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10 Questions to Ask Your Business for Lasting Growth

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Every organization has a strategy. For some, it’s a meticulously crafted document; for others, it’s an unspoken understanding. But the real test of any strategy is whether it lives beyond the boardroom. How often do great plans get lost between departments or diluted by daily pressures? True growth happens when strategic intent is perfectly aligned with operational reality. This requires asking tough, practical questions that bridge the gap between the vision and the execution. To help you stress-test your own alignment, we’ve gathered some of the most important questions to ask businesses to ensure your strategy is more than just a presentation—it’s a living, breathing part of your culture.

Is your business ready for 2023? A new year can be a time to reflect and chart a course forward. As a leader in your organization, it’s critical to take stock of where you’ve been, what you stand for, and how you can reinvent your business for the future. If you want to achieve extraordinary impact for customers, investors, and society, we can help with strategies to do that.

10 Questions to Ask Your Business for Lasting Growth

Here are 10 questions that can help to steer internal conversations with teams to help your business get ahead.

1. Where Does Your Business *Really* Compete?

A “field of play” refers to where your brand might reasonably fit, unencumbered by the boundaries of categories. For instance, Tesla’s field of play is not just cars, or transport, but intelligent energy. Rather than being bound by strict category definitions, consider how your business might exist in a larger context.

What’s one thing our competitors do better than us?

Understanding the competitive landscape is essential for any business that wants to lead its market. This question isn’t about imitation; it’s about honest assessment. Taking a hard look at what your competitors excel at provides clear insights into where your own organization can improve. It forces you to admit where gaps might exist in your product, service, or customer experience. By gathering this kind of competitive intelligence, you can pinpoint specific areas for improvement and develop strategies to strengthen your own offerings, ensuring you meet and exceed the expectations of your customers.

If a competitor wanted to take us down, what weak spot would they attack?

Every business has vulnerabilities, and the first step to protecting your organization is recognizing them. This question encourages you to think like an adversary and stress-test your own strategy. It helps you find your business’s weaknesses before a rival can exploit them. These weak spots could be anything from an over-reliance on a single supplier to a gap in your digital customer experience or a part of your brand that doesn’t resonate. By proactively working to identify your vulnerabilities, you can fortify your market position and build a more resilient business that’s prepared for competitive pressure.

2. Is Your Tech Truly Serving Your Customers?

Today technology is reinventing the core of businesses. Consumers are now empowered decisionmakers. In what areas could your business benefit from better utilizing technology? How would your consumer relationships change? What would be the impact on your business’s category? Finding new tech solutions can have wide-ranging implications.

3. Are You Making Space for Experimentation?

Those who can achieve transformational growth do so by experimenting at scale and integrating learnings as a systemic capability. Does your business test out new ideas regularly? Do you have a process for utilizing feedback from experiments? Think about how you can incorporate experimentation into your regular processes to help identify new areas for growth or improvement.

4. Are You Building Relationships or Just Transactions?

The focus of value creation has shifted from driving transactions to driving interactions. It’s not enough to simply accomplish a task for a customer. Brands and businesses deliver real value when they achieve something more or create greater connections. Consider how your company uses brand technology, ownable experiences, data, purpose, and hyper-personalization.

What frustrates our customers the most?

It’s a tough question, but a necessary one. The most dangerous problems are often the ones you don’t hear about, because as research shows, many unhappy customers leave without complaining. They simply stop doing business with you. To get ahead of this silent churn, you have to proactively seek out friction points. Ask for direct feedback through surveys, interviews, or informal check-ins. Identifying these frustrations is the first step toward designing a better customer experience that not only solves problems but also builds genuine loyalty. When you show customers you’re listening, you turn potential detractors into advocates.

What is our customer retention rate?

Acquiring new customers is exciting, but retaining your existing ones is where sustainable growth happens. It’s a critical metric for the health of your business because it’s far more cost-effective. According to American Express, it can cost 5 to 25 times more to attract a new customer than to keep a current one. A low retention rate can signal deeper issues with your product, service, or overall brand promise. Tracking this number helps you understand customer loyalty and the long-term value you’re creating. A strong focus on retention is a core part of any successful business strategy, ensuring your company is built for lasting success, not just short-term gains.

5. How Do You Balance Today’s Needs with Future Growth?

Now more than ever, organizations need to learn how to optimize their current business model, while building a new one. So called “ambidextrous organizations” are those that can compete in the present while creating possibilities for the future.

