Never Let a Good Crisis Go to Waste: Lessons from Milwaukee’s Historic Flooding

For weeks now, Milwaukee and Waukesha Counties have been dealing with the aftermath of historic flooding. More than 10 inches of rain fell in a single day – rivers surged over their banks, streets became waterways, and thousands were left in the dark. It was devastating.

But as Winston Churchill famously said during World War II, we must “never let a good crisis go to waste.” He wasn’t celebrating hardship; he was reminding us that disruption often forces the changes we’ve been postponing.

For local business owners, these storms were more than just a weather event — they were a wake-up call. Property damage, disrupted operations, and shaken confidence are real and immediate challenges. Yet even in the middle of this catastrophe, there are lessons worth carrying forward. We can’t control the weather, the economy, or sudden industry shifts. What we can control is how well we prepare, how we respond under pressure, and how we adapt once the skies clear.

Stress-Test Your Operations Before the Next Storm

The infrastructure of both Milwaukee & Waukesha were completely overwhelmed by this event – drainage systems, warning networks, emergency response, etc. A crisis exposes weaknesses in ways a normal business cycle never will.

Did operations grind to a halt because key people or systems weren’t accessible? Did cash reserves run out faster than expected? Did supply chain dependencies become bottlenecks?

These painful realities can serve as a “stress test,” showing where the cracks exist and where reinforcement is needed.

Ask yourself: If my primary location were inaccessible for weeks, how would operations continue? Do I have alternative suppliers or distribution channels if a key partner fails? Could my team pivot quickly to remote work if systems went down? Where are the single points of failure that could bring my business to a standstill?

Action: Identify and address your business’s pressure points now. Build redundancy into critical systems, diversify vendors & supply chains, and clearly document contingency plans so they’re usable under stress. Test those plans through tabletop exercises or full crisis simulations at least once a year — because the worst time to find out a plan doesn’t work is during the real event.

Improve Crisis Communication Before You Need It

During the floods, delayed or incomplete information meant some residents weren’t warned in time. In business, late or unclear communication can multiply losses.

Ask yourself: If I had to deliver critical instructions within the next hour, how confident am I that every employee, customer, and vendor would actually receive and understand them? Do I have current contact information? Are there clear communication chains so messages don’t get stuck waiting for approval? Could my business continue if phone lines, email servers, or a key decision-maker were suddenly unavailable?

Action: Build a communication strategy that works under pressure. Maintain accurate contact lists and back them up in multiple places. Use layered channels: text alerts, email blasts, phone trees, even private social groups. No single outage should derail the message. Train spokespersons for both internal and external communication, and run periodic drills to ensure the system works when speed matters most.

Build Financial Sandbags to Withstand the Surge

Cash flow reserves, diversified revenue streams, proper insurance coverage, and disaster recovery plans all move from “nice-to-have” to “must-have” after an event like this. Just as homeowners place sandbags to keep water out, businesses need buffers to keep crises from washing them away.

Ask yourself: If revenue stopped tomorrow, how long could my business continue paying employees, covering fixed costs, and meeting obligations? Do I have alternative revenue sources or contingency plans to keep cash flowing if my primary stream is disrupted?

Action: Go beyond a rainy-day fund. Build a cash reserve that covers 3–6 months of core expenses, secure flexible credit lines before you need them, and stress-test your financials against worst-case scenarios. Monitor early-warning signs like declining receivables, customer churn, or margin compression, so you can respond before a trickle of risk becomes a flood.

Spot the Competitive Opening

While some companies freeze during crises, others pivot and capture market share. In the wake of this flood, recovery efforts will require contractors, materials, logistics, and services. Businesses ready to meet urgent demand will move ahead.

Ask yourself: After a disruption, which urgent needs in my industry are most likely to spike? Which of my competitors will be too slow to respond? Could I scale capacity, shift offerings, or repackage services quickly to meet those needs? Do I have relationships with vendors, partners, or contractors who could help me deliver faster than the market?

Action: Anticipate “surge demand” before it happens. Build scenarios for how your customers’ priorities might change and outline specific ways your business could adapt. Identify the resources, partnerships, or inventory you’d need in place to move quickly. Keep a playbook of pre-approved messaging and streamlined decision-making processes so when the moment comes, you can act with speed and clarity while others hesitate.

Turn Temporary Fixes into Lasting Resilience

Milwaukee & Waukesha leaders are already discussing infrastructure upgrades for future storms. Businesses should do the same – converting short-term crisis responses into permanent improvements.

Ask yourself: Which of the stopgap measures actually revealed a better way of operating? Am I willing to make those changes permanent, even if they require investment or disrupt old habits? What risks or inefficiencies did this event expose that I can no longer afford to ignore?

Action: Don’t slip back into “business as usual.” Document what worked and what failed while the experience is fresh, and translate those insights into concrete improvements. Update policies, refine workflows, and invest in tools or training that make your business stronger long-term. Embed resilience into your culture by regularly revisiting lessons learned and rewarding teams that innovate under pressure.

The Bottom Line

The recent storms remind us that control is an illusion. But preparation, adaptability, and foresight are very real tools we do control. If Churchill was right (and history suggests he was) then this crisis holds an invitation: let’s build stronger, more resilient businesses that can withstand whatever storms lie ahead. The next time the waters rise, your business will already be standing on higher ground.

At Oak Hill Business Partners, we help owners stress-test operations, build resilience, and position their companies for long-term value and growth. Let’s talk about how to turn today’s challenges into tomorrow’s opportunities. Contact us today to start the conversation.

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Erik Owen is the President of Oak Hill Business Partners and has over 20 years of professional experience in Finance and Accounting, Administration, and General Management.  You can call Erik at 262.299.5526 or email him at erik.owen@OakHillBP.com.

Oak Hill Business Partners is a boutique management consulting firm serving middle market, closely held companies. Based in Milwaukee, WI, our partners focus on helping growing companies become scalable by applying functional excellence in finance & administration, sales, marketing, and operations.  Oak Hill also helps company owners plan and execute transition/exit planning holistically. Oak Hill partners work with a team of advisors including wealth and legal advisors to help owners understand their options for transition in the business and execute the plan that meets their specific needs.