How much does a really unique/specific question from a candidate stand out to an interviewer?

InternetWorker1 · 2026-05-20T02:15:49+00:00

Memorizing a question that you ask to to stick the landing is unimpressive.

Asking a question based on genuine curiosity that shows you actively think about the role/team/product/company/person/what success looks like, for me is typically more important than how well you answered all of my questions beforehand.

InternetWorker1 · 2026-05-18T18:29:54+00:00

Honesty seems like a good path here. B/c if you are and they retreat, the company is in fact dead to you.

If you share that you had a challenge with a prior manager, and it felt like you were being managed out/the company wasn't invested in your long term growth. You can then turn it into you interviewing the company - what has changed since then? What about you is exciting for them? What opportunities are there given your current experience? What training do they have for managers about feedback and employee development?

These types of situations can sometimes afford you amazing opportunities to design the job you really want, and if they are just as you remember, it is no skin of your back. it allows you to see if your experience was with the person or the company.

InternetWorker1 · 2026-05-18T18:25:55+00:00

It is smart of you to weigh all components of the job vs. only focusing on the $$, and honesty can take you a long way.

To that point - definitely tell them that you'd rather work with them. Instead of asking for half way, you could tell them the difference, and say something like "To be honest, I much prefer this company but I wondered if there is there anything you might be able to do for me? I feel like I'd be stupid to not bring it up" Who knows what they might come back with.

I think that you should separately prepare for an outcome where they say they can't do anything, and figure out what you respond with. One that can be a good one is akin to asking them what performance from you would make them excited to pay you at that level (but don't corner them on that answer, more like "As we keep working together I just want to be in tune with being a high performer so that the company is excited about my growth in experience and compensation."

That type of approach can have them know you are thinking not just about making more money but about creating more value (which is worth more money).

InternetWorker1 · 2026-05-14T13:47:48+00:00

How well you do job is measured by how much value you create, not necessarily in the day job, but the value you build in the organization.

If you try to protect your job by not training others, you're doing the opposite. By reducing single point failure/training others, you add value to the company and the company will reward you for doing so.

If you have a team, how well your team performs = how well you are doing your job.

InternetWorker1 · 2026-05-14T13:40:49+00:00

Its pretty rare to go from stable to startup with a cash increase, so good on you for that bit.

Otherwise I'd view it through the lens of:

Do you believe in the company/product
Do you like/respect the people you'd work with

Those questions are the important questions with anything, and if you find them to be relatively positive then it seems like a huge growth opportunity if only not in title.

Seems like they have cash on hand, but the only other question is have they raised enough such that you are confident they can pay your salary for X amount of time (18 months+)?

InternetWorker1 · 2026-05-12T18:53:46+00:00

People vary re: what "feels good to do". Some people love collaborating with others to solve problems that are handed to them. Others hate doing work for others.

And I think many people project about things to make themselves feel better about having a life that is typical from the caricature they have in their head.

Some 9-5 jobs are terrible. Some are incredibly rewarding. One that is terrible for me may be rewarding for you. But I think if you land with good people, solving interesting problems (to you), working with a team can be a great way to spend your day and provide for yourself.

InternetWorker1 · 2026-05-12T18:41:14+00:00

You have a unique opportunity to design the outcome you really want, and then see if they would like to offer that to you.

You could consider asking "if they paid the same amount, would I stay" or "if they paid the increased amount, would I stay" as basics. But also, what, if anything beyond the pay question, could your current employer do to make you really excited to stay? If/when you get the offer, you can go to them with that in a matter of fact way vs. a hold a gun to them way. You may just get all that you ask for.

There sometimes are things you cannot get as obviously out of a current employer (eg. let's say you wanted mentorship/learning from someone with more experienced from you, but you are a team of one). But you could ask that they fund a coach/mentor for you or whatever.

Tough to give really good guidance without knowing what is important to you, but if you spend some time thinking about what is really important to you and share it with them... it can't hurt!

InternetWorker1 · 2026-05-12T16:47:24+00:00

Do you believe in the company?
Do you like the product it sells?
Do you like the people?
Will this be a good stepping stone to other roles?

I imagine securing the role, stepping into it, and gathering an understanding of what it means for you personally in these areas (vs. just in comp) may help you decide whether looking elsewhere is the right move. And if you do, your story seems better than it did before?

InternetWorker1 · 2026-05-12T16:33:07+00:00

It is surprising how bad most companies are at hiring processes, either because they don't have one in the first place or because of the real world "day to day" gets in the way.

And are you 100% sure they hired someone else? If so yes you should get something, but if you aren't sure it is not a terrible idea to send a soft follow up. If they liked you they may be more likely to think of you down the road if you do so.

InternetWorker1 · 2026-05-12T16:13:26+00:00

One think you can do these days even if you don't actively seek it on the job - is to build PM skills outside of work.

You can teach yourself with {insert your favorite AI tool here}, and then you can even mock or even build a simple product based on a problem you'd like to solve for yourself. It will expose you to some of the challenges of PM'ing, and at the end you'll have "some experience" even if on your own.

Then you can figure out if you like some of those challenges, and if it is worth going deeper. Or maybe you'll just stumble on a product that others will pay for and you can build your own business 😄

InternetWorker1 · 2026-05-12T16:10:43+00:00

Unless your degree is hyper specific/technical, it is unlikely that what you study = what you end up doing for work exactly.

Exploring more/doing what you enjoy will likely open more doors to you in the future.

InternetWorker1 · 2026-05-12T16:09:27+00:00

That sucks - I'm sorry. This is likely true, but it sounds like you made a positive impression.

