7 Mid-Year Questions for Small Business Owners

Why a Mid-Year Business Check-In Matters

We’re halfway through the year, time for a mid-year business check-in for small business owners. If you’re like most entrepreneurs, you’ve been busy juggling sales, operations, marketing, and maybe even carving out a bit of rest.

However, here’s the truth: if you don’t pause to assess how things are going, you may be spending too much time reacting and not enough time steering your business forward with intention.

A quick mid-year review can help you catch small issues before they become big problems, realign your goals, and enter the second half of the year with more clarity and confidence. It doesn’t have to be fancy, just a quiet moment with your numbers, your gut, and your vision.

When I did this myself, I realized one of my projects had hit all its goals, while another had quietly fallen behind. It wasn’t due to a lack of effort, just a shift in priorities. That kind of insight can change your direction.

Whether you’re running solo, managing a small team, selling products, offering services, or a mix of all three, these questions can help you reset, refocus, and move forward with purpose.

1. Am I on Track with My Goals?

Start with the big picture:

• What did I set out to do this year?
• What’s already been accomplished?
• What needs to shift based on how things have evolved?

Tip: It’s okay to update your goals. Progress isn’t always a straight line, and adjusting doesn’t mean failing, it means leading with intention.

 2. How Are My Finances Looking?

Now’s the time to pull out your spreadsheets or open your accounting app. Ask yourself:

• Am I making the revenue I expected?
• Are expenses creeping up in certain areas?
• How’s my cash flow—steady or stressful?

Look for patterns, not just totals. You might find you’re overspending on subscriptions, delivery fees, or seasonal inventory.

Need help? Talk to a business coach who can walk through your financials with you. They can help you identify red flags or spot growth opportunities.

3. What Are My Customers Telling Me?

Your customers’ needs may have changed. So consider:

• What kind of feedback am I getting?
• Are customers returning, or dropping off?
• Am I still solving the right problems?

For example, I noticed a few clients had stopped opening emails. When I asked why, they said inbox overload. So I changed my subject lines—short, clear, and actionable. Open rates went up right away.

Try this: Send out a short survey or schedule 1:1 chats with a few loyal customers.

4. Is My Marketing Still Working?

Marketing trends shift fast, especially online. Ask yourself:

• Which channels are still bringing in leads?
• What’s underperforming?
• What’s one new tactic I could try this month?

Summer is a great time to test something fresh. Think: limited-time offers, new campaigns, or even a simple brand refresh.

Explore options: Our on-demand marketing classes can enhance your strategy and help you discover what’s working now. Check out our calendar to start learning at your own pace.

5. Are My Systems and Support Still Serving Me?

Whether it’s your tech stack, task list, or part-time help, ask:

• Is everything running smoothly, or am I always putting out fires?
• Are important tasks slipping through the cracks?
• Am I spending time on what truly matters?

This is where I saw the need to automate and delegate. Even handing off one recurring task gave me back time for big-picture planning.

Feeling overwhelmed? It might be time to reorganize, outsource, or upgrade your tools.

6. How Am I Doing?

Let’s be real—you are the engine behind your business. Consider:

• Am I energized, or just exhausted?
• Do I have space to think strategically?
• Am I still enjoying what I do?

When I reflected on this, I realized I hadn’t taken a full day off in weeks. No wonder I felt burned out.

Remember: Your mindset matters. Your health matters. Your joy matters.

7. What’s My Vision for the Rest of the Year?

This is your chance to pause and plan forward:

• What do I want to achieve by December?
• What would success look and feel like?
• What’s one small action I can take this week to move closer?

Pro tip: Write your top three goals on a sticky note. Keep it where you’ll see it daily. Let it guide your decisions.

Final Thoughts

You don’t need a retreat or a weekend getaway to do this mid-year business check-in. Just take an hour, grab a coffee or a notebook, and give yourself the gift of clarity.

Need a hand?
Download our free Mid-Year Business Check-In Checklist, or schedule a coaching session to talk it through. We’re here to help you finish the year strong, and on purpose.