20 Questions You Should Be Asking in Every Interview

Too many hires/promotions are based on superficial impressions or narrow descriptions of job tasks.  It’s time to level up as an interviewer and start focusing more on “fit.”

Hiring/Promoting is One of Your Most Important Responsibilities

Hiring and promoting employees is one of the most important things a leader does.  In Good to Great, Jim Collins emphasizes the importance of “First Who, Then What.”  According to Collins, “Those who build great organizations make sure they have the right people on the bus and the right people in the key seats before they figure out where to drive the bus.”

In the past 3 decades of my career, I have interviewed hundreds of people for hundreds of positions.  As I reflect on these decisions and how they turned out, I’m convinced we can make better decisions when we spend more time discussing how people make decisions and how they work with others.

Qualifications Get You in the Door

Every position has some basic qualifications that must be met.  Even the most basic positions will have requirements like being at least 18 years old, a valid driver’s license, etc.  For more advanced positions, you might require candidates to have passed the bar exam or to be a certified public accountant.

I’d encourage you to keep qualifications requirements relatively low.  You might not need to require advanced degrees, certifications, and 15 years of experience.  Raising requirements reduces the number of applicants, often without increasing the odds of picking a winner.

Evaluating these basic qualifications shouldn’t be part of your interview.  Your HR department should screen candidates and verify this before you meet with the candidates.

What Makes a Good Fit?

Unfortunately, not every hiring and promotion decision I made worked out. 

One third of the time when things don’t work out, it was due to things that are almost impossible (or unethical) to predict when interviewing.  For example, a health or family issue; an incredible job offer from someone else; or someone choosing to be dishonest and unethical.

Most of the time, though, the reason it doesn’t work out has more to do with how they like to work and how they work with other people. 

Cultural Fit

How a person likes to work, and how they work with others is often described as “culture.”  Many people define culture in very different ways.  I prefer the definition by MIT’s Edgar Schein who defined organizational culture as, “a pattern of shared basic assumptions that the group learned as it solved its problems of external adaptation and internal integration, that has worked well enough to be considered valid and, therefore, to be taught to new members as the correct way to perceive, think, and feel in relation to those problems.”

In simpler terms, culture is how things get done within an organization. Through trial and error, organizations generally settle on consistent practices on how to get stuff done. Some organizations embrace structure, planning, and collaboration while others prioritize creativity, speed, and initiative. Sometimes there is a moral element to culture – some organizations have no tolerance for being in the “grey” area on legal issues while others like Enron embrace and celebrate disregard for laws. However, most cultural elements are amoral – communicating via e-mail/text/instant message is not inherently more or less moral than communicating via phone call or in person.

Be careful, though, when focusing on fit. As with many things, this can be a double-edged sword that damages organizations too. Wharton’s Adam Grant encourages us to “stop hiring on cultural fit. That’s a great way to breed groupthink. Emphasizing cultural fit leads you to bring in a bunch of people who think in similar ways to your existing employees….It’s wiser to…hire on cultural contribution. Instead of looking for people who fit the culture, ask what’s missing from your culture, and select people who can bring that to the table.”

Know Thyself

Before you interview candidates and assess how they like to do things, you first need to understand how you like to do things and how you would like the person in this position to do things.  Different positions will have different requirements.  If you’re hiring a security guard you’re probably looking for someone who views rules and authority differently than your new head of R&D.

The Golden Mean

Generally, you’re not looking for someone on the fringes who is described as “extremely…” or “hard core…” 

Aristotle emphasized the “golden mean” where people have enough, but not too much, of a virtue.  For example, courage is a virtue.  Too little courage is cowardice. But, too much courage is reckless.  Many virtues are only virtues when used in moderation. You never want outright cowardice or recklessness.  However, you don’t always want to be right in the middle either.  Sometimes you want someone closer to the reckless end of the spectrum, and other times you need someone closer to the careful end of the spectrum.

The questions below are not yes/no good/bad questions.  These aren’t questions like, “Do you believe in being honest?” or “Do you believe in working hard and being a team player?”  Instead, these questions are more focused on describing a landscape of contrasts and identifying where employees see themselves and how that fits your needs.

