The Best Discovery Questions You Likely Aren’t Asking

In sales, especially in the print/promo world, your success often comes down to the quality of your questions.

And while most sales reps do ask questions, they often stop at the basics:

• Quantity?

• Colors?

• Sizes?

• Logo placement?

These questions are important, but they’re only allowing us to quote the job. They won’t help you understand the customer’s true motivation or create a standout buying experience.

If you want to close more deals and stand out from your competitors, you need to go deeper. Here are the best discovery questions you're likely not asking, but should be.

1. “What’s the bigger goal behind this order?”

This question instantly shifts the conversation from a transaction to a solution.

Maybe they’re trying to:

• Build brand awareness at an event

• Create team unity with consistent workwear

• Raise funds through a merch campaign

When you understand the why behind the order, you can tailor your recommendations and become a partner instead of just a vendor.

Other options here:

1. What are you hoping to accomplish with this order?

2. What’s most important to you?

3. If you had to stack rank quality, turn-around time and cost, from most to least important where would they land?

2. “What’s worked (or not worked) with past printers?”

This tells you exactly how to win the job and what pitfalls to avoid.

If their last provider missed deadlines, make your reliability a key selling point. If they loved the creativity but needed more structure, you can build confidence by showing your process.

3. “Besides yourself, who else is involved in this process?”

Most reps forget to uncover the full decision-making process.

If your contact isn’t the only one signing off, you need to know who else to influence, whether it’s a finance director, coach, or marketing manager. This helps you close deals faster and avoid last-minute surprises.

4. “What would make this project a big win for you?”

This question opens the door to emotion, expectations, and opportunity.

You’ll learn what really matters, maybe it’s looking good to their boss, getting a killer turnout for their fundraiser, or pulling off an event without stress. When you align your solution with their definition of success, it’s easier for them to say yes.

5. “What are your biggest worries or concerns about placing this order?”

This question builds instant trust. It shows you care and gives you the chance to overcome objections before they stall the deal.

If they’re worried about print quality, timelines, or price fluctuations, you can address it proactively and show you’re a professional who gets it.

6. “What happens if you don’t move forward with this project?”

This is a subtle way to tap into urgency and consequences.

You might discover that missing this order would impact an event, cost them sponsorship, or frustrate their team. Now you’re not just selling apparel, you’re helping them avoid a bigger problem.

7. “How do you like to communicate during a project?”

This simple question can save so much frustration down the road. Some clients prefer phone calls. Others live in their inbox. Some love DMs.

Meeting your customer where they are makes the process smoother and shows respect for their workflow.

Conclusion

The right questions don’t just help you sell, they help you build trust, reduce objections, and deliver a better customer experience.

If you’re tired of stalled deals and generic conversations, level up your discovery game. Ask deeper, smarter questions that uncover what really matters.

You’ll close more confidently, stand out from the competition, and turn more one-time buyers into lifelong customers.

Try adding just one of these questions to your next call, you might be surprised what you learn.