From Startups to Big Tech: What To Look Out For?

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Hey folks, I'm just driving to the office. It's Thursday. Going to go to experience dev subreddit for this topic. And this one is about transitioning from startups to big tech, which is something I have a little bit of experience doing. I say a little bit because I've only done it once cuz I guess that's how that works, right? If you do it, it's startups to make big tech. And so I was reading this person's post. Um, I think some of it comes down to they're trying to adjust to what seems like a very fast-paced startup culture into a larger like significantly larger company where things are it's more of like a it's like a big machine, right? like and that means that it often feels like because of the mass of the machine, it's moving uh much slower. Uh there's many more things going on in parallel, right?

So overall, there's a lot of stuff that gets done, but um it seems like when you zoom in on some parts of it, it often feels like it's going very very slow. So I wanted to talk through this because I think that there's different reasons that this happens. I think there's different things that you can factor in for like how do you avoid this? Are some of these things unavoidable? Um they ask kind of in their post like you know is it like is this just how it is? Like maybe it's not for me and like it's a misalignment in terms of like you know working culture or what? Like they go on to say that like uh from like a compensation perspective they're like I literally tripled my total compensation to come here so it seems like unwise to not stay but they're like

what the hell's going on right so top comment was basically like hey man that's how big tech is so like you know get that bag and I don't know Like this kind of stuff bothers me a little bit because it's like like yes, if that's I mean if that's how you look at things then sure but I I don't really align with and I'm not saying it's right or wrong. Like I I just don't personally align with like do the thing that you don't like doing and then it happens to pay a lot so you're just going to keep doing that for forever. Like I think that you can and probably should do that thing because if it's paying really well and it's not like you hate it then like sure. But I would just I have said this in other videos. I just hope that people get more out of their career than that because we do our careers for so long.

Maybe that means and I mean this genuinely maybe that means for this person they do what that for a little bit. they find that they're making great money and then they're like, I can actually retire early or I can go do something later that I actually do really want to do. Like I think that's a great strategy as long as you end up doing something that you genuinely want to do and enjoy doing because I just think that otherwise it's like that's a pretty I don't know. I feel feel that's kind of like a depressing life, but that's not for me to decide for other people, right? So, I'm just kind of sharing that's my perspective on it. So, at least on the surface, hey, like if you don't hate this and the money is really good and like maybe that does turn into something that you really enjoy, great.

Maybe that affords you the opportunity to do other things in life because the pay is great. Great. I just genuinely hope that uh the net effect of staying in such a position is that you know your overall life is better. That's really I mean if you get that I feel like that's that's winning. So um slowness big tech red tape what's going on with all this stuff. Um I I mean I will be very transparent and say that going from when I was at a startup uh talked about this in other videos like for context started when it was like roughly seven people and stayed till it was roughly 250ish and I not because anyone forced me but I worked non-stop for basically 8 years right like around the clock every day like on weekends uh working late like just I love to work there

was lots to do there was lots of things to ship lots of things to fix like there's it was just chaos right and like the goal was like trying to organize the chaos and move forward but there was genuinely lots of chaos and I say that like chaos I realize sounds like a negative word a bad word but I don't mean chaos everything was terrible I just mean there's so much going on right we were moving moving forward. We wouldn't have grown. They wouldn't have IPOed if we weren't moving forward. They wouldn't have, you know, bought got bought back to private for billions of dollars if we weren't moving forward. Things moved forward. It's just that there was so much going on that it was chaos. It was non-stop things happening. And if you're in an environment like that that feels like there's constantly stuff like go go go like you go from that into an environment where things seem to No, you're not going.

No, no, no. You get a finger wag. Absolutely not. Light turned green and I'm driving through the intersection and this woman started to to drive into the intersection to turn right. But I got to do my my most favorite move, which is the eye contact and finger wag to let them know, no, no, no, you don't get to do that. Um, okay. So, things can and will move slower, but it's not like I realize that a lot of people have this experience and then that's like all you hear about. So when you hear about people working in big tech, it seems like the rule is that everything's just slow and like these people were kind of saying in the comments, it's like whatever. Everyone's just pretending to work and pretending to be busy and like get that bag, right? But um I'm sure there are people like it it becomes easier to sort of blend in in environments like that.

So I'm I'm not here to say like, oh no, no one's doing that. I'm sure there are lots of people in a huge company that do that. So, I'm sure there are people doing that. Um, I don't, you know, I'm not suggesting anyone do that. Again, I don't imagine that's a fulfilling career. So, just I don't I just don't know why you wouldn't do something that keeps you busy that you enjoy that also pays you. Uh, maybe that's hard for people to find, but I think that there's other things that happen in terms of things moving slower than you might expect at like a startup. Uh, and it's not always like that. And you know, I can just to give you a super quick example, like actually not even specifically, but like I've worked on two platform teams over the past 5 years at Microsoft and like if there's an incident, you get to see just how fast we can and have to move.

