3 Keys to Navigating Business Crossroads

Every leader faces crossroads: scale, sell, restructure, or transition leadership. These choices carry risk and demand courage, especially amid volatility and disruption.

Putting off big decisions — like who will lead next, whether to buy or sell, or how to use new technology — can cost you years of progress. The reality is that you can’t control everything. But with a structured, strategic approach, you can move decisively, even when the path ahead is uncertain.

Here’s what to consider when you face a business crossroads.

Preparing for Strategic Growth

Growth starts with what you know. McKinsey research shows 80% or more revenue gains come from strengthening your core business.

This all begins with an understanding of your current state. Look to:

• Cash flow: Know your true liquidity position. Analyze payables, receivables, and conversion cycles.
• Processes: Invest in automation, reporting enhancements, and data integration. Reassess operational blind spots that slow down operations.
• Supply chain: Build flexible sourcing and responsive logistics capabilities.
• What-if scenarios: Stress-test your business model under different cost or tax scenarios.
• Critical business systems: Ensure systems are up-to-date and able to connect data in real time.

Once you’ve outlined your current situation, you can explore future opportunities and create tactical steps toward your desired growth goal.

When these critical steps are taken, the impacts are substantial. Research indicates that leaders who prioritize strategy and innovation see their organizations grow over 10% annually on average.

Considerations for Scaling and Expansion

A growth mindset often means looking for opportunities to buy, sell, or expand – and understanding when to decide it’s the right move.

It’s about shifting from “growth at all costs” to “growth with clarity and purpose.” Consider:

• Evaluate strategic fit: Does the opportunity align with your core strengths and market positioning?
• Stress-test decisions: What happens if growth outpaces infrastructure or talent capacity?
• Balance risk and reward: How do you allocate capital to maximize returns without jeopardizing liquidity?
• Build agility: Can your systems and processes adapt quickly, and can automation or AI help?

Navigating Ownership and Leadership Transitions

Whether planning succession or preparing for a transaction, clarity and timing are everything. Regardless of your “next,” concrete steps today can give you greater flexibility amidst market changes and economic uncertainties.

Potential buyers want to see:

• A well-defined org chart and succession plan.
• Signed employment and compensation agreements for key employees.
• Clearly documented key relationships and responsibilities.

This type of early planning allows you to prepare for what’s next — and what you don’t know is coming. Yet Gartner reports only 51% of board directors say there’s a plan for the current CEO’s succession.

Unplanned changes often expose governance gaps, create uncertainty, and lead to rushed decisions that compromise long-term goals. Consider this: businesses in the U.S. lose more than a trillion dollars every year due to voluntary turnover. In addition, a lack of clear strategy or direction – which is shared openly with employees – can lead to wasted direction, time, and resources.

Critical Considerations for Continuity

Align leadership development with business strategy, stress -test timing options, and communicate with transparency.

• Clarify roles and timelines: Define who leads, when, and under what conditions.
• Valuation and timing strategy: Factor in market conditions and tax implications.
• Transaction readiness: Ensure systems and financials are digital-ready for due diligence.
• Stakeholder confidence: Maintain trust and engagement throughout the transition.

The Personal Impact of Ownership Transitions

Continuity isn’t just a business issue — it’s personal. Protecting enterprise value often goes hand in hand with safeguarding family wealth.

Recently, we helped a family-owned business protect future value by moving shares into an irrevocable dynasty trust. Based on projected growth, those shares could have climbed from $25 million to more than $800 million over 30 years — creating a significant estate tax liability. Early planning preserved wealth, aligned with family goals, and ensured continuity for generations.

Resilience for the Future

In a world of volatility and disruption, organizations must be prepared for multiple futures. Research shows that nearly 80% of organizations need to adapt every 2-5 years to stay relevant.

Markets shift, technologies evolve, and regulations change faster than traditional models can accommodate. Leaders who anticipate a range of scenarios — best case, worst case, and everything in between — position their organizations to act decisively rather than react defensively.

You can’t control what the government will do next week, but you can identify volatility hotspots and proactively prepare.

Start by asking:

• Where are we most vulnerable to things we can't control?
• What can we do today to build flexibility and resilience in our organization?
• How can we empower our leaders to act boldly, even in uncertainty?

Then consider:

• Investing in leadership, teams, and systems that are agile and future-ready.
• Running “what if” scenarios to see how your business responds.
• Making sure your systems and processes can flex when needed.
• Having backup plans for things like regulatory shifts, supply chain issues, and more.

Resilience isn’t about guessing the future — it’s about being prepared for whatever the future brings.

Critical Considerations

Ask yourself:

• Scenario planning: What happens if demand drops, costs rise, or regulations tighten?
• Change leadership: Do you have the governance and communication structures to drive adoption?
• Future-ready skills: How will you close gaps in data, digital, and leadership capabilities?
• Early warning indicators: What signals will prompt you to pivot before risk becomes reality?
• AI for agility: Can machine learning models help identify early warning signals, optimize resource allocation, and automate responses to market changes?

Your Tech and Tool Infrastructure Matters

The tools and tech you choose today will shape what you can do tomorrow. Effective technology enables real-time visibility across systems, and precise financial reporting supports better decision-making. 95% of CFOs say improving reporting significantly enhances their strategic decision making.

Ask yourself:

• Can your ERP or accounting system generate timely, accurate data?
• Are customer, vendor, and employee records centralized and transferable?
• Is your tech infrastructure scalable and secure?
• Do you have real-time visibility into your financial records?
• Do you have to make a significant number of manual adjustments or reconciliations?

Only once the foundation is secure can you build upon it with AI and automation technologies.

Ready to Prosper?

At crossroads, hesitation is costly. With a structured, integrated approach — grounded in smart technology investments, talent development, and scenario planning — you can act decisively, protect value, and create durable growth.

The question isn’t just “Where to from here?”. It’s “How do we prosper in the face of uncertainty?”.

Let’s navigate your crossroads together.