I've mentioned a few times on The Simple Dollar that I have conducted a substantial number of job interviews in the past. Although the jobs I usually hire for are technical in nature, most of the truly telling (and thus truly valuable) interview questions were non-technical questions. A great interview question reveals the nature of the person you're hiring - honesty, reliability, ability to communicate intelligently and quickly, and so on.

Over time, I've collected a pretty good pile of questions that I use in almost every interview. Here are twenty five of the most reliable ones, along with a tip or two for each one that illustrates what makes a good answer - and what makes a bad one. Hopefully, the discussion here will provide some insightful questions for interviewers, as well as some things for potential job applicants to think about. If you can easily answer all of these questions, you shouldn't have much to worry about in the interview. At the end, I give a checklist of "homework" a potential interviewer should do before a big interview.

First, stupid answers to stupid questions.

A lot of questions that are asked at job interviews are really stupid and have obvious answers to them. "What's your greatest weakness?" That's not a question that's ever going to get a truly honest answer, and mostly it's just going to draw something bogus like "I'm a workaholic!" Interviewers ask these questions because they're "supposed" to, but they usually don't give any useful information. "Do you consider yourself successful?" The answer is always yes. "Are you a team player?" The answer is always yes. "How long do you plan on working here?" The answer is always long-term. "What's more important, the work or the money?" The work is always more important.

It's easy to identify a nonsense interview question - is it easy for you to give a very generic and canned answer that reveals nothing about you? If it is, then don't sweat the question and worry about ones that actually matter.

1. Tell me about yourself.

This basically just serves to make the person comfortable and gives me a chance to figure out how they talk. This is a question that every interviewee should be prepared to answer, so you should be able to deliver a steady answer here. Have something clear in mind for this one before you even go in the door. The "best" answer highlights aspects of yourself that make you stand out from Joe Average in a positive fashion. Make a list of four or five of the biggest ones, then work that into a thirty second bit.

2. Tell me what you know about us.

This question simply tries to determine if the person being interviewed has done their homework. An exceptional candidate will be able to deliver a lot of information about the company, but mostly this eliminates people who didn't even bother to do minimal checking - these are people we don't want. In other words, before you go to an interview, know what the organization is.

3. What sets you apart from other people that might apply for this job?

The answer is usually already known to the interviewer based on the resume, but this is a chance for you to really sell yourself. Most interviewers will usually sit back and see how well you can sell. On occasion, surprises can be good here, but this can be tricky - if it's something that should have been on your resume, why was it not on your resume? You're better off knowing what the cream of the crop of your resume is and just listing it out.

4. Describe to me the position you're applying for.

This is a "homework" question, too, but it also gives some clues as to the perspective the person brings to the table. The best preparation you can do is to read the job description and repeat it to yourself in your own words so that you can do this smoothly at the interview.

5. Why are you interested this position?

This is actually something of a trick question, because it's just a way of re-asking the second question (what you know about the company) and the fourth (what you know about the position). It's asked because it tells whether people give flippant answers to questions (things like "because I'm a people person") or whether they think about things and give a genuine question. This is a good question to formulate an answer for in advance - basically, just come up with a few things that seem intriguing to you about the company and the position and reasons why they interest you.

6. What aspect of this position makes you the most uncomfortable?

Most people think this is some sort of filter, but it's rarely used that way. This is actually an honesty question. No one on earth will like every aspect of every potential job - it's just not in us. Location? Working hours? People? The company's too big? The company's too small? Honesty really works here - I'd prefer to hear a genuine reason for discomfort (particularly one that comes from real observation of the company) than a platitude that isn't really a discomfort at all. A good way to answer is something like "I've never worked in a company this large before" or "I've heard some strange things about the corporate culture" or "The idea of working for a startup at such an early stage makes me nervous."

7. What was the biggest success you had at your last job?

8. What was the biggest failure you had at your last job?

It's usually good to pair these questions, but the important one is the biggest failure. The best applicant is usually someone who will admit that they made a disaster out of something (they're fairly honest and willing to admit errors) and that they learned from it, an incredibly important trait.

