You can’t fix what you don’t acknowledge. That’s true for relationships, health, and absolutely for your business. Most entrepreneurs get so caught up in the daily grind that they forget to pause and check in with what’s actually working and what’s quietly bleeding money, energy, or opportunity.
Here’s the thing: asking yourself the right questions at the right time can be the difference between a business that survives and one that thrives. These aren’t the fluffy, feel-good questions you see on motivational posters. These are the real, sometimes uncomfortable questions that force you to look at your business with fresh eyes.
What follows are twenty questions that will make you think, make you squirm a bit, and hopefully make you take action on something you’ve been avoiding.
Business Questions to Ask Yourself
These questions cover every angle of your business from finances to customer satisfaction to your own sanity. Take your time with each one and answer honestly.
1. Are You Making Money or Just Staying Busy?
There’s a huge difference between activity and productivity. You might be working twelve-hour days, responding to every email within minutes, and checking off tasks like a machine. But at the end of the month, are you actually profitable?
Look at your numbers. Strip away the vanity metrics and focus on what matters: revenue minus expenses. If you’re constantly busy but your bank account isn’t reflecting that effort, something’s broken. Maybe you’re spending too much time on low-value tasks or saying yes to clients who drain your resources without paying appropriately.
Track where your time goes for one week. Seriously, write it down. Then assign a dollar value to each activity based on what it actually generates for your business. You’ll be shocked at how much time you waste on things that don’t move the needle.
2. Who Is Your Customer, Really?
Most business owners think they know their customers. They’ll rattle off demographics like age, location, and income level. That’s surface stuff. Do you know what keeps your customers up at night? What problem are they desperately trying to solve when they find you?
Your marketing will never hit the mark if you’re guessing at this. Spend time actually talking to your customers. Not surveys—actual conversations. Ask them what they were struggling with before they found you. Ask them what almost made them choose a competitor instead.
The answers you get will completely change how you talk about your business. You’ll stop using your own jargon and start speaking their language. That’s when sales get easier.
3. What Would Happen If You Raised Your Prices Tomorrow?
Fear keeps most business owners charging less than they should. You’re worried customers will leave, competitors will undercut you, or you’ll price yourself out of the market. But have you actually tested this?
Clients who choose you solely based on price are the worst clients to have. They’re high-maintenance, constantly negotiating, and gone the second someone offers them a deal that’s five dollars cheaper. Your ideal customers value quality, service, and results. They’ll happily pay more if you deliver.
Try this: raise your prices by 15% for new clients only. Keep existing clients at their current rate if you’re worried about backlash. Monitor what happens. Chances are, you’ll lose a few price-shoppers but gain better clients who respect your work. Your revenue might actually increase even with fewer clients.
4. Are You Solving a Real Problem or Creating Noise?
The market doesn’t need another me-too product. It needs solutions to actual problems. Look at what you’re offering and ask yourself honestly: Does this solve a pressing need, or is it just something you think is cool?
Sometimes entrepreneurs fall so in love with their idea that they forget to validate whether anyone actually wants it. You might think your new app feature is genius, but if your users aren’t asking for it and won’t pay for it, you’re wasting development time.
Get ruthless about cutting things that don’t serve your customer’s core need. Every product line, every service offering, every feature—it should either solve a problem or generate revenue. Preferably both.
5. What’s Your Unfair Advantage?
Every successful business has something competitors can’t easily copy. It might be your network, your expertise, your location, your technology, or even your personality. What’s yours?
If you can’t answer this quickly, you’re in trouble. You’re competing on price or features, both of which can be matched by anyone with enough time and money. Your unfair advantage is what makes you the obvious choice for your ideal customer.
Maybe you have fifteen years of experience in a niche industry. Maybe you’ve built relationships with key suppliers that give you better pricing. Maybe your personal story resonates with your target market in a way that creates instant trust. Figure out what this is and lean into it hard. Make it central to your brand and messaging.
6. How Dependent Are You on One Revenue Source?
If your biggest client disappeared tomorrow, would your business survive? What about your main product or service? Concentration risk is one of the most dangerous positions a business can be in, yet so many owners ignore it because things are going well right now.
Diversification isn’t about doing everything. It’s about not putting all your eggs in one basket. If 80% of your revenue comes from one client, one product, or one marketing channel, you’re one bad month away from disaster.
Start building alternative revenue streams before you need them. This doesn’t mean launching twenty new products. It means intentionally cultivating multiple clients, multiple products, or multiple marketing channels so that no single failure can sink you.
7. Are You Building a Business or Buying Yourself a Job?
Many entrepreneurs escape the corporate world only to create an even more demanding boss: themselves. If you can’t take a vacation without everything falling apart, you don’t have a business. You have a job with extra steps and no benefits.
