Strategic Questions by Corporate Life Cycle Stage and Cash Flow Component

STARTUP PHASE

Core Operating Cash Flow

1. What is your current cash burn rate, and how many months of runway do you have with existing funding?
2. How do you track progress toward operational breakeven, and what metrics indicate you’re moving in the right direction?
3. Which operational activities are consuming the most cash, and are these aligned with your strategic priorities?
4. How sensitive is your cash burn to changes in customer acquisition costs or delays in product development?
5. What operational milestones do you expect to achieve before generating consistent positive cash flow?

Working Capital Cash Flow

1. How are you currently financing your inventory buildup, and what terms have you negotiated with suppliers?
2. What payment terms are you offering customers, and how do these compare to industry standards?
3. As sales grow, what systems do you have in place to manage accounts receivable aging?
4. Have you considered factoring or early-payment discounts to accelerate cash collection?
5. What is your strategy for managing seasonality or cyclicality in working capital needs?

Capital Expenditure

1. What are your most critical near-term capital expenditure needs?
2. Have you analyzed the ROI of owning versus leasing key equipment?
3. How are you prioritizing capital expenditures with limited available cash?
4. What technology investments are essential for your business model, and which could be deferred?
5. How do you distinguish between growth-oriented and maintenance capital expenditures at this stage?

Investment Activities

1. Are you considering acquiring any complementary technologies or talent through small acquisitions?
2. What strategic partnerships might require capital investment in the near term?
3. How do you evaluate potential returns on R&D investments?
4. Have you considered licensing technology rather than developing it internally?
5. What is your approach to protecting and monetizing intellectual property?

Debt Activities

1. What debt financing have you secured to date, and what are the terms and covenants?
2. Have you explored government grants, subsidized loans, or other non-dilutive funding sources?
3. What assets could potentially serve as collateral for secured financing?
4. How do you balance the trade-offs between dilutive equity and restrictive debt?
5. Have investors provided convertible notes or other debt-like instruments that will affect future financing?

Equity Activities

1. What is your current capitalization table structure, and how might it evolve with future funding rounds?
2. How do you plan to structure employee equity compensation as you grow?
3. What milestones must you achieve before considering the next equity raise?
4. Have you established relationships with potential investors for future funding rounds?
5. How do you communicate value creation to current and prospective investors?

GROWTH PHASE

Core Operating Cash Flow

1. As you scale, which aspects of your operations are showing economies of scale, and which are not?
2. How are you reinvesting positive operating cash flow to accelerate growth?
3. What operational inefficiencies have emerged as you’ve grown, and how are you addressing them?
4. How do your gross and operating margins compare to more mature industry peers?
5. What is your strategy for balancing growth investments against cash flow stability?

Working Capital Cash Flow

1. How is rapid growth affecting your working capital cycle and cash conversion period?
2. What credit terms are you extending to new customers, and how do you assess credit risk?
3. As you expand into new markets or channels, how are working capital requirements changing?
4. What inventory management systems have you implemented to prevent overstocking or stockouts?
5. How are you leveraging supplier relationships to optimize payment terms while ensuring supply chain reliability?

Capital Expenditure

1. What capacity expansion investments are planned for the next 12-24 months?
2. How do you prioritize between expansion capex and efficiency improvement investments?
3. What is your framework for evaluating the timing of major capital expenditures?
4. How do you assess whether to build new facilities or lease existing ones?
5. What technology investments will be required to support your current growth trajectory?

Investment Activities

1. What criteria do you use when evaluating potential acquisition targets?
2. How do you value synergies when considering acquisitions?
3. What is your approach to post-merger integration to ensure value capture?
4. Are you considering international expansion, and how would you fund it?
5. What alternative investment opportunities might compete for capital with your core business expansion?

Debt Activities

1. How do your current debt ratios compare to industry benchmarks?
2. What diversity in debt funding sources have you established?
3. How are you managing interest rate risk in your debt portfolio?
4. What debt covenant compliance issues might arise with your growth plans?
5. How do you balance the use of revolving credit versus term debt?

