6 Questions Every Smart Small Business Owner Asks

June 24, 2025

(Your success may depend on how honestly you answer these)

When you want to get to know someone better and have a great conversation, what do you do?


You ask them questions, of course. Questions get the conversation started and they show you have an interest in the person you’re speaking with.


The same is true of your business.


Asking and answering questions about the operation of your business can increase your efficiency and knowledge. By taking the time to perform a self-audit, you will get to know your business and process better and that means greater alignment with the needs of your target audience.


Get to Know Your Business with These Questions


When you first start your business, you probably stitched it all together on the fly in the least expensive way you could. After all, most of us aren’t backed by angel investors from the start. We cut corners to get going, to make things happen. It’s fine in the beginning. Bootstrapping is nothing to be ashamed of. But it can leave you at a long-term disadvantage.


That’s why at some point in the growth of your company, you need to ask yourself:


What Am I Proud of?

Questioning what you’re most proud of in your business can help you get to the root of your business story. Your story can help you connect with your target audience and increase your revenue. Take some time to think about how and why you help and what makes you beam with pride. Then incorporate that into your marketing.



What Do I Feel Ashamed Of?

Conversely, it’s important to know where you think your weaknesses are. If you’re ashamed of something that means you don’t feel like you’re doing your best and putting forth your best effort. Why is that? Is it because you’re not the best person suited for that activity or responsibility? Now that you’ve built your business, could someone else be doing that?


What Feels Clunky or Delayed?

When you talk to other businesses, watch videos on the subject, or hear others describe their operations, is there something that feels behind the times in your business? Could something run smoother or be more efficient? Don’t ask yourself how you would do it, just note the specific things that could make a difference. Look for the friction in your operations, administration, and/or sales process.


What’s Still Manual That Shouldn’t Be?

Tech has come a long way in the past five years. If you’re still using the same tools you did in 2020, it may be time for a revamp. Conversely, if there’s something you’re doing manually that takes a lot of time and coordination, find out if it can be streamlined with new technology. Chances are it can.


What Do You Hate Doing?

Is there something you hate doing in your business? Why is that? Again, is it competency, time, or resources? Maybe you hate invoicing, for instance, because you don’t see yourself as detail oriented and that’s a role where it’s required. You’re probably right. Get someone else to do it. Maybe you hate doing the books, but you have to be the one to do it. Look into ways that would make it more enjoyable for you such as using dictation.


What Bad Reviews Are You Getting?

Is there something in your operation that everyone hates? Are most of your imperfect reviews about the same thing? If so, it sounds like there’s a sticking point in your process. How can you remedy it so that you and your customers will be happier?


Like relationships, and items for that matter, it’s necessary to revisit the way things work periodically and ensure they’re functioning at their highest levels. Without occasional introspection and examination, your business could wither. Before you make sweeping change, asking yourself these simple questions can help you prioritize the change that is most needed and most likely to yield the best results.



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Christina Metcalf is a writer and women’s speaker who believes in the power of story. She works with small businesses, chambers of commerce, and business professionals who want to make an impression and grow a loyal customer/member base. She is the author of The Glinda Principle, rediscovering the magic within.

