How to Do Strategic Planning During Uncertainty

📢 Thinking Through Policy Uncertainty: A Strategic Imperative for Business Leaders In times of great geopolitical and policy uncertainty—like the one we are witnessing today—business leaders must sharpen their ability to distinguish the signal from the noise. With shifting alliances, evolving trade policies, economic fragmentation, and security risks shaping the global landscape, how should leaders consider what matters most? Here’s where to start: 🔹 Focus on Structural vs. Cyclical Change – Not all policy shifts have the same weight. Some are fundamental shifts in global power structures, while others are short-term political maneuvering. Leaders must ask: Is this a momentary disruption or a realignment that demands a strategic pivot? 🔹 Identify the Intent vs. the Impact – Governments make bold statements, but the real question is whether they have the political will, economic leverage, and regulatory mechanisms to implement those policies effectively. Bluster does not equal execution. Distinguish rhetoric from reality. 🔹 Look Beyond Borders – Policy changes in one country often trigger ripple effects across industries, supply chains, and markets. A new trade restriction, for example, doesn’t just affect exporters; it reverberates through global pricing, logistics, and investment strategies. 🔹 Scenario Planning, Not Guesswork – No leader has a crystal ball, but those who think through multiple contingencies will be best positioned for success. What happens if tariffs rise? If economic blocs realign? If new sanctions emerge? Having a strategy for different scenarios creates agility in uncertainty. 🔹 Follow the Money & Markets – Watch how capital moves. Global investors, multinational corporations, and financial markets often react before policies take full effect. If businesses are shifting supply chains or hedging investments, that’s a sign of where the real risks and opportunities lie. 🔹 Security, Stability & Strategic Foresight – Policy uncertainty isn’t just about commerce; it has deep implications for operational risk, cybersecurity, and corporate security strategies. Leaders must assess vulnerabilities beyond the balance sheet. The Bottom Line? In this era of uncertainty, success belongs to those who don’t just react but anticipate. Those who ask the right questions. Those who embrace complexity rather than fear it. The future isn’t predetermined—but strategic leaders shape how they navigate it. What’s your approach to policy uncertainty? Let’s discuss. 👇 #Geopolitics #BusinessStrategy #PolicyUncertainty #GlobalTrade #Leadership

"Should we hire or should we cut?" is a question I'm hearing often from small business owners right now, which is fair given the mixed economic signals. Some clients are seeing their best quarters ever. Others are watching pipelines thin out. Everyone seems to be asking, "How do we plan for what we can't predict?" This is where scenario planning becomes your survival tool; not just hoping for the best, but modeling the reality of different futures. Here's what we walk our clients through: 🌳 The Growth Scenario: For example, if revenue is expected to be up, we’re looking at potential team expansion and higher overhead. Looking at what that does for cash flow given the changes to expected expense changes. 🌱 The Steady Scenario: Where flat growth is expected and we plan to maintain current team, we’ll want to optimize margins and prepare for inevitable per team member increases. There will likely be some percentage increase YOY but we expect the core costs to stay the same. 🍃 The Contraction Scenario: On the other hand, if revenue is expected to go down, we want to look at strategic cuts that allow the team to run efficiently while preserving cash. For our clients, this is usually a mix of team, professional services, and travel. We also want to ensure that the resources kept are used efficiently. Each scenario gets its own financial mode where we map out cash flow, runway, and break-even points for 3, 6, and 12 months ahead. The command center for this? Fathom. We've been using Fathom since the beginning of Little Fish Accounting and it lets us build the scenarios in real-time with clients, showing exactly how each decision ripples through their financials. No more spreadsheet gymnastics or gut-feeling guesses. Ultimately, the founders who survive uncertainty aren't the ones with crystal balls—they're the ones with clear models and decisive action plans. And we're glad to be the builders 🧱

