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Busy seasons expose assumptions, better questions fix them

Turn conversations into clarity.

Spring is one of those seasons where everything can hit at once. Team uniforms. Academic awards. Booster club orders. Last-minute emails that start with “Hey, quick question…” and end with a tight deadline. If you run a decorating or personalization business, you already know this rhythm. The pace picks up, expectations rise, and it gets tempting to assume you already know what customers want so you can move faster. That temptation is where trouble starts.

Most missed opportunities during busy seasons are not production problems. They are conversation problems. We think we know what the customer values, so we rush to solutions. The customer thinks we understand them, so they hold back on what really matters. Somewhere in the middle, clarity slips and stress fills the gap. You start to resent the business coming in, and the customer wonders if they made the right choice choosing you.

Here is the good news. Your customers are already telling you what they want. You do not need a fancy survey, a new CRM, or a big research project. You just need to learn how to hear what is actually being said and ask better questions at the right moments. Slowing down and being intentional during those customer interactions will be worth the extra time or interruptions.

This mindset shift is a real competitive advantage, especially during chaotic seasons. It reduces back-and-forth, builds trust faster, and turns one-time orders into repeat relationships. And again, no fancy survey, expensive research projects, or cumbersome AI-driven CRM system needed.

The message beneath the message

One of our mastermind members shared an email thread that looked simple on the surface. The customer said they were “holding off” and wanted to explore other options. That phrase alone can trigger doubt. Is the price wrong? Did she miss the mark? Are they going elsewhere?

When she slowed down and looked closer, something important showed up. The customer never said the offer lacked value. They never said they did not want to work together. What they did say, more than once, was that they wanted “more dynamic, higher-impact options” and less effort spent on things they hoped someone would stumble across.

That single phrase told her almost everything. It revealed their desire for visibility and momentum. It revealed their fear of wasted time and money. It revealed the filter they use to make decisions. And with that, we were able to see the deeper desires of the customers, and that helped her redesign the value proposition she was offering, which changed their relationship for the better.

All that value would have been lost if the emotional reaction to being told no had driven the response. Instead, she slowed down and asked better questions. She replied to the “holding off” message with curiosity. She asked, “I’m curious what unexplored options you’re considering. I’m not trying to sell you more. I want to understand what our customers are looking for so we can serve you better. If you’d be open to it, I’d love your feedback.” For this to be of value to you, you must stop taking words at face value and start listening for patterns. When you explore with curiosity instead of defensiveness and pushing, then confusion drops and confidence rises.

Mindset as a competitive advantage

Many business owners think feedback means surveys, analytics, or reviews collected once a year. Those tools can help, yet they are often used as shields. They feel safer than real conversations. The clearest signals show up in everyday emails, texts, counter conversations, and DMs. Busy seasons actually give you more data, not less. You just need to look at it differently.

The shift is simple. Instead of asking, “What did they say?” start asking, “What are they really telling me?” When you train yourself to listen this way, you begin to spot the desires underneath the words. You also start seeing fear with more compassion. That changes how you show up. Less defensive. More curious. More helpful.

The great part is, this mindset shift creates a very valuable change in you and your employees when you crave feedback. That curiosity builds more connection with your customer. The connection builds trust, and trust builds repeat business. Sign me up!

A simple conversation formula that works

There is a pattern you can use in almost any customer interaction, especially when someone hesitates or slows down. Start by noticing repeated words or ideas. Customers rarely repeat things by accident. Words like fast, reliable, eye-catching, less stress, higher impact, or predictable results point directly to what they value.

Then notice the contrast they make. Customers often tell you what they are moving away from just as clearly as what they want. Phrases about wasted effort, confusion, missed deadlines, or lack of response can reveal their true pain points.

Once you see those two pieces, respond with curiosity, not pressure. A simple question like, “Can you tell me more about what high impact looks like for you right now?” opens the door. It tells the customer you are listening and that your goal is to serve, not push.

From the example question from the mastermind member, the value came from a genuine question about the options the customer was exploring. She clearly stated the goal was understanding, not selling. The response she received gave her more clarity than any survey could have. That single question reduced back-and-forth, strengthened trust, and gave her language she could use across her business.

Turning conversations into clarity

Once you start listening this way, you will quickly gather insights that make your business feel simpler. Keep a running list of customer phrases. Use their exact words, not your interpretation. Over time, patterns will jump out at you. Those phrases belong in your website copy, your quotes, and your follow-up emails.

Compare those desires to your current offer. Sometimes you already deliver what they want, yet you have not explained it clearly enough. Other times, a small adjustment can make your offer feel more aligned with a customer’s needs.

This is where many small businesses overcorrect. They think clarity requires a full overhaul. It does not. Often, one tweak, one added explanation, or one small upgrade makes the difference. When customers see themselves reflected in your language, trust grows fast.

Busy seasons reward better listening

Spring sports and academic awards seasons amplify everything. Any busy season typically comes with tight timelines, emotional customers, proud organizations, and real pressure to get it right. Our natural response is to put our heads down, work harder, and move faster in an effort to protect ourselves. This is exactly when asking better questions matters most, and we have to recognize our human nature and welcome the protection, but understand the reality that less danger is ahead when you slow down to listen. Maybe the tight timelines are only assumed, or maybe the strong emotions have nothing to do with you, and your willingness to listen makes a deeper connection.

When a customer says they are “just checking” or “not sure yet,” that is not a delay. It is an invitation. It is a moment to ask one thoughtful question that brings calm instead of chaos — NOT SELLING! When it turns into a competition or a way to close more business, your customers will see right through it and bolt the second they can.

When you respond from a place of service, you create a relationship rooted in trust, respect, and care. That kind of relationship reflects deeper values that customers these days are begging to be connected with.

I invite you to start by looking back at a few recent customer messages. Find one phrase that stands out that might be a desire, a frustration and simple ask. Write it down. Then make one small adjustment. Update a line in your quote. Add clarity to a product description. Ask a better question in your next reply.

When you stop guessing and start listening, your business becomes easier to run and more enjoyable to grow.

Aaron Montgomery

Aaron Montgomery

Our Success Group

Aaron Montgomery is a business facilitator and author of The FUNdamentals of Business Success and The Gratitude Shift: A Simple Path to Find More Peace and Joy. With nearly 30 years of experience guiding small businesses, Aaron helps people fall back in love with what they do each day. For more visit ConsultAaron.com.

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