9. Tell me about the best supervisor you've ever had.

10. Tell me about the worst supervisor you've ever had.

These two questions simply seek to figure out what kind of management style will work best for this person and also how that person is likely to manage people. Let's say I work in an organization with a very loose-knit management structure that requires a lot of self-starting. If that's the case, I want to either hear that the "best" boss was very hands-off or that the "worst" boss was a micromanager. On the other hand, if I came from a strict hierarchical organization, I might want to see the exact opposite - a "best" boss that provided strong guidance and a good relationship or a "worst" boss that basically left the applicant to blow in the wind. Your best approach is to answer this as honestly as possible - the interviewer will have a good idea of the corporate culture and, frankly, if you try to slip into a company where you don't match the culture, you'll have a very hard time fitting in and succeeding. These questions might be worded as "what kind of management style works for you."

Another tip: highlight positives in all of the bosses you discuss. Never turn the interview into a bash-fest of anyone. Your worst boss should have a very small number of specific flaws and they should mostly relate to diverging expectations from you, not in bad character traits. Bashing someone during an interview just reflects poorly on you, so don't jump for the bait.

11. Tell me about the most difficult project you ever faced.

The interviewer could usually care less what the exact project is. The question is mostly looking to see if you have faced serious difficulty and how you overcame it. For most people, this isn't their biggest success or biggest failure, but something that they turned from a likely failure into some sort of success.

12. What do you see as the important future trends in this area?

This works well for some positions - technical ones and leadership ones - and not well for others. It should be pretty obvious from the type of job you're applying for whether this question might be asked. If it is, it's easy to prepare for - just spend a half an hour reading some blogs on the specific areas you're applying for and you'll have some food.

13. Have you done anything in the last year to learn new financial-wellness/things/improve yourself in relation to the requirements of this job?

This is a great "deer in the headlights look" question, as most people simply don't have an answer. The best way to handle this question is simply to always spend some time working on your skills in whatever way you can. Write open source code. Participate in Toastmasters. Take a class. If you put effort into improving yourself every year, you'll not only have a strong resume, but this question will be a non-issue.

14. Tell me about your dream job.

Never say this job. Never say another specific job. Both answers are very bad - the first one sends the warning flags flying and the second one says that the person's not really interested in sticking around. Instead, stick to specific traits - name aspects of what would be your dream job. Some of them should match what the company has available, but it's actually best if they don't all perfectly match.

15. Have you ever had a serious conflict in a previous employment? How was it resolved?

This question mostly looks for honesty and for the realization that most conflicts have two sides to a story. It also opens the door for people with poor character to start bashing their previous employer, something which leaves a bad taste in most interviewers' mouths. The best way to answer usually involves telling the story, but showing within it that there are two sides to that story and that you've learned from the experience to try to see the other person's perspective.

16. What did you learn from your last position?

Although it's fine to list a technical skill or two here, particularly if your job is very technical, it's very important to mention some non-technical things. "I learned how to work in a team environment after mostly working in solo environments" is a good one, for example. There should be no job where you learned nothing, and the interviewer is expecting that you learned at least a few things at your previous employment that will help at your current one.

17. Why did you leave your last position?

Mostly, this is looking for conviction of character. A strong, concrete answer of any reasonable sort is good here. "I wanted to move on" is not a strong answer. Downsizing is a good answer, as is a desire to seek specific new challenges (but be specific on what challenges you want to face). Minimize your actual discussion of your previous position here, as you'll be very close to a big opportunity to start bashing your previous position.

18. Tell me about a suggestion that you made that was implemented at a previous job.

Since these answers usually are heavily involved with the specifics of the previous position, the specifics aren't really important. What's most important is that you actually have been involved in making a suggestion and helping it come to fruition, ideally with some success story behind it. Having done so indicates that you're willing to do the same at this position, which can do nothing but improve an organization. Not having an answer of some sort here is generally a sizeable negative, but not a "do or die" negative.

19. Have you ever been asked to leave a position? Tell me about the experience.

Obviously, it's great if you can answer "no," but it's usually not a deal breaker if the answer is "yes." In fact, a "yes" answer can be turned into a positive - it's a great way to show that you've made mistakes and learned valuable lessons from them. Be honest here, no matter what, but don't spend time bashing the people that let you go. Only discuss them with respect, even if you're angry about what happened.

20. Have you ever had to fire anyone? Tell me about the experience.

This is a question that is mostly looking to see if you have empathy for others. Take it dead seriously when answering - it should not have been an easy choice or an easy experience, but one that you handled and survived. Do not bash the person you fired, either - be as clinical as possible with the reasons.