So it's not like there's an in inability to move fast, right? Um I'm sure there are teams because like Microsoft, that's where I work. So as an example, there there's so many teams at Microsoft across the entire organization, right? There's so many people, so many teams. I'm sure there are teams that absolutely cannot move fast and they have some type of incident and they go, "Oh we just learned how fast we can't move." And so like I can't sit here and say like therefore you know every team is like this but I can say on the teams I've been on like uh the one example specifically I worked on the deployment team for office 365. I did that for three and a half years and we choose to go slower than like than what our technology allows for. We choose to go slower because we're rolling changes out in a controlled way.

We measure the changes. Uh but you know, if we have an incident and we need to go fast, like we need to be able to go fast forwards and back, right? Like the technology itself can go faster, but we have policies and things in place, ways that we work that are slower than that. And it's a conscious decision, right? Like what we don't want is like even though our technology might support it, we don't want a developer to have a change press a button and it's across the entire world in like minutes and then we're like, "Oh, wait. The change is broken and like it's on every single capacity across the planet." Like we actually want to ensure that people put into their uh their process by default like we bake it in for them that you can't do that. You're going to have to let me in, buddy.

Thank you. Um so like that's just one example, right? So if you were working on a change and our deployment system is deploying your change, by definition, we force you to go slower than the technology allows for by definition. So there's one simple example of like that's going slow. When I worked at a startup, you could technically uh like some of the teams I was on, you could take any build, like if we committed code and it, you know, spat out a build, you could take that build and ship it, right? Put it on the website, let customers download it, set the automatic update so customers get it. You could do that. You could do that multiple times a day, like directly to customers. You could. And like sometimes we would hot fix things and then we would hot fix right after that because we found a handful of additional bugs that we want to do.

And so we would generally air on the like in a startup generally air on the side of just like moving fast. Not trying to be negligent obviously but trying to move fast. There was a heavy bias for action because we had the agility to be able to do it and if we made a mistake, we had the agility to be able to correct it. But when you're at a massive scale, the even if you have agility, it's not like it's not the same level of agility. There's too many moving pieces and too many things that can be impacted. So, I'm just right now talking about technology, right? I'm assuming what this person's really more focused on is like getting work done. Now, I already gave you the example that if you're a a partner team of ours building a service on what I was just describing, by definition, your software development life cycle will be slower by definition because you will have changes rolling out over a period of time.

And like odds are you're probably not just sitting there going, "Well, I can't start my next work because I'm just waiting for this thing to roll out." Nope. You're probably, rightfully so, getting started on the next thing while the change is rolling out. Right? So again, by definition, you start to bake in like generally what I would not encourage many uh teams or individuals to do, which is like having more work in progress. That change is rolling out. It might not be perfect though. you might encounter an issue. You still have to watch for signals and monitor things and you might have to go make changes to it. You might have to turn off your flight, right? So, it's not like once the code is rolling, you're like, "Well, I can just cover my eyes and never look at that again." No, like you still have to pay attention to it, but you probably want to get started on your next set of work.

So already in the software development life cycle that's kind of lengthening that uh that flow of things. Um I noticed and I I can only speak for my experience at Microsoft. I cannot speak for other tech companies and only obviously as I'm talking I can't speak for all of Microsoft just the area that I work in. But I've noticed that like uh there's I don't know like leaning towards like longer planning cycles and even when I was in a startup we did like quarterly um for like an organization it was quarterly I think and um and then you'd have like your sprints and stuff within the team and I I don't know like I'm I haven't been there for for 5 years but I I wonder as the company's growing a lot. The overhead for doing that kind of thing feels like a lot to the people that are organizing it.

