Example Answers to “Describe a Challenge You Overcame”

Example Answers to Describe a Challenge You Overcame

Example Answers to Describe a Challenge You Overcame: Highlighting positive qualities rather than negative and make yourself sound amazing.

A popular question in job interviews is “Describe a challenge you overcame.” Some people find this question difficult to answer, but this question actually gives you an excellent opportunity to let your best self shine. The trick is understanding the purpose behind the question and then crafting an answer that makes you stand out (in a good way, not a bad way). The purpose of this question is not to describe an impossible challenge in painstaking detail. The purpose of this question is to let the employer know why they should hire you: because you are a creative, critical thinker who knows how to overcome challenges. 

What is this Question Actually Asking? What is the Purpose Behind this Question? 

People make a common mistake when they hear this question because they do not truly listen to the whole question. They hear the word “challenge,” and they jump straight to that part of the question, forgetting about the part that asks how they overcame the challenge. With all interview questions, just like with questions on a school test, it’s important to read (or listen to) every word of the question and to break down what the question really means. It’s good to look for keywords in interview questions, but you have to think from the employer’s perspective. The keyword here is not a “challenge.” The keyword is “overcame.” 

The purpose of this question is not to describe a challenge you faced. The purpose of the question is to describe how you overcame the challenge. Employers know that people have faced challenges in the past. They do not need to hear all the unbelievable details of your challenges. They are definitely not interested in hearing you bash your old job or your old boss (because that suggests that you might bash them, too, if they hire you). They are interested in hearing how you respond to challenges. They want to know whether or not you are someone who can deal with challenges. Your job in responding to this question is to show that you are a creative, critical thinker who can take a less than ideal situation and turn it into a success (without panicking). 

How to Choose an Answer to this Question? 

As with all the interview questions, you want your answer to make you stand out (in a good way, not in a bad way). 

It’s tempting with this question to start with the challenge. It’s tempting to think of the worst thing that ever happened to you and then describe in detail how difficult it was and how frustrated you were. This is NOT the best way to answer this question. If you do this, you will likely spend too much time describing the challenge and not enough time describing how you overcame the challenge.  A better way to approach this question is to think of a time when you succeeded, despite all odds. The bulk of your answer should be about how you responded, NOT about the challenge itself. Keep the description of the challenge to a minimum. Don’t share too many details, especially anything that makes it seem like you are bashing your old boss or old company. State the necessary facts about the challenge, then move quickly along to how you responded to it. It’s best to avoid mentioning details about the challenge that you did NOT overcome and stick to the details that you DID overcome. 

Because this is an interview question, it’s usually best to describe a challenge and response from either work or school. You’re trying to make it seem like your ability to overcome challenges is a transferable skill. This means if you are applying for a job as a teacher, for example, you might want to describe a teaching-related challenge or at least a challenge that somehow relates to being a teacher. If you describe a cooking-related challenge rather than a teaching-related challenge, the person who is interviewing you will have more trouble seeing how your skills will translate to the position you are interviewing for. 

As with all interview questions, keep the requirements and the job description in mind while answering. Most employers state explicitly in their job advertisements what they’re looking for, so your response should indicate that you have those qualities. For example, if they are looking for someone who has strong classroom management skills, you might want to focus on how you overcame a classroom management-related challenge (without violating any student privacy guidelines, of course).  It might be appropriate to describe a challenge and response that is not related to work or school in some cases. Use your discretion when doing this. At the very least, it should relate somehow to the job you are applying for. For example, if you are applying for a job as a cook, it could be appropriate to describe a cooking-related challenge at home rather than at work. 

Example Answers to Describe a Challenge You Overcame

Example Answer (for a Teaching Job)

A challenge I overcame was teaching college courses during the Covid-19 pandemic. The pandemic hit mid-semester, and all classes were suddenly moved online. Normally when we teach online classes, students sign up online and are required to complete an online learning orientation on the first day of classes. When the pandemic hit, nobody was prepared for online learning, and students were frustrated that they would no longer be receiving the face-to-face instruction they had signed up for. This move to online classes was necessary for safety reasons, but it did present a significant challenge to me as a teacher. I responded to this challenge by taking a variety of actions. First, I made the online orientation available to all my students and required them to take it as a graded assignment. The university did not require this, but I thought it must be important because students normally receive online learning orientation. I made it a graded assignment because that is the best way to make sure that students would actually complete it. This orientation taught students how to use most online platforms that we would use in the class. 