6. Are Your Actions Aligned With Your Strategy?

Strategy is nothing without action. But how often is your company engaging in actions that aren’t aligned with your strategy? Or vice versa? How much strategic thinking does your business have simply sitting in PowerPoint decks? Figure out how to activate this thinking in the real world.

7. Are You Collaborating for Shared Success?

The value chain doesn’t just end with your product or service. There are opportunities to grow beyond your brand through collaborating with other businesses, or even starting other businesses to create shared value. Applying an ecosystem lens may open opportunities you hadn’t previously considered.

8. Can Your Team Explain Your Mission in 20 Seconds?

Every business needs a North Star to guide what they do, and how they do it. Powerful brands and businesses are the ones who can quickly articulate why they do what they do. Going beyond that are brands who have a higher purpose, or a mission that society can connect to. How strong is your North Star?

9. How Will You Keep Your Best People?

We are in an ongoing war for talent. As companies look to retain and attract top talent, it’s not enough to think about what’s working well enough today. Think about what you will have to do in the next three years to keep your team motivated.

10. Will Your Business Still Be Relevant Next Year?

In a world of changing technology and consumer needs, companies that fail to reinvent themselves or parts of their business get left behind. How could your business anticipate what’s coming next? How can you build something for the future? Vivaldi’s team of strategists is always happy to discuss these questions in depth with you. We want to help create the next generation of your business. Reach out to our team.

Questions for Financial Health and Profitability

A strong business strategy is built on a clear understanding of your financial reality. While top-line revenue is exciting, true sustainability comes from profitability, healthy cash flow, and a smart financial structure. Getting an honest look at the numbers isn’t just a task for the finance department; it’s a leadership responsibility that informs every major decision, from product development to marketing spend. These questions are designed to cut through the noise and get to the heart of your company’s financial well-being, ensuring your plans for growth are built on solid ground. Answering them honestly will help you identify both hidden risks and untapped opportunities.

What is the true financial state of the business?

Before you can plan for the future, you need a precise snapshot of the present. This means looking beyond the surface-level profit and loss statement. Start by asking, “What is the company’s current financial status and cash flow?” A profitable company can still fail if it runs out of cash. Next, get a handle on your liabilities by asking, “What is the debt situation?” Understanding your debt obligations is critical for managing risk and making future investments. Finally, look at the trajectory of your income. Are revenues rising or declining? A clear-eyed view of these three areas—cash, debt, and revenue trends—provides the foundational knowledge needed for any sound business transformation.

Which parts of the business are most profitable?

Not all revenue is created equal. To allocate resources effectively, you need to know which products, services, or customer segments are actually driving your profits. Begin by asking, “What are the most significant business expenses?” This helps you understand your cost structure. Then, you can determine the “profit margin for the most profitable products or services.” You might discover that your best-selling item isn’t your most profitable one, or that a niche service is quietly generating a significant portion of your net income. This analysis allows you to double down on what’s working and re-evaluate or reprice the offerings that are dragging down your profitability.

Is your pricing strategy built for growth?

Your pricing does more than just cover costs; it communicates your brand’s value, positions you in the market, and directly impacts your growth potential. It’s worth asking your team, “What is your pricing strategy and why?” If the answer is “that’s what our competitors charge” or “it’s what we’ve always done,” it’s time for a deeper look. A strategic approach to pricing considers the value you deliver to customers, your long-term financial goals, and the overall market landscape. Your pricing model should be a dynamic tool that supports your growth ambitions, not a static number that holds you back from reaching your full potential.

How effectively do your teams generate revenue?

Your people are your greatest asset, but it’s crucial to understand how their efforts translate into financial results. Asking “How effectively do employees generate revenue?” isn’t about micromanaging individuals but about evaluating the efficiency of your entire revenue-generating engine. Are your sales and marketing teams properly aligned and equipped with the right tools? Are there internal processes creating friction that slows down the sales cycle? By examining the connection between your team’s activities and financial outcomes, you can identify opportunities for better training, improved processes, and more effective sales enablement that helps everyone succeed.

Questions for Operational Efficiency and Processes

A brilliant strategy can easily be derailed by clunky, inefficient operations. The internal processes that run your business are the engine of your growth, and if that engine is sputtering, you’ll never reach your destination. Leaders often get so focused on the “what” and “why” that they overlook the “how.” Taking the time to scrutinize your daily workflows, challenge legacy systems, and remove internal friction is one of the most powerful things you can do to prepare your business for the future. A streamlined organization isn’t just faster and more profitable; it’s also a better place to work, which helps you keep the talented people you need to thrive.

