How to Answer Classic Interview Questions

Career Blog

businessman holding clipboard with drawing question mark

Hiring managers aren’t always experts at the hiring portion of their title. For many replacing a team member or adding a new one is a dreaded, time-consuming task taken on as infrequently as possible. It’s an understandable sentiment. After all, they have day jobs and the complexities of sourcing, hiring, onboarding, and training can be major distractions.

Of course savvy HR and business leaders understand that this investment can pay healthy dividends if it allows you to enhance your team’s performance or acquire a missing skill set. Still strategy is a hard sell for time-pressed, tactic-minded middle managers.

So what does this dilemma mean for the job seeker? In a word predictability. Unless the manager has received quality interview training you shouldn’t expect a great deal of variety in questions received. Here’s a few of the more common questions and insights on how to answer them.

  1. Tell me about a key accomplishment of which you are proud. This is an impact question designed to provide insight into your values. The most important point of this answer (it’s a character-driven anecdote after all) is the why? Sure, you have to tell the interviewer what you did and when, but the meat comes from why you chose to spend your energy on that endeavor and what impact the result had on you and others.
  2. Tell me about a time you made a mistake. A good interviewer is looking for several things with this question; are you humble enough to admit that you’ve made an error or two along the way; are you confident enough to provide a real, job-related example instead of a throwaway line; are you ambitious enough to demonstrate how you learned from that mistake; and are you sharp enough to put a process in place to not let it happen again. Candidates should see this question as an opportunity to showcase their grit, perseverance, and ingenuity.
  3. Tell me how you handled a difficult situation. Candidates often assume this is a leadership/management question. Many times however, it’s a process question designed to test your critical thinking and judgment. Give the hiring manager an example of the situation you faced, the exact steps you took to resolve it, and why you made those decisions. Highlight any roadblocks and how you overcame them. Then share the result. Feel free to screen anything that is confidential or too personal. Again it’s about process not content.
  4. Give a time when you went above and beyond the requirements for a project. Candidates often botch this question by failing to provide a brief backstory. Before you can showcase how you went beyond the role, you have to first set the parameters of the job. This is a story-based question so you have to set the scene, provide tension, and demonstrate a climactic resolution that paints you as the hero. For example; was there a time you filled in for a manager, came up with an idea to save the company money, or heroically secured supplies when a vendor botched a delivery?
  5. What was your biggest failure? This is a spin on question two, but the stakes are higher based on word choice used: failure vs. mistake. A savvy interviewer might even infer something about the manager’s if not the organization’s risk tolerance. Be smart about your response. Give a real, meaningful example, but one that happened early in your career. Then shift gears and focus on what you’ve learned since then and how you and your current company benefited from that experience.
  6. Tell me about a time when you disagreed with your boss. This is another process question with a side order of conflict management. What interviewers are really looking for is: can this candidate build and sell a compelling business case? Most people will tell stories of how they convinced the boss of their idea and subsequently saved the world, but remember content is second tier. Hiring managers are looking for the resolution: how you formed your position, how you presented your case, and how you (ego-free) got to the best solution for the company.
  7. What are some of your leadership experiences? Anyone can rattle off the manager positions they’ve held or the volunteer work they performed, but leadership is measured on impact. People should be changed (for the better) for having interacted with you. And, if you’re lucky, you should’ve evolved as well. The key word in the question is experience. Share that story.

Need a career coach? Contact me via

Be sure to check out my latest book The Introvert’s Guide to Job Hunting and follow me on Twitter at @timtoterhi

Share This Article


Leave a Comment


Pin It on Pinterest