Look at your role in the business. Are you the only person who can do critical tasks? Are you involved in every decision? Do sales stop the moment you’re not actively selling? These are all signs that you’ve built a job, not a business.
A real business has systems, processes, and people who can run things without you. Start documenting how you do things. Hire people smarter than you in areas where you’re weak. Build processes that anyone can follow. Your goal should be to make yourself less essential, not more.
8. What Are You Measuring and Why?
Most businesses track the wrong metrics. They obsess over vanity numbers like social media followers or website traffic while ignoring the metrics that actually predict success. What gets measured gets managed, so if you’re measuring the wrong things, you’re managing your business poorly.
Focus on metrics that directly tie to revenue and profit. Customer acquisition cost, lifetime customer value, conversion rates, profit margins. These numbers tell you whether your business is healthy or just looks healthy.
Every week, you should know exactly how many leads you got, how many converted, what you spent to get them, and what they’re worth over time. If you can’t rattle off these numbers without checking a dashboard, you’re flying blind.
9. Who on Your Team Shouldn’t Be There?
You know who they are. That employee who does just enough to not get fired. The contractor who’s always late with deliverables. The partner who’s checked out but still collecting their cut. Keeping the wrong people around is costing you more than their salary. It’s costing you in morale, productivity, and opportunity.
Great people leave when they have to carry dead weight. Your best employees get frustrated when they see someone slacking without consequences. Every day you delay the difficult conversation is another day your team culture erodes.
Make the hard decision. Have the tough conversation. Exit the wrong people gracefully but firmly. Your business—and your remaining team members—will thank you.
10. What Are Your Customers Complaining About That You Keep Ignoring?
Customer complaints are gold. They’re telling you exactly what’s broken in your business, usually before it becomes a crisis. Yet most business owners get defensive, make excuses, or dismiss feedback as outliers.
Look at your recent complaints or negative reviews. Strip away your emotional reaction and look for patterns. Are multiple people saying your checkout process is confusing? That’s not a coincidence. Are customers mentioning slow response times? That’s a system failure, not a fluke.
Fix these issues and you’ll see immediate improvements in customer satisfaction and retention. Better yet, reach back out to the people who complained and tell them you fixed it based on their feedback. You’ll turn critics into advocates.
11. What’s Your Cash Runway?
Revenue doesn’t pay the bills. Cash does. Profitable businesses go under every day because they run out of cash before their receivables come in. How many months could you operate if revenue went to zero tomorrow?
Calculate your monthly burn rate—fixed costs plus variable costs minus any passive income. Then look at your cash reserves. That’s your runway. If it’s less than three months, you’re in a dangerous position. Six months is better. Twelve months give you breathing room to weather storms and capitalize on opportunities.
Building cash reserves feels impossible when money’s tight, but it’s exactly when you need it most. Even setting aside 5% of revenue can build a buffer over time. Cut unnecessary expenses, negotiate better terms with suppliers, and get aggressive about collecting payments faster.
12. Are You Saying No Enough?
Opportunities are everywhere. New projects, new clients, new partnerships, new ideas. Saying yes to everything feels productive. It’s actually killing your business. Every yes to something mediocre is a no to something great.
Look at what you said yes to in the last month. How many of those things moved you closer to your main goal? How many were distractions disguised as opportunities? The most successful business owners are ruthless about saying no to good opportunities so they can say yes to great ones.
Create criteria for what you’ll say yes to. Revenue potential, alignment with your goals, time investment, and excitement level. If an opportunity doesn’t meet most of your criteria, it’s a no. Protect your time and energy like the finite resources they are.
13. What Systems Are Broken That You Keep Manually Fixing?
Every time you manually fix something, you’re choosing to fix it forever. That recurring problem with invoicing, that client onboarding process that always has hiccups, that inventory tracking nightmare—these aren’t one-time issues. They’re system failures that you’re Band-Aiding instead of actually fixing.
Stop fighting fires and start installing sprinkler systems. Document the problem, identify the root cause, and create a process or system that prevents it from happening again. This might mean investing in software, hiring someone, or completely redesigning how you do something.
The time you spend fixing broken systems now will free up hundreds of hours in the future. Plus, you’ll stop making the same mistakes that frustrate your customers and team.
14. How Much of Your Revenue Is Predictable?
One-time sales are exciting. Recurring revenue is life-changing. If every month feels like starting from zero because you have to hunt for new business, you’re on a revenue roller coaster that will eventually exhaust you.
