It’s too hard to find the best interview questions. Even though it’s widely acknowledged that “hiring right” is the make-or-break duty of every growing business, finding the perfect interview question requires sifting through a compendium of books, blogs, and brains.

As a boss, what I want is a broad list of great interview questions, organized by the quality I wish to evaluate (e.g., “hard worker,” “focused,” “team player”). So that’s what I’ve compiled, below.

Read more about the methodology at the bottom of this post, following the questions. tl; dr it involved selectively extracting from all the best books and blog posts I could find in a week of research.

Part one: the most sought-after traits in employees

The most sought-after traits have been broken into four tiers, based on the frequency with which they were mentioned in first-page search results. If you only have an hour for your interview, you probably don’t want to go very in-depth on more than 3 different areas. A popular strategy at bigger companies is to share different areas of evaluation between the team. It helps to ensure that you won’t miss a fatal weakness of the applicant.

If you are going to interview collaboratively, remember that some questions are duplicated between sections. Don’t be that interviewer who repeats a question from the previous interviewer.

Tier One

There is one talent that almost every blog & book regards as critical. Apparently, businesses don’t want to hire a candidate that causes drama and resists management?

• Team player. Are they friendly, agreeable and upbeat?

Tier Two

These qualities were cited by 75% of publications surveyed, which is to say they are important to virtually every company. “Honesty” is one of the hardest qualities to evaluate in an interview context, but I’ve found a handful of questions to penetrate the interview defenses.

• Adaptable. Are they flexible and eager to learn?
• Trustworthy. Shun the crooks.
• Culture fit. Does their personality match the company’s values?

Tier Three

Qualities that were mentioned by roughly half the sources surveyed. Many of the most critical talents Bonanza seeks are located here.

• Communicator. Do they know how to wield language and be tactful?
• Leadership. Does this candidate have the tools to be a leader?
• Ambitious. Every business wants a team that is self-motivated and hard-working
• Focused. Can they possibly eschew Facebook, Twitter, IM, Hacker News, et al. for eight hours?
• Problem-solving. Can they work autonomously, surmounting challenges and making decisions lacking manager intervention?
• Intelligent. Does this candidate have the raw smarts to be proficient at their job?
• Organized. Can they keep track of the details and prioritize among choices?

Tier Four

These qualities weren’t mentioned as consistently across articles surveyed. It is my personal judgement that they are still important to assess, depending on the role being filled.

• Passionate. Are they excitable? Do they love their work?
• Creative. Can they figure out novel solutions to problems?
• Stable. Loyalty and dependability are essential to team morale.
• Invested in us. Have they done the homework on the company they’re appyling to?
• Meat & potatoes. Miscellaneous questions not to forget.

Part 2: My favorite interview questions

This list is the culmination of a week spent combing the internet and popular books for great interview question. I have attempted to choose my favorite versions of the classic questions (e.g., “What’s your weakness?”) such that the version chosen gives the candidate the opportunity to talk in the realm of specific examples.

Do note: some questions apply to more than one category, so are listed more than once. Don’t make a fool of yourself in a collaborative interview by asking the same question twice. Use your communication skills to coordinate questions with your teammates.

Team player, friendly, agreeable, upbeat

1. What do you think makes a person likeable?
2. How would a co-worker who likes you describe you?
3. How would a co-worker who dislikes you describe you?
4. What qualities in your co-workers bother you most? Do you appreciate most?
5. If I were to ask your current boss what your greatest strength is, what would he or she tell me?
6. What do you have Strong Opinions about?
7. Describe the boss who would get the very best work from you.
8. What changes have you made in working with others to be more effective at work?
9. What could you have done to improve your relationship with your worst boss?
10. What’s a time you disagreed with a decision that was made by your boss? How did you handle it?
11. Tell me about a time you had a conflict with a co-worker, and how you handled it?
12. How do you deal with a difficult customer?
13. What do you feel an employer owes an employee?
14. Give an example of a time you misjudged someone
15. When was the last time you were angry?
16. Can you describe a time when your work was criticized?

