Oh, now it’s urgent? Cute.

It's miscommunication like this that causes mass go back to the office. This is the reason.

This is why RTO is a thing.

This is it. This is why, is because we, we gotta get together. This doesn't need to happen. It doesn't need to be this way. It doesn't need to be this way. We can't do this because otherwise then, can you imagine going back in the office every day again?

I'm sorry, I couldn't, I couldn't think of anything else to do but laugh when you said that. You're listening to Off the VPN, the show where two work besties get real about working in What's up, Jasmine?

What's up, Allison?

How's it going?

Terrible. You know, it's— this is the first day there's a little bit of sun. It has been raining every day. April is my least favorite month. I'm so sorry to anyone who was born in April or really, like, likes April. I have, like, journal entries of me being in, like, elementary school talking about how much I dislike April. Like, that's, that's how much I hate This is dark rainy days. I know some people love rainy days. I'm the complete opposite. If there's no sun, I am done.

Yeah, I shut down. Look at that. Wow, a natural poet here today on Off the VPN. Who knew? Finger fans. Shall we forget the awfulness of April and jump into a juicy story?

Yeah, you wanna, you wanna dive right in. You're ready. You must be, you must be ready to go.

I'm ready to go.

Are you? Are you okay?

I mean, I'm with you. Like the—

oh, this is also terrible for you.

Yeah, the sun not being out for like 5 consecutive days does major personality damage to me. Like, I'm trying to claw my way out of it. We'll see if I make it.

I don't know.

It's rough. All right, let's do it. I have a story for you, and today's story is about everyone's favorite dynamic duo. I would say in general in the workplace, but also especially in tech. Two things, miscommunication and deadlines.

Oh, it's gonna be fucking PM is one of them or Scrum Master.

So there is a PM involved in today's story, but that's not the dynamic duo. No, the dynamic duo was miscommunication and deadlines.

Oh, wow. I thought you meant like the dynamic duo. That's one of the output. Oh yes, for sure. Miscommunication and deadlines for sure.

Yeah.

Or should we call them targets or deadlines in this? Deadlines is crazy.

It's more of a deadline.

Yeah. Oh no.

You're gonna find out it's a deadline for sure.

Even worse.

Even worse. Worse. Even worse. Yeah. But so at the center of today's story is a developer who we're going to call Logan.

Oh, Logan.

You got any fun, fun nicknames for Logan?

I mean, I was thinking like, uh, Wolverine. Okay, that's the name of Wolverine. I don't remember Wolverine's last name, but I'm pretty sure it's Logan, right?

I think that sounds right. Yeah. Okay, so Logan, aka Wolverine, is the main character of today's story.

Um, he's a mutant.

Yeah.

Uh, titanium or whatever, the vibramium is like the type of thing.

All right. Yeah.

All right. Who else we got?

That's the only person entering stage left for the moment.

Okay. All right. So in comes Wolverine stage left.

In comes Wolverine stage left. He has been working at a smaller software company for about 2 years and is one of 10 developers. So Logan, AKA Wolverine, is working at a small company, maybe similar to early Jellyfish days like us, and because this company is small, it's a people need to wear many hats situation. And Logan specifically spends the majority of his time helping to maintain healthy and happy clients. And in addition to like one-off bug fixes, but also like, you know, smaller to medium-sized feature requests. In other words, his work is extremely reactive, right? Like a customer comes in, they want a thing. Logan's like, okay, I can like go and do that. It'll take me a day and a half, whatever. And so larger scale development projects or like anything that happens on the longer time horizon is like actually pretty rare for the type of work that Logan at least is doing. So one day Logan shows up to work and his manager is like, we're gonna change all of that. Not only do we want you to keep doing those things, but we'd also like you to work on a side project. And Logan's like, all right.

All right.

Yeah. Logan's like, all right.

So not reactive, maybe more proactive, more, more thought beefy. Okay.

That's right. And without going into too much of the technical details here, basically this side quest is going to be to integrate a new platform into the product. So my understanding is that this product that the company sells has a bunch of like third-party integrations.

Oh yes.

And typically how they spin these up per client, it's like very bespoke. It's a lot of like manual work to, for every single like new client onboarding to set up any bespoke integration. And so Logan SideQuest is, hey, there's this new platform that basically if you can integrate this into our product, it will just like remove all of that bespokenness and we'll basically be dealing with like a single set of APIs.

Got it. So here's a, another third-party platform they wanna bring in to unionize or unify all of the other integrations and platforms. That's allegedly, this would make it easier to onboard customers to be able to add integrations themselves. Is that what you're saying?

Exactly.

All right. Okay. Exactly.