Second, I implemented virtual (Zoom) office hours to replace my regular face-to-face office hours. We were not allowed to go to campus physically, so I could not host office hours in my office like I normally do. Some students are comfortable emailing questions, but other students express themselves better verbally rather than in writing. Because of this, I wanted to give you the option to speak with me over Zoom rather than email. I created a recurring Zoom link for my normal office hour times and posted it on the class webpage with instructions on joining. I also checked my email regularly, of course, because many students did continue to ask their questions over email. Third, I adapted my assignments for the web. One assignment was originally meant to be a multimedia presentation that students would perform in front of the class. Instead of this, I still had them create a multimedia presentation and post it on the course discussion board. The discussion board also took the place of our regular, face-to-face discussions that we would have in class each day. The essay assignments remained the same, but I did create more explicit instructions and assignment sheets for these since people have more trouble understanding directions when they are not in the room with the person giving the directions. 

Lastly, I overcame this challenge by listening to my students and being understanding of their needs. I granted extensions on assignments when they needed it because online learning was new to most students in the class. I granted a couple of Incompletes at the end of the semester for those students who were unable to complete the work by the deadline. Although a teacher’s job is to get students to learn and meet the standards, their job is also to be there for students. I do not underestimate the power of understanding the role model figure who meets student needs, especially in international crises. At the end of it all, not a single student failed the class. I take this as evidence that I overcame the challenge of teaching suddenly online during the pandemic. I accomplished this by caring about my students and prioritizing their success.


This answer is strong. It is relevant to the job that the person is applying for: they are interviewing to be teachers, so they answered the question with an experience from teaching. Also, it focuses mostly on how the person responded to the challenge, rather than spending a lot of time complaining about the challenge itself. This person lists a few different things they did to respond to the challenge, which makes it seem like they have many good ideas. They also showed that they went above and beyond since they shared orientation with their students that was not required by the university. Lastly, this person provides evidence that they successfully overcame the challenge by describing their work’s positive results. Employers love to see evidence that you have accomplished the same things that you will be asked to accomplish at their business if they hire you. 

Example Answer #2 (for an Administrative Assistant/Office Manager Job)

I am a very organized person, so one thing that was really challenging for me in the past was when I lived with my brother while we were both attending college. I love my brother, but he is not an organized person, so living with him as a roommate was tough. 

The way I overcame this challenge was first by having a heart-to-heart with my brother. I told him it bothered me when he put dishes away in random cupboards rather than following the organizational system I had created. I keep different types of dishes in different cupboards; otherwise, I can never find anything. At first, I was worried my brother would think I was overreacting for bringing this up, but he didn’t. I think it’s because I explained why it bothers me that he would randomly put things away: it confused me, and it took extra time to find anything. I even added that if my tasks were streamlined and took less time, that would mean I would have more time to spend with him, my beloved brother! I think putting a positive spin on things always helps. I like to compliment someone, then criticism, then another compliment. If you give criticism, sometimes people do not react well, and the problem only becomes worse because they refuse to see your side of it. So, my people skills and communication skills helped me overcome this challenge. 

I also showed my brother what the inside of my dresser drawers and my closet looked like. I explained the logic behind each organizational choice and pointed out that it did not take me very long to find a specific outfit. In contrast, it took him a very long time to find his favorite clothing items because they were always on the floor, on a chair, or shoved into a random place in the closet. My brother may not have re-organized his own closet, but he did agree to follow the organizational system I had created for the spaces we shared, including the kitchen. This made my life less stressful, and I think it saved us both time in the end! Plus, my brother wasn’t mad at me for sharing my concerns because I did it cordially and professionally.


This answer is strong because it is relevant to the type of job the person is applying for. Here, the applicant chose to describe an experience, not from a job, but they did pick something related to an administrative assistant or office manager’s skill set. Administrative assistants need to be organized, and they also need to have a cordial and professional personality. This applicant demonstrated both of those qualities in their answer. This applicant, just like the first one, did not waste a lot of time describing the challenge. This person even noted that they love their brother to avoid seeming like they were complaining about an annoying roommate. This person showed that their actions helped themselves and their brother, which makes it seem like they are a team player and a positive person. This answer highlights a lot of qualities that people look for in an Administrative Assistant. 


Employers ask many different job interview questions, but what they’re secretly asking every time is, “Why should we hire you?” That’s why they’re interviewing people in the first place: they need to hire someone, and they want to learn more about what you can do to help them.  The bottom line with this question is that you should be highlighting your positive qualities rather than the negative qualities of whatever challenge you faced. The point is not to complain; the point is to make yourself sound amazing. The challenge itself does not need to be something earth-shattering. What needs to be earth-shattering is how you overcame the challenge, however small. 

Also read: Tricky Strategic Interview Questions To Throw Applicants Off Balance.

Example Answers to “Describe a Challenge You Overcame”

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