The Importance of Experience When Teaming with AI in Strategic Planning for Lower Middle Market Companies

[Editor's Note: Lower Middle market companies have unique characteristics that require critical thinking and experience to yield the best results when using AI in strategic planning. We hope you find this article useful - dpm] Artificial intelligence is rapidly reshaping how companies approach strategic planning. From market analysis to scenario modeling, AI tools promise faster insights, broader perspectives, and more data-driven decision-making. For lower middle market companies—often operating with lean teams, limited resources, and high execution risk, the appeal is clear. Yet AI is not a strategist. In the lower middle market, experience is essential when using AI in strategic planning, and that experience often comes not only from internal leadership but from an experienced strategic planning consultant who understands both the tools and the terrain. The strongest outcomes emerge when AI is paired with seasoned judgment—internally and externally.  AI Is a tool, not a decision-maker or a substitute for judgement. AI excels at processing large volumes of information, identifying trends, and generating strategic options. It can evaluate markets, analyze customers, model pricing, and stress-test assumptions far faster than traditional approaches. What AI cannot do well is understand organizational culture, leadership dynamics, or execution realities. It lacks awareness of past initiatives, informal decision-making structures, and the human factors that often determine whether a strategy succeeds or fails. Experienced leaders—and experienced consultants—know that strategy rarely fails because of poor analysis and often fails because of misalignment, timing, or execution. AI informs decisions; experience determines whether those decisions are realistic and actionable. Lower middle market companies have some unique characteristics. Many AI tools are trained on generalized datasets reflecting public companies or large enterprises. Lower middle market firms operate under very different conditions where customer concentration is higher, management teams are lean, systems and data are imperfect, and capital decisions can be existential. An experienced strategic planning consultant brings pattern recognition from dozens of similar companies and situations. They understand that what might work at scale often breaks at $20–$100 million in revenue. Their role is to translate AI-generated insight into strategies that fit the company’s true constraints—leadership bandwidth, cash flow sensitivity, and owner risk tolerance. Experience shapes better questions. AI’s usefulness depends heavily on the quality of the questions (prompts) it is asked. Knowing which questions matter—and which assumptions to challenge—is a function of experience. Seasoned consultants help leadership teams: ·    Frame the right strategic questions. ·    Identify blind spots in internal thinking. ·    Challenge data that looks precise but is directionally wrong. ·    Focus on decisions that will actually move the needle and add value. For example, AI may suggest aggressive geographic expansion based on market growth data. An experienced consultant may recognize that talent limitations, customer service risk, or operational complexity make that path dangerous. Experience reframes the discussion from “Where can we grow?” to “Where can we grow without breaking the business?”  Pattern recognition matters more than prediction. AI is effective at prediction based on historical data. Experienced consultants contribute something different: pattern recognition shaped by real outcomes across multiple companies and cycles. They have seen: ·    Strategies that looked compelling but failed in execution. ·    Growth initiatives that strained culture or cash flow ·    M&A plans that underestimated and inadequately planned for integration risk. This perspective allows consultants to act as a strategic filter—helping teams avoid attractive but unwise paths. In the lower middle market, avoiding the wrong move can be as valuable as selecting the right one. Speed requires judgment and facilitation. AI dramatically accelerates strategic planning by enabling teams to test more scenarios in less time. However, speed without judgment increases risk. An experienced consultant plays a critical facilitation role by: ·    Slowing decisions that require alignment. ·    Helping teams prioritize clarity over optimization. ·    Ensuring strategy translates into executable initiatives with clear accountability. They use AI to broaden thinking and pressure-test assumptions, while applying experience to determine what deserves action. This balance is essential in environments where recovery from a bad decision is costly. Strategy is also about Trust and Alignment. In many lower middle market companies, strategy is a trust exercise involving boards, lenders, family owners, and employees. Data alone does not create confidence. Experienced consultants bring credibility, objectivity, and the ability to translate AI-driven analysis into clear, human narratives. They help to align stakeholders, manage differing agendas, and ensure the strategy is understood and owned—not just approved. The future of strategic planning in the lower middle market is not AI-driven or consultant-driven—it is collaborative. The strongest results come when leadership teams, experienced consultants, and AI tools work together. Companies that succeed will not be those that adopt AI fastest, but those that integrate it thoughtfully with seasoned leadership and external perspective. We can help.  Mead Consulting Group has worked with scores of organizations and leaders to help them move to develop a highly- functioning management team that plans and acts strategically and accomplishes its goals. If you would like to learn more about how we can help your organization, please contact me at meaddp@meadconsultinggroup.com or (303)660-8135. For more information, see some of our success stories with organizations from $10M to $250M.  Best regards, Dave Mead