20 Questions

  1. Cooperative vs Challenging: “Some teams prioritize friendly relationships and unity above everything else.  Other teams prioritize critical feedback and internal competition.  Which do you prefer?”
  2. Tight vs Loose: “Some organizations have tight cultures with strong social norms and little tolerance for deviance.  Others have loose cultures with weak social norms and lots of variety.  Would you describe the teams you’ve led as having tight or loose cultures?”
  3. Structured vs Flexible: “Some groups are extremely rigid and structured.  Everything is thoroughly thought out and planned and plans are strictly followed.  Other groups are extremely flexible and accommodating and open to new ideas and always willing to change directions at the drop of a hat.  Which of these groups drives you crazy?”
  4. Logic vs Gut: “Many leaders require data and a spirited debate from all sides before making important decisions.  Other leaders make quick decisions relying mostly on their instincts.  Which leader would you rather work for?”
  5. Big Picture vs Details: “Some people are so focused on the big, big picture that they are disconnected from reality.  Others are so focused on the little details that they can’t see the forest through the trees.  Which of these people are you more likely to be accused of being?”
  6. Strategic vs Tactical: “Some employees are like athletes who love to work in the system and be on the field scoring points.  Others prefer to work on the system devising new strategies and plans for the players on the field.  Which role do you excel in?”
  7. Explore vs Exploit: “Every successful business has 2 phases.  In the first phase, they are exploring lots of ideas and designs and processes and business models.  Once they find a winning combination, they exploit the value of that idea by scaling it up and getting a return on their investment.  Which phase gets you the most excited?”
  8. MVP vs Thorough Plan: “When some organizations launch a new project, they focus on building a Minimum Viable Product (MVP) where they quickly throw stuff out to see what sticks and then make lots of quick adjustments and improvements.  Other organizations are more like Apple and thoroughly research and perfect each product and only bring world-class products to market.  Which approach do you think our organization should be using?”
  9. Singles vs Grand Slam: “In baseball, some teams’ use a strategy focused on small gains that consistently get batters on base.  Other teams swing for the fences and are always trying to hit home runs.  Which team would you rather play on?”
  10. Offense vs Defense: “Some teams win by having a good enough defense and the best offense, while others win by having a good enough offense and the best defense.  Which approach do you think is the best way for us to double our profits in the next 5 years? Do we need to be more focused on defending what we’re already doing well, or more focused on exploring new products/services/markets?”
  11. Lone Genius vs Opinion Poller: “Some leaders are ‘lone geniuses’ who have a 6th sense for making great decisions.  These leaders often become ‘geniuses with a thousand helpers’ and can be very successful.  Other leaders surround themselves with people who are smarter than they are and help those others work together to make the best decision.  If I were to survey your former employees, would they be more likely to describe you as the former or the latter?”
  12. Lion vs Mouse: “I’ve worked with several great leaders who are strong, confident lions who command respect the moment they walk in the room.  I’ve worked with other great leaders who would be better described as mice who are more like Socrates and claim to know nothing and ask lots of questions.  Which type of leader do you think is more likely to produce the best results in our industry?”
  13. Individual vs Team: “If you were setting up a bonus plan for your employees, would you prefer a plan where each employee is bonused based on their individual performance, or a plan that was simply based on the overall performance of the team?”
  14. Aspirational vs Content: “Suppose you had two job offers at two companies for positions similar to the one you are interviewing for now.  The main differences between the 2 positions are one pays more and has an incredible 401k program but almost no chance of being promoted within the next 5 years, while the other pays less but you have a good chance of being promoted in 12-18 months.  Which position would you choose?”
  15. Emotional vs Stoic: “I’ve worked in very emotional cultures with lots of yelling, crying, people pounding their fists on the tables, storming out of meetings, using colorful language, etc.  I’ve also worked for organizations where this type of behavior is considered unprofessional, inappropriate, and rarely seen.  Which organization are you more likely to thrive in?”
  16. Levels of Initiative: “In our organization, we refer to a ‘Levels of Initiative’ pyramid with 6 levels of initiative: (1) Wait to be told, (2) Ask, (3) Recommend, (4) Do it and report immediately, (5) Do it and report routinely, and (6) Do it!  In general, what level of initiative do you prefer in your employees?  In general, what level of initiative does your current boss prefer from you?”
  17. ABC: “Jack Welch famously divided his employees up into 3 categories – A players who got significantly bigger bonuses and raises and promotion opportunities, B players who got ‘normal’ treatment, and C players who got no bonuses or raises and had be either coached up or out.  What do you think of this approach?”
  18. Work Hours: “Some cultures value the early starter.  They say the early bird gets the worm and if you are always in your seat before the boss arrives you are viewed as someone with a lot of potential.  In contrast, other cultures value night owls who are always still at their desk when the boss leaves and who send e-mails at 11pm.  Some employees put in 8 hours a day, 5 days a week while others work significantly more and are almost always willing to work nights and weekends whenever an important project comes up.  What do you prefer and expect from your employees?”
  19. Communication Style: “If you had an employee who thinks they have a great idea for improving the business, how would you like them to communicate this idea to you?  Would you want them to tell you about it the next time they bumped into you in the hall?  Would you prefer they e-mail it to you?  Or, would you prefer they schedule an appointment and come prepared with something in writing?”
  20. Work/Life Balance: “I have a friend who told me, ‘This isn’t a job, it’s a ministry!  I love this job, the work we do, and the people I work with!  I love all the happy hours and extracurricular events we do together after work and on the weekends!’  I have another friend I’ve known for years but still don’t really know what he does for work other than that he works for some big company downtown.  But I do know he’s a huge Denver Broncos fan, his family loves traveling and goes on a big vacation every summer, and they’re super active in their kids’ schools and activities.’  Which of these friends would you rather have as your boss?”

Tough Decision

Hiring and promotion decisions are tough!  There are no easy answers, especially when filling senior positions.  There’s no easy way to grade the answers to these 20 questions.  There are very few right or wrong answers. 

Increase Your Odds

Deciding who to hire/promote will be much easier if you include some of these questions in your next interview.  Pick 3 to 5 of your favorite questions above and use them in your next interview.  I promise it will help shine some light in critical areas, and with this additional insight it will be much easier to see who is most likely to succeed!

Two more bonus tips for increasing your odds:

  1. Panel: Use a diverse panel of 3 to 6 people for every interview.  It’s always good to get multiple perspectives.
  2. Questionnaire: After the interview, require panel members to fill out a brief questionnaire before discussing the candidate together as a team.  It’s helpful to require members to form and document their own opinions before being influenced by others’ opinions.  Keep the questionnaire short and simple.  Ask about the key attributes/skills required to succeed in the position using an objective measure (yes/no, scale of 1 to 10, average/above avg/below avg, etc) and a space to explain the score given.

You can always reach out to our team at DPX for help defining the needs of the position, structuring the interview questions and the post-interview questionnaire, finding candidates, and interviewing candidates.  Our team has broad networks and decades of experience to help!