Top 10 Progressive Insurance Interview Questions: The Complete Guide with Sample Answers and Insider Tips

You just got the email. Progressive wants to interview you for that insurance position you applied for, and suddenly your excitement mixes with a healthy dose of nerves. You’ve heard Progressive has a rigorous interview process, and you want to make sure you’re ready.

Here’s what you need to know right away: Progressive uses something called Targeted Selection, which is a fancy term for behavioral interviewing. This means they won’t accept vague, generic answers. They want specific stories from your past that demonstrate how you’ll perform in the future.

The good news? Progressive is incredibly transparent about their interview process. They actually send candidates preparation materials and tell you exactly what they’re looking for. If you prepare properly, you have a massive advantage.

In this guide, we’ll walk you through the top 10 Progressive interview questions you’re most likely to face, complete with sample answers that sound natural (not robotic). We’ll also share insider tips from Glassdoor reviews and Progressive’s own resources to help you stand out. By the end of this article, you’ll know exactly how to structure your answers, what Progressive evaluates, and how to turn your interview into a job offer.

Let’s dive in.

What Makes Progressive Interviews Different?

Progressive doesn’t do traditional interviews where you can wing it with generic answers. They use the Targeted Selection model, developed by DDI, which focuses entirely on behavioral questions.

The philosophy is simple: your past behavior predicts your future behavior. If you successfully handled difficult customers in your previous role, you’ll likely do the same at Progressive. If you adapted well to change before, you’ll adapt well to their fast-paced environment.

This is where the SOAR Method comes in. Unlike the traditional STAR method you might know, Progressive teaches SOAR, which stands for Situation, Obstacle, Action, and Result.

Here’s how it breaks down:

Situation (30 seconds or less): Set the scene. What was happening? Where were you working? What was the context?

Obstacle (woven into situation): What challenge or problem did you face? What made this situation difficult?

Action (about 2 minutes): What specific steps did YOU take? This is the meat of your answer, where you demonstrate your skills and decision-making.

Result (30 seconds or less): What happened? What did you learn? How did it turn out?

Interview Guys Tip: Progressive actually sends candidates a link to their behavioral interviewing guide before your interview. Don’t skip this resource! It’s like getting the answer key before the test. They want you to succeed, so use their materials.

To help you prepare, we’ve created a resource with proven answers to the top questions interviewers are asking right now. Check out our interview answers cheat sheet:

The Top 10 Progressive Interview Questions (With Sample Answers)

1. Tell me about yourself

This question starts almost every Progressive interview. They’re not asking for your life story or where you grew up. They want to understand your professional journey and why you’re sitting in front of them today.

Why they ask this: It’s an icebreaker that helps them assess your communication skills and see if you can present yourself clearly and concisely.

Sample Answer:

“I’m currently working as a customer service representative at a retail bank, where I’ve spent the last two years helping customers with account questions, resolving complaints, and explaining financial products. Before that, I completed my business degree with a focus on management.

What I love most about my current role is problem-solving for customers, especially when they’re frustrated. There’s something really rewarding about turning a negative experience into a positive one. I’ve consistently received high satisfaction scores and was actually recognized last quarter for having the highest customer retention rate on my team.

I’m interested in Progressive because I want to take my customer service skills into an industry that’s innovating how people think about insurance. When I learned about Progressive’s technology-driven approach and commitment to employee development, it felt like the perfect next step for my career.”

What they’re really evaluating: Can you communicate clearly? Do you connect your background to their role? Are you genuinely interested in Progressive specifically?

Learn more about crafting the perfect response in our guide on how to answer tell me about yourself.

2. Tell me about a time when you had to deliver bad news to a customer. How did you handle it?

This is a classic Progressive question because insurance often involves difficult conversations. Claims get denied. Coverage has limitations. Premiums increase. They need to know you can handle these moments with empathy and professionalism.

Sample SOAR Answer:

“In my previous role at a cell phone retailer, I had a customer come in expecting a full refund on a damaged phone. After reviewing the situation, I discovered the damage wasn’t covered under warranty because it was accidental, not a manufacturer defect.

