25 questions to ask during your next interview: Ladders 2019 Interviews Guide

They don’t feel very threatening to ask and yet they can produce reams and reams of insight.

To best understand company culture, the types of people who are successful there, and the particular requirements or desires for the position itself, I’ve assembled the following 25 questions for you to ask the HR person, the recruiter, the hiring manager, and the other people you interview.

These are useful because they are open-ended enough for an answer to be revealing, while relevant enough to the context of an interview to seem sensible. They don’t feel very threatening to ask — they allow you to feel sharp — and yet they can produce reams and reams of insight into the heart of the operation and its people.


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With that, here are your 25 easy-to-ask, revealing-to-answer questions to take to an interview:

1. What’s the biggest change your group has gone through in the last year? Is the strong economy growing your business? Or not yet?

2. Which competitor worries you the most?

3. If I get the job, how do I earn a perfect score on my performance review? What are the key accomplishments you’d like to see in this role over the next year?

4. What are the three things I can contribute in the first 100 days to make you feel great about hiring me? What are the most important things to the success of this role overall?

5. What’s your (or my future boss’s) leadership style?

6. How does sales / operations / technology / marketing / finance work around here? (I.e., groups other than the one you’re interviewing for).

7. What type of people are successful here? What type of people are not?

8. What’s one thing that’s key to this company’s success that somebody from outside the company wouldn’t know about?

9. How did you get your start in this industry? Why do you stay? (Asked well — i.e., asking the question and then not interrupting at all — this question alone can have your interviewer chatting away for 10 or 20 minutes of fond reminisces.)

10. What are your group’s best and worst working relationships with other groups in the company? What are the pain points you have to deal with day-to-day?

11. What keeps you up at night? What’s your biggest worry these days?

12. Who are my customers (internal or external) and how do they measure me / us? Who views me (my team) as a customer (internal or external)?

13. What’s the timeline for making a decision on this position? When should I get back in touch with you?

14. The economy is strong, unemployment is down, and there’s a lot of hiring demand out there. Among all the roles that you could have prioritized, why did you decide to prioritize this one instead of the others you could have hired for?

15. What is your reward system? Is it a star system / team-oriented / equity-based / bonus-based / pat-on-the-back-based? Why is that your reward system? What do you hope to get out of it, and what actually happens when you put it into practice? What are the positives and the negatives of your reward system? If you could change any one thing, what would it be?

16. What does success for this group / team / company look like in one year? In five years?

17. What information is shared with the employees (revenues, costs, operating metrics)? Is this an “open book” shop, or do you play it closer to the vest? How is information shared? How do I get access to the information I need to be successful in this job?

18. Looking ahead, if we are going to have a very successful year in 2020, what will that look like? What will we have done in the time before then to make it successful? How does this position help achieve those goals? (This question helps show your ability to look beyond today’s duties to the future more than a year away.)

19. How does the company / my future boss do performance reviews? How do I make the most of the performance review process to ensure that I’m doing the best I can for the company?

20. What is the rhythm to the work around here? Is there a time of year that it’s “all hands on deck” and we’re pulling all-nighters, or is it pretty consistent throughout the year? How about during the week / month? Is it pretty evenly spread throughout the week / month, or are there crunch days?

21. What type of industry / functional / skills-based experience and background are you looking for in the person who will fill this position? What would the “perfect” candidate look like? How do you assess my experience in comparison? What gaps do you see?

22. What is your (or my future boss’) hiring philosophy? Is it “hire the attitude / teach the skills” or are you primarily looking to add people with domain expertise first and foremost?

23. Is this a new position, or an existing position? If new, why was it created and what are the expectations? If an existing position, where did the prior person go? What were the things that person did really well, that you hope to see in the next person? What are the things you hope will change?

24. In my career, I’ve primarily enjoyed working with big / small / growing / independent / private / public / family-run companies. If that’s the case, how successful will I be at your firm?

25. Who are the heroes at your company? What characteristics do the people who are most celebrated have in common with each other? Conversely, what are the characteristics that are common to the promising people you hired, but who then flamed out and failed or left? As I’m considering whether or not I’d be successful here, how should I think about the experiences of the heroes and of the flame-outs?

You may want to score these answers along the framework I created above, or on a framework of your own making. Or you may focus entirely on the qualitative side of your conversations.

In any event, this list of questions enables you to come to (every) interview with a few good questions. Even though I’m usually the final person to meet a candidate here at Ladders, I’m always surprised when people I’m interviewing say they don’t have any questions for me. Sure, it’s understandable that you’ve already met four of my colleagues and they’ve answered a lot of the open questions you had about Ladders, but, really? You have absolutely no good questions for me? Not even just asking me the exact same ones to see if our answers vary? It’s common enough, though, that it seems three interviews in one day is about as long as a candidate can maintain their ability to ask questions.

It’s also a shame, because asking questions in interviews is only 50% about addressing your needs, explaining the role to you, and satisfying your curiosity. The other 50% of asking questions is showing your capability for critical thinking about the company, the industry, and the role. Using your question time to show off your good noodle by asking (brief) insightful questions, is a much better use of the time than saying that you have no questions. And even if you do run out of questions, there is the great, all-purpose, anytime, anyplace question to ask: “Is there anything else I should’ve asked but didn’t?”

This article is adapted from Ladders 2019 Interviews Guide: 74 Questions That Will Land You The Job (Ladders, Inc. , 2019). Purchase the Kindle Single for immediate download here.*

*Disclosure: Ladders from time-to-time uses affiliate links. At no additional cost to you, we will receive a commission if you click through and make a purchase.


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Marc Cenedella|is the Founder, Executive Chairman and CEO of Ladders, Inc., the comprehensive career resource dedicated to helping professionals ‘Manage, Market and Move-up’ in their careers