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If you had questions which would affect your decision to work for a given company, would you wait until interview before asking them or would you prefer not to waste their time (and yours) by asking them earlier? If you did ask prior to interview, would you prefer to approach that via email or some other means?
Consider circumstances where you had a lot of interviews to attend.
This depends entirely on what the question is, and on how likely the company is to meet your needs. An important aspect is whether they can choose to meet your needs. If they simply are or are not [whatever] then ask as soon as possible - it can't be changed and it's a deal breaker. But the more they could choose to [whatever] then the more there is to be gained by waiting until they know you, and want you, and might be motivated to agree to [whatever] in order to get you.
Classic "ask right away, before even applying if you can" questions include:
Classic "wait until the very end of the very last interview" questions include:
You should identify where your questions fall on this spectrum. A restaurant isn't likely to change from Argentinian to Chinese cuisine; a software development shop isn't likely to change "stacks"; a retail outlet isn't likely to switch to being open 24 hours a day, even if that's what it takes to get you on board. Ask these sorts of questions early. Dress code, remote work, getting training and conferences - these things are sort of in the middle. They might start to bend to get a great candidate, but if you ask about them too soon you might just be told "no" because they don't yet know you're a great candidate. Finally, money and easy benefits are always negotiable, so don't ask about them before they know what you're worth.
There is usually an exploratory point in the recruiting process where the recruiter/interviewer will talk to you at a high level to decide whether you're enough of a fit to interview. These conversations are often over the phone or face to face. This is the point at which you should ask your deal breaker questions. (They're asking you their deal breaker questions now, too.)
If you don't think of your deal breaker criteria until the interview, the best time to discuss them is after they ask you if you have any questions, which is usually at the end of the interview. If they don't give you a chance to ask questions, you should ask if you can ask a few questions before you leave.
Keep in mind that many companies' interview processes involve non-managers who are not able to talk about pay or benefits. If these are your deal breakers, you should address them either up front in the screening process or after an offer has been made.
Fit the order of what you ask and when to who you are talking to.
In my line of work, for example, it's not unusual for the interview process to be:
Establish contact w. a recruiter (let's say it's external to the company). Provide resume and agree to have it shared w. the company. Answer basic questions to help recruiter sell you.
Contact is made with the first line of recruitment internal to the company. Pass that communication sequence.
Go through some number of interviews (phone, video, in person) with some number of stakeholders within the company. Usually this includes the person to whom you will reporting and a sampling of the people you may be working with. Other types of analysis may be used (coding exercise, testing, presentations, etc)
Get a debrief from some variety of recruitment. Debrief ends in offer
The goal I have with make or break questions is to aim to get answers that are both accurate and time saving for everyone involved (but especially me!). It does me no good if the answers are not accurate, so I focus on that as a priority.
Here's how I'd break the questions down by phase in the above process:
They can't be a great representative of the company. Don't expect accurate answers about work at home and child care - for example.
They do however, have the ability to verify:
contract vs. non-contract - this has to be explicitly clear to them before they start recruiting.
ball park of salary - it's true that I would not start at the negotiation but I've been called for positions that are 10,000s less that I would even consider. I usually give a ball park ("I'm looking in the mid 100K range") nothing too specific, but I really don't want the conversation to go past this phone call if we're on two different pages.
size and riskiness of company
location and existence of relocation package
must start by XYZ date. You can't easily get agreement on the latest you could possibly start yet (and who knows how long the process will take?), but you can be clear and say "I'm looking to start by XYZ date - any job that can do this will be my first pick".
They tend not to have much maneuverability. There's always the option of going forward with something that sounds like a no go, but which you may negotiate into something good. But that's at the risk of wasting your time.
It never hurts to verify that the external recruiter is not sleazy. Besides, it makes you sound like researched and you care when you run through the description of the position that you have so far. Go through all the elements of set 1 that mattered to you.
It's also a good time to check on the Y/N of benefits - time off, health care, child care on campus -- all the stuff you may be able to read in a brochure from the HR department. Try not to scrutinize - try to hit the stuff that is make or break.
For the most part, the company will not create special benefit packages for YOU. It's been done in the right time and place, but I would not expect it to be the norm, so this a good time get info on the non-negotiable stuff.
This is the time when it's good to interview your boss. There's a huge bunch of make or break stuff that relates to the boss/employee relationship.
Keep in mind, however that you can't really get to a negotiation that is in your favor until your potential boss has gotten the feedback of his fellow stakeholders. He's probably not going to negotiate while he's in evaluation mode.
Now is when you actually have some ability to influence outcomes. Maybe work at home options are unusual, but now that they've met you, they are willing to consider a trial. Maybe you will get a higher or lower salary package based on the value they think you will deliver.
It is the very end of the process, however.
There are a few cases where you may wish to wait, even on make or break conditions until your first day. One such thing is non-visible disabilities. Prejudice against groups of people with disabilities has lead many to get the job first, and ask for accommodations later.
An interview is a bit of a negotiation.
You are offering yourself and your skill set, they are offering opportunity and benefits.
Any negotiation involves give and take and a bit of horse trading. There may be certain things that are deal breakers for you, some that you may be willing to be flexible on depending on how sweet the deal is.
Also as a negotiation at any stage either side may walk away and decide the deal is not for them.
You may not always know what the triggers for this are at the start, it involves a bit of exploration. You may also find after talking to them that things you think are deal breakers for you are not.
Say you needed flexible working hours due to child care. You may think that is a deal breaker, but if you insist on 'flexible hours', you could miss that the work place has a Creche or other child care incentives.
Salary is another thing, if you insist on X amount of money, you may miss that the company pays less but provides a huge amount of other incentives.
So talk and listen. Work out if you want this job and how much it is worth for you, they will be deciding the same thing about you. Discuss issues as they come up. Or if they don't come up and you feel it is a big issue for you then raise it.
The company may have a different set of priorities and culture from previous employers. Some things you may think are big deals may not be and vice-versa.
One final thing to remember about this, is to make sure that things you agreed on are in writing (if not in the contract itself). It is all to easy to a manager to change (or change their mind), and a deal that you though you had to be forgotten (I know from personal experience).