The obstacle was that this customer had driven 45 minutes to our store specifically for this refund and was already frustrated. I knew I needed to deliver disappointing news while still keeping their business.

I started by acknowledging their frustration and explaining exactly why the damage didn’t qualify for warranty coverage, using their actual phone to show them the specific damage indicators. Then I shifted to solutions. I explained our device protection plan options and found a certified refurbished model at a significant discount. I also waived the restocking fee as a goodwill gesture.

The customer left without the free replacement they wanted, but they purchased the refurbished phone and signed up for the protection plan. They actually thanked me for being honest and helpful. It taught me that delivering bad news is about being transparent while focusing on what you CAN do, not just what you can’t.”

Key points to emphasize: Empathy first, clear explanation, solution-focused approach, positive outcome even when saying no.

3. Describe a situation where you had to adapt to an unexpected change at work or school. How did you handle it?

Change happens constantly in insurance, whether it’s new technology, policy updates, or shifting team structures. Progressive wants people who roll with change instead of resisting it.

Sample SOAR Answer:

“Last year, my company merged two customer service teams, which meant our team of four suddenly became a team of ten. We’d all developed our own systems and processes, and suddenly we needed to unify everything.

The biggest obstacle was that we had completely different approaches to case management. My team used a shared spreadsheet system while the other team relied entirely on email tags. Neither system would scale to ten people, and we were getting duplicate work and missed follow-ups.

I volunteered to research CRM solutions and presented three options to our manager, comparing features and costs. Once we selected a platform, I created training documentation and ran practice sessions with small groups. I also set up a ‘buddy system’ pairing someone from each original team to help everyone adjust.

Within a month, our average response time actually improved by 20% despite the transition chaos. The best part was seeing the two teams blend into one cohesive unit. I learned that change is smoother when you give people clear processes and support, not just throw new systems at them.”

What good looks like: Taking initiative, bringing people together, focusing on measurable results, showing leadership even without a formal title.

4. Tell me about a time when you had to go above and beyond your job responsibilities to get something done.

Progressive’s culture values people who don’t just punch the clock. They want employees who take ownership and do what needs doing, even if it’s not technically their job.

Sample SOAR Answer:

“I was working as a server at a busy restaurant when our event coordinator called in sick on the day of a 50-person wedding rehearsal dinner. The manager was scrambling because no one else knew the event details or setup requirements.

The obstacle was that I’d never coordinated an event before, and I was also scheduled to serve my regular section that night. But I knew if we messed up this event, we’d lose future wedding business.

I came in two hours early to review the event notes and coordinate with the kitchen. I completely reset the private dining room, confirmed the menu with the bride’s mother, and created a timeline for service. During the dinner, I checked in regularly while still managing my regular tables. I even stayed an hour past my shift to ensure cleanup was perfect.

The bride’s family was thrilled with how smoothly everything went, and they booked their actual wedding reception with us. My manager gave me a bonus and started training me on event coordination. It showed me that stepping up when needed not only helps the team but opens doors for your own growth.”

Common mistakes to avoid: Don’t make it sound like you regularly do other people’s jobs or that you’re a martyr. Focus on a specific situation where going above and beyond made real impact.

Interview Guys Tip: When discussing going “above and beyond,” Progressive wants to hear about your thought process, not just that you “worked hard.” What made you decide to step up? How did you prioritize? What was the business impact?

5. Give me an example of when you had to prioritize multiple tasks with competing deadlines. How did you handle it?

If you’re interviewing for claims, customer service, or any client-facing role, this question is almost guaranteed. Insurance professionals juggle multiple cases, customers, and deadlines constantly.

Sample SOAR Answer:

“During finals week of my senior year, I was juggling three major projects due the same week while working 25 hours at my campus job. I also had committed to leading a volunteer event that Saturday.

The obstacle was that everything felt equally urgent and important. I couldn’t drop any of these commitments without major consequences, but I physically didn’t have enough hours in the week to do everything perfectly.

First, I listed everything out with actual deadlines and estimated time requirements. I realized one project was due Thursday but presentations weren’t until Monday, giving me weekend time. I then talked to my manager about shifting two of my work shifts to the following week. For the volunteer event, I delegated setup tasks to two other volunteers instead of trying to do it all myself.