21. Are you applying for other jobs?

This is an honesty question. I'm looking for "yes," but people who are trying too hard to feed me a line of nonsense answer "no." The best way to answer is to say "Yes, in much the same way that you're interviewing other people. We're both trying to find the best fit for what we need and what we want." If your answer is truly no, then say so - "No, I'm actually happy with my current position, but there were a few compelling aspects of this job that made me want to follow up on it" and list those aspects.

22. What do you feel this position should pay?

Surprising to many, this is often not salary negotiation. In most cases, the person you're interviewing with has little control over the final salary you'll get. It's usually used as a reality check - if you're hiring a janitor and they expect $80K, you can probably toss the resume right then and there. At the same time, a highly-skilled programmer selling themselves at $30K is also setting off some warning bells. A good answer is usually on target or a bit on the high side, but not really low or insanely high. I'd get an idea of the asking rate for the position before I ever go to the interview, then request about 30% more.

23. Where do you see yourself in your career in five years?

This is something of a "junk" question, but it is useful in some regards as it filters for people with initiative. A person who answers something along the lines of "I'm going to be successful in this position that I'm interviewing for!" is either not incredibly motivated to improve themselves or isn't being totally honest. I'd rather have an answer that involves either promotion or some level of enterpreneurship - strong organizations thrive on self-starters. The only problem for potential interviewees is that some companies - weak ones, usually - don't want self-starters and are particularly afraid of people who dream of becoming entrepreneurs. Talking about promotion is thus usually the safest bet if you're not familiar with the culture, but I personally love it when people interviewing talk about entrepreneurship - that means they're the type that will be intense about succeeding.

24. What are your long-term goals - say, fifteen years down the road?

This is a great late question because it tells you whether the person is a long-term thinker or not. People that plan for the long term are usually in a good, mature mental state and will often wind up being stronger workers than people without long-term plans.

25. Do you have any questions about this job?

Yes, you do have questions about this job. Not having questions is a sign that you aren't really that interested in the position. Thus, your job as an interviewee is to have a few questions already in mind when you walk in the door. Most interviewers are happy to answer most anything you ask them - just make sure your questions are intelligent ones, though.

Do Your Homework!

Here are the things you should do in advance of any interview that will help you handle almost all of the questions above.

Work on a very brief description of yourself that you can bust out at any interview. The big trick is to mention things that are unusual or even unique to you, but stick to the things that are either positive or (at worst) neutral - keep the negatives to yourself unless they're tied to a big positive. A thirty second spiel will do.

Research the company by visiting their web site and finding out exactly what they do. Good things to read include the company's most recent annual report and their Wikipedia entry (if they're big) or just by Googling the company's name and location (if they're small). If it's a startup, just try to absorb as much as you can from whatever sources you can get, but if it's truly a tiny startup, don't sweat it if you can't find much information.

Research the position by reading the job posting very carefully and looking up any pieces that you don't know. You might also want to refresh yourself on what's cutting edge in the areas covered by the job posting by reading up a bit if you're not already familiar - blogs and news sites are a good place to start. You should also get a good grip on the regular starting salary for this type of job by searching around for similar jobs near your location.

Know how you match the position by taking the pieces of the company information you found and the job posting and matching them to your skills. Do about five of these, as these are going to be silver bullets during the interview. Also, identify at least one thing that makes you uncomfortable about the company and position and think about why it makes you uncomfortable.

Always work to improve your skills by participating in activities that sharpen the key skills you need for the field you're in. Are you in public relations? Join a Toastmasters group. Are you an administrative assistant? Do volunteer work for an organization that could use your skills but does things in a different way (the same goes for many tradespeople). Are you a programmer? Contribute to an open source project.

Have a few questions about the position in mind when you walk in the door. This creates a strong impression during the interview that you are actually interested in that specific position, which is a big positive for you. Questions of all kinds are good here, but the best ones usually address corporate culture and technical specifics of the job.

Do not bash your previous job. If there are specific things about your last job that really, really irritate you, spend some time trying to think of positives about it. Know when you go in that your previous job will likely be discussed at least to a degree, and be prepared to discuss it without being negative. Look for positives, and also be able to state the reasons for leaving as clinically as possible.

Be honest, above all else. If you make up things at your interview and you slip at all, the interviewer will toss your application in the trash. Instead, just try to focus on the positives of what you already have. If you've made it to the interview, there's something the organization likes about you. Don't waste time inventing stuff to say.