Look at ways to add predictable revenue to your business model. Retainers, subscriptions, maintenance contracts, membership fees. Anything that creates ongoing payments from customers. Even if it’s not your entire business model, having 30-40% of your revenue be predictable changes everything.
You can plan better, invest more confidently, and sleep easier knowing you’re not starting from scratch each month. Your business becomes more valuable too, since predictable revenue is worth more to potential buyers than sporadic sales.
15. What Would You Do If You Had No Fear?
Fear makes you play small. Fear of failure, fear of criticism, fear of success, fear of looking stupid. You’re making conservative decisions because you’re protecting yourself from potential pain. But safe decisions rarely build exceptional businesses.
That bold marketing campaign you’ve been considering. That new market you’ve been eyeing. That product pivot you know makes sense, but feels risky. What’s really holding you back? Usually, it’s not logic or data. It’s fear wearing a logical disguise.
Run the actual numbers. What’s the worst that could realistically happen? Most of the time, the downside is manageable while the upside is massive. Make fear-based decisions consciously, not unconsciously. If you’re going to let fear win, at least acknowledge that’s what’s happening.
16. Are You Profitable on Paper or in Reality?
Accounting profit and actual profit are two different things. Your P&L might show profit, but if your cash is tied up in inventory, receivables, or equipment, you’re not really profitable. You’re just moving money around.
Real profitability means you can take money out of the business without hurting operations. It means you’re generating more cash than you’re spending, consistently. It means your margins are healthy and sustainable, not dependent on cutting corners or underpaying yourself.
Review your financials with a critical eye. Are you including your own labor in your cost calculations? Are you accounting for depreciation, taxes, and replacement costs? Are your margins thick enough to weather price increases from suppliers? If the honest answer to any of these is no, you’re not as profitable as you think.
17. What Do You Need to Learn That You’re Avoiding?
Every business owner has knowledge gaps. Maybe it’s financial literacy, maybe it’s digital marketing, maybe it’s management skills. You’ve been getting by without really understanding these areas, but it’s limiting your growth.
The things you’re avoiding learning are usually the exact things holding your business back. You avoid them because they’re uncomfortable, complex, or make you feel incompetent. But that discomfort is a signal pointing you toward where you need to grow.
Identify your biggest knowledge gap and commit to filling it. Take a course, hire a coach, read books, find a mentor. You don’t need to become an expert, but you need to understand enough to make informed decisions and know when someone is feeding you nonsense.
18. How Are You Different From Your Competitor Down the Street?
If your answer is “better service” or “higher quality,” you’re basically the same. Everyone says that. Your customers can’t tell the difference between your “better service” and your competitor’s until after they’ve already made a purchase decision.
Real differentiation is clear, specific, and visible before someone buys. It’s in your positioning, your pricing, your process, your guarantee, your niche, or your brand. Southwest Airlines differentiates on price and point-to-point routes. Apple differentiates on design and ecosystem. What’s your thing?
Stop trying to be everything to everyone. Pick a lane and own it. Be the fastest, the most specialized, the most premium, the most convenient, the most innovative. Just be something specific that matters to your ideal customer.
19. When Was the Last Time You Actually Talked to a Customer?
As businesses grow, owners get further removed from customers. You’re dealing with operations, finance, hiring, and strategy. Someone else handles customer service. Someone else does sales. You’re running the business, but you’re losing touch with the people who make it possible.
This is dangerous. Your team filters information. They tell you what they think you want to hear or what they think is important. You miss the nuance, the emotion, the real problems and opportunities that only come from direct contact.
Block time every week to talk to customers. Not just the happy ones. Especially talk to the ones who cancelled, the ones who complained, and the ones who bought once but never came back. These conversations will give you insights worth thousands of dollars.
20. Are You Running Your Business or Is It Running You?
This is the ultimate question. Do you control your schedule or does your business dictate your life? Do you make proactive decisions or constantly react to crises? Are you building something sustainable or just surviving day to day?
If you feel like you’re always behind, always stressed, and always wishing you had more time, something needs to change. Your business should serve your life, not consume it. Success means nothing if you’re miserable, burned out, and missing out on everything outside of work.
Take an honest look at your life balance. When was the last time you took a real day off? When did you last do something just for fun? How’s your health? Your relationships? If your business success is coming at the cost of everything else, you’re not succeeding. You’re slowly destroying yourself while building something you’ll eventually resent.
Wrapping Up
These questions aren’t meant to be answered once and forgotten. Your business changes, markets shift, and what worked last year might be holding you back now. Come back to these questions quarterly and answer them honestly.
The businesses that thrive are the ones led by owners who ask hard questions and take action on the answers. You don’t need all the answers right now. You just need to start asking better questions and be willing to change based on what you discover.