Retail interviews are a chance to show more than just your work history. They reveal who you are, what drives you, and how well you can connect with others. 

For Dave Thompson, retail is both personal and purposeful. His wine shop, Deep Red Wine Merchant, located in Chicago’s Avondale neighborhood, blends education with his love for horror film culture. 

His approach to customer service, sourcing, and storytelling demonstrates how to craft answers that connect and serve as a compelling guide to standing out in any retail job interview.

Read on to learn eight comprehensive tips inspired by his approach.

1. Share Your “Why” With Heart 

When asked, “Why do you want to work in retail?” go beyond surface-level answers. Think about the passions or life experiences that brought you here.

Dave built Deep Red Wine Merchant around two deep interests: wine and horror films. He didn’t try to fit into a mold. Instead, he created a different concept where customers can learn, explore, and relax in an environment that’s authentically him.

He said, “I wanted to create a space that was very comfortable and very approachable… especially if you’re just starting out.”

So what’s your why? Whatever it is, use it in your retail interview. To prepare, do the following: 

• Think about a moment that made you love retail—was it helping someone find the perfect gift, solving a tricky customer need, or the energy of a busy store?
• Tie that moment to something personal—maybe your love for organizing, storytelling, fashion, food, or connecting with people made retail feel like the right fit.
• Explain how passion shows up in your work—share how it feels to create a welcoming space, offer thoughtful recommendations, or build trust with regulars. 

Telling your story with confidence can help potential employers see how you’ll bring joy and connection to their retail space.

2. Turn Unique Interests Into Professional Strengths

Retailers love candidates who bring fresh perspectives. One of the best ways to stand out is by leaning into what makes you unique. When asked, “What makes you different from other applicants?” don’t shy away from personal passions. Instead, use them to paint a fuller picture of how you think, connect, and contribute.

Take Dave Thompson, for example. His lifelong love of horror films is a lens through which he sees the world, and it directly shapes the atmosphere at Deep Red Wine Merchant. From the shop’s name (inspired by an Italian horror classic) to the way he talks about wine, Dave draws powerful connections between horror’s layered storytelling and wine’s nuanced flavors.

When preparing for interviews, think about what energizes you outside of work and how that passion naturally shows up in how you serve or solve problems. That’s how you gain a competitive edge.

3. Go Deep on Product Knowledge

When a hiring manager asks, “Tell me about a product you love,” it’s less about what you choose and more about how you describe it. This question is designed to reveal how you think, how you communicate, and how you help others connect with what you’re selling. Your goal should be to bring the product to life.

Dave Thompson excels in this area at Deep Red Wine Merchant. When he talks about wine, he takes the customer on a journey. 

You can approach your answer the same way:

• Start broad: Introduce the product by discussing why people love it. Is it versatile, nostalgic, or a seasonal favorite? It could solve a common problem or spark a specific emotion, such as comfort, excitement, or indulgence. This sets the stage for the deeper dive.
• Narrow it down: Now break the product into its components. Talk about the color, scent, material, flavor, or how it functions in everyday life. This is where your expertise truly shines, demonstrating that you’ve paid attention to what makes the product special.
• Make it interactive: Consider how you’d explain it to an unsure customer. Would you use comparisons, sensory language, or ask them a question to engage them? The best retail employees inform and engage customers.

If you’re heading into an interview, choose a product you love and practice describing it as you would to a friend or a first-time customer. Your ability to connect over something simple can make you stand out as a knowledgeable, thoughtful, and enthusiastic candidate.

4. Frame Inclusion and Values as Priorities

If you’re asked, “What kind of environment do you want to work in?” or “What matters to you in retail or your job?”, this is your opportunity to talk about values, what you stand for, and how that translates into the work you do. Today’s retailers are looking for employees who understand the importance of culture, inclusion, and delivering meaningful customer experiences.

Dave Thompson makes it a priority to source wines from queer, Black, and Latinx winemakers because he believes those voices deserve space and recognition in an industry that often overlooks them.

In your interview, you can take a similar stance. Instead of focusing solely on sales or brand alignment, discuss wanting to work in a place that reflects the community it serves. Demonstrating that you value diversity, fairness, and inclusion can set you apart as someone who brings understanding and compassion to the retail floor.

5. Be Transparent About How You Handle Challenges

Retail work comes with its fair share of challenges, and interviewers are aware of this. That’s why questions like “Tell me about a time you handled a difficult situation” or “How do you manage change?” are so common. These moments are about showing that you can stay grounded, flexible, and focused when things don’t go as planned.

When you’re preparing to answer this kind of question, think about a time when something at work didn’t go smoothly. Perhaps it was a delayed shipment, a challenging customer interaction, or an unexpected schedule adjustment. Be specific about how you responded. Did you problem-solve on the fly, rally your team, or communicate transparently with a customer? 

Employers aren’t expecting perfection; they’re looking for people who can face change with clarity and confidence. If you can show that you’re someone who steps up rather than shuts down, you’ll make a strong and lasting impression.

6. Talk About Learning as a Lifelong Game

If you’re asked, “Where do you see yourself in five years?” it may be tempting to focus on climbing the ladder, but employers are often more interested in how you plan to grow, contribute, and stay engaged. They want to hear that you’re someone who sees retail as more than a short-term job and an opportunity to build skills, deepen your knowledge, and support the team around you.

When you’re preparing to answer this question, think about what you’re eager to explore. Maybe it’s learning more about visual merchandising, becoming a product expert, planning in-store events, or eventually mentoring new team members. 

A thoughtful, growth-focused answer tells employers that you’re motivated and ambitious, without sounding like you’re in a rush to leave. It shows them you’re here to invest time and be there for the long haul.

7. Demonstrate Your Commitment to Customer Education

Interviewers love to ask: “How do you create a great customer experience?” or “How do you help customers make informed decisions?” These questions assess your ability to guide, educate, and empower individuals throughout the buying process.

You can highlight moments where you’ve helped a customer better understand a product. Maybe you broke down a skincare routine in everyday language so someone new to the brand felt confident trying it.

Or maybe you asked thoughtful questions that helped a customer choose the right tech accessory for their needs. These kinds of examples demonstrate that you listen, simplify when necessary, and guide people to the right decision.

Being someone who helps others feel more informed and less overwhelmed will always stand out in retail.

8. Stand by Ethical Sales Practices

If you’re asked, “What’s your sales style?” don’t just say you’re persuasive. Be specific, and if integrity matters to you, say so proudly.

Instead of pushing sales, Dave helps people find what fits their taste and encourages them to come back when they’re ready.

Structure your response like this:

• “I believe in asking questions, listening carefully, and making recommendations based on what the customer is looking for.”
• “If something isn’t a good fit, I’d rather help a customer explore other options, even if that means they don’t make a purchase that day.”
• “Long-term trust is more important to me than short-term gains.”

It doesn’t matter what you’re selling. Demonstrating that you value honesty and customer satisfaction above all else will help you excel in the interview. Take a page from Dave’s book: lead with sincerity, guide with care, and trust that customers will appreciate your sales style because they feel respected.

Conclusion

Dave Thompson’s story proves that when you lead with passion, purpose, and empathy, your answers in retail interviews can stand out from the crowd.

By preparing thoughtful responses rooted in your experiences and values, you’ll go beyond generic answers and show retailers why you belong on their team.

Remember: retail interview questions are an opportunity! Use them to share your story, and you’ll walk into your next interview with confidence and clarity.

Want to learn more about other Illinois retail leaders? Read inspiring stories from retailers across Illinois who are making a difference.

If you loved learning about Dave’s story and know a retailer who deserves recognition, Nominate A Retailer to submit your nomination!