The problem though here is that in Logan's assessment, he's like, this is not a one, it's not a one-man job. Like side quest or no side quest, like this is going to touch multiple parts of the existing system. It's going to be a big effort. Like, I hear you on the side quest thing, but it feels like we should probably have like more than one person making some of these decisions about how it all works. Like. Are you sure we don't want like another person on this? Uh, what are, what are your thoughts on that?

I feel like it totally, like you're, this is a 10-person company, so I feel like most things are single-person tasks. And I think how I would look at this is like a lot of stuff when we were early stage, we could not get away with now, right? We have. Massive amounts of customers. There's a lot more thoughtfulness, but there's a lot more things you could get away with. Like, if I needed, for example, to take the app down for a couple hours back when we were like a Series A, yeah, that's probably a lot— like, that's probably a thing I could do versus something, you know, now.

Like, I—

we could— I could not do that. I'd make a lot of people upset, right? So I think that Why I'm saying this is I think if they're feeling like this is a big job, like how can we cut it up? Explain like where this is. Make sure you get, say, hey, like I want someone else to think about this with me as a thought partner. I remember I used to do that back in those days, like, hey, so here's this idea, what do you think? Have people like collaborate, but you gotta kind of figure out how to do it on your own.

Yeah.

Because you're limited in resources. We don't have like giant dev teams to go off and do a project. But that's the fun part is it makes you be more creative about your resources, right? Like you're very smart about how to get something done quickly with basically nothing, right? So I think like this person needs to figure out how to make it happen and less about I need another person.

But then again, like they might be seeing something that I'm not.

So I, I wouldn't lead with, I need another person.

Yeah. And to give Logan some credit, I think that was more of an internal thought. I don't think he was like, no way, like I need other people if you want me to do this. I think he was like, okay, so just to be clear, like this is a side quest. How many hours a week are we talking? What are you thinking? Like he's asking those types of questions and his manager is basically like, yes, confirmed. This is a side quest. Not only is it a side quest, but it's not a high priority. So like in your downtime, throughout the week, like maybe give it a few hours and let's just send, make sure that you send progress updates to myself and the other main stakeholder who cares about this, which is our CTO.

Interesting.

And Logan's like, okay, so not gonna have to ask for other people. It's not like time critical. They just kind of want me to start chipping away at this thing week over week. What are you thinking?

I think if you know it's a big job, it needs focus and attention. So, and if it's a low priority, that doesn't make sense.

And then really quickly, what is, what do you think a good medium for providing updates to your manager or your CTO might be?

Probably like a one-on-one. I mean, especially when you're small and then you have like a standup.

Okay, great. So what I'm hearing is synchronous communication.

Yeah.

What they do is they decide to use a Slack channel exclusively. And so the usual interaction pattern for how this goes is that Logan writes a thoughtful update including like week over week what progress has been made and what blockers he's run into. And in return, he gets just a thumbs up. Okay, so, so basically Logan's like, all right, I'm, I'm just like talking into the void here. I'm on my own, whatever.

But like, are they like fully remote?

I do not know that.

I, I will say, I wonder what it must be like. Like, we were all together. I remember being like in person. I don't know what it'd be like to do And I, you know, I'm, I love working from home, but I'm like, I can't even imagine. You have to make more active effort when you're remote. So like async, especially when you're trying to move that fast with something that small and being that scrappy, like the importance of communication is even higher, I think.

Yeah. And like, this is a small company. You have to imagine there are synchronous meetings happening, like you mentioned standups and stuff. So, you know, I, I'm questioning the Slack thing here a little bit, but also I know the end of the story, so you'll see why in a second.

Um, whatever.

There's some other issues with Logan and this project, even though it's not a priority, right? He's like still expected to like chip away at it. And so sometimes he'll ask technical questions to other senior folks, like other senior devs, I guess, again in Slack, and it takes like days to get responses. But he's not really worried because again, everybody was sort of in on the fact that like, this is not a high priority. To be clear, Logan, your other—

anxiety, because there's some— I remember the deadline and missing communication. I know where this is going. I'm—

you know where this is going.

Anxious.

Yeah.

Who needed it? What deal? What deal is this attached to that this specific integration? I'm already, I'm already like.

You already know the drill.

Who did we say was gonna give us like X amount of money if we gave this particular situation, but for some reason they gave it to the one guy, said it's like low priority, chip away at it, not that important? Oh no.

Yeah, you're, you, you're exactly, you're exactly right. You've read the signs, you know what's coming. But like, Logan right now is not worried. He's like, we all agreed this is not a high priority, so it's okay if people take days to get back to me. And everybody knows this is a side project for me, so it's okay if I give an update one week that doesn't really have a lot of information on it. Like everyone knows, like I'm working on this when I have downtime and some weeks I just don't have downtime cuz he's still look like doing all the other critical, more reactive customer work.

