Think about a time you overcame a challenge or obstacle. Describe the experience in two or three sentences.

Life’s not an easy ride. Actually for some people it presents a series of obstacles. Overcoming one challenges, they are immediately confronted with another one. And while I sincerely hope it isn’t the story of your life, you will no doubt face some obstacles in your teaching job, or in any corporate job you try to get at the moment. Hence it cannot surprise you that interviewers will ask you at least one question about dealing with challenges, and now we will look at such.

Before proceeding to 7 sample answers, let me give you some basic guidelines. First, the bigger the obstacle the better. If you managed to overcome extreme adversity in your life or work, that’s the situation to narrate. Second, give credit to people who helped you on your way. Teamwork is important in each school and company, and hiring managers are looking for people who can hand a helping hand to their colleagues, but also accept help when they need it (aren’t too proud to ask for help). And last but not least, include numbers and data in your answer, to give it more credibility. You can make something up, or at least “add some spice to your story”, to make it more interesting and memorable. In order to make it also believable, however, add numbers and facts (for example when exactly it happened, who was involved, etc).

Let’s proceed to 7 sample answers. I focus mostly on shorter answers, since that’s what they often ask you to do–to describe the experience in two or three sentences. They may ask follow up questions though, hence it is important to have it covered, and know how you’d answer such questions…


7 sample answers to “Think about a time you overcame a challenge or obstacle. Describe the experience in two to four sentences.” interview question

  1. I’ve overcome one in my last teaching job. We weren’t on the same page with the principal and I struggled to get my message over while I wanted to make the school better. But I did not give up, looked for compromises, and eventually won their favor and managed to get a green light for my ideas. It helped me to improve the engagement in the lessons by 50% within six months, and also to almost eliminate problems with discipline.
  2. I am trying to overcome one right now, struggling to get a job in these competitive times. Have sent probably fifty job applications, and not just randomly–I carefully researched each offer, and came up with a unique cover letter and everything, but struggle to get an interview, let alone a job. Anyway, as you can see I continue to try and experiment, and I am determined to succeed, even though I know it isn’t easy to get a decent job once you are 55 years old and nearing retirement.
  3. I faced the most important challenge of my life three years ago–battle with cancer. And I must confess I was the one responsible for it, since I had a bad lifestyle, terrible diet, stressed too much, simply I did everything wrong. Had to change my life from the basics, and undergo a strenuous therapy, but I stood my ground and with the help of doctors, psychologist and my family, step by step I not only beat the cancer, but also started to live a more balanced life.
  4. Winning the trust of my students in my last teaching job was a big challenge. The discipline levels were really low, many students came from broken families, and the school administrators didn’t have a good system in place to deal with such disruptive behavior. I could have run away from the classroom crying, or just sit and let the students do whatever they want. But I decided not to, and introduced new concepts of teaching, using technology, playing educational games, involving students in the way they liked to be involved, recognizing their individuality. It worked, the discipline improved, and I was one of the few teachers who managed to win both trust and respect of this class.
  5. I am still waiting for the fist big challenge of my life. Of course just graduating from college was a challenge, since I am not the most gifted student and had to work extremely hard to make it happen, and to earn my degree. But I know bigger challenges await me in the workplace, and am ready to face them with open arms, since I know we learn the most in challenging times.
  6. I went through a complicated divorce recently, which was a hard challenge, both physically and mentally. But it is behind me now and I prefer to look ahead, and focus on the future, instead of dwelling on the past. I hope to find new friends and new thoughts in my new job with your company.
  7. I had to overcome a big challenge in my last sales job. The sales targets were extremely ambitious, and many people quit after month one. But I did not let it discourage me, worked harder than others, and eventually became one of the best salesmen in the company in 2022. Having said that, the pressure was eventually too much and impacted me health-wise, which is the reason why I quit and am looking for a new job right now.


Final thoughts

Two to four sentences isn’t much to describe any situation, let alone such a tricky one as overcoming the obstacle. Remember though that they don’t specify how long the sentences should be. You can describer the situation in three short sentences, and in three compound sentences, each having fifty words or even more! Be creative and do not let the instructions to discourage you from sharing more details with the interviewers.

What’s more, do not limit yourself with obstacles from work. The biggest obstacles we often face in personal life–relationship problems, health issues, problems with children, and so on. In my book they all make for a great answer to this interview question, and you can demonstrate on them your “never give up” attitude... Hope it helps, and do not forget to check also answers to other tricky interview questions:

Matthew Chulaw
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