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

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