Small Business Strategy Check In: 10 Questions to Help You Reflect

I’ve been making the rounds, talking to small and local business owners a lot recently. Let me just say, y’all are the most passionate, dedicated, relentlessly optimistic business people out there. You’re not just running a business, you’re trying to make your community better while you’re at it. That kind of commitment deserves some love. (Also, a reminder to everyone else: Shop local.)

That passion, though, comes with a lot of plate spinning. For most small business owners, carving out time to think strategically feels like a luxury. I recently sat down with a mother–daughter team navigating a booming market while the mom is eyeing retirement and the daughter is figuring out how to make the business her own. It’s exciting. It’s emotional. And it’s overwhelming. When the day-to-day is coming at you fast, it’s easy to let the current carry you without much intentionality. That works… until it doesn’t.

Ironically, when business is good, being intentional about what’s next can feel like a waste of time. Why slow down when things are working? But planning now is how you turn inevitable ebbs and flows into mostly flows. You don’t need a 40-page growth plan or a consultant speaking in buzzwords. You just need a clear-eyed look at where you are and where the opportunity actually is.

Here are ten questions that can help you do exactly that:

1. What are you extremely good at today?

2. What product or service is your most profitable today?

3. If you had to pick one, what’s the biggest thing holding back growth right now?

   1. I know there are new customers out there, but they don’t know who we are and I don’t know how to find them

   2. We can’t handle taking care of more customers with our current staff/facilities/inventory

   3. There aren’t enough people who need what we sell to keep the business growing

4. Where does the majority of your business come from today? 

   1. Repeat customers

   2. New customers via referrals/word of mouth

   3. New customers from marketing (ex: participating in events, social media activity, advertising, etc)

   4. Honestly, I’m not sure

5. What does your BEST customer look like? Another way to think about it: If you could have 100 more customers, who would you clone? (What do they buy? How often do they buy? Why do they buy? And what matters most to them?)

6. Is your current best product or service actually meeting the needs of that best customer?

7. How do you (or your business owner) spend the majority of your time at work? 

8. Have you tried any of these tactics to promote your business in the past year? Rate: not used; used and I don’t know if it worked/did not work; or used and worked

   1. Events/promotions that you create (ex: St.Patty’s day menu at your restaurant that doesn’t usually serve that kind of food; weekend away package to your resort that bundles lodging, dining, and an activity; “Spring Cleaning” special for your HVAC company to promote annual service packages)

   2. Organic social media (posts that you create on any social media platform and do not pay for)

   3. Digital advertising (posts on social media that you do pay for, ex: boosting a post in FB, running ads on Google)

   4. SEO (search engine optimization)

   5. Email marketing, including a newsletter

   6. Local advertising (ex: billboard, ad in local magazine)

   7. Event participation (ex: trade shows, locally organized events like organize, extended holiday shopping hours)

   8. Sales outreach (calling or emailing individual customers or prospects to drive business)

   9. Direct mailings

   10. Buying leads from an industry partner, like Zillow, Angi (previous Angie’s List), Yelp

   11. Reputation management (getting reviews on Google, FB, Trip Advisor, etc.)

   12. PR (working to get coverage in the news media, appearances on podcasts, or other speaking engagements)

   13. Influencer marketing (aligning with an industry influencer for paid promotion to their audience)

9. Are there any big changes in your market coming in the next 12-18 months? For example: new competitors; leadership change/want to sell the business; you have a new product/service coming; the demographics of your service area are changing because of gentrification, etc. 

10. One year from now, what will your business look like if you had a “successful” year? 

As a card-carrying Gen X’er, I was a huge fan of those “choose your own adventure” books. Remember them? At various points throughout the story, the reader would get to choose what the main character did next: ”If you want to enter the dark, scary forest, turn to page 124. If you want to hightail it home for reinforcements, turn to page 136.” Well, as a small or local business owner, you’re living in a choose your own adventure series. So be intentional about it and build the business you want! 

We’d love to help you choose your next right adventure. If you’d like to chat through the answers to these questions, fill out the form below. We can schedule a (virtual or in-person) free coffee chat to talk about it. Sometimes an objective, fresh set of eyes can help you think about things in a whole new way.