“Can you share a moment when a customer interaction completely changed your small business approach? What lesson did you learn and how would you advise other entrepreneurs to remain open to such insights?”
Here is what 15 thought leaders had to say.
Proactive Outreach Transforms E-Commerce for Baby Boomers
About two years ago, an elderly customer called us frustrated because she’d been trying to buy a rattan dining set for three days but kept abandoning her cart. She said “I love what I see, but I feel lost clicking around – can someone just walk me through this?” That call lasted 45 minutes, and by the end she’d placed a $2,800 order.
That interaction made me realize we were losing a massive chunk of our target market – baby boomers who have buying power but struggle with e-commerce navigation. I immediately implemented a system where we proactively reach out to anyone who shows shopping activity but doesn’t complete their purchase within 24 hours.
The results were staggering – our conversion rate for customers over 55 jumped 40% and our average order value increased because these customers tend to buy complete room sets rather than individual pieces. We went from treating e-commerce like a hands-off vending machine to creating what I call an “in-person digital experience.”
Now every employee takes full ownership of customer relationships from first contact to delivery. These customers often come back directly to their rep for future purchases and refer their friends specifically to that person, creating a loyalty loop that traditional e-commerce rarely achieves.
Nino Russo Alesi, Acting CEO, Rattan Imports
Client Feedback Reveals Missing Layer in Team Building
Years ago, I was speaking with a client who had just completed one of our team-building
programs. I expected the usual feedback, but instead, she told me something that stopped me in my tracks. She said, “This was great, but I wish it had helped us understand why we communicate the way we do.” That single comment altered my perspective on our business. We had been focusing on critical practical skills, but we were missing the deeper layer that drives behavior: insight into self and others. That led us to rework how we design our programs. We started building tools that help people not just do better but understand themselves better, too. It made our offerings more personal and effective.
For other entrepreneurs, I’d say this: treat feedback like gold. Don’t just listen for compliments or complaints. Listen for the unmet need hiding underneath. Sometimes the insight that transforms your business doesn’t come from a strategy session or trend report. It comes from someone simply telling you what didn’t quite click. Stay curious, even if it stings a little. That’s where the real growth begins.
Bradford Glaser, President & CEO, HRDQ
Simple Order Process Change Drives Immediate Growth
I once had a devoted client tell me that my ordering procedure was too difficult. Although I believed my approach was sound, I made the decision to streamline it in light of their suggestions. Orders grew right away. The lesson? Real-world adjustments may be necessary for even well-designed procedures. I would advise other business owners to pay close attention to what their consumers have to say. Consider every encounter as an opportunity to gain knowledge. Remain adaptable, modest, and receptive to constructive criticism since seemingly insignificant things have the power to change your company completely.
Dhari Alabdulhadi, CTO and Founder, Ubuy Germany
Small Projects Create Big Business Transformation
About five years ago, I had a consultation with a homeowner who was preparing to sell her house. She kept apologizing for “wasting my time” because she only wanted to replace window treatments in two rooms – not the whole house makeover I typically handled.
That conversation completely shifted how I thought about our business model. I realized we were inadvertently intimidating customers who had smaller projects, making them feel like they weren’t “big enough” clients for us. This woman’s honesty made me see we were losing tons of potential customers who assumed we only did large installations.
We immediately changed our messaging and process to welcome projects of any size. Now about 40% of our business comes from these smaller jobs – homeowners doing guest rooms, single bathrooms, or preparing just a few rooms for sale. These clients often become our biggest advocates and refer us for much larger projects later.
The lesson hit me hard: customers will tell you exactly what’s wrong with your approach if you actually listen without getting defensive. Most entrepreneurs miss these golden insights because they’re too busy explaining why their current system works instead of hearing why it doesn’t work for real people.
George Huizinga, Owner, Zinga’s
Resilience Messaging Outperforms Crisis Communication Strategy
When COVID-19 hit in 2020, I watched our clients panic and either go completely silent or send tone-deaf “in these difficult times” messages. Then one Fortune 500 client called us frustrated because their crisis messaging felt stale just weeks after launch.
That conversation made me realize consumers adapt faster than brands think they do. We pivoted from helping clients with crisis messaging to what I called “resilience messaging”—focusing on normalcy and future planning instead of dwelling on difficulties. Our data showed 64% of Twitter users actually wanted brands to keep advertising because it provided comfort.
This taught me that customer sentiment moves in waves, not linear progressions. Now I track social listening data weekly instead of quarterly, and we help brands stay ahead of emotional shifts rather than react to them. When everyone else is stuck in one mindset, that’s your opportunity to lead the transition to the next phase.
