July 27, 2021


10 Killer Interview Questions

Two people sitting across from each other in an interview

Barry Moltz

Small Business Expert, Shafran Moltz Group


Finding the right team members may be one of the most important tasks we face as small-business owners. A big part of that can be asking the right questions during the interview process.


And yet small-business owners can be lousy interviewers, because we sometimes tend to talk too much. We may be so used to selling prospects on our company, we may forget when it’s our turn to listen.


Here are 10 questions that may help you find the perfect person for your business, if you listen carefully to the answers.


"What do you hope to learn at this company in this position?"


“Learn” is the operative word here. By phrasing the question this way, you can accomplish two things: One, gauge how interested the interviewee is in growing and improving—always a valuable quality in an employee. And two, see how you might tailor the role to support their development. Such a consideration is key to engaging employees long-term, And in the event the candidate is weighing multiple offers, it may help tip the scales towards you.


What to look for in an answer: Do their individual goals match the company’s goals? Can you see ways to support the individual’s development that would benefit both them and the business? If yes, it may be a strong fit.


"Tell me about a time when …?"


There are a lot of people who can give "good interview." They can talk in generalities, but you may still wonder what the candidate really contributed to the achievements on their resume. This targeted question works because it requires a specific example. For instance, if interviewing someone for a sales position, consider asking, "Tell me about a time when you won a customer from a competitor." If it’s a customer service rep, maybe ask, "Tell me about a time when you kept a customer from leaving the company."


What to look for in an answer: As much detail as possible in the example that the candidate gives. Try to get names, dates and specific results as appropriate.


"What is your most significant career accomplishment?"


This can be a challenging question, because it requires people to narrow it down to one thing. Others don't like to brag about their achievements.


What to look for in an answer: Don’t settle for an answer like "I've done a lot of great things in my career." Try to get them to narrow it down to one. Look for their level of ownership, pride and what they value. Compare to see if this matches the company’s culture.


"If you could start your career over, what would you do differently?"


This may allow you to gauge how the prospective employee makes major decisions. The answer can reveal if they like the path they're currently on.


What to look for in an answer: Do they hold onto the past, or are they able to learn and move forward toward another result? Do their individual goals match your company’s goals? Can you see ways to support the individual’s development that would benefit both them and the business? If yes, it may be a strong fit.


"What frustrates you the most (or really gets you mad)?"


It can be easy for people to do their best when things go well, but how are they when things inevitably get frustrating?


What to look for in an answer: How they channel their frustration toward something positive, especially in a team environment.


"What do you know about the company?"


This can show if they're serious about the opportunity and if they were prepared before the interview.


What to look for in an answer: If they give you a blank face or they answer, "not much," move on to the next person. Anyone who's not prepared enough even to learn about the company on the Internet may not be worth hiring.


"Tell me about the worst relationship you had with the people you worked with in your last job."


Many people can brag about things that go well, but how did they handle a bad relationship at their last company?


What to look for in an answer: Do they take 50 percent of the responsibility for the bad relationship, or do they place blame on the other person? How did they resolve it productively?


"Is it better to be perfect and late on a task, or imperfect and on time?"


Most small businesses need things to be completed on time for customers, not necessarily perfect.


What to look for in an answer: While there is no "right" answer, make sure that whatever they say matches your company’s culture.


"Explain something to me that you think is complicated."


This may be an important question, since a critical skill of anyone who works on a team is how they explain things to others. 


What to look for in an answer: It doesn't matter what they explain (it could be sports or a cooking recipe), but what can be important is whether they're effective in making you understand.


"Is there a question I haven't asked you, but should?"


This can be a good catch-all question at the end of interview. This may ensure that the candidate expresses everything they want to say and nothing is missed.


What to look for in an answer: Anything that's way out of line with the flow of the rest of the interview could be a warning sign. For example, if they bring up a strange fact or achievement about themselves, be wary.


Photo: Getty Images

Don't do business without it