Ask HN: Should I tell my boss Im looking for other work?

In a growing tech firm, there's always going to be technical debt. It's probably foolish for a startup to optimize very far beyond the end of the runway. Getting into the air is the first big problem, staying in the air may require doing the flappy bird, until the jet engines arrive. Facebook was written in php. Reddit in Common Lisp. StackOverflow ran production and development on a single box even while scaling.

Sure the system may need a complete rebuild in several possible futures. That doesn't make the company unviable or growth infeasible. Sales velocity trumps a great deal of technical debt.

Unless the overall company culture is one of unhappiness, a good manager will usually be able to intuit who is looking for work elsewhere...or just assume everyone is.

My advice, for what it is worth, is to announce that you are leaving when you are ready to leave. And then leave. There's nothing to be gained by sitting on the fence about the change. Nothing to be gained by hanging around. Line things up and then move.

Good luck.

There are some common problems that could ultimately run a company into the ground.

One is that a prototype demo that was only intended for securing funding is used as a production system.

Another is that a codebase grows organically for many years without any attempt to refactor it into something smaller. I've seen that a whole bunch of times.

"Dave, I have a question about Spellswell's code."

"Sure, what?"

"It has this custom allocator" - SPWAlloc or some such - "that is just a bottleneck that adds twelve bytes to the requested allocation, then asks malloc for that amount of memory."

That is, every single allocation was twelve bytes bigger than it needed to be.

"I did that so Spellswell would stop crashing."

After I finished beating my boss senseless with a baseball bat, I revised SPWAlloc so it called through directly to malloc, without adding anything to the requested allocation.

Of course it started crashing all over the place, which was a huge PITA back in the System 7 days, but then I fixed all those bugs. That only took me a day or two - all manner of buffer overruns, off-by-one errors &c.

"Then again, it is a business and they will survive without me"

Exactly. Always think about yourself first here. It is ok if you leave. Just don't tell your boss until you have another job. Once you get a job, serve your notice and leave gracefully. Keep it simple.

Don't tell your boss you're looking. You're not required to do so by law or convention, and the results are unpredictable, but veer toward the negative.

If you want to be particularly decent to your boss, be willing to stay on a fairly long time after you give notice (up to a month, say.) Since the typical transition time is two weeks, that's generous on your part. They may take you up on it, or not.

>but the company is under staggering technical debt. Unfortunately the leadership team comes from a predominantly sales background and don't seem to understand how large a problem technical debt can be.

This is every programming job ever.

This is going to be very dependent on your relationship with your boss(es) - I don't think there's a one-size-fits-all answer to this.

FWIW here's my experience: I was a banquet manager before returning to school to switch careers and a few months into school (long enough to be "sure" about switching) I thought I would tell my boss I wanted to become a software developer and had returned to school to pursue that. I assured her it wouldn't require any adjusting of my schedule (I would schedule my school around work) and that I wasn't planning on leaving the hotel until I finished my degree (i.e. years). Her response was that if I was going to leave [eventually] she'd rather it be sooner so she could hire my replacement and so I gave my two weeks notice that day.

If you think there's any chance their response would be along the lines of what I experienced I'd suggest not letting them know until you find something and then give the standard two weeks.

[Also, I don't want the above to make it sound like I left on a bad note, she was supportive and encouraging of me and she coordinated a nice going away lunch for me and we all grabbed drinks after my last shift, etc]

My maternal grandmother was an elementary school teacher back in the 1920s or so. Back then it was SOP for female teachers to be fired if they got married.

So when grandma and grandpa got married, she didn't tell anyone at her school. To the extent any of her coworkers knew about grandpa, they thought the two of them were just dating.

When grandpa graduated medical school, they had the principal of granda's school over for dinner to celebrate.

"I'd like to introduce you to my husband."

She quit her job on the spot, and the two of them left the state.

I don't understand why you say it is very dependent on the relationship with the boss. You only give a negative example for telling the boss. Was the positive side getting a free lunch without a job?

> You only give a negative example for telling the boss.

I gave the only relevant example I had, which happened to be negative [it actually worked out extremely well for me but that's another story] and cautioned the OP if they thought that was a possible reaction they're better off waiting and giving two weeks once they find something.

If they know their boss better than I did (we had only worked together a few months) they may be able to gauge the response better than I was, which is why it depends on the relationship.

