I’vementioned a few times on The Simple Dollar that I have conducted asubstantial number of job interviews in the past. Although the jobs Iusually hire for are technical in nature, most of the truly telling (andthus truly valuable) questions were non-technical questions. Agreat interview question reveals the nature of the person you’re hiring– honesty, reliability, ability to communicate intelligently andquickly, and so on.

Over time, I’ve collected a pretty good pile of questions that I usein almost every interview. Here are twenty five of the most reliableones, along with a tip or two for each one that illustrates what makes agood answer – and what makes a bad one. Hopefully, the discussion herewill provide some insightful questions for interviewers, as well assome things for potential job applicants to think about. If you caneasily answer all of these questions, you shouldn’t have much to worryabout in the interview. At the end, I give a checklist of “homework” apotential interviewer should do before a big interview.

First, stupid answers tostupid questions.
A lot of questions that are asked at job interviews are really stupidand 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 aworkaholic!” Interviewers ask these questions because they’re“supposed” to, but they usually don’t give any useful information. “Doyou consider yourself successful?” The answer is always yes. “Are you ateam player?” The answer is always yes. “How long do you plan onworking 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 question – is it easy for you togive a very generic and canned answer that reveals nothing about you?If it is, then don’t sweat the question and worry about ones thatactually matter.

1. Tell me about yourself.
This basically just serves to make the person comfortable and gives me achance to figure out how they talk. This is a question that everyinterviewee should be prepared to answer, so you should be able todeliver a steady answer here. Have something clear in mind for this onebefore you even go in the door. The “best” answer highlights aspectsof yourself that make you stand out from Joe Average in a positivefashion. Make a list of four or five of the biggest ones, then workthat into a thirty second bit.

2. Tell me what you know aboutus.
This question simply tries to determine if the person being interviewedhas done their homework. An exceptional candidate will be able todeliver a lot of information about the company, but mostly thiseliminates people who didn’t even bother to do minimal checking – theseare people we don’t want. In other words, before you go to aninterview, know what the organization is.

3. What sets you apart fromother people that might apply for this job?
The answer is usually already known to the interviewer based on theresume, but this is a chance for you to really sell yourself. Mostinterviewers will usually sit back and see how well you can sell. Onoccasion, surprises can be good here, but this can be tricky – if it’ssomething that should have been on your resume, why was it not on yourresume? You’re better off knowing what the cream of the crop ofyour resume is and just listing it out.

4. Describe to me the positionyou’re applying for.
This is a “homework” question, too, but it also gives some clues as tothe perspective the person brings to the table. The best preparationyou can do is to read the job description and repeat it toyourself in your own words so that you can do this smoothly atthe interview.

5. Why are you interested thisposition?
This is actually something of a trick question, because it’s just a wayof re-asking the second question (what you know about the company) andthe fourth (what you know about the position). It’s asked because ittells whether people give flippant answers to questions (things like“because I’m a people person”) or whether they think about things andgive a genuine question. This is a good question to formulate an answerfor in advance – basically, just come up with a few things thatseem intriguing to you about the company and the position and reasonswhy they interest you.

6. What aspect of thisposition makes you the most uncomfortable?
Most people think this is some sort of filter, but it’s rarely used thatway. This is actually an honesty question. No one on earthwill like every aspect of every potential job – it’s just not in us.Location? Working hours? People? The company’s too big? Thecompany’s too small? Honesty really works here – I’d prefer to hear agenuine reason for discomfort (particularly one that comes from realobservation of the company) than a platitude that isn’t really adiscomfort at all. A good way to answer is something like “I’ve neverworked in a company this large before” or “I’ve heard some strangethings about the corporate culture” or “The idea of working for astartup at such an early stage makes me nervous.”

7. What was the biggestsuccess you had at your last job?
8. What was the biggest failureyou had at your last job?
It’s usually good to pair these questions, but the important one is thebiggest failure. The best applicant is usually someone who will admitthat they made a disaster out of something (they’re fairly honest andwilling to admit errors) and that they learned from it, an incrediblyimportant trait.

9. Tell me about the bestsupervisor you’ve ever had.
10. Tell me about the worstsupervisor you’ve ever had.
These two questions simply seek to figure out what kind of managementstyle will work best for this person and also how that person is likelyto manage people. Let’s say I work in an organization with a veryloose-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 veryhands-off or that the “worst” boss was a micromanager. On the otherhand, if I came from a strict hierarchical organization, I might want tosee the exact opposite – a “best” boss that provided strong guidanceand a good relationship or a “worst” boss that basically left theapplicant to blow in the wind. Your best approach is to answerthis as honestly as possible – the interviewer will have a goodidea of the corporate culture and, frankly, if you try to slip into acompany where you don’t match the culture, you’ll have a very hard timefitting in and succeeding. These questions might be worded as “whatkind of management style works for you.”

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

11. Tell me about the mostdifficult project you ever faced.
The interviewer could usually care less what the exact project is. Thequestion is mostly looking to see if you have faced seriousdifficulty and how you overcame it. For most people, this isn’t theirbiggest success or biggest failure, but something that they turned from alikely failure into some sort of success.

12. What do you see as theimportant 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 ofjob 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 blogson the specific areas you’re applying for and you’ll have some food.

13. Have you done anything inthe last year to learn new things/improve yourself in relation to therequirements of this job?
This is a great “deer in the headlights look” question, as most peoplesimply don’t have an answer. The best way to handle this question issimply to always spend some time working on your skills inwhatever way you can. Write open source code. Participate inToastmasters. Take a class. If you put effort into improving yourselfevery year, you’ll not only have a strong resume, but this question willbe a non-issue.

14. Tell me about your dreamjob.
Never say this job. Never say anotherspecific job. Both answers are very bad – the first one sends thewarning flags flying and the second one says that the person’s notreally interested in sticking around. Instead, stick tospecific traits – name aspects of what would be your dream job.Some of them should match what the company has available, butit’s actually best if they don’t all perfectly match.

15. Have you ever had aserious conflict in a previous employment? How was it resolved?
This question mostly looks for honesty and for the realization that mostconflicts have two sides to a story. It also opens the door for peoplewith poor character to start bashing their previous employer, somethingwhich leaves a bad taste in most interviewers’ mouths. The best way toanswer usually involves telling the story, but showing within it thatthere are two sides to that story and that you’ve learned from theexperience to try to see the other person’s perspective.

16. What did you learn fromyour last position?
Although it’s fine to list a technical skill or two here, particularlyif your job is very technical, it’s very important to mention somenon-technical things. “I learned how to work in a team environmentafter mostly working in solo environments” is a good one, for example.There should be no job where you learned nothing, and the interviewer isexpecting that you learned at least a few things at your previousemployment that will help at your current one.

17. Why did you leave yourlast position?
Mostly, this is looking for conviction of character. A strong, concreteanswer of any reasonable sort is good here. “I wanted to move on” isnot a strong answer. Downsizing is a good answer, as is a desire toseek specific new challenges (but be specific on whatchallenges you want to face). Minimize your actual discussion of yourprevious position here, as you’ll be very close to a big opportunity tostart bashing your previous position.

18. Tell me about a suggestionthat you made that was implemented at a previous job.
Since these answers usually are heavily involved with the specifics ofthe previous position, the specifics aren’t really important. What’smost important is that you actually have been involved in making asuggestion and helping it come to fruition, ideally with some successstory behind it. Having done so indicates that you’re willing to do thesame at this position, which can do nothing but improve anorganization. Not having an answer of some sort here is generally asizeable negative, but not a “do or die” negative.

19. Have you ever been askedto leave a position? Tell me about the experience.
Obviously, it’s great if you can answer “no,” but it’s usually not adeal breaker if the answer is “yes.” In fact, a “yes” answer can beturned into a positive – it’s a great way to show that you’ve mademistakes and learned valuable lessons from them. Be honesthere, no matter what, but don’t spend time bashing the people that letyou go. Only discuss them with respect, even if you’re angry about whathappened.

20. Have you ever had to fireanyone? Tell me about the experience.
This is a question that is mostly looking to see if you have empathy forothers. Take it dead seriously when answering – it should nothave been an easy choice or an easy experience, but one that youhandled and survived. Do not bash the person you fired, either– be as clinical as possible with the reasons.