It's probably moved to like to like a semester like half year or uh perhaps even like yearly planning, right? Because there's overhead to it. And I honestly think that that's like the wrong direction. I think that having some strategic stuff uh very high level strategic stuff um you know at longer intervals is great to realign on things but I think that you need to do more frequent planning personally uh I think that's one of the things that when your organization starts to move towards like really long planning cycles there's a lot of waste and I believe the sort of uh idea is that hey if we move to longer planning cycles we have less overhead we'll just plan really effectively but like you're bullshitting yourself like the only thing that's going to be true if you plan for 6 months at a time or a

year at a time the only thing that's going to be accurate is the fact that you're not going to get what you're planning done that's the only thing and I could guarantee it every time it's just not going to be the reality too much changes on time horizon like that. It's just ridiculous. So, when you lengthen the period of time for planning to try and say like, "We're just going to do it more effectively and not have this overhead," you're lying to yourself because you're saving time in one spot and you're making everything else so much worse in terms of uh efficiency and and overhead, right? Because you did all this work for planning, right? all this time and effort goes into it and then your plans change and it's like well why the hell did we take so long planning all this stuff and

I'm not saying there's no benefit to doing the planning it's just that I think you need to keep it higher like the the further out the timeline is the more like highlevel brainstorming like north star kind of discussions to have and like that's it keep it super high level and just acknowledge like your plan is not actually a plan it's really just like a brainstorming discussion and trying to align on like on things that are valued, a direction, a rough direction to go in. That's all. So, I think that this kind of stuff creeps into big tech a lot. Um, and I don't I'm sitting here being like I don't have a solution for this, but I think like all things when it comes to a culture, I've talked about culture a lot in most recent videos on this channel. Um, I talk about it from the perspective of a team, but like the same thing applies to an entire organization and beyond, right?

Like the culture is made up of actions that are taken repeatedly and consistently. You observe the culture. So if your organization or company has a culture of doing things that slow down and it feels ineffective, it is that way because that's like the majority case, right? And like it doesn't get better unless you try driving change in the other direction, the direction that you want to see it happen. And no, you don't just do it by yourself. No, it doesn't just happen by you snapping your fingers and making it. You know, you can't just say, "And now we do it and it happens." Um, you kind of have to lead by example, demonstrate that it works effectively, get other people bought into it, and it's a thing that happens over time, and like that could be a monumental or like seemingly impossible thing to to try and do at scale, right?

like it just the reality of it there would be so much friction to try and overcome to get people bought into that. Now I can say that in the five years that I've been at Microsoft I have heard of even and in a positive way like things moving to more frequent regular planning cycles and I'm like very much bought into that because what will happen is that if you take like when you're at a smaller company and you only have like you know one team or a couple teams or something the the overhead that you have for teams like trying to like focus on their priority ities and then like still I don't know like enable other teams to like you know if you have to deliver work for them or you have to collaborate or whatever it is like the more teams you add

in just like if you have a team of people the more people you add in you start to become less efficient the cost and the tax the overhead for trying to coordinate across teams just goes up and up and up. So, it's just like if you can find ways to be more effective and shorter in your planning cycles, I think that can help tremendously. But I'm not sitting here saying like that just solves the problem. It doesn't. When you have many teams with many people with interconnected dependencies, it's going to move slower, right? And like what you can try making trade-offs in other ways where you're like, "Okay, well, we'll just like we'll work in isolation." And it's like, "Okay, but you might be paying for that down the road or the the company might be paying for that down the road because three teams built the same thing in isolation.

So like that's wasteful, right?" So it's interesting. It's not like a a simple trivial problem to solve, but like the nature of how these things are structured and how they operate is different. And there is a spectrum to all of this. It's not like it's just binary or at a small company it just like everything works easily and at big companies everything's just It's just not like that. There's going to be spectrums of these things. But I think personally from like a what do we do about this kind of perspective, I think that what you can do is like not be quiet about it. Like what happens is that people get complacent about because they see it and they're like, "Well, that's impossible to change." Like you're telling me that you're suggesting that I'm going to try influencing our organization to do things differently. There's people have been here that like 25 years.

Do you think they're going to start changing? Well, I mean, your option otherwise is to do nothing. Okay. And so you do nothing. What do you think has a better chance of success? Statistically, you do nothing or you do something. Even if you're doing something is very minimal in terms of moving the needle on the, you know, the direction you want to go, it's still something. And I think that if you have enough people that do this over time, you can shift things. It's just that it's ridiculously hard. But otherwise, you don't do anything. So, my personal experience has been that yes, things do move slower. Uh I've noticed this with with planning. I've noticed this with coordinating with other teams.

um you know you might have a situation where something comes up on your team and you're like okay within our team we can we can pivot pretty quick right we feel good about that our team culture is good for that we worked really hard on that so within your team you might feel great like okay change in priorities something came up like okay you know we're going to we're going to be on top of this but then you realize like okay in order to go do whatever we need to focus on like we need to coordinate with these two teams, right? Like they're critical in ensuring we can move forward on this, but those two teams, they're not effective at pivoting. They're like, "Look, we got these roadmap items. We have to deliver on them.