Typically I would never disclose you are looking for another job . . . things might be chummy with your boss(es) while you're all on the same team, but once they know you're leaving they could can you on the spot, lock you out of your workstation and send you on your way.

This could result in a loss of pay between hey I might leave, you're fired, and finding your next gig. Plus it is a little harder to find a job when you don't have one. Keep things positive. No: Our code sucks, we need to do things the right way. Yes: If we improve this our clients will have less downtime and it will reduce churn and increase LTV.

In the mean time while you're looking you could start a movement to improve things at your existing company. Maybe it would help out your friends and girlfriend's employment outlook. Most companies are receptive to hey we can improve things for the clients/subscribers by doing this, this and this.

Good luck, stay on the down low.

Definitely not. There is a possibility that it will sour your relationship with your boss (why take the risk?). Best to quietly find another job and resign in the appropriate manner and move on.

Don't tell your boss.

If people do get pushed out you'll be first to go even if you haven't found something better yet. Beyond that you will be treated differently and probably for the worse.

Even the boss is your friend, don't tell. The middle ground is 2 weeks notice. If the company wants to lay off, their middle ground is just 30 minutes notice with the security escorting you out.

2 weeks is the responsible, non bridge burning way of giving the company warning.

I run a slightly bigger startup than the one you're at and FWIW, I really appreciate it when employees tell me that they are looking for work elsewhere. If you are an engineer (I assume you are since you are talking/worrying about technical debt) you are extremely employable. You will probably get a much better opportunity if you are able to look around while at your current company. Interviewing behind your companies back can be logistically tough and can lead to a worse offer.

It's possible that your company might march you out the door if you tell them you are leaving. I think this would be a real asshole move and not in their interest but it could happen. If this puts you in a major financial bind it might not be worth the risk, but if you are ok with this I think it is probably better for you to let them know.

I don't think you have an obligation to let them know but I think it's probably in your interest.

I lead a team of 6 designers and developers, and have frequently told my team that I understand they won't work for me forever, and if they ever decide to leave I would be happy and excited for them (and I honestly meant it).

A few days ago one of my best developers told me she is talking to another shop, and while it stung for a second ("oh man it's going to be hard to replace her," "this is the worst time for someone to leave," etc.) I was genuinely excited for her and I talked to her about her options and helped her weigh the differences. I tried as hard as possible to be unbiased.

I think if you have this sort of expectation with your boss, you should talk about it - a good leader has a responsibility to be a mentor and a coach, and should help you work through decisions like this.

Of course, if you have any concerns about repercussions, or believe that talking through it would only help your employer, don't do it.

The middle ground is just telling them you're unhappy. Maybe there's something they can do?

(The "looking around" part is implied).

He's unhappy that it looks like the company may just collapse under their feet.

Sure, sure. There's not much they can do then. But, maybe they'll give him some more money to stay (for a few months), and he can use that to get even more at his next job.

I'm going to go a different direction from the rest of the commenters so far. How long have you been with your girlfriend? Are you thinking this girl could be around for the long haul? No reason to give up a good job because of a girl, especially if you don't think she's going to be around 5 years down the road.

I find that every good young worker that has only been somewhere under a few years is always keeping their eyes open for a better situation. It should be assumed everyone is looking if the company has good management - your boss probably is too.

No way, not until you're ready to give notice.

I gave Live Picture roughly five months advance notice. My resignation letter pointed out the reasons I would be leaving, and that I would do so once I was assured that the product I was working on - also called Live Picture - was In The Can.

I didn't give Geonex Verde any notice. Although the verbal offer for my next position gave me plenty of time to give notice, there were some delays in getting a real written offer letter.

We had just bought some new printers. Back in the old days when I was but a pollywog, one had to write one's own printer drivers. I suggested to my boss that I do so, but he said there was a higher priority project that I should complete first.

However had I left without writing the printer driver, the company would have been quite screwed. So I wrote the driver in secret. My very last day at the company I presented the company president with some sample prints.

"Hey, these hardcopies look great!"

"Thanks. I have some bad news for you Scott..."

Consider as well that resigning in protest might really be the ethical thing to do. Don't just write a rant or a flame, but a well though out, lucidly composed letter - then email it to everyone else in the company. I've done that as well. But if you do this, be prepared to get fired on the spot.

You could then - maybe, hopefully - take comfort in your protest resignation saving the company.

No