Adaptable, flexible, eager to learn

1. What do you think are the most important attributes of successful people? How do you rate yourself in those areas?
2. If you could change one thing about yourself by snapping your fingers, what would it be and why? Do you have a plan for
3. making that improvement?
4. Tell me about competitor (or similar) businesses you kept up with in your past position. What did you glean from them?
5. When have you failed? Describe what happened and what you learned from it.
6. How do you take advantage of your strengths?
7. How do you compensate for your weaknesses?
8. What’s the most interesting thing you’ve learned in the past year?
9. If you were starting college today, what classes would you take? (Alternative: What would you like to learn more about in the next year?)
10. What books are you reading? (Alternative: What industry publications are your favorites?)
11. Tell me about the last time you took a risk? Was it the right decision? What did you learn?
12. How do you keep up with changes in your field?
13. What was the most useful criticism you received?
14. How do you measure your own success?

Trustworthy, honest

1. Have you worked in a position where you felt you weren’t given enough to do?
2. What was the most useful criticism you received?
3. If I were to ask your current boss what your greatest weakness was, what would he or she tell me?
4. Tell me about the last time you had to make an unpopular decision
5. When have you failed? Describe what happened and what you learned from it.
6. Tell me about a work incident in which you were totally honest, despite a potential risk or downside.
7. What’s your greatest fear about this opportunity?
8. Where does your boss think you are now? [Ed: answer doesn’t matter, smell of truthfulness in response does]
9. If I looked through your web browser history, what would I learn that isn’t on your resume?
10. Tell me about some of the gaps in your employment. How did these come about?
11. May I contact your current employer? May I contact your references?
12. Why shouldn’t I hire you?

Culture fit, compatible personality

1. Describe the boss who would get the very best work from you
2. What will make you love coming to work here everyday?
3. What type of work environment do you prefer?
4. What gets you excited outside of work?
5. If I looked through your web browser history, what would I learn that isn’t on your resume?
6. Assume that you come to work here. One year from now you go home one Friday evening thinking that accepting this job was the best thing you ever did. What happened during the year for you to feel that way?
7. How much time per week do you spend working alone? Do you think it should be more or less?
8. How competitive are you?
9. Do you have a favorite quote?
10. What unique experiences separate you from other candidates?
11. What are the most important rewards you expect to get from your career?
12. Where do you see yourself in five years?
13. Which areas of your work are most often praised?
14. Tell me about the funniest role you’ve had on a job/project?
15. When you are on vacation, what do you miss most about work?
16. How would you describe yourself to a stranger at a party?
17. How do you incorporate fun into your day?

Communicator, tactful

See also: “Team player”

1. Why are you leaving your current job?
2. Have you given presentations to your peers, either at work or in other contexts?
3. See that picture frame on the wall? Sell it to me.
4. What’s a time you disagreed with a decision that was made by your boss? (Alternate: If you know your boss is 100% wrong about something, how would you handle it?)
5. If you feel strongly about an idea, but a person doesn’t agree with you, what tactics would you use to persuade them?
6. What’s your greatest fear about this opportunity?
7. Describe a time where you put in extra effort to make sure a person with whom you were communicating had really understood your point.
8. Describe a situation in which you dealt with a difficult customer
9. Why shouldn’t we hire you?
10. What do you think we could do better or differently?

Leadership

1. How do you motivate people?
2. What do you think are the most important attributes of successful leaders?
3. Tell me about the last time you had to make an unpopular decision
4. Tell me about the last time you fired someone
5. How do you decide what tasks to delegate to whom?
6. How do you bring other team members into your process? (Alternate: How do you get others on board with your decisions?)
7. Did you inaugurate new processes in your previous position? Tell me about them
8. Have you been in charge of a budget? How did you balance priorities?
9. What’s the most difficult part of being a manager for you?
10. What do your reports find most difficult about your management style?
11. How do you set expectations with your reports or peers? How do you handle a situation where a report fails to meet expectations (e.g., consistently missing deadlines)?
12. Describe a situation where you successfully resolved a conflict with a team member.
13. Would you rather be liked or feared?
14. Describe a crisis you faced at work. What was your role? How did you resolve it? What were the results?
15. Do you have a management philosophy? No.

Ambitious, self-motivated, hard-working

See also: “Invested in us”

1. What would your first 30, 60, 90 days look like in this role?
2. What extracurricular activities were you involved with in college? Since?
3. What side projects have you done? What was the biggest?
4. Tell me something that happened at work in the last year that made it a truly great day.
5. Have you been promoted in past jobs? How did these promotions come about?
6. Describe a situation in your past job where you were proactive? (Alternate: Give me an example from a previous job where you’ve shown initiative)
7. When did you first start doing [the job’s requirement]? [Ed note: if they started doing it before required in school, suggests self-starter]
8. How do you keep up with changes in your field?
9. How competitive are you?
10. What are your short range goals and objectives?
11. Give me an example of a goal you set in the past and how you went about reaching it?
12. Where do you see yourself in five years?
13. Do you take work home with you?
14. How ambitious are you? No.

Focused, tenacious

1. What are your strategies for making the most of your day?
2. What do you do when things are slow? (You are lacking for projects)
3. What do you do when you’re burned out to rekindle your spark?
4. If you’re struggling with an idea, how do you break through and find a solution?
5. How do you pass time while waiting for [job specific pause point, like compiling a program]?
6. Describe a time where you put in extra effort to improve a business process to be more efficient?
7. What percentage of your time is spent on each of your job responsibilities? [Answer matters less than whether they seem to keep track of it]

Problem-solving, self-sufficient, autonomous, decisive

See also: “creative.”

1. Describe a time when you were asked to do something you weren’t trained to do. How did you handle it?
2. Tell me about a time when you made a decision without all the information you needed.
3. Can you tell me about a time when you discovered a more efficient way to do a routine task? Have you done this repeatedly?
4. What are some of the Google tricks you use to find answers to your questions?
5. How do you decide whether to message your boss when you have a tough problem?
6. How many dentists are there in Poland?
7. How would you build a toaster for a blind person?
8. See that picture frame on the wall? Sell it to me.
9. Tell me about the last time you took a risk? Was it the right decision? What would you have done differently?
10. Can you think of a time where you were forced to take charge when your manager wasn’t available?
11. Have you worked in a position where you felt you weren’t given enough to do?
12. What was the most important task you’ve ever had?

Intelligent, proficient, competent

1. What are you especially good at compared to others?
2. Have you been promoted in past jobs? How did these promotions come about?
3. What’s the one accomplishment you’re most proud of? Why?
4. What is your greatest professional achievement?
5. What’s your greatest fear about this opportunity?
6. Tell me something that happened at work in the last year that made it a truly great day
7. How would you rate yourself in terms of speed, quality, and self-direction? [Ed: Can they answer a multi-part question?]
8. In what college courses did you get the worst grades? Why? How do you think it’ll effect your job performance?
9. Tell me about the last time you took a risk? Was it the right decision? What would you have done differently?
10. What do you consider to be the most important aspect of your craft?
11. What do you consider to be the most misunderstood aspect of your craft?
12. If I asked a co-worker friend what made you most valuable to the team, what would they say?

Organized, detail-oriented

1. What would your first 30, 60, or 90 days look like in this role?
2. Tell me about the first 60 minutes of your typical day
3. What are your strategies for making the most of your day?
4. Have you been in charge of a budget? How did you balance priorities?
5. What do you do when you begin a project? How does this help the project go successfully?
6. What tools do you use to maintain organization? How do you keep lists?
7. Tell me about a project where you noticed a small detail that made a big difference?
8. What percentage of your time is spent on each of your job responsibilities?
9. Describe the top of your desk
10. Do you always double-check your work? What’s your system for deciding?

