Strategic Questions for Scaling Small Businesses

Leading to Growth

Business owners leading companies with $5–$10 million in annual revenue often find themselves at a critical inflection point. They have moved beyond the startup phase, yet breaking through to a mid-sized or large enterprise brings new challenges. Many are actively seeking guidance on strategy, growth, scaling operations, leadership development, and overcoming organizational hurdles. We see this reflected in Google search patterns – for example, “How to advertise your business” was the most Googled business query in New York state​ (business.centurylink.com), indicating a strong interest in marketing and growth tactics. Likewise, terms like “how to scale a business” or “business growth strategy” yield a flood of results, showing that owners are searching for ways to take their business to the next level.

Research from reputable sources (U.S. Chamber of Commerce, Harvard Business Review, Forbes, Inc., etc.) and small business surveys highlights a consistent set of growth barriers and questions on these entrepreneurs’ minds. Key challenges include securing financing, building the right team, expanding the customer base, and managing the complexities of a growing operation​. Some concerns are openly discussed – like how to obtain capital or improve sales – while others are more “under-the-radar,” shared in peer groups or forums (for instance, the struggle of a founder to delegate control of the business as it grows​ (for more, see: sheridanguerrette.com).

This report distills findings from search query analysis, common scaling barriers, and peer discussions into five strategic diagnostic questions. These are the crucial questions that business owners in the $5M–$10M revenue range are asking – or should be asking – as they chart a path to sustainable growth. Each question is paired with insights and data from experts and surveys, and they serve as a guide for both business owners and strategy consultants to focus on what matters most when scaling up.

Common Growth Challenges for Small Businesses Scaling Up

Before delving into the strategic questions, it’s important to understand the landscape of challenges that prompt these questions. Studies and surveys find that small and mid-sized businesses face a recurring set of obstacles when attempting to scale:

• Financial Constraints: Difficulty maintaining cash flow and obtaining growth capital is a top-cited barrier. One survey noted that “maintaining cash flow and securing funding” is one of the biggest challenges for small businesses (​dubll.com). Limited financing can stall expansion plans, making “How will we pay for growth?” a pressing concern. Economic conditions like inflation and rising interest rates have heightened these worries – in late 2024, 56% of surveyed owners said inflation was their biggest concern, with revenue growth being the next highest​ (entrepreneur.com).

• Talent and Leadership Gaps: As companies grow, they often outgrow the “wearing all hats” model of the founder doing everything. It becomes critical to attract skilled employees and develop leaders. A Forbes Business Council panel identified “skill and efficiency gaps” as a major obstacle for growing small businesses (​dubll.com). Many businesses struggle to hire or train people fast enough, leading to burnout of existing staff and the founder becoming a bottleneck. In fact, companies around the ~$5M mark often plateau because the owner is still involved in every decision and task – eventually stretching themselves too thin​ (sheridanguerrette.com). This makes building a strong management team and delegating authority a key imperative for growth.

• Marketing and Customer Growth: Scaling up revenue requires reaching new customers or markets, yet many smaller firms under-invest in marketing. Business advisors observe that a lot of owners rely on word-of-mouth or their own sales efforts and keep marketing spend low – just enough to sustain current revenue​(gierschgroup.com). This can limit growth. It’s telling that marketing questions are popular in search queries; for example, business owners frequently ask how to effectively advertise or use social media for growth (​business.centurylink.com). Overcoming this means formulating a robust customer acquisition strategy and possibly increasing the marketing budget to drive “explosive growth”​(gierschgroup.com).

• Operational Scalability: As a business expands, informal processes that worked for a small team start to break down. Many growing companies face internal confusion or inefficiencies because they lack standardized processes and systems. An Inc. analysis of companies scaling from “a few million to tens of millions” notes that running on ad-hoc decision-making becomes a bottleneck as the company scales, and implementing standard operating procedures (SOPs) is essential for consistency and efficiency (​inc.com). Similarly, unclear roles and responsibilities can cause tasks to get dropped or duplicated, so defining an org structure is crucial​ (inc.com). Another often-cited issue is technology: a significant number of small businesses have been slow to adopt new tools or software, leading to “lack of technology utilization” as a growth inhibitor​ (dubll.com). In short, scaling up requires investment in better systems, whether that means software, automation, or simply more structured workflows.

• Maintaining Culture and Quality: A softer but important challenge is preserving the company’s culture, customer experience, and quality standards during rapid growth. Fast growth can strain a company’s culture as new employees flood in and processes change. Leadership experts advise that “company culture is what leaders should focus on the most during times of growth”, because strong relationships and shared values help reduce growing pains when formal processes are still catching up (​en.clear.sale). Owners of growing businesses often worry privately about how to avoid the team culture souring or the customer service slipping as they scale. While this may not always surface in public forums, it is a concern echoed in high-growth peer groups and articles (​en.clear.sale).

Understanding these challenges provides context for the strategic questions below. Each question addresses one or more of these pain points. A strategy consultant, in an initial conversation with a potential client, might use these questions to diagnose the business’s situation and priorities. Likewise, a business owner can use them as a self-assessment to identify gaps in their growth strategy.

Five Key Strategic Questions for Business Owners Scaling to Mid-Size

Below are five critical questions that emerging mid-sized business owners (around $5M–$10M revenue) are asking – or should be asking – as they plan for growth. These questions have been distilled from common search queries, expert analyses, and real-world experiences of entrepreneurs who successfully scaled up. Each question is accompanied by insights into why it matters: