Navigating the Shift from Complicated to Complex Problem-Solving

Todd McLees
9 min readOct 2, 2023

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Summary: This article focuses on the OODA Loop — a time-tested framework for decision-making and problem-solving in complex environments. We’ll offer top tips and practical strategies to refine your complex problem-solving skills using this framework as our guide. By the end, you’ll have actionable steps to navigate and thrive in a world that refuses to stand still.

The world has undergone a seismic shift — from merely complicated to profoundly complex. In a complicated world, problems could be solved through expertise and linear thinking. But in today’s complex world, problems are not just puzzles to be solved; they are webs we must navigate. These challenges are multifaceted, interconnected, and often volatile, requiring a new breed of problem-solving skills.

Enter complex problem-solving, a skill set that has moved from the periphery of professional competencies to the core. It’s no longer sufficient to be an expert in a particular domain; you need to be a maestro of adaptability, capable of conducting a symphony of skills ranging from analytical acumen to emotional intelligence.

Understanding the OODA Loop: A Framework for Navigating Complexity

The OODA Loop, which stands for Observe, Orient, Decide, and Act, was initially developed by military strategist John Boyd for combat operations. However, its principles have been widely adopted in various fields, from business to healthcare, as a way to make better decisions in complex and rapidly changing environments.

The OODA Loop is not a linear process but a continuous cycle, emphasizing the dynamic nature of complex problem-solving. It encourages adaptability, quick thinking, and a multi-disciplinary approach to tackling challenges.

Fig.1 – OODA Loop, a Complex Problem Solving Framework

Observe

The first step in the OODA Loop is to observe. Observing involves gathering data from multiple sources to understand the situation at hand. In a business context, this could mean analyzing market trends, customer feedback, and internal metrics. The key is to collect diverse and relevant information to form a comprehensive view of the problem.

Orient

Orientation is the process of making sense of the data you’ve collected. It involves filtering the information, interpreting it, and placing it within the context of your own experiences, biases, and insights. It’s the stage where emotional intelligence and critical thinking come into play, helping you understand the facts and nuances of the situation.

Decide

Once you’ve oriented yourself, the next step is to decide on a course of action. Deciding is where analytical skills are crucial. You need to evaluate the possible solutions, weigh the pros and cons, and choose the best course of action based on the information available.

Act

The final step is to act on your decision. This step involves implementing the chosen solution and observing the results, which feeds back into the first step of the loop. The OODA Loop is iterative; you continue to go through these steps, refining your approach as you gather more data and learn from your actions.

Getting the Most Out of OODA Loops

Now that we’ve laid the groundwork with the OODA Loop, let’s dive into actionable strategies that can help you become a master of this technique for complex problem-solving.

Enhance Your Observation Skills

Tip: Regularly update your data sources and invest in tools that can provide real-time analytics. Observation is the first step in the OODA Loop, and it’s crucial to get it right. The better your observation skills, the more accurate your understanding of the problem will be. Consider using advanced analytics tools that can provide real-time data, and make it a habit to consult multiple sources to get a well-rounded view.

Cultivate Contextual Awareness in Orientation

Tip: Engage in activities that broaden your perspective, such as cross-disciplinary training or cultural exchange programs. Orientation isn’t just about understanding the data; it’s about understanding its context. The more diverse your experiences and perspectives, the better you interpret information. Consider cross-disciplinary training or even cultural exchange programs to broaden your contextual awareness.

Make Data-Driven Decisions

Tip: Use decision matrices or other analytical tools to evaluate your options objectively. When it comes to deciding, nothing beats a data-driven approach. Utilize analytical tools like decision matrices to weigh the pros and cons of each option to ensure that your decisions are intuitive and backed by solid data.

Implement Agile Action Plans

Tip: Adopt agile methodologies to make your action plans flexible and adaptable. The ‘Act’ phase is where the rubber meets the road. Implementing agile methodologies can make your action plans more versatile, allowing you to pivot quickly if the situation changes. That flexibility is particularly useful in complex environments where variables can change rapidly.

Iterate and Learn

Tip: Conduct a retrospective to identify what worked and what didn’t after each OODA Loop cycle. The OODA Loop is a continuous cycle, and each iteration offers a learning opportunity. After you’ve acted, take the time to review the outcomes and understand what worked and what didn’t. This retrospective will feed into your next OODA Loop, making each cycle more effective than the last.

By adopting these tips and strategies, you’ll become proficient in using the OODA Loop and elevate your complex problem-solving skills to an indispensable level in today’s volatile, uncertain, complex, and ambiguous world.

The Illusion of Linear Problem-Solving:

In a world that loves straightforward answers, we’ve been conditioned to view problem-solving as a linear path to resolution. It’s the assembly line model applied to cognitive work: identify the problem, find a solution, implement it, and move on. But this model is a relic, a carryover from an era where problems were less dynamic and more isolated.

The truth is, we’re not dealing with assembly lines; we’re navigating mazes. In a complex world, problems are rarely isolated events that can be neatly solved and put away. They’re interconnected, evolving, and often laden with unforeseen consequences. The linear model fails because it doesn’t account for this complexity. It’s like trying to solve a Rubik’s Cube by only turning one side.

So, if you find yourself stuck in the “assembly line” mindset, it’s time to break free. The world has moved on to a more intricate dance of cause and effect, and your problem-solving approach needs to keep pace. The OODA Loop, as we’ve discussed, offers a more cyclical and adaptive model better suited for the world we live in today.