Passionate, excitable

1. What excites you about our company?
2. What gets you excited outside of work?
3. Describe the boss who would get the very best work from you.
4. What are the most important rewards you expect to get from your career?
5. If you had unlimited money, what would you be doing?

Creative

1. Tell me about the last time you took a risk? Was it the right decision? What would you have done differently?
2. Tell me about the last time you found a unique solution to a long-standing problem.
3. Tell me about the last time you figured out how to save your company money? Did they heed your advice?
4. Did you inaugurate new processes in your previous position?
5. What improvements might you make to our business?
6. Where do you draw inspiration for your craft from?

Stable, loyal, dependable

1. Why are you leaving current job? Have you brought your concerns with your job to the attention of your boss?
2. Is this the first time you’ve thought about leaving? What made you stay before?
3. Why have you had so many jobs?
4. How do we know you’ll stick around?
5. Will your current job be surprised to hear you’re leaving?
6. What aspect of our job appeals to you least?
7. How does your ideal job stack up to what we’re offering?
8. Have you been absent from work more than a few days in any previous position?

Invested in us

1. What about this job most excites you?
2. What about this company most excites you? (Alternative: What do you know about the company?)
3. What do you think we could do better or differently?
4. What advantage do we have over our competitors? (Who are our competitors?)
5. How does your ideal job stack up to what we’re offering?
6. Where do you see yourself in five years?
7. What criteria are you using to choose companies you interview with?

Misc, administrative

1. Tell me about yourself
2. Which areas of your work are most often praised?
3. Is there any question I haven’t asked you that I should?
4. Salary range expectations?
5. When can you start?
6. Are you considering other offers?

Methodology

Settling on the definition for what makes a “great” interview question is a subjective affair. There were a couple rules I applied. I wanted questions that lead the candidate to talk about a specific example; questions like “what’s your management style?” (a common question amongst my sources [1]) are too vague to expect worthwhile insights in return. When in doubt, I considered whether I would be annoyed to get asked the question in an interview (e.g., “Give us one word that describes you“). If so, it’s not on the list. 80% of questions evaluated are not on the list.

Once I decided what I was after, I purchased a handful of Amazon’s top-rated interview books, and visited tens of Google’s top ranked pages on interviewing. Most of my sources are linked in the footnotes [1][2].

Building a dataset from my research, I sought to make two determinations:

1. What are the top 15 qualities that employers seek in an employee?
2. What are the most succinct questions to evaluate those qualities?

The first goal was tricky, because often, sources will refer to the same idea in slightly different ways (e.g., “adaptable,” “flexible,” or “willing to learn”). Some qualities, like “problem-solving” and “creative” feel distinct, but related. In these cases, I added links between the two categories to help the reader find related questions.

Still here? Hello!

I’d wager you would pass the “hard-working” and “tenacious” evaluation phases of the interview. So why not check out the many jobs Bonanza is hiring for at the moment? Everyone loves an interview where they know the questions in advance. 🙂

Also: if you have a favorite interview question that I haven’t listed here, please share it in the comments! Around 10% of the questions above were from my personal collection, indicating there are likely still more good questions lurking out there.

Footnotes

The philosophical side of me woke up a bit disgruntled this morning. It had processed that last blog post during my 6 hours of rest, and it concluded that what I had written ultimately spelled the unraveling of capitalism as we know it. “For you see,” says philosophical side, “if a company’s profit represents only the gap between the contributions of its workers and their actual pay, then any company that isn’t losing money is operating unjustly. And any company that is losing money won’t be operating for long.” Ah, guilty as charged. So how’s about I speak more precisely?

The root of that equation remains true. A company’s profit still represents the difference between the contributions of its workers and their pay. The crucial detail here is that in this definition, a company’s “workers” also includes its top brass — the people making the deals (the other crucial detail is that some of that profit is mitigated by taxes, risk, etc. boring!). In a perfectly just company, the gap between workers’ contributions and compensation represents the value that the company’s principal shareholders bring, because they are ultimately the ones that will reap that profit.

