In today’s fast-moving business environment, technical skills and experience are no longer the only qualities that matter. Grit is the determination to push through obstacles, stay focused on goals and maintain a positive mindset during challenges, and it has become a key trait for success. Gregory Hold, Founder & CEO of Hold Brothers Capital¹, recognizes that companies that want to build resilient teams need to identify candidates who have this inner strength from the start.

Grit is not always easy to spot on a résumé or through standard interview questions. It reveals itself through how people respond to pressure, recover from setbacks, and stay committed when conditions are tough. To find candidates with true resilience, hiring managers need to ask the right questions, ones that go beyond surface-level answers and give insight into how a person thinks and acts during difficult times.

1. Can you describe a time when you faced a significant setback at work? How did you respond?

This question helps uncover how candidates handle failure or disappointment. The focus is not on whether they succeeded in fixing the problem, but on how they approached it. Look for signs of accountability, reflection, and proactive steps to move forward.

2. Tell me about a goal you pursued over a long period. What kept you motivated?

Resilient people often have experience with long-term goals that require sustained effort. Their response to this question reveals their commitment, focus, and the strategies they used to stay on track. It also gives insight into what inspires them and how they measure personal success.

3. Describe a situation where you had to learn something difficult to achieve a goal. What did you do?

This question shows how candidates deal with challenges that require new skills or knowledge. It highlights their willingness to step outside their comfort zone and their ability to persevere through learning curves. Look for examples that reflect curiosity, effort, and problem-solving.

4. Have you ever worked on a project that didn’t go as planned? What was your role in addressing the challenges?

Every professional encounters a project that hits roadblocks. The key is how they responded when things did not go smoothly. This question helps gauge whether a candidate stays engaged, contributes to solutions, and remains focused on team success even when plans change.

5. What is the toughest piece of feedback you’ve received? How did you apply for it?

Receiving and applying feedback is a critical part of growth. People with grit see feedback as an opportunity, not a threat. This question helps identify candidates who are open to learning, resilient in the face of critique, and capable of adjusting without losing confidence.

6. Tell me about a time when you had to advocate for your ideas despite resistance. What was the outcome?

This question explores both perseverance and communication. Resilient candidates stand by their ideas when they believe in them, but they also listen and adjust as needed. The response provides insight into how they balance confidence with collaboration.

7. Describe a time when you managed stress during a high-pressure period at work. What strategies helped you cope?

Stress is part of the most demanding roles. What matters is how a candidate manages it. This question helps reveal practical techniques they use to stay focused and maintain performance. It also shows their level of self-awareness and ability to recognize when they need to regroup.

8. Can you share an example of a risk you took that did not work out as you hoped? What did you learn?

Taking risks requires courage, and resilience helps people bounce back when outcomes fall short. This question uncovers how candidates process disappointment, extract lessons, and apply them to future decisions. Look for evidence of reflection and growth rather than defensiveness.

9. What’s the most challenging team dynamic you’ve experienced? How did you help improve it?

Resilience is often tested in team settings, where personalities and pressures can be combined. This question provides insight into how candidates contribute to healthy team environments and work through interpersonal challenges. It highlights empathy, patience, and persistence.

10. Tell me about a personal or professional passion that you’ve pursued despite obstacles. What kept you going?

This question looks beyond job-specific experiences to understand a candidate’s inner drive. Passion projects often require grit, especially when faced with setbacks or limited resources. The answer reveals what matters to the candidate and how they stay committed to meaningful goals.

Evaluating Responses for Signs of Grit

When listening to candidates’ answers, hiring managers should look for certain patterns that point to resilience. These include taking ownership of actions, demonstrating problem-solving under pressure, showing self-awareness about weaknesses and setbacks, and describing constructive ways they moved forward. Responses that highlight learning, growth and steady effort, even in the face of difficulty, signal the kind of grit that helps people succeed in demanding roles.

Creating an Interview Environment That Supports Honest Dialogue

To get genuine responses, it is important to create an interview setting where candidates feel safe sharing both successes and struggles. Framing questions as opportunities to learn about problem-solving rather than as tests of perfection helps put candidates at ease. This approach encourages openness and leads to more meaningful conversations.

Hiring managers should listen carefully not only to what candidates say, but how they say it. Tone, body language, and level of detail can all provide clues about how a person really approached a challenge. Follow-up questions can help clarify points and deepen understanding.

Beyond the Interview: Supporting Grit in the Workplace

For companies such as Hold Brothers Capital, hiring grit is just the start. Organizations also need to create environments that nurture resilience. It includes providing support during tough periods, offering growth opportunities, and recognizing the effort people put into overcoming obstacles. When teams see that grit is valued, they are more likely to embrace it in their daily work.

According to Gregory Hold, “hiring managers who focus on grit help build teams that can weather challenges, stay committed to goals, and contribute to a culture of persistence and growth. These qualities make a real difference in a competitive landscape.”

Asking the Right Questions to Build Stronger Teams

Grit helps individuals and teams stay steady during uncertainty, recover from setbacks, and keep moving toward success. The right interview questions give hiring managers insight into a candidate’s true resilience. By focusing on specific, experience-based questions, organizations can identify people who will not only meet challenges head-on but also help shape a stronger, more adaptable team for the future.

¹ Hold Brothers Capital, is a group of affiliated companies, founded by Gregory Hold.