Overview

Business leaders often excel in their areas of expertise, but many overlook critical risks that can impact long-term success. At the recent Blind Spots in Business panel, five industry experts shared actionable strategies to help business owners uncover and address the hidden vulnerabilities in their operations, people management, legal infrastructure, insurance coverage, and personal finances. Their message was clear: by identifying blind spots early and assembling the right team of professionals, business owners can reduce risk, protect assets, and build resilient organizations.

Meet the Experts

• Jon McGraw, President, Buttonwood Financial Group, LLC
  Serves as Family CFO to successful families and business owners. Specializes in protecting wealth, coordinating complex financial strategies, and preparing clients for life’s biggest transitions.
• Tandra Stacer, Producer, Haas & Wilkerson Insurance
  Focuses on commercial insurance risk, helping companies align coverage with operational realities so they’re protected when it matters most.
• Sara Gertsema, Unit Leader, Personal Lines, Haas & Wilkerson Insurance
  Brings expertise in personal risk management for high-net-worth individuals, ensuring business owners protect their personal assets with care.
• Michael Griffin, Attorney, Dysart Taylor
  Advises businesses on contracts, compliance, and litigation. Helps clients avoid costly exposure and solidify legal foundations.
• Roger Dusing, PhD, Senior Consultant, OMNI Human Resource Solutions
  Helps organizations resolve HR blind spots, improve leadership, ensure compliance, and align talent strategy with business growth.

Key Insights by Topic

1. HR Blind Spots: Leadership, Culture & Retention

Dr. Roger Dusing highlighted one of the most pressing challenges in today’s workforce: disengagement. According to Gallup, nearly half of employees are actively disengaged and seeking new roles. The root cause? A lack of effective people management.

Supervisors are often promoted based on technical skill, not leadership ability. As a result, many managers lack the training to coach, mentor, and motivate employees. When leadership focuses only on operations and not on culture, businesses suffer high turnover, low morale, and increased risk of compliance violations.

What You Can Do: Invest in leadership development, prioritize emotional intelligence, and ensure your senior managers are building strong relationships with their teams. Culture starts at the top.

2. Insurance: Gaps in Coverage Can Be Costly

Tandra Stacer and Sara Gertsema shared real-world examples of business owners who mistakenly believed they were fully insured. The reality is more nuanced.

Many commercial properties are undervalued, which means businesses may receive far less than expected in the event of a loss. Auto policies often lack Hired Auto Liability coverage, leaving companies exposed when employees use personal vehicles for work. On the personal side, business activities are not covered by a personal umbrella policy - a critical misunderstanding among many entrepreneurs.

What You Can Do: Review policies annually with a broker who understands your operations. Check valuations, exclusions, and title ownership. If you don’t know what a coverage type means - ask.

3. Legal: The Cost of Complacency

Attorney Michael Griffin emphasized the legal risks of doing business with outdated documents or no legal agreements at all. From partnership disputes to vendor relationships, too many businesses rely on informal agreements or internet templates.

Common mistakes include not having a buy/sell agreement among business partners, improperly titled assets, and failing to update shareholder or operating agreements as the business evolves. In worst-case scenarios, these oversights lead to litigation or loss of legal protections.

What You Can Do: Establish core legal documents early and revisit them every 2–3 years. Don’t rely on internal staff or CFOs to draft legal documents—engage an attorney who understands your business.

4. Personal Finance: Concentration Risk & Missed Opportunities

Jon McGraw addressed the importance of separating personal and business finances. Many business owners are overly reliant on their business as their primary asset - a classic case of concentration risk.

Without diversifying wealth outside the company, business owners put their personal financial future at risk. From tax planning to multigenerational transfers, the earlier owners start strategizing, the more options they have to protect their families.

What You Can Do: Start pulling income out of the business and investing in other vehicles. Create a plan for how the business integrates with your broader financial goals, including estate planning and retirement.

5. Transition Planning: Culture, Communication, and Continuity

Both Dusing and McGraw discussed the overlooked risks during leadership and ownership transitions. On the people side, incoming leaders often fail when they don’t embrace the company culture or establish relationships. On the personal wealth side, many owners delay planning until after a sale, missing the chance to structure deals in a tax-efficient and legacy-minded way.

Assumptions about generational succession often go untested. Business documents may assume children will take over, but those conversations never happen. The result? Conflict, confusion, and missed opportunities.

What You Can Do: Start transition planning early. Engage the next generation in discussions. Evaluate leadership fit before a hire and align cultural expectations in the onboarding process.

6. AI & Operational Innovation

The panel briefly touched on the role of artificial intelligence across industries. While AI can streamline workflows, enhance hiring processes, and support legal drafting, it must be used responsibly.

Privacy concerns are paramount, especially in financial and legal settings. Organizations must ensure that sensitive data is never input into public AI tools, and that outputs are always reviewed by qualified professionals.

What You Can Do: Begin exploring AI for efficiency, but with human oversight. Use private, secure environments and develop internal policies around responsible use.

Final Takeaways: What Every Business Owner Should Do Next

• Tandra: Make sure your broker understands your operations in detail.
• Sara: Conduct annual reviews with your insurance, legal, and financial teams.
• Michael: Every multi-owner business needs a buy/sell agreement. Review it regularly.
• Roger: Your people managers drive the culture. Train and support them.
• Jon: Identify your biggest blind spot and commit one hour a month to fixing it.

Conclusion

Every business has blind spots. Whether it’s a missing legal document, underinsured asset, disengaged team, or lack of succession planning, these gaps are preventable. By assembling the right team of professionals and reviewing your business through a multidisciplinary lens, you can reduce risk and build a business that not only grows, but endures.

Ready to learn more? Contact one of the panelists or your trusted advisor to begin addressing your own business blind spots today.

Disclaimer
This material is intended for informational purposes only and should not be construed as legal, tax, investment, or insurance advice. The views expressed by panelists are their own and do not necessarily reflect those of their respective firms. Before making any financial or business decisions, you should consult with qualified professionals who are familiar with your unique circumstances. Past performance is not indicative of future results.