What had induced me to carelessly paint profit as an illustration that high performers were not fairly compensated was that it’s usually true. But only of high performers. This axiom can be witnessed at most any company, but it is perhaps easiest to illustrate at technology companies, if only because that’s where I’ve witnessed it. The gap in productivity between a company’s most productive programmer and least productive programmer is usually around 10x (This is not an exaggeration; if anything, it is an understatement. Unless they are damn good at hiring, a gap of 10x is usually observable by the time a company reaches 20 or so programmers. See Paul Graham’s earlier linked articles for some exlanation of how this is possible).

The gap in salary between a company’s most productive programmer and least productive programmer? Perhaps 2x, at most 3x. Blame methods of evaluation, blame economies of scale, blame the rain, but the reality is that a programmer who is 10x better than another programmer who makes $40,000 is not getting paid $400,000. They’re probably getting paid $70,000, and hopefully, working with a boss who lavishly praises their contributions on a regular basis.

But the bottom line is that $330,000 of that programmer’s productivity is being manifest as profit for the company (or $330,000 of that programmer’s productivity is paying for the 8 overcompensated crappy programmers, if you prefer). This is not a “good deal” for the highly talented individual. But I admittedly mispoke in attributing all profit to inequity. In actuality, some profit is absorbed by future investment, some by past and future risk, and some by the shareholders who will take that profit. The rest? That is inequity.

I still need a bona fide “second in command”-type partner.

How much time to invest on this search and how to go about in on a day-to-day basis? I’ve gotten some interesting opinions on this from different people I’ve asked. When I started a thread about it on Biznik yesterday, I got one opinion (from the esteemed Mr. Pierre Leonard) that I should become a more active presence in community boards to make the people come to me, and one opinion (from the esteemed Mr. Kelly Hobkirk) that I’d be better off to just focus on building the business. Of course, both of these opinions were coming from people who don’t have an intimate knowledge of the business or its current state of affairs. But independently of my situation, they make excellent points to be weighed in the overall argument of how much time to invest, and where to invest it.

However, my prevailing opinion remains that, despite the small army of helpful consultants and rad programmers and able web designers that are already contributing to this project, having an equally-contributing, self-motivated co-founder is a critical path requirement to get where we’re going at the rate I want to get there.

The next frontier of exploration was actually proposed to me by none other than my girlfriend, the lovely KT. And it’s a damn good idea: students. Yeah, they aren’t going to step in with years of experience or a rolodex of industry contacts. But as I’ve found, those assets tend to go hand-in-hand with financial responsibilities and monetary expectations. I think there’s a reason that young co-founders flock together (Bill Gates and Paul Allen, anyone? Or their arch-nemeses, Sergey and Larry?): it’s that they’ve got fire and they’ve got freedom. Of course, more seasoned co-founders can make something work if they’ve got a cache of money and cred piled up between them, but whuppersnappers on step 29 of 800 don’t have such frivolities (observe: blog sarcasm) at hand.

In the next couple days, I’ll post a link on here to my newest student job listing. But in a nutshell, my pitch to students will be the same as my pitch to every bright person employed by a company they don’t have a share in: why do you think you’re getting paid? So few smart people seem to “get” that their salary is inherently less than their value. If their salary equalled their value, then “profit” for their company would not exist. I find it ironic that when most people hear their company is profitable they will rejoice in this fact, perhaps boasting about it to their friends; when in fact, this profit represents the difference between what the sum of the employees are earning and what the company is reaping from those efforts. The bigger the profit, the bigger the discrepancy in what people earn vs. what they produce (and in a perfect world, would be entitled to). So my pitch, quite simply, is that join us and you can be the benefactor of your excellence.

It’s the pitch that ultimately persuaded me to stop thinking like an employee.