Small Business Mid-Year Checklist: 13 Questions Every Entrepreneur Should Be Asking

Summer is upon us. Before you take a well-deserved break, make time to reflect. Are you running your business as well as you could be? Use this 11-question small business checklist to evaluate your progress.

Male small business owner checks stock in shop using digital tablet
Author By the Roll Editorial Team on June 12, 2023
Reading Time 3 min read

Summer is upon us. Before you take a well-deserved break, make time to reflect. Are you running your business as well as you could be? Use this 11-question small business checklist to evaluate your progress.

1. Are your customers happy? Even the best businesses struggle to keep customers happy from time to time. Review any complaints you've received so far this year. Are there repeating patterns? Also, consider surveying your customers using a free tool such as SurveyMonkey. You can't address problems you can't (or won't) see.

2. Are your employees happy? It's impossible to keep everyone on the payroll happy, but research shows that happy employees tend to perform better. Have you talked with your team lately? Find out if there are frustrations you could remove with a small amount of effort and investment and then make the changes. In the meantime, check out these five must-have solutions to boost employee retention.

3. Are your partners happy? Unless you are a solo operator in a services business, odds are you have suppliers and fulfillment partners. Think win-win here. When was the last time you had a check-in call with your top supplier? Have you asked about how profitable it is for them to carry your products? What do they hear about your competitors? Running your business is like managing a network of relationships. Treat your partners with respect and they may surprise you with the value they deliver in return.

4. Are your benefits up to date? Simple changes to benefits- and perks can improve your ability to retain and motivate key employees. What could you add without much new cost? A modern small business payroll solution such as Roll by ADP can make adding perks such as same-day payment for hourly employees as simple as flipping a switch.

5. Is your marketing funnel full? Think about how new customers find you. What do you spend to get those leads? Can you lower that cost through social media marketing? What about search advertising or adding existing customer testimonials to your blog? A healthy, well-stocked pipeline of new leads is the lifeblood of a growing business. Checking to make sure you have one is a must for your mid-year checklist.

6. Is your business adequately staffed? Every small business has pain points. What tasks could you either eliminate or improve? Hire to ease the pain and then be aware there will be some staff you'll want to keep long-term — even if you're running a seasonal business. Upgrading your onboarding and benefits now can be a great way to keep high performers engaged while also planning for a profitable future.

7. What investments aren't paying off? Summer is an excellent time to review all your operations. Think big and small. Are your shipping costs appropriate? Do you have too many or too few people providing support? Does your tech infrastructure need an upgrade? Budgets and financial statements tell the big picture story of your small business, operational details provide the context to help you make better use of capital.

8. Where should you invest next? Understanding what's not working is half the story. Your small business checklist should include a careful review of what's creating value for you and your customers. These are the areas where you can choose to invest. Be creative! Instead of concentrating capital in one project, try funding a few, measure the results of each experiment, and then concentrate on the most successful.

9. Do you need to re-forecast the budget? The more committed you are to growth, the more planning you'll need to do. Your budget is the blueprint for funding your plan. As you go through your mid-year checklist, take notes on what budget items could be affected by your fine-tuning — you'll recalculate all the line items later, first you need to take stock. Then, use the re-forecasting process to assess your ambition. How much change are you looking at? Is it realistic that you'll come back from vacation ready to make so many adjustments? A good budget is a working document. Let it serve you, not control you.

10. Are you up-to-date on taxes? Don't take chances on underpaying taxes. The Small Business Administration can direct you to local experts who can help you stay compliant, including qualified CPAs. There are also excellent tools such as Roll by ADP for automating and managing your business tax filings, which can be important if you file quarterly. (Which you should.)

11. Are your legal agreements up-to-date? Legal filings shouldn't be refreshed as frequently but a review of your key documents — including articles of incorporation, lease agreements, credit arrangements, and the like — is worth adding to your mid-year checklist. You can do this with or without an attorney, but paying for a short consultation to make sure everything is in order can be worthwhile if you've not seen a lawyer in a few years. 

12. What contracts need to be updated? If you're in business, you have contracts. And if you've been in business for a while, you probably have old contracts that need reviewing, updating, and (maybe) terminating. Make a thorough contract review a regular part of your small business checklist. The same holds true for compliance forms and documents. The larger and more distributed your company becomes, the more often you should be reviewing agreements and obligations. Every six months is a good cadence.

13. Is the business what you hoped it would be? Finally, be honest with yourself and your family. This is your business after all and you're giving a significant chunk of your life to growing it. Check-in with yourself and those you love to make sure that you're on the right track — and if not, think about what changes would make you happy.

"In my occupation, I love what I do but have enough responsibilities to manage without adding more. I’m a therapist, I don’t want to be a payroll manager. The ease and simplicity of Roll gives me more time to remain focused on doing what I love to do but helps me do what I need to do without the extra back-end work." - Lynnette, owner of Maxx Therapy Solutions.

Business isn't just business. For many entrepreneurs, it's a lifetime affair of long hours, deep dedication, and family involvement. It's personal for them, and it may be for you too. A good mid-year check-in can help to make sure the business you're running today is on the way to being the one you dreamed of on the day you started.

Business Basics • Small Business • Technology
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