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Medium: @christinametcalf

Facebook: @tellyourstorygetemtalking

Instagram: @christinametcalfauthor

LinkedIn: @christinagsmith

November 3, 2025
With the holiday season approaching with the speed of a bullet train (holiday prep, year-end sales pushes, family gatherings, budget reviews, etc.), it’s no surprise many of us feel our blood pressure and tension rise, while our patience comes crashing down. While this season is one of the most exciting of the year, it brings lots of extra stress. But what if some of that stress was unavoidable? Maybe we can’t keep that troublesome relative away but we can borrow wisdom from the minimalist movement and writer Joshua Becker’s article, “The Stress We Needlessly Bring into Our Lives.” Here are four practical reframes you can share with your team and apply to your own workflow, designed specifically for business juggling multiple moving parts in busy months ahead. 1. Stop Comparing—Start Aligning It’s tempting to look at other businesses and feel like you’re falling behind. Maybe their social media looks polished, their storefront’s decorated like a movie set, or their sales numbers seem untouchable. But comparison steals focus. Your business has its own rhythm, audience, and goals. Instead of chasing what others are doing, take stock of what’s working for you. Consistency and authenticity will always outlast temporary trends. 2. Simplify Your Season Overcommitment is one of the biggest stress traps. For business owners, that often means piling on extra promotions, extending hours you can’t sustain, or saying yes to every collaboration that comes along. You might be busy and pulled in many directions but it’s unlikely you’ll feel accomplished if you overcommit yourself to trying to do it all at the same time. Imagine if you wanted to paint your entire house. If every day you woke up and painted a different area for one hour, it would be a very long time before the house would feel complete. At the end of a month, you will have put in 30 or so hours in painting but you may not even have an entire room finished. You’ll feel depleted and dissatisfied even though you spent a month working on it. This year, try doing fewer things better. Focus your efforts on what brings in customers or builds lasting relationships. Simplifying isn’t a step back; it’s a strategy for quality and control and doing more of what works, not more of a little bit of everything. 3. Build Breathing Room Into Your Calendar Every business has busy seasons, but nonstop hustle doesn’t equal progress. Schedule short breaks or “quiet hours” each week to regroup, brainstorm, or catch up. You’ll make better decisions when you’re not rushing from one task to the next. Encourage your employees to do the same. A calm, focused team provides better service and represents your business more positively, especially during the holidays, when stress levels tend to spill over. 4. Reevaluate Expectations The pressure to please customers, employees, and family can quickly become overwhelming. But not every long-standing tradition or offer is worth the toll it takes. If a particular sale or event no longer delivers value, it’s okay to let it go or reinvent it. Communicate changes early and clearly, and most customers will understand. When expectations are realistic, everyone wins. 5. Redefine Success for the Season This time of year, we tend to measure success by numbers—sales totals, event attendance, new clients. But remember, success also looks like closing the year without burnout, keeping your team motivated, or maintaining great customer experiences through the chaos. As Becker notes, “We can’t control everything. We can only control our choices.” Choose the ones that keep you steady, clear-minded, and ready for what’s next. Running a business is demanding, and the holidays only amplify that reality. As your Chamber, we encourage you to slow down where you can, focus on what truly matters, and give yourself credit for how far you’ve come. You’ve built something worth protecting—your time, your team, and your wellbeing included. As we move into the holiday season, we’re here to support your continued success, one thoughtful choice at a time. Let us know how we can help.  Read More: Meeting Customer Needs: Inexpensive Sensory-Friendly Ideas for the Holiday Season Simplify Seasonal Staffing for Small Business Season Turning Gift Returns and Exchanges into Business Opportunities
November 3, 2025
As a business in our town, we want to help you this holiday season. But we also need some assistance from you. As part of Small Business Season (November 1- December 31), we’re trying to bring awareness to the importance of shopping local. Every time someone buys from a business in our town, something bigger happens than a simple transaction. Those dollars circulate through the community, supporting local jobs, funding community improvements, and creating a stronger local economy. According to studies, for every $100 spent at a locally owned business, roughly $68 stays in the community (as opposed to $43-48 when you buy online). That money helps pay employees, supports local charities and children’s programs, and keeps the lights on for other small businesses. It’s a powerful reminder that shopping local isn’t just about convenience or sentiment. It’s an investment in our shared success. As Small Business Season kicks off, it’s a great time to think about how your business fits into that story. Whether you run a retail store, a restaurant, a service company, or a home-based business, you play a part in shaping the local economy both as a provider of products and/or services and as a supporter of our community. Why It Matters to You, to Us, to Everyone It’s easy and convenient to order online but it doesn’t do as much for our community. That’s why this Small Business Season, we’re trying to educate our residents on the importance of where they spend their money. We’re asking you to help get the word out. When people understand the impact of their purchases, they’re more motivated to support local businesses. Suddenly the convenience of hitting a button doesn’t look as appealing as the appreciation they see in your eyes. How can you help? We have an easy way that you can start today. Tell Your Story You want to put a face and personality behind your business and that starts with storytelling. Share: Your personal “why.” What makes your business unique. What you love about being local. How you contribute to the community. What your family or staff loves. A picture of something in your business (or your holiday décor). Why you started your business or talk about someone who helped you along the way. What keeps you inspired. What local causes you support and why. A favorite business memory or that point you realized you were meant to do what you’re doing. These personal details are what turn shoppers into loyal supporters in the same way that getting to know someone better builds the relationship. Speaking of building relationships, here are two simple ways to start showing up in the community (and don’t be afraid to wear your branded apparel when you do): Collaborate with nearby businesses to amplify each other’s messages about buying local. We can help you with introductions, if you need them. Display a “Small Business Season” sign or “Chamber Member” sign and encourage customers to share photos when they visit. The more we work together to elevate small businesses and help our residents (and visitors) understand why every purchase here has a purpose, the stronger our community becomes. Can we count on you to be part of this message? ------------------ Looking to read more about Shop Local? - Announcement Post - 16 Questions to Use to Prepare for Small Business Season Success - Maximizing momentum From Small Business Season
October 29, 2025
November 1st – December 31st, 2025