Right, right.

So Lulu's not worried, but a few months into the project, you know what would've helped?

What if they had this? Do you know what, like, would help provide visibility during this, that he was doing so much, as we know, what would we call KTLO work? Bugs?

What? I feel a sales pitch.

I feel like you know the answer. I feel like you know the answer. Why don't you, why don't you, why don't you answer? Because, you know, I wish I was wearing my jellyfish t-shirt right now. I feel like, um, I'm like This sounds like a very— I don't know. I feel like maybe there's a solution here.

There is definitely a solution. Go to jellyfish.co. Get a demo today. Yeah, 1000%.

You're right.

We are sponsored by Jellyfish. Hashtag ad. We're a few months into the project and enter scene— stage left. Stage right. I don't know. Yeah, right. Product manager. A product manager comes up to Logan.

What is the project manager's name?

Whatever you want it to be.

Can it be— oh, maybe we should keep with the X-Men theme. Can it be Professor X?

Professor X.

Okay, so Professor So prefer, we'll just call him X for short.

Yeah. Okay. Okay. So X, our product manager at this company, tells Logan, hey, I'd love to onboard a new customer using your new integration platform instead of us needing to build another one-off bespoke integration to onboard this customer. And Logan, AKA Wolverine, is like, sure, that'd be cool, but also just so you are aware, there's some important elements here that are not production ready yet. And like, also, btw, not sure if you knew this, but this is like a side project for me, so I'm not really working on it consistently and I can't really tell you when I'm going to be able to get to them. Reasonable. The PM says, okay. And then Logan, sorry, X says, okay. And then Logan basically doesn't hear anything else about it for a while. So he just like continues going on as he's been going on. He puts in a couple hours a week when he has spare time. He's just doing his thing, right? No. Enter a random Wednesday morning. Logan shows up to work at his desk and has a DM from his CEO waiting for him. Oh, what are you imagining?

I mean, probably reinforcing that this is now a priority or something. I don't know. I don't know. I don't know. I don't know. But I'm, I'm like, oh, I'm uncomfortable.

Yeah.

Tell me. I don't want to. I don't want to know. Please tell me.

So the CEO just has a simple question for Logan.

Oh, not a question. Is it a leading question? Please don't be a leading question.

And this question is, where is the integration visible in the app? I can't find it.

No, no, no.

The context behind the question is that the CEO wants to demo it to a new client, and that new client is the same one that the PM X was talking about weeks prior. Really quickly, how are you— how would you handle this situation? Like, what are— what are some—

wow, that's crazy.

First response, wow, that's crazy.

I'd be like, I mean, I just— I'd keep it a stack. Like, I'd be like, what do you mean? I'm like, there's no integration live.

Yeah. Like, where did you get this information?

Question mark. I'd ask them a question back. That's crazy.

Yeah.

And then I would DM my boss and be like, actually, no, I would screenshot it, send it to my boss. I'd be like, so why is this happening? And I'd have them deal with it at this point. I'm just the IC.

No, that's, that's not—

isn't there 10 people? Like, what? Yeah, not giving 10 people vibes.

10 developers. 10 developers.

Oh, 10 developers. That's still different.

That's still a small company though. Okay, so obviously Logan is confused. Uh, yeah, we can all agree that this is not— I mean, what would you do? Left field. What would you do if you got like a message I mean, I would definitely sweat for, for a while at my desk and like panic maybe a little bit. But I think ultimately I'd be like, this is like our miscommunication here. Like the game of telephone has like been screwed up so badly that we need to just, I would just be like, we need to just address this now and like, not like make any major decisions, but I'd be like, do you have time to hop on a call? Like, I think we need to just clear some things up first. Um, that would probably be my go-to, but I would be like freaking out for sure. Cuz that level of misalignment is like, how did we even get here? Something is really off. But yeah, so eventually though, like what happens in Logan's case, I, I don't know exactly what he did immediately, but Logan, AKA Wolverine, eventually shows up to a meeting with this CEO and they have a synchronous conversation. The CEO shows up and says, I need you to drop everything else you're doing. It's not just that, but the CEO sets a deadline.

Oh no, I don't like where this is going.

The CEO gives Logan a specific date and he's like, we need this in production ASAP, but get it done by this day and we're good. Logan is like, Logan is spiraling. Rightfully so.

Logan is—

first of all, wait, how many days?

How long?