I created a hour-by-hour schedule for the week, blocking specific times for each project. I also used my lunch breaks for smaller tasks like responding to volunteer emails. Everything got done on time, I maintained my 3.8 GPA, and the volunteer event was our best-attended one that semester. The experience taught me that prioritization isn’t just about working harder, it’s about being strategic with your time and asking for help when you need it.”

What they’re looking for: Actual organizational systems, communication with stakeholders, delegation skills, and realistic self-awareness about limitations.

Explore more strategies in our behavioral interview questions guide.

6. Describe a time when you made a mistake at work. What did you do?

This question makes everyone nervous, but here’s the thing: Progressive knows everyone makes mistakes. They’re evaluating whether you take ownership, learn from errors, and prevent them from happening again.

Sample SOAR Answer:

“In my first month as a pharmacy technician, I accidentally entered the wrong quantity for a prescription refill. Instead of a 30-day supply, I processed it as a 90-day supply. Fortunately, our pharmacist caught it during final verification before it went to the patient.

The obstacle was that I felt mortified. I’d made an error that could have cost the pharmacy money and potentially harmed our patient relationship. I also worried about losing my job so early on.

I immediately apologized to the pharmacist and asked her to walk me through exactly where I went wrong. I realized I had skipped a verification step in our system that would have flagged the discrepancy. I then created a personal checklist that I kept at my workstation for the first three months, forcing myself to double-check every entry before moving forward.

I didn’t make that type of error again, and after six months, the pharmacist told me I’d become one of the most accurate technicians on the team. That mistake taught me that systems and checklists aren’t just bureaucracy, they’re how we protect ourselves and our customers from human error.”

Turning a negative into a positive: Notice how this answer shows accountability, immediate corrective action, prevention measures, and long-term improvement. That’s the formula Progressive wants to see.

7. Tell me about a situation where you had to work with a difficult team member or customer.

Conflict happens. Progressive wants to see that you can handle interpersonal challenges professionally without burning bridges.

Sample SOAR Answer:

“I worked on a group project in college where one team member constantly missed meetings and didn’t complete his assigned portions on time. This put extra pressure on the rest of us, and tensions were rising.

The obstacle was that confronting him directly risked making the situation worse, but ignoring it meant we’d either fail the project or have to do his work ourselves. We only had two weeks until the final presentation.

Instead of complaining to the professor or having the group gang up on him, I asked to meet with him one-on-one for coffee. I approached it with curiosity rather than accusation, asking if something was going on that made it hard to participate. Turns out he was working two jobs to pay for school and felt overwhelmed but didn’t want to ask for help.

We restructured his assignments into smaller, more manageable pieces and set up check-ins every two days instead of weekly meetings. He started contributing consistently, and we ended up getting an A on the project. I learned that most ‘difficult’ people aren’t intentionally causing problems, they’re usually dealing with challenges you don’t see. Leading with empathy instead of frustration usually works better.”

What NOT to say: Avoid badmouthing anyone. Don’t make yourself the hero and them the villain. Show emotional intelligence and problem-solving skills.

8. Why do you want to work at Progressive?

This isn’t the time for generic answers about “great company culture” or “competitive salary.” Progressive wants to know you’ve done your research and you’re genuinely interested in them specifically.

Sample Answer:

“I’ve been really impressed with how Progressive has innovated in the insurance industry, especially with tools like Snapshot and Name Your Price. Insurance can feel complicated and overwhelming to customers, and I love that Progressive focuses on transparency and giving people control over their coverage options.

What really attracted me to this role is the combination of technology and customer service. I read about Progressive’s investment in AI tools to help claims adjusters work more efficiently, which means they can focus more on the customer relationship rather than administrative tasks. That balance of innovation and human connection is exactly where I want to grow my career.

I also appreciate that Progressive promotes from within and offers clear career paths. Several Glassdoor reviews mentioned the strong training programs and mentorship opportunities, which tells me this is a company that invests in employee development, not just fills positions.”

What makes this answer work: Specific product/service knowledge, connection to your values, shows you’ve researched the company culture, mentions what you’ll gain (not just what you’ll give).

