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    Startups & Entrepreneurship

    If You’re Not Asking Your Employees These Questions, You’re Leaving Money on the Table

    adminBy adminJune 5, 2026No Comments8 Mins Read
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    If You’re Not Asking Your Employees These Questions, You’re Leaving Money on the Table
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    Opinions expressed by Entrepreneur contributors are their own.

    Most operators are sitting on valuable business insights every single day — and they don’t even realize it.

    I see it all the time when I walk into a business or work with a franchise. Customers consistently leave the same add-ons untouched or throw them away. Employees answer the same questions multiple times a shift because something is unclear. An operational process slows everything down during peak hours and the team quietly develops workarounds to keep things moving.

    These moments are easy to dismiss, but they’re not random. They’re signals pointing directly to opportunities to improve performance, efficiency and customer experience.

    The patterns become obvious once you start looking for them. The people doing the work see them every day. They know where customers get confused, where time gets wasted and where the experience falls short. The problem isn’t a lack of insight. It’s that most leaders aren’t asking for it—or creating an environment where it gets shared.

    There’s a reason shows like Undercover Boss resonate with so many leaders. Executives step into frontline roles and, often for the first time, hear what’s really happening inside their businesses. Employees openly share frustrations, inefficiencies and missed opportunities that leadership never saw. The lesson isn’t that you need to go undercover. It’s that people will share valuable insights when they feel safe speaking up and someone takes the time to listen.

    After years of running my own franchise locations and now working with brands that rely on frontline teams, I’ve learned that most businesses don’t have an idea problem. They have a listening problem. Your employees already know what’s working and what isn’t. The question is whether you’re creating the conditions to hear it.

    Why leaders overlook what’s right in front of them

    Most leadership models are built around directing. Leaders train people, enforce standards and focus on execution. That’s necessary for consistency. But when communication becomes one-directional, awareness suffers. The people closest to the customer stop sharing what they see and leaders lose visibility into what’s actually happening on the front lines.

    Frontline employees interact with customers all day. They hear the same questions repeatedly, notice hesitation and see where expectations don’t match reality. They experience where processes break down under pressure and where inefficiencies create friction. That perspective is difficult to replicate through reports, dashboards or performance metrics.

    The problem isn’t that employees lack insight. It’s that most organizations don’t consistently ask for it.

    What changed how I led my own business

    I didn’t always operate this way.

    When I owned my Edible Arrangements franchises, I approached leadership as many operators do. I believed my job was to have the answers. When something wasn’t working, I responded by tightening expectations, increasing accountability and giving more direction. That approach only took me so far.

    The shift happened when I started asking a different question. Instead of focusing on what my team was doing wrong, I began asking what they were seeing that I wasn’t. One employee pointed out something in our sales process that I’d completely overlooked. We used to ask customers whether they wanted their strawberries dipped in chocolate and then whether they wanted all of them dipped or only half.

    It sounded helpful. In reality, it was lowering our sales. She noticed that most customers weren’t looking for a cheaper option. They were buying gifts and had already committed to spending. But once we introduced the idea of dipping only half the strawberries, many customers defaulted to it simply because it was presented as a choice.

    We changed the script and simply offered chocolate-dipped strawberries. Nothing else changed. The product stayed the same. The customers stayed the same. Our average ticket increased.

    That experience taught me a valuable lesson: the people closest to the customer often see opportunities that leadership misses.

    Small observations can drive immediate gains

    The same thing happened in our operations. At one point, I accepted a certain amount of product waste as the cost of doing business. Then a team member pointed out that we consistently prepared more chocolate than we needed, especially during slower periods.

    Her suggestion was simple: prepare smaller batches and replenish based on actual demand. We made the change and the waste dropped almost immediately.

    What struck me wasn’t how complicated the solution was. It was how obvious it seemed once someone said it out loud.

    I see this pattern everywhere

    This isn’t unique to my business. I was once leading a training session for a large group when an employee suggested moving a buffet table from against a wall to the center of the room so people could access it from both sides. A simple adjustment dramatically improved flow and shortened lunch service.

    I couldn’t help but wonder how many times that employee had noticed the problem before feeling comfortable enough to speak up. I’ve seen similar examples in restaurants, retail stores and franchise systems.

    In one restaurant chain, it was a busser — not a manager — who noticed that many guests never used the straws and coffee creamers automatically provided with drinks. The team began asking customers whether they wanted those items instead of distributing them by default. Waste decreased. Costs dropped. The guest experience remained unchanged.

    The insight didn’t come from a consultant, a report or a new technology platform. It came from someone working closest to the customer.

    Your team is a real-time feedback system

    Every shift, your employees are gathering information. They’re observing customer behavior, identifying friction points and adapting in real time to keep operations running smoothly.

    Most organizations rely heavily on data to understand performance. Data is important, but it only tells you what’s happening. Your employees can often tell you why it’s happening. If you want to improve performance, you need both.

    How to ask questions that actually produce insight

    If you want meaningful input from your team, you have to be intentional about how you ask for it. General requests for feedback rarely produce useful answers because they’re too broad.

    Instead, focus on patterns and lived experience:

    • Where do customers seem confused or hesitant?
    • What slows things down?
    • Which parts of the process feel harder than they should?
    • What are customers trying to change, customize or work around?
    • What are customers consistently asking for — or throwing away?
    • Where do you see inconsistency in how we deliver the experience?

    One of my favorite questions is also the simplest: “If you were responsible for improving results today, what would you fix first?” Questions like these do more than generate ideas. They encourage employees to think like owners rather than operators.

    How to put this into practice immediately

    You don’t need a complicated system. You need consistency. Start by choosing one shift this week and asking your team two or three focused questions about what they’re seeing. Listen for patterns rather than one-off comments. Repeated observations usually point to the biggest opportunities. Then test one idea. Keep it simple. The goal isn’t perfection — it’s momentum.

    Finally, close the loop. Let your team know what changed because of their feedback. When people see that their input leads to action, they’re far more likely to continue contributing.

    The connection to performance most leaders underestimate

    This isn’t about creating a feel-good culture. It’s about driving better business results. When employees feel heard, engagement increases. Higher engagement leads to better execution. Better execution creates a stronger, more consistent customer experience. Leaders who understand this don’t view listening as a soft skill. They view it as a performance advantage.

    Your next breakthrough may already be inside your business

    Many leaders spend their time searching for new strategies, tools, and ideas to improve performance. Those things can be valuable. But they’re often overlooking opportunities that already exist inside their own organizations.

    The insights that drive meaningful improvement are frequently embedded in the daily experiences of the people serving your customers. The leaders who outperform their competitors aren’t necessarily the ones with the best ideas. They’re the ones who ask better questions, listen more closely, and act on what they learn.

    If you do that consistently, you may discover that the solutions you’ve been searching for have been there all along.

    Most operators are sitting on valuable business insights every single day — and they don’t even realize it.

    I see it all the time when I walk into a business or work with a franchise. Customers consistently leave the same add-ons untouched or throw them away. Employees answer the same questions multiple times a shift because something is unclear. An operational process slows everything down during peak hours and the team quietly develops workarounds to keep things moving.

    These moments are easy to dismiss, but they’re not random. They’re signals pointing directly to opportunities to improve performance, efficiency and customer experience.

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