Where are you wasting time, money, or resources?

This question requires radical honesty and a willingness to look in uncomfortable places. Waste can hide in plain sight—in redundant software subscriptions, inefficient meetings that drain calendars, or manual processes that could be automated. Encourage your team to think critically about their daily work and ask, “Where are we wasting the most time, money, or resources?” Creating a culture where people feel safe to point out these inefficiencies is the first step. The goal isn’t to place blame but to collectively identify and eliminate the silent profit killers that are holding your organization back from its full potential.

What is your biggest bottleneck and how can you remove it?

In any system, there is always one primary constraint that limits the output of the entire system. Identifying this constraint is key to making meaningful improvements. Ask your leadership team, “What is our biggest bottleneck, and what’s the first step to removing it?” It could be a person who has to approve everything, a slow software system, or a poorly defined handoff between departments. The power of this question is its focus. Instead of trying to fix everything at once, you concentrate your energy on the one thing that will have the biggest positive impact on the entire workflow once it’s resolved.

Which processes are overly complicated?

Complexity is the enemy of execution. Over time, simple workflows can become burdened with unnecessary steps, approvals, and exceptions. It’s essential to regularly ask, “What processes feel unnecessarily complicated, and how can we simplify them?” This directly challenges the “we’ve always done it this way” mentality that can stifle innovation and efficiency. Often, processes were designed to solve a problem that no longer exists. By questioning their purpose and seeking the simplest possible path forward, you can make your organization more agile, reduce employee frustration, and speed up your ability to deliver value to customers.

How do you define and measure success?

If you don’t have a clear destination, any road will get you there. A surprising number of teams operate without a shared, specific understanding of what they are trying to achieve. It’s a foundational leadership responsibility to ask, “How does the company define and measure success?” This goes beyond vague goals like “grow the business.” It means defining the key performance indicators (KPIs) that truly reflect the health and progress of your organization. When everyone understands the metrics that matter most, they can align their daily actions and make smarter, more autonomous decisions that move the entire company in the right direction.

Strategic Questions for Major Business Initiatives

While optimizing current operations is vital, lasting growth often comes from making bold, strategic moves. Launching a new venture or acquiring another business are high-stakes initiatives that can define your company’s future. Before committing significant capital and resources, it’s critical to ask the tough questions that challenge your assumptions and stress-test your strategy. These questions aren’t meant to create roadblocks; they are guardrails designed to increase your chances of success. They ensure your big bets are grounded in market reality, competitive insight, and a clear-eyed assessment of the risks and rewards involved in any major growth initiative.

For Launching a New Venture

Launching something new is exciting, but passion alone doesn’t guarantee success. A disciplined, strategic approach is essential. Before you write the first line of code or design the first prototype, you need to validate the core assumptions of your business case. This means moving beyond your own vision and getting deeply in tune with the market you hope to serve. The right questions at this stage can save you from building something nobody wants to buy.

Are you solving a real “painkiller” problem?

The most successful products and services are “painkillers,” not “vitamins.” Vitamins are nice to have, but when budgets get tight, they’re the first thing to go. Painkillers solve an urgent, expensive, or frustrating problem that customers are desperate to fix. Ask your team, “Is this a real problem that needs solving?” If the problem you’re addressing isn’t a top priority for your target audience, gaining traction will be an uphill battle. Focus on creating solutions that customers can’t live without.

Is the market large enough to support your goals?

A brilliant solution for a tiny market is a passion project, not a scalable business. You need to be realistic about the size of the opportunity. Ask yourself, “Is there a large enough market to help my business reach its revenue goals?” This involves more than a quick Google search. It requires a thorough analysis of the Total Addressable Market (TAM) and a realistic assessment of the share you can capture. Ensure the potential reward is worth the risk and effort you’re about to invest.

How will you stand out from the competition?

Unless you’ve invented something entirely new, you will have competitors. Simply being different isn’t enough; you need to be better in a way that matters to customers. Ask the tough question: “Who are my competitors? How do I beat them?” Your competitive advantage could come from a superior product, a more innovative business model, a stronger brand, or an exceptional customer experience. Define your unique value proposition clearly and ensure it’s something you can defend over the long term.

