Whether you’re an agency recruiter, a corporate recruiter, or part of an internal HR team, the interview stage of the hiring process is one of the most critical points in making a successful hire.
And when it comes to structured interviewing, behavioral-based interviews—especially those built around “tell me about a time when” questions—remain one of the most effective ways to assess how candidates actually perform on the job.
What Is a Behavioral-Based Interview?
A behavioral-based interview is an interviewing technique where the interviewer asks candidates to describe how they handled real situations in the past to better predict how they’ll perform in similar situations in the future.
Rather than focusing solely on skills, credentials, or hypothetical answers, behavioral interviews aim to understand:
How candidates respond under pressure
How they handle mistakes and setbacks
How they work with others
How they learn and adapt
In other words, behavioral interviews help project candidates into the real responsibilities of the role—not just the job description.
Why “Tell Me About a Time When” Questions Matter
“Tell me about a time when” interview questions are foundational to behavioral interviewing because they:
Encourage candidates to share real experiences
Reveal patterns of behavior, not rehearsed answers
Provide insight into decision-making, accountability, and growth
These questions are far more revealing than yes-or-no or hypothetical questions like:
“Do you work well under pressure?”
A better question is:
“Tell me about a time when you had to work under extreme pressure.”
‘Tell me about a time when you failed’ interview questions
These are similar to “tell me about a time you made a mistake” interview questions, but with one difference. They deal with a situation that is bigger and more impactful. Making a mistake could be a smaller incident that had little to no bearing on a candidate’s job performance. Failing, on the other hand, represents adversity on a larger scale.
For example, you can make a mistake while attempting to complete an important project and that project could still be a success. That’s different than the project itself becoming a failure, either through a single mistake, or more likely, a string of them.
You never going to hire a job candidate who has never made a mistake, nor who has never failed. So you might as well find out what mistakes and failures are in their past, so you can determine how they reacted to them. Did they respond in a positive fashion? Or did they allow their mistakes and failures to adversely affect their future performance?
“Tell Me About a Time When You Made a Mistake”
There’s no such thing as a perfect candidate.
Every professional—no matter how experienced—has made mistakes. What matters most is how they responded, what they learned, and how they applied that learning moving forward.
Asking candidates to describe a mistake helps you understand:
Accountability
Emotional maturity
Problem-solving ability
Growth mindset
Mistakes and adversity are inevitable. A candidate’s response to them often determines long-term success far more than technical skills alone.
“Tell Me About a Time When You Failed”
Failure-based questions go a step further than mistake-based questions.
A mistake might be a small misstep. Failure, on the other hand, usually represents a larger challenge—such as a missed goal, a failed project, or a poor outcome despite effort.
No strong candidate has never failed. The key is discovering:
How they processed the failure
Whether they took ownership
How they adjusted their approach afterward
Did they learn and improve—or did the failure negatively shape future performance?
What Are “Tell Me About a Time When” Interview Questions?
“Tell me about a time when” questions are behavioral interview questions designed to uncover a candidate’s character, work habits, and problem-solving approach.
They prompt candidates to share stories from:
Past jobs
Education
Team environments
Challenging or high-pressure situations
These stories help recruiters and hiring managers evaluate fit, not just qualifications.
You should ask both:
Positive questions (strengths, initiative, leadership)
Challenging questions (mistakes, failures, conflict)
For example:
Tell me about a time when you made a positive change at work.
Tell me about a time when you failed at work.
Be sure to take structured notes so you can compare responses consistently across candidates.
When Should You Ask These Questions?
You can—and should—use “tell me about a time when” questions at multiple stages of the recruiting process:
Pre-Interview / Phone Screening
Behavioral questions help narrow the candidate pool early and provide valuable insight before advancing candidates to your client or hiring manager.
Live Interviews
During in-person or video interviews, behavioral questions allow you to:
Observe body language
Assess communication skills
Evaluate authenticity and confidence
25 “Tell Me About a Time When” Interview Questions
A strong behavioral question typically:
Asks about a real situation
Prompts reflection on outcomes and learning
Here are 25 examples you can tailor to your job order:
Tell me about a time when you reached a goal at work. How did you achieve it?
Tell me about a goal you didn’t reach. What happened?
Tell me about a time when you fell behind on your work. How did you recover?
Tell me about a time you led a team. What challenges came up?
Describe a time you disagreed with your manager. How was it resolved?
Tell me about a time you didn’t get along with a co-worker.
Describe a time you were unprepared for a meeting or presentation.
Tell me about a time you had to adapt to a new system or process.
Describe a time you took initiative. What was the result?
Tell me about a miscommunication at work and how you handled it.
Describe the most stressful situation you’ve experienced at work.
Tell me about a time you solved a difficult problem.
Describe a time you noticed a co-worker made a mistake.
Tell me about a mistake you made and how you fixed it.
Describe a time you had to make a quick decision.
Tell me about a decision you regretted.
Describe a time doing the right thing negatively impacted you.
Tell me about a time you went against your better judgment.
Describe a time your work was personally criticized.
Tell me about a time you juggled multiple projects.
Describe a time you influenced someone’s thinking.
Tell me about a team you struggled to work with.
Describe a time you struggled with work-life balance.
Tell me about a complex problem you had to solve.
Tell me about a time you wanted to quit—and what kept you going.
Managing the Interview Process with the Right ATS
Interviewing and selecting the right candidate is far easier when your recruiting process is supported by the right technology.
TE Recruit™ is an ATS + CRM built specifically for recruiting agencies, designed to support structured interviews, candidate evaluation, and consistent decision-making—without enterprise complexity or bloat.
With TE Recruit, recruiting agencies can:
Standardize interview workflows
Capture structured interview notes
Use pre-screening questions
Compare candidates objectively
Maintain visibility across the hiring process
Because TE Recruit is built for growing recruiting agencies, it scales with your team while remaining easy to use and recruiter-first.
If you’d like to see how TE Recruit supports more effective interviewing and candidate evaluation, you can:
Start a 30-day free trial
Or request a live demo with a product specialist