Check out our detailed guide on answering why do you want to work here for more strategies.

9. Describe a time when you had to learn something new quickly. How did you approach it?

Insurance is complex and constantly evolving. Progressive needs people who can learn on the fly and adapt to new systems, products, and regulations.

Sample SOAR Answer:

“When my retail store implemented a new point-of-sale system, we had three days of training before going live during our busiest season, Black Friday week. The old system had been in place for five years, and everyone was comfortable with it.

The obstacle was that this new system was completely different, with multiple screens and processes that felt counterintuitive. I was worried about slowing down transactions when we had lines out the door during holiday shopping.

I took detailed notes during training and created a quick-reference guide with the most common transactions. I also came in an hour early for three days before the launch to practice on the system when the store was quiet. I made mock transactions, processed returns, and even deliberately created errors so I’d know how to fix them under pressure.

When we went live, I was one of the fastest adopters on the team and actually helped train colleagues who were struggling. My manager asked me to turn my quick-reference guide into an official training document for new hires. The experience taught me that the best way to learn something new is hands-on practice combined with creating resources that break complex processes into simple steps.”

Demonstrating growth mindset: This answer shows initiative, preparation, helping others, and turning learning into a transferable resource. That’s exactly what Progressive wants.

10. What questions do you have for us?

Never, ever say “No, I think you covered everything.” Not having questions suggests you’re not truly interested or haven’t thought critically about the role.

Why this matters: Your questions reveal what you care about and whether you’re thinking long-term about this opportunity.

Smart questions to ask:

• “Can you walk me through what the first 90 days typically look like for someone in this role? What would success look like at the 30, 60, and 90-day marks?”
• “How does Progressive support ongoing learning and development? Are there opportunities to earn certifications or cross-train in different areas?”
• “What do you think distinguishes team members who thrive at Progressive from those who struggle?”
• “How is success measured in this role, and how often would I receive feedback on my performance?”
• “What do you enjoy most about working at Progressive? What’s been your biggest surprise about the company culture?”
• “What are the next steps in the interview process, and when should I expect to hear back?”

Interview Guys Tip: Ask questions that show you’re already thinking about how to excel in the role, not just whether you’ll get the job. Questions about training, success metrics, and team dynamics demonstrate you’re planning to stick around and grow.

For more ideas, check our comprehensive guide on questions to ask in an interview.

Top 5 Insider Tips for Progressive Interviews

1. Master the SOAR Method Before Your Interview

Progressive explicitly tells candidates they use behavioral interviewing and the SOAR method. This isn’t a secret, it’s literally the game plan they give you. Don’t waste this advantage.

Prepare 5-7 different stories from your past that demonstrate various competencies: customer service, problem-solving, teamwork, leadership, handling change, dealing with conflict, and learning new skills. Practice telling each story using Progressive’s recommended timing: 30 seconds for situation, 2 minutes for action, 30 seconds for result.

Record yourself or practice with a friend. Your answers should sound conversational, not memorized. The goal is natural storytelling that happens to follow a structure.

2. Take the Assessment Seriously (It’s a Real Filter)

According to multiple Glassdoor reviews, many qualified candidates never make it past the pre-employment assessment. This 45-50 minute test includes basic math, vocabulary analogies, personality questions, and a customer service call simulation.

Here’s the insider tip: Take the assessment when you’re focused and alert, not distracted or rushed. One candidate reported being declined after taking it while distracted, then passing easily when retaking it with full concentration months later.

The assessment genuinely filters people out, so treat it like a real test, not a formality.

3. Prepare for the HireVue Video Interview

After you pass the assessment, you’ll likely face an asynchronous video interview. You’ll answer 5-8 behavioral questions on camera with 1 minute to prepare and 3 minutes to respond. You get two attempts per question.

Practice recording yourself answering common behavioral questions beforehand. Get comfortable seeing yourself on camera and speaking without a live person to react to. It feels weird at first, but preparation makes a huge difference.

Set up good lighting, test your camera and microphone, eliminate background noise, and dress professionally from the waist up at minimum. Treat it like a live interview even though it’s recorded.

4. Study the Job Description Like a Roadmap

Progressive’s own interview preparation resources tell candidates to connect their answers back to the job description. This is your roadmap for what they’re evaluating.

