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Big, deep, thorny problems can kill companies. One need only look at global companies that were thriving 50 years ago but now no longer exist to understand that it just takes one complicated problem to sink a business. One deeply complex, intertwined, and/or seemingly unsolvable problem can quickly take a company from thriving to diving to not-surviving in the span of a few short years or even months.
Consider how a failure to adapt to technological changes and market shifts killed Blockbuster, Kodak, Nokia, RIM, MySpace and Borders. Blockbuster famously rejected purchasing Netflix for $50 million, failing to recognize the shift towards online streaming and clinging to its brick-and-mortar rental model. Despite inventing the digital camera, Kodak failed to capitalize on this innovation, fearing it would harm their film business. They underestimated the speed at which consumers would adopt digital photography, leading to their decline and bankruptcy. Nokia and Research-In-Motion (RIM) — maker of the Blackberry — were unable to keep pace with the smartphone revolution. Borders failed to embrace online book sales and outsourced it to Amazon (who ate their lunch). And MySpace just could not compete with Facebook.
Even a single, deeply-complicated disaster or crisis can bring down a company. Reflect on what precipitated the corporate demise of these businesses. In 1987, Texaco’s legal battle resulted in a $10.5 billion debt which forced the company into bankruptcy. In 2008, risky investments in mortgage-backed securities during the housing bubble burst led to Lehman Brothers’ bankruptcy and was a catalyst for the global financial crisis. In 2012, a software glitch in a trading algorithm caused Knight Capital to lose $440 million in just 45 minutes, effectively ending its run as an independent firm. And, a fire at the Rana Plaza garment factory in Bangladesh in 2013 resulted in over 1,100 deaths. It not only led to the collapse of the business but it exposed critical issues regarding working conditions and safety standards in global supply chains. In 2021, a ransomware attack of Colonial Pipeline disrupted fuel supply to nearly half of the US East Coast, causing panic buying and fuel shortages. And in 2023, losses on bonds and a subsequent bank run triggered the collapse of Silicon Valley Bank and led to the FDIC placing the bank in receivership. This is just a handful of the companies that faced one complex, seemingly unsolvable problem… and went under as a result.
Solving problems is surely one of the most important things a company’s leadership does. But solving deeply complicated, intertwined, and seemingly unsolvable problems in business is tricky. Most would advise taking a structured, methodical approach… a slow slog that requires persistence, adaptability, empathy, positivity and an understanding of the data. Why? Complex problems rarely have easy solutions, so business owners must persevere through challenges. They must be flexible and willing to adapt their approach as they learn more about the problem and potential solutions. And they must understand the impact of the problem on those involved, including employees and customers. As they consider options, they must use data and analysis to inform their decisions and validate their approach. And, throughout it all, they need to maintain a positive attitude while focused on finding solutions. So, what does this look like in reality?
Traditional Problem-Solving Steps in Business
The key strategies are:
1. understanding and defining the problem. For this, leaders must go deep, thoroughly dissecting the issue and mapping out the objectives, scope, and constraints. The goal is to drill down to the root cause, identifying the actual cause or causes of the problem rather than the symptoms. A problem tree analysis can be helpful here.
2. acknowledging and listing all related issues. They must identify the perceived problems and then divide the complex issues into smaller, more manageable pieces to make it less intimidating and reveal hidden solutions.
3. gathering pertinent information and analyzing the data. The team must collect relevant data from various sources, including interviews with staff and vendors, documentation, existing processes, and stakeholders.
4. validating the data. The business leader must ensure accuracy, reliability, completeness, and timeliness of the facts, figures, and files collected. Utilizing techniques like data visualization, statistics, models, or algorithms to process and interpret the data, leadership can then spot patterns, trends, relationships, causes, and effects from the data.
5. generating and evaluating possible solutions. This involves encouraging creative thinking and exploring multiple perspectives to brainstorm potential solutions. Then the team must consider alternative solutions that may not have been initially discussed. For this, analysts must leverage technology to crunch the data and simulate the options discussed. Stakeholders must think outside the box and consider unconventional solutions, even experimenting with new methods. And they must evaluate the feasibility, effectiveness, and potential risks of each proposed solution.
6. developing and implementing a detailed Plan. This seems logical. The team must outline steps, objectives, milestones, and timelines for implementation. Instead of committing significant resources to one solution, the company should make low-risk “small bets” to test ideas and see what works. Recognizing that solving complex problems is often an iterative process, they must make adjustments based on feedback and results. The team must test, refine and scale the chosen solution.
7. communicating and collaborating with the team. Maintaining open and transparent communication with stakeholders, including clients, throughout the process is key. Leaders might also seek outside expertise or collaborate with others to gain fresh perspectives. In these discussions, it is important to manage expectations, being transparent about the complexity of the issue and setting realistic timelines.
8. monitoring and learning. They will need to continuously assess the effectiveness of the chosen solution and make adjustments as needed. It’s important to take time to reflect on the experience, learn from it, and document findings for future reference.