My advice: set up simple social listening alerts for emotional keywords around your industry, not just brand mentions. The clients who started talking about “future planning” and “getting back to normal” three weeks into lockdown outperformed competitors who stayed in crisis mode for months.
Maria A. Rodriguez, VP, Comms and Marketing, Open Influence
Listen for What Remains Unsaid in Pitches
A few years back, a founder came to us, completely deflated after a string of investor rejections. She had a strong product, decent traction, and still couldn’t crack the code. We initially approached it like any other pitch deck job—refine the slides, sharpen the narrative, align it with the usual VC appetite. But halfway through, I caught myself tuning out during one of her explanations. That was the moment it hit me—we weren’t really listening either. We were polishing a surface without digging into what really mattered to her and her vision. So, we scrapped the deck and spent a few evenings just talking, no slides, no templates—just understanding her story.
That pivot in how we approached client interaction completely reshaped how spectup works today. We now begin every engagement by deeply immersing ourselves in the founder’s mindset before touching any strategy or deliverable. The lesson? Listening isn’t just about what’s said—it’s about catching what’s unsaid and leaning into it. For other entrepreneurs, my advice is simple: treat customer confusion or pushback as gold. It’s rarely about the obvious fix. It’s often your blind spot calling.
Niclas Schlopsna, Managing Consultant and CEO, spectup
Protection-First Content Strategy Builds Customer Trust
About two years ago, a Florida homeowner left me a voicemail that completely changed how I approach content at SunValue. She was crying because she’d been scammed by a solar company that promised her $200/month savings but delivered a system that barely worked. She found our educational content and said it was the first time anyone had explained solar honestly without trying to sell her something.
That conversation made me realize we were still too focused on technical specs and not enough on protecting people from bad decisions. I immediately shifted our entire content strategy to a “protection-first” approach, creating guides that teach homeowners how to spot red flags and ask the right questions before signing anything.
We launched our “Solar Scam Prevention Guide” and started leading with warnings about common industry tricks instead of leading with product benefits. Our consultation bookings increased 46% because people trusted us more when we prioritized their protection over our sales pitch.
The lesson hit me hard: people don’t need another company trying to convince them to buy solar—they need someone who helps them buy solar safely. Now I tell every solar business owner to spend more time teaching customers how to avoid bad installers than explaining why their panels are better.
Nina Golban, Search Engine Optimization Copywriter, SunValue
Inconvenient Request Reveals Profitable Global Opportunity
About 18 months ago, I had a guest from Nigeria reach out after hearing our podcast, asking if we could record at 3 AM my time to accommodate her schedule. Initially, I thought this was unreasonable and almost declined.
But I decided to try it once. That conversation became one of our most downloaded episodes, and it opened my eyes to something huge—we were completely ignoring international listeners who made up nearly 40% of our audience but couldn’t participate in live recordings due to time zones.
This single interaction led us to create flexible recording schedules and offer multiple time slots for international guests. Our global download rate increased by 67% within six months, and we started landing sponsorship deals specifically targeting international markets.
The biggest lesson: your most inconvenient requests often reveal your most profitable opportunities. Now when someone asks for something that feels difficult, I ask myself what market segment they might represent that I’m currently missing. That 3 AM recording taught me that accessibility isn’t just good ethics—it’s smart business.
Favour Obasi-ike, Project Scheduler, Work & PLAY Entertainment
Home Sample Delivery Transforms Flooring Business
A elderly customer couldn’t visualize how our hardwood would look in her home, so we started our free sample delivery service. She was overwhelmed visiting showrooms, but seeing samples in her actual lighting changed everything. That conversation led to our two-day delivery promise because I realized people need to experience flooring in their space. It’s now our biggest differentiator and has transformed how we serve customers.
Dan Grigin, Founder & General Manager, Elephant Floors
Customer Language Trumps Keywords in Marketing Success
My biggest wake-up call came from a SaaS client who was hemorrhaging money on Google AdWords. After three months of “optimizing” their campaigns using standard best practices, they were still burning $8,000 monthly with barely any qualified leads. I was confident in our approach until they said something that stopped me cold: “Your keywords look perfect on paper, but you’ve never actually talked to someone who uses our software.”
That week I spent four hours on sales calls with their prospects, listening to actual language people used when describing their problems. Turns out we were targeting “project management software” when real users were searching for “stop missing deadlines” and “team chaos solutions.” The disconnect was massive.