Equity Activities

1. What is your timeline for potential public offering or other liquidity events?
2. How do you communicate growth metrics to existing investors?
3. What is your strategy for timing and sizing follow-on equity raises?
4. How are you managing investor expectations about cash burn versus growth?
5. What equity-based incentive plans have you implemented for key management?

MATURITY PHASE

Core Operating Cash Flow

1. How stable and predictable is your core operating cash flow, and what factors drive variability?
2. What operational excellence initiatives are you pursuing to enhance margins?
3. How do you balance cost control with maintaining competitiveness and innovation?
4. What recurring revenue streams have you developed to stabilize cash flow?
5. How have you optimized your geographic or product mix to maximize operating cash flow?

Working Capital Cash Flow

1. What working capital efficiency metrics do you track, and how have they trended over time?
2. How do your inventory turns and days sales outstanding compare to best-in-class competitors?
3. What technology systems have you implemented to optimize working capital management?
4. How do you manage working capital needs across different business units or geographies?
5. What supplier financing programs have you established to optimize payment terms?

Capital Expenditure

1. How do you balance maintenance capex with growth investments at this stage?
2. What is your process for evaluating the ongoing ROI of previous capital investments?
3. How do you determine the optimal timing for equipment replacement or facility upgrades?
4. What percentage of cash flow are you committing to capital expenditures, and why?
5. How do you evaluate build versus buy decisions for new capabilities?

Investment Activities

1. What is your approach to strategic acquisitions at this stage in your corporate life cycle?
2. How do you evaluate adjacent market opportunities versus core business investments?
3. What is your framework for international expansion or new market entry?
4. How do you manage your portfolio of non-core investments?
5. What investment opportunities are you pursuing to prepare for future market changes?

Debt Activities

1. What is your target capital structure, and how do you optimize your debt profile?
2. How do you manage refinancing schedules to minimize risk and cost?
3. What mix of fixed and floating rate debt do you maintain, and why?
4. How do you leverage your improved credit profile to reduce borrowing costs?
5. What contingent financing arrangements do you maintain for strategic flexibility?

Equity Activities

1. What is your capital allocation strategy regarding dividends versus share repurchases?
2. How do you determine the appropriate dividend payout ratio?
3. What triggers would lead you to adjust your dividend policy?
4. How do you structure share repurchase programs to maximize shareholder value?
5. What mechanisms have you established for managing shareholder activism?

EARLY DECLINE PHASE

Core Operating Cash Flow

1. Which product lines or business segments are experiencing declining cash flows, and why?
2. What operational restructuring initiatives have you identified to stabilize cash flow?
3. How are you adjusting your cost structure to align with changing revenue patterns?
4. What metrics do you use to distinguish between cyclical downturns and secular decline?
5. Which operational investments could potentially reverse negative cash flow trends?

Working Capital Cash Flow

1. How are you adjusting inventory management practices as growth slows?
2. What changes have you made to credit policies and collection practices?
3. How are you managing supplier relationships as you optimize payment terms?
4. What working capital release initiatives have been most successful?
5. How are you monitoring customer payment behaviors for early warning signs?

Capital Expenditure

1. How have you reprioritized capital expenditures as cash flow tightens?
2. What criteria do you use to distinguish between essential and deferrable investments?
3. How are you extracting additional value from existing capital assets?
4. What sale-leaseback opportunities have you identified?
5. How do you balance short-term cash conservation with maintaining competitive capabilities?

Investment Activities

1. Which business units or product lines are candidates for divestiture?
2. How do you determine whether to close or sell underperforming operations?
3. What criteria do you use to identify core versus non-core assets?
4. What is your timeline and process for planned divestitures?
5. How do you value businesses in declining markets for potential sale?