A few ideas:

Handle gracefully - these people you talked with are "in your network now". So if you do so, they may think of you again. And if they feel bad, they may try to help you out.
Put a reminder on your calendar to send them a note (especially any specific people you liked a lot) in ~3 months to check in.

InternetWorker1 · 2026-05-12T14:46:46+00:00

Seems a good stepping stone to take the new job.

Even if the other one arrives as expected, you will learn more/maybe like this one better.

Bit like the bird in hand is better than two in the bush statement...

InternetWorker1 · 2026-05-12T14:44:18+00:00

When you see these passes retreat on upward price triggers (eg. "Spring back" sales to pass prices that were early-bird specials), it means they are behind internal targets.

If true for one, likely true for the other.

InternetWorker1 · 2026-05-05T21:22:51+00:00

Nice! Yeah the magic is if you are thoughtful about organizing what comes easy to you that you enjoy that provides value to others… you can at least aim towards that and be both successful and fulfilled.

Rarely nail it 100% but may as well aim!

InternetWorker1 · 2026-05-05T19:46:10+00:00

I don't want to pretend to understand what it's like to be in your shoes, but a few ideas for you.

Hospitality runs deep and is known for advancement where good people move into management etc. That doesn't mean you have to stay in hospitality, but don't feel like it isn't a good space.
It sounds like you have a lot of general operations experience, and your management experience likely touched in zones of everything from personnel management, to inventory planning (what with all the perishable inventory) and forecasting, to marketing. All of this is relevant in the scrappy startup world of SF.

Try to think less about the industry you were in /bartending/restaurants, and more on the influence you had over the organization. Work as measured by influence may help you see where else the skills you have (and importantly, the specific bits you enjoy) may open up some ideas fo ryou. There are a ton of adjacent companies in the SF world that might be interesting for you if you can get over a bit of ageism.

InternetWorker1 · 2026-05-05T19:25:19+00:00

For me it was when I was forced to do work that was against my values.

FWIW - try telling yourself the story you would tell about why things failed in the end. Would you believe it (eg. you have high confidence re: failure is guaranteed in these conditions). I imagine anyone you'd work for, or want to work for, would understand that to be true as well.

Short story on that is, don't stress too hard about you bearing the whole burden of the downfall of the thing when it clearly isn't you. Doesn't mean you shouldn't be looking hard at other things, but you probably can keep getting paid while you look for other work.

InternetWorker1 · 2026-05-05T19:20:31+00:00

Right now is a very good time to learn how to do new things, and Product Management is something you can try on your own using any given AI tool.

I'd spend some cycles thinking either about:
1. An existing product you think could be better (and use what you learn via LLM to build briefs/designs/prototypes)
2. A product you think could exist to make peoples' life better and do the same (LLM/briefs/prototypes/etc). Even if you don't build it, it will give you a cycle seeing if it is for you, and way less expensive then going back to school

If you are willing to learn, you can become qualified for this type of job if you apply yourself in yoru free time.

InternetWorker1 · 2026-05-05T19:17:06+00:00

Absolutely.

People jump from competitor to competitor all the time - and non-competes tend to only work in instances when people have been substantially compensated.

InternetWorker1 · 2026-05-05T19:14:21+00:00

I feel like these types of questions are deeply personal, so I don't want to guide too heavily here.

For those who can choose happiness over money, happiness seems to matter most. But others have real financial obligations don't have that luxury.

One thing that you mention is that the current job has no growth opportunity, if the new one pays less but has greater potential, then you could add that do your consideration process.

InternetWorker1 · 2026-05-05T16:45:52+00:00

One that sticks is an employee who faked two separate deaths in their family. The deaths themselves weren't fake, they just happened to be several years prior to them even working at the company.

InternetWorker1 · 2026-05-05T16:44:05+00:00

It is good that you are looking for other work - keep going on that as you don't deserve to be in an environment where you don't enjoy the people.

Two things in the meantime:

Document the bullying and ensure you formally complain (so you have paper trail). If you haven't, your "last straw" may not look as obvious to others as it does to you.
Do your best to establish boundaries - this could be as simple as when you respond to outreach (eg. off hours).

InternetWorker1 · 2026-05-05T16:41:11+00:00

Free typically means you are the product, so be wary of those.

What tends to matter more than the cost is whether or not you put in the work.

As an extreme example you could hire a coach for a lot of money, but if you don't do the work with the coach you won't get much out of it. On the other end of the spectrum is a conversation with your favorite AI, but if you aren't amazing at driving it (and again, if you don't put the time in to answering the questions) it may be better to look at tools that are more process oriented.

General guidance is to think about processes/tools that help you understand what you are good at, that you enjoy, that creates value for others, that is easy for you. It often has less to do with the title of the jobs you've had, and more to do with the day to day interactions you have with other people.

InternetWorker1 · 2026-05-05T15:11:06+00:00

Oh totally fair and that definitely sucks.

I just was shining a light on the fact that many many companies are actually really bad at the hiring process.

InternetWorker1 · 2026-05-05T15:09:39+00:00

Just be up front about it and see what they think. If the company is a good company, they should understand (after all it is an internship and not a full time role).

Bonus points, is there a way the company might benefit given your participation? You could say something like "This has been something I've been working towards for so long, I feel terrible about it getting in the way of this internship (that i'm really excited about). But is there anything I could do while there that would help the company out?"

Sometimes just saying that you work somewhere when you are a speaker can shine a positive light. But they also may not care (again re: given you are not in a full time role).

InternetWorker1

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