We rebuilt the entire campaign around pain-point keywords instead of feature-based terms. Within 60 days, their cost per lead dropped 73% and they started getting 40+ qualified sales calls monthly. That single client interaction taught me that customer research isn’t a one-time setup task – it’s ongoing intelligence gathering.
Now I require all our account managers to listen to at least two client sales calls monthly before touching any campaigns. The language gap between what businesses think customers want and what customers actually search for is where most marketing budgets die.
Magee Clegg, CEO, Cleartail Marketing
Customer Insight Launches Custom Cabinetry Factory
A significant moment for me at Bestonlinecabinets occurred early on when a customer suggested we start manufacturing our own cabinets instead of relying solely on third-party suppliers. This feedback made us realize that while we aimed to simplify the online shopping experience, we were missing a crucial opportunity to control quality and design. Listening to our customers guided us in launching our own custom cabinetry factory in 2014 and helped us build our reputation for offering the best hardwood kitchen cabinets at affordable prices.
The lesson here is clear: stay receptive to customer insights, as they can lead to transformative changes in your business model. I encourage other entrepreneurs to actively seek and embrace feedback, as it can open doors to innovations that truly resonate with your audience.
Josh Qian, COO and Co-Founder, Best Online Cabinets
One Email Complaint Doubles Business Referrals
One honest customer email did more for our business than months of strategy sessions.
A client told us, “I love your service, but I had to guess my way through the submission process.” That feedback hit hard. We’d assumed our onboarding was intuitive—but it wasn’t. We rebuilt it from the ground up, adding step-by-step guidance and proactive check-ins. Not only did satisfaction scores jump, but referrals doubled.
I’m David Quintero, CEO of NewswireJet. That moment taught me to treat complaints as clarity—and to build systems that listen louder than we talk.
David Quintero, CEO and Marketing Expert, NewswireJet
Donor Storytelling Beats Displays for Repeat Gifts
My entire donor recognition approach flipped after a conversation with Martha, the development director at a prep school in Connecticut. She pulled me aside during a demo and said “Chase, your software is beautiful, but you’re solving the wrong problem. We don’t need fancier displays – we need our donors to feel remembered after the check clears.”
That hit hard because I’d been obsessing over touchscreen features instead of relationship depth. We immediately pivoted from one-time recognition moments to ongoing donor storytelling. Instead of just displaying names on digital walls, we started showcasing donor impact journeys – showing how their contributions evolved over time and what specific outcomes they enabled.
The results were massive. Our pilot schools saw repeat donations jump 25% within six months, and our own ARR grew from $800K to $2.4M as word spread. One school told us that 40% of their new donors came through referrals from existing supporters who felt genuinely valued by our system.
My advice: stop asking customers what features they want and start asking what problems keep them up at night. The gap between what people say they need and what actually drives their behavior is where breakthrough products live. That single conversation with Martha taught me that emotional connection beats technical sophistication every time.
Chase Mckee, Founder & CEO, Rocket Alumni Solutions – Digital Record Board
Education-First Approach Transforms Tax Practice
I’ve been running my accounting practice for 19 years, and one conversation completely flipped how I approach tax strategy education. A chiropractor, Dr. Ken Meisten, came to me frustrated after two previous CPAs left him owing $3,300 in taxes with zero guidance on saving money.
When I dug into his situation, I realized he wasn’t just missing deductions—he had no clue about the fundamental difference between employee and business owner tax systems. After restructuring his approach and going back three years, we got him an $18,000 refund instead of owing money. But here’s what changed everything: he said “I wish someone had explained this years ago instead of just preparing my returns.”
That moment made me realize most business owners are drowning in compliance when they should be swimming in strategy. The average household saves $4,000-$8,000 annually when they understand business tax systems, but accountants typically just prepare returns without teaching the “why” behind the deductions.
Now I lead with education first, compliance second. I wrote “More Relaxing Less Taxing” and created our membership program because that one frustrated chiropractor showed me people don’t need another tax preparer—they need someone to teach them how money actually works in America’s two different tax systems.
Courtney Epps, Owner, OTB Tax
Microsoft Office 365 Enhances Remote Work Balance
My work often requires me to be on the go, juggling tasks and deadlines. With the rise of remote work, finding productivity software that supports my work-life balance has become essential. After trying various options, I’ve found Microsoft Office 365 to be the best fit. It provides all the tools I need as a real estate agent, along with features tailored for remote work and better work-life balance.
One standout feature is Teams, which makes communication and collaboration with colleagues and clients effortless. During the pandemic, it’s been especially useful for scheduling virtual meetings, sharing updates in real-time, and even offering virtual property tours to potential buyers.
Zach Shepard, Principal, Braddock Investment Group Inc