Clearly, this shows a methodical way of tackling complex, complicated business problems. It’s also a slow process. But sometimes, part of the problem is that there isn’t time to take the slow road. This is especially true if past leadership has ignored a growing concern and wasted valuable time that could have been used to explore options and take small bets to test paths forward.
When a problem is particularly complex, that’s when it’s valuable to try a radically different approach. This is sometimes referred to as “cutting the Gordian knot.” The “cutting the Gordian knot” approach in business is a metaphor derived from the legend of Alexander the Great. He was presented with a complex knot, and instead of trying to untangle it, which would have taken a long time, he simply cut through it with his sword. (Preserving the cord really didn’t matter.)
Business Problems that are Gordian Knots
What kinds of problems might require a different approach? Cybersecurity attacks. Compliance challenges. Marketplace unpredictability. Economic instability. AI and Blockchain technology. Political upheaval. Labor shortages. So how does a company cut through one of these thorny problems?
In a business context, “cutting the Gordian knot” involves a quick and decisive approach. This approach involves taking bold, unconventional action, bypassing the complexities of the problem. Instead of focusing on untangling the knot, focus would be placed on redefining the problem to fit the available solutions or discovering new ways to solve old problems by looking at the core issue. The key is prioritizing immediate action and making bold decisions. Emphasis is on summoning the courage and confidence to take decisive steps when faced with seemingly insurmountable challenges and high doses of risk and fear. The steps to apply this approach in business are far more streamlined.
Current Case in point: Tomatoes
Florida tomato farmers are facing significant challenges due to 2025 tariffs on Mexican tomatoes, leading to price drops and crop losses. The threat of tariffs, even before their implementation, caused Mexican suppliers to flood the U.S. market with tomatoes, driving down prices for Florida farmers. It has led to a price collapse. Florida tomato farmers are now facing a situation where the price of tomatoes has dropped to $3 or $4 per box, while they need around $10-$11 per box to break even. Some farmers are even resorting to plowing over their crops due to the high cost of picking and packing, making it more economical to let them rot. For many of those farm businesses, this could mean bankruptcy. This could also impact other parts of the tomato supply chain, such as distributors, wholesalers, and retailers, as well as restaurants with customers who are used to year-round availability of fresh tomatoes. It might also lead to job losses in the tomato industry in other states like Arizona and Texas, where many warehouses and distribution centers handle Mexican tomatoes. And it could seriously impact the food industry.
Added to the tariff problem is the issue of taste. The reason the US had imported more tomatoes from Mexico than buying Florida-grown tomatoes had to do with taste. Florida tomatoes were considered less desirable than Mexican tomatoes due to differences in growing practices, soil and varieties. Florida tomatoes were frequently harvested green and treated with ethylene gas to ripen for uniform color. This process impacted flavor compared to vine-ripened Mexican tomatoes. Florida varieties were also bred for characteristics like disease resistance and suitability for shipping and processing (e.g., machine slicing for burgers). This also impacted flavor. And Florida’s sandy soil and high humidity present challenges, requiring fumigation to prevent disease and pest issues. Notwithstanding, Florida tomatoes were chosen over Mexican tomatoes in the past because Mexican vine-ripened tomatoes are grown in the summer season. And Florida produced virtually all the fresh-market, field-grown tomatoes in the US from October through June each year, accounting for about 50 % of all fresh tomatoes produced domestically. So if Mexican tomatoes are no longer available and Florida growers go bankrupt, that could drastically affect the food industry. Consider all the items made using tomatoes like salsa, marinara sauce, soups, etc.
Now there’s a Gordian Knot of a problem. How does the food industry and Florida tomato growers solve this problem? Florida tomato growers could improve the quality of their produce by focusing on proactive disease management, selecting appropriate varieties, and implementing proper postharvest handling procedures. Such strategies, combined with ongoing research and adaptation to changing market conditions, could contribute to a more sustainable and successful Florida tomato industry. But that would take time.
So, what does cutting the Gordian Knot of this problem look like? Try an entirely different approach. Grow tomatoes hydroponically. By growing tomatoes hydroponically, it would be possible to cultivate them without soil, using a nutrient-rich solution and a soilless medium. This method offers advantages like faster growth, higher yields, and reduced risk of soilborne diseases. It also allows tomatoes to be grown year-round in Florida and other warm-climate states and reduces farm-to-table time, which would ensure better taste and lower cost. And it allows tomatoes to be grown in areas that aren’t necessarily set aside for agriculture. That slices right through the problem and positions both the farmers and food industry to be able to grow using less water, pesticides, and land, which is sustainable despite increasingly hotter temperatures and unpredictable weather. It is out-of-the-box thinking for a particularly complicated problem.
The next time business is facing a complex, time-sensitive and business-threatening challenge, rather than burying the proverbial head in the sand, try cutting the knot with a fast, radical solution. As the late Steve Jobs, founder of Apple, put it, “Simple can be harder than complex. You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.”
Quote of the Week
“We will make bold rather than timid investment decisions where we see a sufficient probability of gaining market leadership advantages.”
Jeff Bezos, Founder, Amazon
© 2025, Keren Peters-Atkinson. All rights reserved.
