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Questions to Ask Before Joining a Startup

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Re: Questions to Ask Before Joining a Startup

#281

Earlier quoted context omitted.

I don’t understand what you’re (sarcastically) trying to get at here. That if you ask questions you can’t get a reasonably high salary?

oh it means that you won't get hired

It seems like you have the perception that top talent is easy to hire. In my experience that hasn't been true at big or small companies, and if a candidate is exceptional companies will go the extra mile to get them. And if we're talking about early stage startups the power dynamic is totally reversed - the senior candidate actually has a ton of negotiating power because a startup can't compete on salary with FAANG companies, and good candidates know it.

Good senior people are selective and want to know a lot about the companies they might be joining. If they didn't ask perceptive questions I'd think it was a red flag.

I mean seriously, a startup is trying to hire a senior engineer, is offering less base salary than Google, stock with an average value of nothing and they don't even want to answer the hard questions? How would they ever hire anyone good?

The only people I'd give a pass on not knowing asking good questions in an interview are interns or new grads.

Re: Questions to Ask Before Joining a Startup

#282
post #4

I've been thinking about low-friction options for getting a sense of the engineering quality. I don't think I'm alone in thinking that technical debt and bad software development practices are a top concern. Being quite senior now, I'd feel comfortable asking: 1 - To see their CI dashboard 2 - To see a sample of their production systems stdout & stderr 3 - Asking to review a recent non-trivial commit (with the person…

In the context of a startup, I would expect almost all of those to be disappointing. But maybe that's what you're hoping to see. In my opinion, if you're a start-up and you've got all those boxes checked, you're possibly doing the right things in the wrong order, and that's a red flag for me. What I hope to hear are responses like, "so this is how we're doing CI. It's awful, almost non-existent. But that's because at…

I don’t disagree with you, not entirely. When I was younger, it was all about sprinting full out as long as possible and that is a company that is either going straight to the moon of more often bursting in to flames. I’m quite a bit older and more senior now too and I think there are two slices of startup time, you put in your 45hours doing whatever it is the company needs, often running like hell. Then there is the 5-15 extra hours a week a startup can take and I absolutely think those need to be spent on dividend earning things, logging, ci, documentation, better testing, tooling, etc.

Thing is, it can go to the moon or it can flame out but there is this giant middle part of the spectrum where there are good exits and those exits often involve supporting your product and having well documented and tested technology is a positive. Trust me on this, it really sucks to get bought and then explain that it’s going to be a year and a rewrite to do the 10 things the buyer wanted yesterday.

Re: Questions to Ask Before Joining a Startup

#283
Awesome post. Definitely good timing as I was about to start an Ask HN around this as I go through the process.

I've also asked about early exercise (83(b)) and term sheets, if there are bad terms i.e. liquidation pref, anti-dilution etc but not all companies are willing to share this info.

Also, I am curious about why companies don't just have a black box formula output generator, with your equity offer value, saying this is our projection and based on our current termsheet if the company exits at this value your options are worth X, with the option of dilution built in.

Re: Questions to Ask Before Joining a Startup

#284
post #66

Earlier quoted context omitted.

In the context of a startup, I would expect almost all of those to be disappointing. But maybe that's what you're hoping to see. In my opinion, if you're a start-up and you've got all those boxes checked, you're possibly doing the right things in the wrong order, and that's a red flag for me. What I hope to hear are responses like, "so this is how we're doing CI. It's awful, almost non-existent. But that's because at…

This. As I always say, "If you are building a startup, over-engineering is a far bigger sin than creating technical debt."

Unfortunately I’ve met some people that take that mentality to a macho extreme in the form of “if you want to be STARTUP, you should actively avoid doing anything that resembles forethought.”

Re: Questions to Ask Before Joining a Startup

#285
I think it’s important to note that in many situations, money > equity.

90% of startups fail.

If you have two options, one being getting payed your preferred rate, and another being taking a huge pay cut for equity.. experience tells me to take the money every time and you’ll have made the right choice 90% of the time.

For most people money on hand today is way more important than future money that may never even materialize. And if you’re not most people, there will be future opportunities to buy into the company one way or another if you want to be an investor. You don’t even need to invest in the company you work for, there might be better investments that your real money that you get from the job can afford.