🚨 Uncertainty is near an all-time high 🚨 Since 1985, the U.S. Federal Reserve has tracked an uncertainty index—and it's now skyrocketing, fast approaching its pandemic-era peak. But you can THRIVE in these conditions. Here are 8 ways to do it: 🔹 1. Uncertainty Matrix – Map out what’s certainly known, certainly unknown, unevenly recognized in your organization, and critical blind spots. 🔹 2. Scenarios – Develop a few truly distinct scenarios (not just based on your company’s outcomes, but on market shifts). What actions can you take today to thrive in each future scenario? 🔹 3. Portfolio Plan – Assess the risk level, risk type, and maturity of your investments. Think of it as a diversified portfolio—how will it hold up in different market conditions? 🔹 4. Platforms vs. Products – Shift from rigid products to flexible platforms. Netflix, for example, is a platform that can evolve with the market—traditional broadcast networks do not. 🔹 5. Capture New Markets – Disruptive events create major opportunities. Fintech boomed after the financial crisis—where’s your industry’s next opening? Consider all dimensions: goods companies can grow into non-tariffed services, you can expand geographically, and more. 🔹 6. Agile Planning – Static, annual strategic plans don’t work during high uncertainty. Instead, focus on dynamic strategies that separate fixed priorities from adaptable tactics. 🔹 7. Reduce Inter-Dependencies – Create modular, flexible value propositions that can have both more agility and lower costs. 🔹 8. Put Customers First – Your customers’ Jobs to be Done remain constant—use them as your North Star for strategy, cost reduction, and option development. 📚 Want to go deeper? Our materials on FutureCasting and the book Rogue Waves address approaches 1 – 4, our book Capturing New Markets tackles point 5, our book The Innovative Leader focuses on point 6, and our books Costovation and Jobs to be Done concentrate on points 7 and 8. Dig into them or get in touch for a discussion. Uncertainty = Opportunity. Seize it!! 🚀 #Leadership #Strategy #Innovation #JobsToBeDone #Growth #Agility

Want to know what's dominating CEO conversations? Here is the most recent data for Q1 2025 by Philipp Wegner with IoT Analytics - Hot off the Press as of March 25th! 𝐊𝐞𝐲 𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐬: • 𝐓𝐚𝐫𝐢𝐟𝐟𝐬 𝐓𝐚𝐤𝐞 𝐂𝐞𝐧𝐭𝐞𝐫 𝐒𝐭𝐚𝐠𝐞: CEO mentions of tariffs surged by 190%, surpassing previous peaks as companies grapple with new global trade tensions and policies. CEOs are actively exploring strategies to mitigate or even leverage these tariff impacts. • 𝐔𝐧𝐜𝐞𝐫𝐭𝐚𝐢𝐧𝐭𝐲 𝐒𝐩𝐢𝐤𝐞𝐬: Mentions of uncertainty climbed 49% as geopolitical shifts and trade wars cloud strategic decisions, notably affecting the EMEA region and industrial sector most significantly. • 𝐀𝐈 𝐂𝐨𝐧𝐭𝐢𝐧𝐮𝐞𝐬 𝐑𝐢𝐬𝐢𝐧𝐠 – 𝐄𝐬𝐩𝐞𝐜𝐢𝐚𝐥𝐥𝐲 𝐀𝐠𝐞𝐧𝐭𝐢𝐜 𝐀𝐈: AI remains a priority, with an impressive 275% spike in discussions about Agentic AI—highlighting a strategic shift towards autonomous decision-making technologies designed to boost efficiency and innovation. • 𝐑𝐞𝐜𝐫𝐮𝐢𝐭𝐢𝐧𝐠 𝐇𝐢𝐭𝐬 𝐚 𝐅𝐫𝐞𝐞𝐳𝐞: Amid economic turbulence, CEOs scaled back conversations on hiring by 8% while hiring freeze mentions soared by 286%, signaling cautious approaches towards workforce expansion. 𝐌𝐲 𝐓𝐚𝐤𝐞: CEOs today face complex, interconnected challenges. They’re shifting from optimistic hiring and growth toward defensive positions amidst economic uncertainty and tariff complexities. At the same time, investments in innovative AI, particularly agentic AI, are viewed as strategic ways to navigate these turbulent waters. 𝟑 𝐏𝐢𝐞𝐜𝐞𝐬 𝐨𝐟 𝐀𝐝𝐯𝐢𝐜𝐞: 𝟏. 𝐑𝐞𝐚𝐬𝐬𝐞𝐬𝐬 𝐒𝐮𝐩𝐩𝐥𝐲 𝐂𝐡𝐚𝐢𝐧 𝐑𝐢𝐬𝐤𝐬: Evaluate your exposure to tariffs immediately. Move swiftly to adjust sourcing and production to maintain competitiveness. 𝟐. 𝐒𝐜𝐞𝐧𝐚𝐫𝐢𝐨 𝐏𝐥𝐚𝐧𝐧𝐢𝐧𝐠 𝐢𝐬 𝐂𝐫𝐮𝐜𝐢𝐚𝐥: Strengthen your organization's ability to rapidly respond to geopolitical shifts. Having robust contingency plans can provide stability in uncertain times. 𝟑. 𝐀𝐜𝐜𝐞𝐥𝐞𝐫𝐚𝐭𝐞 𝐀𝐈 𝐈𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭: Quickly identify and prioritize strategic AI investments—especially autonomous, agentic AI solutions—to drive productivity, agility, and market advantage despite hiring freezes. 𝐅𝐨𝐫 𝐦𝐨𝐫𝐞 𝐢𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐨𝐧 𝐭𝐡𝐢𝐬 𝐫𝐞𝐩𝐨𝐫𝐭: https://lnkd.in/eWWMt47K ******************************************* • Visit www.jeffwinterinsights.com for access to all my content and to stay current on Industry 4.0 and other cool tech trends • Ring the 🔔 for notifications!