It's not super clear from the story, but I think the CEO gave Logan like a couple weeks, like another 2 weeks. And obviously this means that Logan has to put down everything else he's been doing and just focus on this full time. Logan goes back after talking to the CEO and is like, okay, how can I get this done in 2 weeks? How can I cut scope? Like Logan is going through all of the motions to try and figure out how are we going to make this deadline work? And even with cutting scope, figuring out how to deliver the bare minimum, again, just for a demo, right? This is for a demo. Logan's like, I'm gonna need 1 or 2 more weeks after this CEO set deadline. He doesn't know how to tell the CEO that though. He doesn't know how to manage everyone's expectations. Right. So, but here's the thing. Yeah. Unfortunately, like so many of our stories, we also end this one on a cliffhanger. All I know about how this ends is that Logan basically freaks out, is wondering if he needs to be pulling all-nighters to get this done, or if he can go back to his manager and the CEO and find a way to say, I need 2 more weeks to do this. All I know is that Logan is questioning absolutely everything about even working here, in addition to how do I move forward in the next day.

There's a lot of red flags. In the air. Like, and the fact the CEO isn't talking to the other people who are setting the deadlines and going directly through— that is just dysfunction at its finest. Like, we, we are very, uh, dysfunctional here, which is sad if it's such a small company. Again, I would not expect this level of dysfunction this early. That is not a good signal. Mistakes happen, that's fine. But like, there is like a layer, I think, of kind of communication jumps that clearly don't need to exist at this level. And I think that's kind of like what I'm seeing.

Yikes. If I'm Logan, I'm like, that's it. I'm calling an all hands. I'm gonna set the record straight on this project. Like, how big is this company? Let's just, yeah, I know everybody has this same information.

I'd be like, no, no, no, no, no. We need to talk like this can't keep happening.

A.

Being like, I also think with like the solution itself, I would probably lean out on my engineer friend, like if not friend, my colleagues, and I'd be like, all right, listen. Yeah. I need to brainstorm how we're gonna get this done. Like, I think like, don't put it all on yourself.

Yeah.

I think maybe if, even if they're not contributing as a developer, but maybe there is some support, they could be like, oh, I could do that. Like I've done that before. Or. You can get input so that maybe there's some shortcut you're not thinking of. So I would probably be like, I'd say in Spanish, I'd be like, guys, CEO literally asked me to do this in 2 weeks. I'm not really sure how. So anyone who wants to help me figure out how I can do that, please do that. I think like sometimes, you know, people take on things and they feel like they gotta do it themselves. I actually think one of the early lessons as a developer is like learning to get support from other people is actually what will make you successful. At least for me, that's a big lesson I learned. Like you can spin your wheels all you want, but I actually think like you have a literal, what do they call that? Like a treasure trove of just people around you to help you strategize. So I would just lean in on that. But then again, the senior engineers weren't answering them. So, um, I don't know.

That's what we're calling an all hands and we're saying like face to face, this is like, I need help now. But yeah, I totally agree with you. That's a thing that you have to learn at some point when you need to ask for help versus how much am I going to gain by staring at this by myself for another like hour or two? Like this is clearly a situation where you bring in, you bring in your colleagues for help. Yeah. I hope Wolverine did that. We don't know.

Yeah, I don't know. That is not fun for— no, it's miscommunication like this that causes mass go back to the office. This is the reason.

This is why RTO is a thing.

This is it. This is why, is because we, we got to get together. This doesn't need to happen. It doesn't need to be this way. It doesn't need to be this way. We can't do this because otherwise then can you imagine going back in the office every day again?

Sorry, I couldn't think of anything else to do but laugh when you said that.

I remember I have fond memories of you coming in in the office just with your ski mask.

Oh, in the winter? I really don't remember doing that. But if it happened, if you say it happened, I believe you. I would do that.

You would. Yeah. And just completely like You'd still have your jacket on walking into stand-up and your backpack. You'd rock right in at 10.

Yeah, I will say, and I shouldn't admit this, the earliest I ever showed up to the office was on my first day of work.

Listen, I work consistently early for much longer than that. But you know what? You gave me the inspiration to be someone who starts late in the day.

But I stayed late. I stayed late. I remember having super late in nights, so I don't want to hear anything about it.

And then we signed off. I don't even know.

No, we can edit.

Well, um, well, until next time, Allison. I'll see you. I'll see you tomorrow.

I'll see you tomorrow. I can't wait. We should— we will record some Off the VPN content in person. Yes, not full episodes, but some.

Which, by the way, follow us on Instagram. We have an Insta now. It's just our— my mom that follows us, so.

And Allison.

Yeah, so, uh, please Actually, I think my mom does follow us on Instagram.

That's actually okay. That's our biggest fan right there. That just broke my heart.

All right. See ya.

All right. See ya. Bye.

Thanks for listening to Off the VPN.

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