For Acquiring a Business

Acquiring another company can be a powerful way to accelerate growth, enter new markets, or acquire new capabilities. However, M&A is notoriously difficult to get right, and a bad deal can have devastating consequences. Thorough due diligence is your best defense against a costly mistake. It’s about looking past the polished presentation and uncovering the true state of the business you’re considering buying. The answers to these questions will help you decide whether to proceed, renegotiate, or walk away.

Why is the business for sale?

This is the single most important question to ask, and you need to dig until you get the real answer. The seller’s story might be about retirement or pursuing other interests, but you need to verify that there isn’t a more troubling reason. Are they losing a major customer? Is a new competitor disrupting their market? Is there a hidden operational problem? Understanding the true motivation behind the sale will give you critical insight into the health and future prospects of the business.

What are the hidden legal and contractual risks?

The biggest liabilities in an acquisition aren’t always on the balance sheet. It’s crucial to ask, “Is the business involved in any lawsuits?” But your legal due diligence shouldn’t stop there. You need to review key customer contracts, employee agreements, and supplier relationships. Are there unfavorable terms that will be difficult to change? Are there change-of-control clauses that could jeopardize key relationships? Uncovering these hidden risks before the deal closes can save you from major headaches down the road.

How reliable are the financial projections?

Every seller presents a rosy picture of future growth. Your job is to separate fact from fiction. When you review the financial models, ask, “What is the quality of earnings, and what is the projected sales for the next year?” Scrutinize the assumptions behind the numbers. Are they based on historical trends and realistic market conditions, or are they based on wishful thinking? A thorough quality of earnings (QoE) analysis will help you understand the true, sustainable profitability of the business and give you more confidence in its future performance.

Frequently Asked Questions

Why is it so crucial to ask these tough questions if our current strategy seems to be working? A strategy that looks great on a PowerPoint slide can easily fall apart under real-world pressure. These questions are designed to bridge the gap between your plan and your operational reality. Think of it as a stress test for your business. It helps you find the small cracks in your foundation—like a process that frustrates your customers or a competitive threat you’ve underestimated—before they become major problems. It’s about ensuring your strategy is resilient and truly embedded in how your teams work every day.

This is a comprehensive list. Where is the best place for a leadership team to start? It can definitely feel like a lot to tackle at once. Instead of trying to answer every question, start where you feel the most friction in your business. If team morale seems low, begin with the questions about talent and mission. If sales have flattened, focus on the sections about your customers and competitors. The most effective starting point is usually the area that’s already causing concern, as that’s where you’ll likely find the most immediate opportunity for meaningful improvement.

Who should be involved in answering these questions? Is this just an exercise for the C-suite? While leadership must champion this process, limiting the conversation to the executive team is a missed opportunity. Your most honest and valuable insights will often come from employees who are on the front lines, interacting with customers, and navigating internal processes daily. Involving a diverse, cross-functional group gives you a 360-degree view of the organization and fosters a culture where everyone feels responsible for the company’s success.

What’s the most common mistake companies make when they try to answer these questions? The biggest pitfall is a lack of genuine honesty. It’s tempting to provide the “correct” corporate answer or to downplay a problem to avoid conflict. This exercise is only valuable if you create an environment where people feel safe to be candid without fear of blame. The goal isn’t to find fault; it’s to find opportunities. True progress begins when your team can openly acknowledge what isn’t working.

After we’ve identified our weaknesses, what’s the best way to turn those insights into action? Identifying the problems is only the first step. The key is to avoid trying to fix everything at once, which leads to paralysis. After your discussions, prioritize the top one or two issues that will have the greatest positive impact on the business if solved. Assign a clear owner to each priority, define what success looks like, and set a specific timeline for a follow-up. This transforms a reflective exercise into a concrete action plan that drives real change.

Key Takeaways

  • Activate Your Strategy: A winning strategy is useless if it stays in a slide deck. Use these questions to translate your high-level vision into daily actions and decisions, ensuring every team is aligned and contributing to real growth.
  • Assess Your Business Holistically: Sustainable growth requires a clear-eyed view of the entire organization. Go beyond revenue numbers to scrutinize your financial health, operational efficiency, and customer relationships to find hidden risks and untapped opportunities.
  • Turn Inquiry into a Competitive Advantage: Don’t wait for a crisis to find your weak spots. Proactively questioning everything from customer frustrations to internal bottlenecks allows you to fortify your business against threats and turn potential problems into catalysts for innovation.

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