Have you ever walked out of a meeting—whether it was with a retail buyer, a job candidate, an investor or even a date—and thought, “Something just didn’t click”?
You had the product, the deck, the resume… but it still didn’t land.
Buyer meetings are not just about showing that you are the right brand for the retailer’s shelves; they are also an opportunity to learn how you both can best work together – OR, conversely if you are not a fit, and would be better spending your time on more relevant opportunities.
This information can only come from a back and forth discussion with the buyer. And the key to uncovering this information is ASKING THE RIGHT QUESTIONS.
Questions Are A Power Tool in Your Retail Sales Pitch
Here’s what most people overlook:
The questions you ask can make you look like a boss or a beginner.
Most people treat a pitch like a performance and the newbies treat it like a monologue. But real success comes from treating it like a conversation.
Asking the right questions—using the right vocabulary and focus—can instantly position you as someone who is retail ready (or job ready). It shows preparation, empathy for the customer’s pain points, and alignment with the person across the table.
At START to SOLD, we teach founders that the difference between a “so-so” pitch and a game-changing one is not about having perfect answers.
It’s about knowing how to ask the right questions and giving good answers.
When you ask thoughtful questions, you show:
- You understand the customer’s world
- You’re serious about a long-term partnership—not just a quick sale
- You’ve done the work to align your offer to their actual needs
Your Dream Buyer May Not Be Who You Think
We don’t pitch just to sell. We pitch to find the right buyer.
Not all buyers are a good fit for you, at this time.
We hear it ALL the time from founders that they want to be in TARGET or COSTCO as their goal. Let’s be real… It’s everyone’s big dream. Like being FAMOUS and RICH.
But the truth is if you get into these large stores TOO early it could crush you with their high quantities and rules you may not be ready to match.
Don’t worry – you can get there – the big times! Growth that lasts and is safe for you as a founder needs to scale like a stair step.
Let’s embrace today! And find our perfect match for this growth phase. You have a unique capacity and ability to manufacture and deliver during THIS current phase of growth. Today – who can you serve with great success? That is your ideal retail store today.
Your questions today should match and communicate with this phase of growth and that ideal retailer. Just like how you have different capacities to deliver, they will have different needs.
Strategic, smart questions also communicate your values, boundaries, goals. It should be a good fit.
The smaller retailer will be able to tell if you are a good fit for them by the questions you ask them because their questions and needs will be different than larger retailers.
Plan questions based on your ideal retailer in this phase of growth. They help you connect with the right person—and repel the wrong one. (These questions should also help determine if the retailer is a cultural fit for your brand, something that can be important for mission-based CPG manufacturers).
Asking smart questions allows you to find your ideal partnership. And when you do, both sides will feel it.
Show You’re Easy to Work With
Listening to the answers – is part of asking questions.
Strategic, smart questions also communicate what you understood AND your ability to truly listen. I’ve seen retail buyers answer a question and the person pitching completely miss the point. That situation resulted in LOST credibility and connection. They didn’t get a call back – because they were bad listeners and showed they wouldn’t be easy to communicate with. It had NOTHING to do with their product fit!
Questions aren’t just about getting answers—they’re about demonstrating leadership. Help the buyer get to the answers you know they need. When you ask smart, relevant questions, you show you’re intentional, thoughtful, and serious. It’s one of the fastest ways to earn credibility when you ask relevant questions in-line with the process of building a business partnership. When you use their vocabulary they know they won’t waste time teaching you new things.
Make Your Plan to Ask to Align, Not Just to Sell
If you’re not finding the success you want in sales or interviews, take a step back and ask yourself:
How can I ask better questions to align myself with my customers?
The best tool is writing out your questions with the same seriousness you use to write out your pitch. Write the questions based on who you are meeting with and to reflect your goals.
Some Examples to Give You a Start
While the specific questions that you should ask will vary depending on several factors, including the categories of your products, your time in business, and current distribution, here are some examples of the types of questions we are talking about. We’re happy to help you further develop the ideal questions for your brand!
1. how many stores are you buying for?
2. what are your current best sellers?
3. What do you think your shoppers are looking for this coming year in our category?
4. what is the price range of products in our category that are you are currently selling
Don’t know where to start? We are here to help you! We have:
- PITCH TEMPLATES for DIY pitch presentation you can tailor to your product category. That includes advice on questions to ask and answer as you prepare.
- 1:1 CONSULTING for strategic and specific advice to write questions for your next pitch.
As one happy satisfied START to SOLD client put it:
“With the right questions I could unlock a new level of connection with a retailer I’ve never had before. We were retail ready before—but now a retailer knows it faster, and I also am confident we are a good fit.”
When you lead with curiosity, strategy, and empathy, your questions become your big advantage.
Your Next Steps:
- Write your presentation to include questions
- Identify your ideal retail partner and order
- Practice active listening during your pitch to impress them you’re a great future partner