Debt Activities

1. How are you preparing for potential covenant compliance issues?
2. What debt maturity concentrations exist, and how are you addressing them?
3. Have you opened discussions with lenders about potential restructuring needs?
4. What options have you identified to extend debt maturities or reduce principal payments?
5. How are you prioritizing debt service against other cash demands?

Equity Activities

1. How are you communicating changing prospects to shareholders?
2. What adjustments to dividend policy are you considering?
3. How do you balance shareholder returns against cash preservation needs?
4. Have you considered strategic investors who might provide fresh capital?
5. What governance changes might help navigate this transitional period?

DECLINE PHASE

Core Operating Cash Flow

1. Which operations remain cash flow positive, and which are consuming cash?
2. What is your timeline for stabilizing or winding down cash-negative operations?
3. How are you prioritizing which product lines to maintain versus discontinue?
4. What steps have you taken to reduce fixed costs and increase variable cost structures?
5. How frequently are you updating cash flow forecasts given the volatility?

Working Capital Cash Flow

1. What inventory liquidation strategies have proven most effective?
2. How are you managing accounts receivable risk as customer behavior changes?
3. What supplier payment prioritization system have you established?
4. How are you preserving critical supplier relationships while conserving cash?
5. What working capital metrics do you monitor daily or weekly during this phase?

Capital Expenditure

1. Have you eliminated all non-essential capital expenditures?
2. What minimum maintenance capex is required to maintain safe operations?
3. How are you monetizing underutilized equipment or facilities?
4. What deferred maintenance issues could create critical operational risks?
5. Have you considered rental or temporary solutions instead of capital purchases?

Investment Activities

1. What is your timeline for divesting remaining non-core assets?
2. How are you packaging assets to maximize value in distressed sales?
3. What intellectual property could be monetized through licensing or sale?
4. How are you maintaining value in operations intended for sale?
5. What minimum investment is required in businesses being prepared for sale?

Debt Activities

1. What debt restructuring negotiations are underway with creditors?
2. How are you prioritizing secured versus unsecured debt obligations?
3. Have you engaged restructuring advisors to evaluate formal reorganization options?
4. What debt-for-equity exchanges have you proposed or considered?
5. How are you managing inter-creditor dynamics in restructuring discussions?

Equity Activities

1. What options have you presented to shareholders regarding the future of the company?
2. Have you explored strategic buyers or private equity firms specializing in turnarounds?
3. What governance changes have been implemented to navigate this crisis period?
4. How are you balancing fiduciary duties to shareholders against other stakeholders?
5. What is your communication strategy with equity holders during this challenging period?

CROSS-CUTTING QUESTIONS FOR ALL STAGES

Transitional Indicators

1. What metrics do you monitor to identify when you’re transitioning between life cycle stages?
2. How do you distinguish between temporary business cycle effects and fundamental business maturity changes?
3. What strategic planning adjustments do you make as you observe transition indicators?
4. How do you communicate life cycle transitions to stakeholders?
5. What organizational changes typically accompany transitions between life cycle stages?

Risk Management

1. How does your risk management approach differ across the cash flow components?
2. What key risk indicators do you monitor for each major cash flow stream?
3. How have you adjusted hedging strategies for currency and interest rate risks?
4. What contingency plans exist for major disruptions to each cash flow component?
5. How do you balance different stakeholder interests when making risk management decisions?

Technology and Innovation

1. How do your technology investment priorities shift across life cycle stages?
2. What digital transformation initiatives are you pursuing to enhance cash flow management?
3. How do you evaluate the ROI of technology investments across different cash flow components?
4. What emerging technologies could potentially disrupt your industry or business model?
5. How do you balance innovation investments against core business requirements?

ESG Considerations

1. How do environmental, social, and governance factors affect each cash flow component?
2. What ESG-related investments are required to maintain competitiveness?
3. How do you measure the financial impact of sustainability initiatives?
4. What ESG-related financing options have you explored?
5. How do you incorporate ESG considerations into major capital allocation decisions?