Small Business Mid-Year Checklist: 14 Questions Every Entrepreneur Should Be Asking

The mid-year mark is crucial for entrepreneurs to pause, reflect and fine-tune their business strategy. Use this 14-question small business checklist to evaluate your progress or be your baseline.

Male small business owner checks stock in shop using digital tablet
Author By the Roll Editorial Team on June 03, 2024
Reading Time 4 min read

The year is halfway over – are you where you want to be? Before you get caught up in the summer slowdown, take a moment for a crucial business health check. This midyear evaluation is your chance to assess your progress, identify areas for improvement, and realign your strategies for a successful second half. Don't let unanswered questions or nagging doubts hold you back. By addressing their key areas, you'll gain valuable insights and set the stage for continued growth and profitability.  

1. Are my customers satisfied and loyal

What to consider: Happy customers are your best advocates. To gauge their satisfaction and loyalty, conduct regular surveys:

  1. Actively solicit feedback and calculate your Net Promoter Score (NPS).
  2. Respond promptly to negative reviews and address client concerns with empathy and professionalism.
  3. Prioritize building solid client relationships- they are the foundation of your business's success.   

2. Is my marketing strategy effectively reaching my target audience and generating qualified leads?  

What to consider: A successful marketing strategy is essential. To gauge its effectiveness, dive into website analytics, social media engagement metrics and campaign performance data. Are you attracting the right kind of visitors? Are they converting into customers? Consider A/B testing different ad copy and landing pages to optimize your campaigns. Invest in search engine optimization (SEO) to improve organic visibility. Feel free to experiment with new platforms like TikTok, online forums and communities, and YouTube shorts to reach untapped audiences.  

3. Are my employees engaged and empowered

What to consider: Your employees are the most asset. Do they feel valued and motivated? Engage in regular one-on-one conversations to discuss their experiences, address concerns and gather feedback. Conduct an employee satisfaction survey to gain deeper insights into their needs and aspirations. Investing in employee engagement and development will pay dividends in productivity and retention.  

4. Are your benefits and compensation competitive

What to consider: Ensuring your team feels valued and supported is paramount in today's competitive landscape. It's not just about the paycheck; it's about creating a package that resonates with their needs and stands out among their options. This involves comparing your offerings with industry standards and considering what innovative companies are doing to attract and retain top talent. Resources like SPARK blog and expert analyses can be invaluable for up-to-date insights and trends. Exploring comprehensive platforms that offer insights into current compensation trends and benefits packages can give you a competitive edge.

These platforms often highlight key strategies and solutions successful businesses adopt, providing a broader perspective on what being competitive truly means in your industry.

5. Are my business partnerships mutually beneficial?

What to consider: Strong partnerships are built on trust, communication and shared goals. Schedule check-ins with key suppliers and partners to discuss their profitability, exchange feedback, and explore opportunities for collaboration or co-marketing. Remember, when your partners thrive, so does your business.  

Also, networking can open doors to new opportunities. Attending industry events, connecting with other entrepreneurs, and proactively seeking out potential partners or collaborators who share your values and complement your skill set. For instance, a fitness instructor could partner with a local health food store to offer joint promotions or workshops.  

6. Am I outsourcing tasks that could be handled more efficiently by someone else? 

What to consider: As a solopreneur or small business owner with limited resources, your time is valuable. Take a hard look at your daily tasks and identify those that require your unique expertise or direct involvement. Could a freelance writer handle your blog posts? Could a bookkeeper manage your finances? Outsourcing non-core functions can free up your time to focus on growing your business and doing what you do best. Consider using platforms like ADP's WorkMarket, or Upwork and Fiverr to find skilled freelancers. When it comes to paying your team, explore comprehensive solutions like Roll by ADP, which offers payroll and HR and allows you to focus on your core competencies. By strategically delegating tasks, you’ll create more time for innovation, strategy and the activities that truly drive your business forward.  

7. Am I fully compliant with all relevant tax laws, regulations, and legal requirements

What to consider: Staying compliant is essential to avoid penalties and legal issues that could derail your business. Consult with legal and tax professionals to ensure you're meeting all obligations. Regularly review contracts and agreements and stay informed about any changes in regulations that may impact on your business operations.  

8. Is my technology infrastructure secure, up-to-date and capable of supporting my business needs

What to consider: A robust and secure technology infrastructure is crucial in today's digital age. Regularly assess your hardware, software, and cyber security measures. Consider cloud-based solutions for scalability and flexibility. Implement automation tools to streamline processes and provide ongoing training to employees on cybersecurity best practices to protect your business from threats.  

9. Is my work-life balance sustainable

What to consider: As an entrepreneur, I find it easy to blur the lines between work and personal life. Evaluate your current work-life balance and adjust as needed. Set boundaries, delegate tasks, and schedule time for activities outside of work to prevent burnout and maintain your overall well-being.  

10. Which investments deliver the highest ROI, and which need to be reevaluated?

What to consider: Assess the effectiveness of your investments in marketing, technology and other areas. Determine which ones generate the most significant returns and which may need to be adjusted or discounted. 

11. Is my sales process efficient and effective at converting leads into paying customers

What to consider: Analyze your sales funnel from the initial context to closing the deal. Are there any bottlenecks or areas for improvement? Streamline your sales process, refine your messaging, and track your conversion rates to optimize your sales efforts. Consider implementing a simple CRM system to manage leads and client interactions.

12. Is my pricing aligned with the value and provide and my financial goals

What to consider: Review your pricing structure and compare it to your competitors'. Are you charging enough to cover your costs and generate a profit? Consider conducting market research to understand your target customers' willingness to pay. Experiment with pricing models, such as tiered pricing or package/bundle deals, to find what works best for your business.  

13. Am I on track to meet my financial goals for the year

What to consider: Review your financial statements, cash flow projections and budget to assess your progress. Are you on track to meet your revenue and profit goals? If not, identify areas where you can cut costs, increase sales or adjust pricing.  

14. Am I maximizing tax deductions and credits available to small businesses?

What to consider: Taxes can be a significant expense for small businesses, but deductions and credits are often available that can help reduce your tax burden. Are you taking advantage of all your eligible deductions, such as home office expenses, business travel costs, or equipment purchases? Are you aware of any tax credits that could benefit your business? Consult with a tax professional or accountant to ensure you're maximizing your deductions and minimizing your tax liability. They can help you identify potential savings and ensure you're complying with all tax laws and regulations.


Taking the time to plan strategically and set goals is crucial for small business success. By reflecting on your long-term vision and breaking down your goals into actionable steps, you'll create a roadmap for the future. This midyear check-up is the perfect opportunity to revisit your business plan, reassess your priorities, and ensure you're on track to achieve your entrepreneurial dreams. Remember, a well-defined strategy is essential for navigating challenges, seizing opportunities and ultimately attaining lasting success.

Business Basics • Small Business • Technology
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