When Growth Stalls: Key Warning Signs
Chairs are often the first call when issues surface. These are the signals that matter most:
• Lack of proactive business and individual tax planning for 2025 to reflect the changes from the One Big Beautiful Bill Act
• Misalignment of business and personal tax planning
• Missed opportunities related to state and local tax and pass-through entity tax elections
• Insufficient preparation or strategy for a potential business sale from a tax perspective
• Consistent pattern of last-minute tax filings and tax surprises
• Moving weak or broken internal processes to an outside provider without fixing them first, creating long-term problems
• Absence of clearly defined service expectations or performance measurements
• Losing visibility and control over company data
• Underestimating how much internal behavior and workflow change is required
• Lack of clear or measurable improvements after outsourcing is implemented
• Customization of the ERP software system expands over time until it becomes unmanageable and very expensive
• Technology implementations do not deliver the expected results
• Data quality is poor, leading to inaccurate outputs and unreliable reporting
• Lack of oversight of software licensing, creating cost and compliance risks
• Assumption that technology alone will solve business problems without addressing process and people issues
• Insufficient cash flow forecasting that accurately demonstrates whether the business can meet its obligations
• Weak financial packages prepared for the bank or investor
• Absence of planning or forecasting for how different interest rate scenarios may affect the business
• Limited understanding of the available lending options and which type of financing is the best fit
• Lack of preparation for the requirements of a merger or acquisition
• No clear understanding of the company’s valuation or a defined roadmap for the business post-transaction
• Unresolved key legal and tax issues which can delay, halt, or disrupt the transaction
• Operational weaknesses in technology, human resources, finance/accounting, and state and local tax compliance that reduce buyer confidence and value
Five Strategies to Turn Challenges into Wins
1. Make Tax Planning a Playbook, not a Fire Drill
Model OBBBA 2025 changes, align business and personal planning, and understand the tax impact of big decisions before they’re made
2. Treat Outsourcing as a Performance Lever
Improve reporting, shorten close cycles, stabilize staff, and outsource noncore functions with clear processes and measurable targets
3. Enforce Technology Discipline
Create a digital roadmap, tighten ERP governance, clean up data, and scale AI only when foundational systems and data are ready
4. Package Your Story for Lenders
Build lender-ready financials, projections, working capital models, and covenant analyses to get the best terms, then work to find the right lender to support your business
5. Run a Sell-Side Process Like a Pro
Spot issues early, run quality of earnings (QoE) reports, structure tax intelligently, and prepare the whole organization — not just accounting and finance for diligence
Why This Matters for Your CEOs
Proactively strengthening tax, finance, tech, and operational foundations helps CEOs:
• Increase valuation
• Smooth capital raises
• Avoid unnecessary surprises
• Build a scalable organization equipped for future growth
Give Your CEOs a Scaling Advantage
If a CEO in your chapter is facing these challenges — or if you want support with diagnosing where their next constraint will appear — we’re here to help.
Our teams work with middle-market CEOs to effectively navigate these challenges and develop a clear roadmap for future growth. We apply integrated tax, tech, finance, and transaction expertise to help them scale with confidence.
Let’s Continue the Conversation
Whether you want to discuss a specific CEO situation, explore diagnostic tools, or get resources for your chapter let’s schedule a call.