21. Are you applying for otherjobs?
This is an honesty question. I’m looking for “yes,” but people who aretrying too hard to feed me a line of nonsense answer “no.” The best wayto answer is to say “Yes, in much the same way that you’re interviewingother people. We’re both trying to find the best fit for what we needand what we want.” If your answer is truly no, then say so – “No, I’mactually happy with my current position, but there were a few compellingaspects of this job that made me want to follow up on it” and listthose aspects.

22. What do you feel thisposition should pay?
Surprising to many, this is often not salarynegotiation. In most cases, the person you’re interviewingwith has little control over the final salary you’ll get. It’s usuallyused 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 thesame time, a highly-skilled programmer selling themselves at $30K isalso setting off some warning bells. A good answer is usually on targetor a bit on the high side, but not really low or insanely high. I’dget an idea of the asking rate for the position before I ever go to theinterview, then request about 30% more.

23. Where do you see yourselfin your career in five years?
This is something of a “junk” question, but it is useful in some regardsas it filters for people with initiative. A person who answerssomething along the lines of “I’m going to be successful in thisposition that I’m interviewing for!” is either not incredibly motivatedto improve themselves or isn’t being totally honest. I’d rather have ananswer that involves either promotion or some level of enterpreneurship– strong organizations thrive on self-starters. The only problem forpotential interviewees is that some companies – weak ones, usually –don’t want self-starters and are particularly afraid of people who dreamof becoming entrepreneurs. Talking about promotion is thus usually thesafest bet if you’re not familiar with the culture, but I personally loveit when people interviewing talk about entrepreneurship – that meansthey’re the type that will be intense about succeeding.

24. What are your long-termgoals – say, fifteen years down the road?
This is a great late question because it tells you whether the person isa long-term thinker or not. People that plan for the long term areusually in a good, mature mental state and will often wind up beingstronger workers than people without long-term plans.

25. Do you have any questionsabout this job?
Yes, you do have questions about this job. Not having questions is asign that you aren’t really that interested in the position. Thus, yourjob as an interviewee is to have a few questions already in mind whenyou walk in the door. Most interviewers are happy to answer mostanything you ask them – just make sure your questions are intelligentones, though.

Do Your Homework!

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

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

Research the company by visiting their web site andfinding out exactly what they do. Good things to read include thecompany’s most recent annual report and their Wikipedia entry (ifthey’re big) or just by Googling the company’s name and location (ifthey’re small). If it’s a startup, just try to absorb as much as youcan 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 verycarefully and looking up any pieces that you don’t know. You mightalso want to refresh yourself on what’s cutting edge in the areascovered by the job posting by reading up a bit if you’re not alreadyfamiliar – blogs and news sites are a good place to start. You shouldalso get a good grip on the regular starting salary for this type of jobby searching around for similar jobs near your location.

Know how you match the position by taking the piecesof the company information you found and the job posting and matchingthem to your skills. Do about five of these, as these are going to besilver bullets during the interview. Also, identify at least one thingthat makes you uncomfortable about the company and position and thinkabout why it makes you uncomfortable.

Always work to improve your skills by participatingin activities that sharpen the key skills you need for the field you’rein. Are you in public relations? Join a Toastmasters group. Are youan administrative assistant? Do volunteer work for an organization thatcould use your skills but does things in a different way (the same goesfor many tradespeople). Are you a programmer? Contribute to an opensource project.

Have a few questions about the position in mind whenyou walk in the door. This creates a strong impression during theinterview 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 technicalspecifics of the job.

Do not bash your previous job. If thereare specific things about your last job that really, really irritateyou, spend some time trying to think of positives about it. Knowwhen you go in that your previous job will likely be discussed at leastto a degree, and be prepared to discuss it without beingnegative. Look for positives, and also be able to state the reasons forleaving as clinically as possible.

Be honest, above all else. If you make up things atyour interview and you slip at all, the interviewer will toss yourapplication in the trash. Instead, just try to focus on the positivesof what you already have. If you’ve made it to the interview, there’s somethingthe organization likes about you. Don’t waste time inventing stuff tosay.