Re: Questions to Ask Before Joining a Startup

#286

Earlier quoted context omitted.

most companies dont ever reach billion dollar evaluations. say they get sold for a reasonable $100M after 4 years. my 1% stake as a founding engineer should gross me $1M (house money). but since there were 3 rounds I generally end up with car money. I've been through this several times, and ended up with car money or nothing, and I dont think I'm alone. a warning to fresh grads that they may not end up retiring after…

But without those 3 rounds, your company likely wouldn't have gotten to the $100M valuation. Sure, if you can get a company to a $1B exit without raising any funding and avoiding any dilution, that is the best case. But, in reality most companies need to raise capital to grow. You accept dilution because the value of your shares should go up assuming the company is executing well and putting the capital to go use (i.…

Right, but consider if OP's other option was a Google/Amazon/Apple with total compensation at $250k a year.

They could have worked in a stable environment with guaranteed $1M in compensation after 4 years, vs unstable and very demanding job with a low likelyhood of $1M total compensation over the same time horizon.

Re: Questions to Ask Before Joining a Startup

#287

Earlier quoted context omitted.

oh it means that you won't get hired

It seems like you have the perception that top talent is easy to hire. In my experience that hasn't been true at big or small companies, and if a candidate is exceptional companies will go the extra mile to get them. And if we're talking about early stage startups the power dynamic is totally reversed - the senior candidate actually has a ton of negotiating power because a startup can't compete on salary with FAANG c…

Exactly this. An employee who thinks he won't get hired, if he asks questions very relevant for him, is probably a bad hire in the first place. And for the top talent employee the startup needs, not answering the questions is a huge red flag. If you are good, you can select between so many options and most of them pay better than a startup.

Re: Questions to Ask Before Joining a Startup

#288
post #72

Earlier quoted context omitted.

I would expect most to be disappointing too, and it's a good idea to avoid those. Proper logging doesn't take more time, it just takes more discipline / giving a damn. People and companies that say: we don't have time to do it right Almost always mean: we don't know how to do it right Talent, not time, is the enemy of quality. (at some point that stops being true, but most companies (startups or not) are soooo far fr…

> Talent, not time, is the enemy of quality. What a refreshingly interesting perspective! How did you come upon this? Anyone care to disagree?

From experience. Not to beat a dead horse in this thread, but logging is still the simplest example to grasp. Good logging takes 0 extra time over bad logging, the only difference is talent.

But you'll see this across the board. People who write well organized, readable, low coupled code do so naturally and at more or less the same speed as people who write piles of poo. They might both achieve the same functional output, but the clean code will pay dividends in the future (and not just long term, even next week when you have to make a little change)

Also, quality is pretty core to a number key principle of the Toyota Production System (which many startups _attempt_ to emulate). Kaizen, muda and jidoka.

Fred Brooks might have written "plan to throw one away; you will, anyhow." But he also wrote: "Study after study shows that the very best designers produce structures that are faster, smaller, simpler, clearer, and produced with less effort. The differences between the great and the average approach an order of magnitude. "

Re: Questions to Ask Before Joining a Startup

#289

the answer to every question on this list: "We are a private company and don't share this information." Outside of the room, the Engineering team laughs at your questions, Operations and the CEO give each other quizzical looks before laughing too, and they go on to the next candidate. You get smug satisfaction for not going with "THAT Company who cant answer simple questions", until a reminder about the rent payment…

If you need to worry that much about the rent payment as a software engineer in current times you either lack skill (in interviewing or on job) or sold yourself way under worth.

Re: Questions to Ask Before Joining a Startup

#290
post #289

the answer to every question on this list: "We are a private company and don't share this information." Outside of the room, the Engineering team laughs at your questions, Operations and the CEO give each other quizzical looks before laughing too, and they go on to the next candidate. You get smug satisfaction for not going with "THAT Company who cant answer simple questions", until a reminder about the rent payment…

If you need to worry that much about the rent payment as a software engineer in current times you either lack skill (in interviewing or on job) or sold yourself way under worth.

There's a ton of circumstances that could put even a software engineer into financial trouble. Don't assume that a software engineer automatically equals a high savings.
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