections. That's like the summary.
And the one thing I remember distinctly about that particular exercise, airing of grievances, is like, yes, there were a lot of times where you gave kind of like a joke grievance about laundry or getting your socks wet, but we also had many instances of people actually sharing like legitimately hard things happening in their lives. And what that did for the rest of the team was basically open up those avenues of conversation to be able to be like, hey, how can I help you this week? Or like, if you need to take the afternoon off, like, let me run that meeting for you, or whatever it is. And so it actually like over time ended up like, I think, allowing us to work a lot better together because we were seeing that human side of each other, which isn't strictly necessary to work better together. But I do think in that specific case, it really did help.
So a question for you guys too is like, how do you know that something needs to fit? Like, how do you gauge a team's health just objectively? Like, what are the kind of signals that say like, hey, something's up here, or this needs improvement? What are the different things that you're thinking about?
So one thing that our team does is we basically take a survey every time we do a retro. Of like where everyone's at on a scale of 1 to 10. We call it our tree scale because for each number it's representative of a different stage of a tree. So like 0 is literally ashes, like you're just melted, you're burning, you're dying. We have a shrub in Manhattan on the lower end as well, which is just, you know, not a great state to be in either. But then on the upper end, you know, it's like a fruit tree or like a giant redwood, that kind of thing. And so Having that has definitely flagged a lot of things for me that I wouldn't have otherwise noticed. And, you know, seeing the ups and downs of like, okay, this person is usually at a 5, so I don't feel too bad seeing that again versus, oh, this person says 10 all the time, but now they're saying 6, like that's kind of low for them. Like, are they okay? And then following up and checking in on that. Whenever I'm talking about, um, team health with people or just like how they're feeling, I try to make it as like casual as possible so it's more approachable. Like having the formal, like, tell me what you're thinking about today. Like, what is the exact, like, problems that you're having? Like, list them out kind of thing is just not conducive to people actually being comfortable sharing with you. So making it like either a fun activity or just like a comfortable environment where people are down to share with each other, I think really has a lot of value. And that's not something you get overnight, right? You have to build that up, but the effort is so worth it. And, you know, eventually people will give you feedback on those processes as well. You know, I'm really comfortable saying like, hey, random team member, um, what do you think about us doing that? Um, and it does help improve those processes over time too. And I've made adjustments based on that and it, you know, it only serves to make us better.
Yeah, no, Sarah, like I completely agree. I think like sentiment is just so important to being able to see that and like look at the trees, I guess, over time. I know something that when we were on the same team, you were team leading, I was managing, um, was also just like sentiment's one thing, but also like how is the team actually performing being a really good signal as well, right? Like engineers are really happy when they're delivering, right? People don't like when their stuff is late, they're frustrated, they're annoyed, they wanna be on the next thing. If things are slogging, they're pissed, like they hate it. But I actually think like that kind of qualitative gut feel and like there's, there's like, how's everybody feeling and pairing that with the actual, like, what, what are we delivering? Are we delivering well? Right? Like, cuz at the end of the day, like we still need to keep our jobs, you know what I mean? So how do we like pair the two and make sure that everyone's feeling good and we're productive?
And they really go hand in hand, like you said, like having those good metrics and just feeling like you're getting things done and you're not thrashing about between like 10 different epics at once. It feels good too. So it really does. Like, if one is going up, it can sometimes just really help with the other.
Well, thank you so much, Sarah, for being here with us today. This was a lot of fun.
I always love chatting with you guys.
We will see you online at work.
Yes. Yes. Thank you so much.
On the VPN.
On the VPN, we will see you. Beautiful. Thanks for listening to Off the VPN.
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