Like, we we simply can't we simply can't change what we're doing to rep prioritize to support you on this." So it's almost like it you know in your situation even if you are like very nimble in terms of navigating and changing priorities you can get completely blocked by a team that's just not able to do that. Now that doesn't mean that's the end of the road. It just means that there's more hurdles to go over. Do you say, "Okay, well that team can't help us." Like, "Hey, that team, like, you might own this area, but if we can staff the work, like, does it make sense? I've seen this kind of thing be successful, right? You can't do it. No problem. We have people that can like that are that can and are willing, but it's probably something you need to own because it falls in your team's area.

So, like, can we partner on this, right? like can you have people review the stuff or work uh you know sign off on the designs and stuff and we'll have a transition plan for later. We've done this the other way where like we've had um you know teams that are like we simply can't when they're talking through stuff we jump into it like there's there's ways to try and make things better but it's also very easy to just if if people don't give a you kind of just fall into the well I guess it is just that way and Like I don't know. I feel like at bigger companies it's a little bit easier to like to just do that. Oh, come on. Absolute dummy. It's like 15 bus lengths in front of that person and they're slamming on their brakes. Like you're going to cause an accident, pal.

Um I feel like at startups you don't like you don't get that choice. You can't be like, "Well, it's just not going to work." Like it's like no, it's we got to find a way to make it work because if we don't, we're screwed. like that could be a that could really affect the company or that could be a missed such a you know huge missed opportunity for the company. Um and in a larger company that might be like okay well this project's going to to fail or be late or something and in the grand scheme of things it's tiny like it sucks but it's tiny. So, I don't know. It's like it's challenging and uh like I said, being transparent, like I feel that things move slower in big tech, it's a really hard adjustment for me. So, I would say like if you're try if you're in a situation like this and you're trying to think like is this the right move?

Like, do you like the work you're doing? Is it interesting? Is it challenging? Do you feel like you have opportunities to grow? If you have never sat down like with yourself and thought about what you want out of your career like currently where you want to head to like if you haven't done these kind of like reflection snapshots I strongly encourage that you do. It might sound kind of like a thing to do but like if you don't know if you don't know what you're trying to get out of your career and stuff then like how do you make a decision on this? So, I recommend that you go through the thought exercise and don't just do it once. Like, do it periodically. It might be every every year, whatever, but don't just do it one time cuz your life circumstances will change. But go through like what are you getting out of this this opportunity?

If you're like, "Hey, look, right now where I'm at in my life, like, yep, this is going to be a good experience, right?" So, like that's at least a check mark. um it moves slower. That's not exciting. So like my engagement level might not be there. Uh the work is so so in terms of interest. So again engagement not might not really be there. It's probably an indicator that's not really sustainable. Just for the record if you're like already I don't know. Probably not. You might say pay is great. Okay. That's a good check mark, right? And you have to do like this pros and cons analysis and figure out like is this the right spot for me? And it might be, you know, it might be worth taking that opportunity being like, "Hey, look, I realize that in a couple years I probably can't take this anymore because like I'm just not engaged in what I'm doing." Okay?

At least like at least you're making a conscious decision and it's not an accident. And then that way when you're partway through, say you're a year in and you do this reflection again, ask yourself the same set of questions. Has the work changed? Are you actually enjoying it more? Are you like at the point where you're like, "Man, I can't take this. Like, I'm not engaged in anything I'm doing. Like, I hate waking up on Mondays and going to work kind of thing." Cuz if you're already feeling that, like, maybe it's time that you start searching. So again, I don't think there's anything wrong in taking a job where it's just like, hey, the money is really good. Um, I just I think that you want to make a conscious decision to do it. So asking I don't know. I feel like asking the internet's not the right move because it's like the internet doesn't know what you want, right?

It's just how it is. Anyway, I think that's all I got on this topic. Um, I'm almost at the office, too, so I'll sign off here. But if you have questions that you want answered on the channel, just leave a comment below. I'm happy to try and go through it. Software engineering career related. Uh and otherwise you can go to codemute.com. You can submit questions anonymously because when you leave a comment, people can see it, right? So up to you. Um and then I have programming tutorials in C and using AI tools at my main channel called Dev Leader. And then the Devleer podcast is where I do my live stream every Monday at 7:00 p.m. Pacific. I also interview other software engineers. One of the most recent episodes has Derek Co. Martin of codeep opinion.com. So go check that out. And um my other channel cuz I got a whole bunch is called Devleer Path to Tech.

Currently that's just ré reviews. So if you want your resume to be reviewed, you can go over to Dev Leader Path to Tech, watch one of the videos, see what the ré reviews are like, and I'll see you next time.