We'll talk more about Machiavelli during Ethics Week, but "The Prince" should be required reading for leaders. This quote on the need for speed is timeless...and timely. I see companies sitting on their hands, paralyzed by uncertainty. Don't be a victim! Stress-test and diversify your supply chain footprint. Map tariff and export-control exposures and build alternative supplier networks in at least two regions. Adopt "optionality" in capital planning. Structured real-option approaches preserve flexibility without paralysis. It's not about acting first, it's acting best...quickly. The action can be small, but iterate and learn. It's only in acting that you can extract commercial truth. What are your real capabilities? Will customers reach for their wallets? How will competitors respond? With this knowledge, you can create options and pivot. Put in the work now so you can strike quickly, and best, when the fog clears. It always does.

The Craft of AI Product Building #3: AI Product Roadmapping Maria Santos stared at the conference room whiteboard, covered in sticky notes, timeline arrows, and more question marks than she'd ever seen in a strategic planning session. As VP of Product Strategy at TransGlobal Logistics, a $2.3 billion supply chain management company, she faced a challenge that traditional planning frameworks couldn't address: developing a three-year AI roadmap that could transform their business while navigating unprecedented uncertainty. The executive directives was both inspiring and daunting: leverage AI to automate 60% of route optimization decisions, predict supply chain disruptions with 85% accuracy, and reduce operational costs by $50 million annually. The timeline was aggressive—full deployment within 36 months to stay competitive with AI-powered logistics startups that were rapidly gaining market share. But Maria realized that conventional roadmapping approaches were fundamentally inadequate for AI initiatives. AI development introduced variables that defied precise scheduling: Would computer vision technology advance enough to reliably identify damaged packages in their warehouses? Could they acquire sufficient high-quality data to train predictive models for global supply chain disruptions? How would emerging regulations around algorithmic decision-making in logistics impact their deployment timeline? Maria Santos's challenge at TransGlobal Logistics captures a fundamental problem facing enterprise leaders today. Tasked with delivering a transformational AI roadmap - she faced a planning nightmare that traditional frameworks couldn't solve. Maria leveraged an AI Product Strategy Framework that leveraged planning for uncertainty as a strategic asset. This Framework addresses the core challenge of maintaining strategic coherence while accommodating AI development's inherent uncertainty. The Multi-Horizon Planning Structure recognizes that AI requires different planning approaches across time scales: detailed 6-month execution plans with validated technical approaches, tactical 6-18 month capability development with flexible implementation paths, and strategic 18+ month vision frameworks that preserve directional clarity while accommodating breakthroughs. The framework treats uncertainty as a strategic variable rather than a planning obstacle, building optionality through multiple pathways to value creation. Dynamic Influence Layers continuously shape strategy evolution through technology trend monitoring, competitive landscape assessment, regulatory environment tracking, and organizational capability development. This creates responsive planning systems that adapt to rapid AI advancement while maintaining stakeholder confidence and strategic accountability. Read more about Adaptive and Dynamic Roadmapping in Chapter 5 of my upcoming book - The Craft of AI Product Building.