Read the job posting carefully and identify 3-5 key competencies they’re seeking. Prepare at least one story that demonstrates each competency. When you answer questions, use language and terminology from the posting when it makes sense.

If the job description emphasizes “customer-focused problem-solving,” make sure your stories highlight how you solved problems while keeping the customer’s needs central. If it mentions “adaptability in a fast-paced environment,” have a story ready about thriving under pressure.

5. Show Genuine Enthusiasm for Progressive’s Mission and Culture

According to Glassdoor reviews, Progressive weighs culture fit heavily in hiring decisions. They want people who are genuinely excited about working there, not just looking for any insurance job.

Research Progressive’s innovation in the insurance industry. They pioneered usage-based insurance with Snapshot, created the Name Your Price tool, and consistently invest in technology to improve customer experience. Be ready to discuss what specifically interests you about Progressive’s approach.

Multiple employees mention Progressive’s personable, supportive culture in reviews. Authenticity matters more than polish here. Be yourself, show genuine interest, and let your personality come through. Progressive wants real people, not corporate robots.

For phone or video interviews, our phone interview tips can help you prepare for remote conversations.

What to Expect in the Progressive Interview Process

Understanding the timeline and stages helps you prepare mentally and logistically.

• Stage 1: Online Application Submit your resume and application through Progressive’s careers site. Tailor your resume to the specific role, using keywords from the job description.

• Stage 2: Pre-Employment Assessment (45-50 minutes) This includes math, vocabulary, personality assessment, and customer service simulation. Take it seriously and in a focused environment.

• Stage 3: Asynchronous Video Interview (HireVue) Answer 5-8 behavioral questions on camera. You’ll have 1 minute to prepare and 3 minutes to respond per question, with two attempts allowed.

• Stage 4: Live Interview with Hiring Manager Usually conducted via Microsoft Teams. Expect more behavioral questions and deeper conversation about your background and the role. This typically lasts 45-60 minutes.

• Stage 5: Potential Final Round or Background Check Some roles require additional interviews. If you advance, you’ll go through background screening before receiving an offer.

Timeline: The complete process typically takes 2-4 weeks from application to offer. Most candidates report hearing back within 1-2 weeks between each stage.

Interview Guys Tip: Stay proactive but patient. If you haven’t heard back within the timeframe they mentioned, it’s completely appropriate to send a polite follow-up email to your recruiter.

Common Mistakes to Avoid

• Skipping the SOAR structure: Progressive evaluates whether you follow their method. Generic answers won’t cut it.
• Rambling or going over time: Keep situation and result sections brief. Focus your time on the action portion where you demonstrate your skills.
• Using “we” instead of “I”: They need to know YOUR specific contributions, not what your team accomplished collectively. It’s okay to mention team context, but be clear about your individual role.
• Not preparing questions to ask: Coming with no questions signals lack of genuine interest or critical thinking about the opportunity.
• Badmouthing previous employers: This is especially important in behavioral questions about conflict or challenges. Stay professional and focus on what you learned.
• Treating the assessment like a formality: Many qualified candidates are filtered out at the assessment stage. Take it seriously.
• Being too rehearsed: Your answers should follow SOAR structure but sound conversational, not memorized like a script.

Wrapping Up

Progressive’s interview process might seem intense, but here’s the beautiful part: they tell you exactly what they’re looking for and how they evaluate candidates. Most companies keep you guessing. Progressive hands you the playbook.

Master the SOAR method. Prepare 5-7 solid stories from your past. Research Progressive’s products, values, and culture. Practice your answers out loud until they feel natural. Take the assessment when you’re focused. Come with thoughtful questions.

Do these things, and you’ll walk into your Progressive interview genuinely prepared, not just hopeful. You’ll know what they’re evaluating, how to structure your answers, and what makes candidates stand out.

The bottom line: Progressive uses behavioral interviewing because they want to see the real you, backed by concrete examples. Authenticity plus preparation equals interview success. You’ve got the preparation part covered now. The authenticity? That’s all you.

Now go review that job description one more time, practice your stories, and show them why you’re the right person for the job.

---