Most of us see interviews as fraught with anxiety. Nearly as nerve-wracking as public speaking, even self-assured candidates worry about creating a favorable (and memorable) impression on the hiring manager.
And there are some interview questions that are harder than others to answer. One of the most dreaded is: “What obstacles have you overcome?”
Why do recruiters ask this? What kind of answer are they looking for? Should you tell them something personal? But how personal is too personal? And what if you don’t have a work-related example? Can you make it up? Should you?
We’ve reached out to experts to help us answer these questions, and here’s what they have to say.
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What are hiring managers looking for generally?
Career transition expert and certified career coach Davida Shensky tells InHerSight that hiring managers are trying to understand you as a potential employee. They’re trying to assess “cultural fit, interpersonal skills, self-awareness, and how you handle yourself in various situations.”
Here’s what that means:
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Cultural fit: They want to know if your values, working style, and personality align with the company culture. (On InHerSight, we recommend “culture add” as an alternative to this.)
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Self-awareness: Can you reflect on your strengths, weaknesses, and past experiences?
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Communication skills: How effectively do you articulate your thoughts? Are you clear and concise?
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Interpersonal skills: They might be assessing how well you get along with others, how you handle conflicts, or how you work in a team.
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Motivation and goals: They’re curious about what drives you and how that aligns with the role and company.
That’s what interviewers are looking for overall. But there are specific traits and skills they look for in responses to specific questions, one of those questions being about overcoming obstacles.
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What are hiring managers looking for in the ‘overcoming obstacles’ question?
Career coach Jennifer Landers tells InHerSight that when hiring managers want you to describe a time you overcame a challenge, “they are looking for insights into your problem-solving skills, resilience, ability to stay composed under pressure, and how you handle difficult situations. They want to see how you approach challenges, the strategies you use to overcome them, and the outcomes of your efforts.”
The problem is, she says, that “most people leave out the most important part—the results!” Your results from handling the situation as you did helps frame it for the hiring manager, defining why it mattered to the organization.
The top four abilities hiring managers look for, Landers adds, are:
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Problem-solving skills: Demonstrating your ability to think critically and come up with effective solutions.
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Resilience and adaptability: Showing that you can handle obstacles and setbacks without becoming discouraged.
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Initiative: Indicating that you can take proactive steps to address challenges rather than waiting for someone else to solve the problem.
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Outcome and learning: Highlighting the positive outcome of your actions and what you learned from the experience.
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How personal is too personal?
Do the examples of overcoming obstacles have to be work-related, or can they be personal? And just how personal is too personal? We asked certified career coach Rosalinde Rosado how to answer this question effectively and appropriately.
“As tempting as it might be to speak about something personal, keep your answer focused on your problem-solving skills and how you connect with people in a work-related environment,” Rosado says. “Describe the circumstances around your challenge and your actions, explaining your solution's value to the employer. What made your solution so different from other approaches? Employers are also looking for characteristics such as the emotional intelligence of future leaders and how well they fit within their culture.”
And what happens if you lack specific experience in the workplace? Executive coach Marina Field, Ph.D., says “you can use examples from volunteering, clubs, or other professionally-oriented experiences.”
When you make it too personal, Landers explains, using family issues or deeply emotional experiences, you risk making the interviewer uncomfortable or even distracting them from your professional qualifications.
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How to keep it professional
Steer away from being too personal by maintaining a tone that is appropriate for an interview setting, even if the question seems casual, says Shensky. How?
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Focus on work-related experiences: Share stories that demonstrate your skills, work ethic, and how you've handled professional challenges.
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Highlight personal strengths: It's okay to talk about your passions or what motivates you, as long as it's tied to how you can contribute to the company.
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Share learning experiences: If you do touch on personal challenges, make sure the emphasis is on what you learned and how it made you a better professional.
Here are examples of answers to the question: "What motivates you?" One answer is too personal, the second is professional:
Too Personal: "I’m motivated by the need to support my family financially, as we’ve been struggling lately."
Professional: "I'm motivated by the opportunity to learn and grow in my field. I thrive on setting goals and achieving them, which is why I’m excited about the chance to contribute to your team."
In a nutshell, keep your responses focused on how your experiences relate to the job and your professional growth. Avoid sharing details that don't contribute to your qualifications or might make the conversation uncomfortable.
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So what’s the best way to answer: “What obstacles have you overcome?”
You need to understand the question completely. “Clarify if necessary, to ensure you know what they’re asking,” advises Shensky. “If a question feels too personal, you can politely ask how it relates to the role.”
Make sure you showcase growth from the situation, she adds. “If you’re discussing weaknesses or challenges, focus on how you overcame them or what you learned.”
Landers recommends the CAR acronym: Challenge-Action-Result.
First, you explain the challenge, setting out your responsibility in the situation. Then you detail the specific action you took to overcome the challenge, and finally you share the outcome and any positive results from actions you took.
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Landers provides an example of how you could answer a question, using the CAR format, about overcoming a tight deadline:
Challenge: "In my previous role as the lead on a project, we had a client request a significant change to the project scope just days before the final deadline. I had to ensure the changes were implemented without delaying the project timeline."
Action: "I quickly assembled the team, reallocated resources, and prioritized tasks. I also communicated with the client to manage their expectations and provided regular updates on our progress."
Result: "We successfully delivered the project on time with the requested changes, which led to positive feedback from the client and a continued business relationship."
The well-known STAR method (Situation-Task-Action-Result) is similar to CAR, except it also briefly focuses on the task you took responsibility for and the goal of your actions.
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Field tells InHerSight that, because the question about overcoming challenges is frequently asked in interviews across industries, you should be prepared to respond if it comes up. “Before you go into an interview, identify a specific example of a professionally related challenge you’ve experienced.”
Preparation using the STAR framework would look something like this:
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Situation: Begin by briefly highlighting the situation by providing background context for the challenge.
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Task: Describe your role in the situation and what you were responsible for.
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Action: What did you do? Describe the steps you took to address the challenge.
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Result: What impact did your actions have? How did everything turn out?
Field says you can anticipate the types of questions an interviewer might ask. “You can do this in a few different ways,” she notes.
“One way is by reviewing the job description and identifying any specific competencies, skills, or experiences that are listed and practice answering questions related to those. Another way is by going to Glassdoor and identifying questions that other people have shared they were asked during their interviews. A third way is by googling common questions asked in interviews.”
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Shensky gives a detailed example scenario of how to answer the question: “Tell me about a time when you faced a significant challenge at work,” using the STAR format.
Situation: Briefly describe the context. "In my previous role as a project manager, we had a situation where a key team member left in the middle of a critical project phase."
Task: Explain your responsibility. "I was responsible for ensuring the project stayed on track despite the sudden change."
Action: Describe what you did. "I quickly reassigned tasks, communicated with the team to manage expectations, and brought in a temporary resource to fill the gap."
Result: Share the outcome. "As a result, we met our deadline with minimal disruption, and the client was impressed with our adaptability."
High performance coach Katie McIntyre says: “The only response better than a STAR format is a STAR(T) format: Situation, Task, Action, Result, Takeaway (what you learned).”
The example McIntyre gives is a candidate finishing their answer with: “One of my biggest takeaways from that project was realizing how profitable it is to view every client as a true partner rather than a company we simply transact with, and that's really served me over the last few years.”