The Case of the Failing Factory: A Real-World Example of Complex Problem-Solving

Imagine a factory where production has inexplicably slowed down. The immediate reaction is to look at the machinery. Is it outdated? Is it malfunctioning? The management’s first instinct is to invest in new, state-of-the-art equipment. Millions are spent, but the problem persists.

Enter a consultant who decides to take a different approach. Instead of focusing solely on the machinery, she observes the entire ecosystem of the factory — from the workers on the floor to the supply chain logistics. She employs the OODA Loop: observing the workflow, orienting by talking to employees, deciding on a few small-scale tests, and then acting on them.

The revelation was surprising. The slowdown wasn’t due to machinery; it was a human issue. Workers were unclear about new protocols, leading to inefficiencies and mistakes. The consultant recommended a reorientation of training programs and better communication channels. Within weeks, production ramped up, exceeding previous levels.

This case study serves as a vivid illustration of why complex problem-solving is so crucial. The factory’s management was stuck in a linear mindset:

  • Identify the problem (slow production).
  • Find a straightforward solution (new machinery).
  • Implement it.

But, the consultant saw the problem as a web of interconnected issues, requiring a more nuanced and adaptive approach. She didn’t just solve the problem; she redefined it, turning a costly failure into a resounding success.

The lesson here is clear: in a complex world, the first solution that comes to mind is often not the right one. It takes a cycle of observation, orientation, decision-making, and action — a continuous loop — to solve the problems worth solving.

A Symphony of Skills: Why Complex Problem-Solving is More Than Just a Solo Act

In the age of specialization, we’ve been trained to believe that expertise in a single domain is the pinnacle of professional achievement. But when it comes to complex problem-solving, being a virtuoso in one field isn’t enough. You need to be a conductor, orchestrating a symphony of skills that harmonize to create a more resonant solution.

Think of it this way: a violinist may be a master of melody, but without the bass of the cello, the rhythm of the percussion, and the harmony of the woodwinds, the music lacks depth. Similarly, complex problem-solving isn’t just about analytical prowess; it’s about integrating a range of skills — emotional intelligence, creativity, and critical thinking — to create a more nuanced understanding of the problem.

Research backs this up. A study from the World Economic Forum lists complex problem-solving as the top skill needed for the future. Still, it also highlights the importance of coordinating with others, emotional intelligence, and critical thinking. These aren’t just add-ons but integral parts of the complex problem-solving process.

So, if you’re still clinging to the notion that your specialized skill set is your only asset, it’s time to expand your repertoire. The challenges of today’s world don’t exist in silos; neither should your skills. As we’ve explored, the OODA Loop is a framework that encourages this kind of multi-disciplinary thinking, urging you to observe from multiple angles, orient through diverse perspectives, decide with analytical and emotional acumen, and act with agility.

In a more interconnected world than ever, complex problem-solving is less a solo act and more a symphony — a harmonious blend of diverse skills that elevates the entire performance.

Actionable Strategies for Complex Problem-Solving

You’ve understood the theory, seen it in action through a case study, and recognized the need for a multi-disciplinary approach. Now, let’s get down to the brass tacks — how do you improve your complex problem-solving skills?

Reframe the Problem

Tip: Before diving into solutions, question the problem itself. Is it really what it appears to be? Use techniques like the “5 Whys” or SWOT analysis to dig deeper into the issue.

Diversify Your Information Sources

Tip: Don’t just rely on familiar sources in the Observe phase of the OODA Loop. Expand your horizons by consulting experts from other fields, reading research papers, or even engaging with social media debates relevant to the problem.

Develop Emotional Acuity

Tip: Emotional intelligence isn’t just for HR seminars; it’s a vital part of the Orient phase. Practice active listening and empathy, especially when gathering qualitative data from team members or stakeholders.

Use Analytical Tools

Tip: In the Decide phase, employ decision-making frameworks like decision trees or cost-benefit analyses to evaluate your options objectively.

Be Agile in Implementation

Tip: Adopt agile methodologies for the Act phase. Start with a Minimum Viable Solution and iterate based on feedback and results.

Learn and Iterate

Tip: After each OODA Loop cycle, conduct a retrospective. What worked? What didn’t? Use these insights to refine your approach for the next cycle.

By incorporating these practical strategies into your problem-solving toolkit, you’re not just tackling issues head-on but evolving your approach to challenges. You’re turning them into opportunities for innovation and growth. And in a constantly shifting world, that’s not just a skill — it’s a superpower.

Seeing Problems as Opportunities

In a world that often feels like it’s spinning faster than we can keep up, the ability to solve complex problems isn’t just a skill — it’s a necessity. From the factory floor to the boardroom, we’ve seen that the most effective solutions often come from reframing the problem, questioning our assumptions, and bringing in diverse perspectives.

But let’s not forget: complex problem-solving isn’t a solo act. It’s a symphony of skills, from emotional intelligence to creativity, that allows us to find solutions and redefine problems. It’s about doing things right and doing the right things.

So, the next time you face an insurmountable challenge, remember: it’s an opportunity in disguise. An opportunity to innovate, collaborate, and demonstrate the uniquely human skills that machines can’t replicate.

By embracing the OODA Loop and the practical strategies we’ve outlined, you’re not just preparing for the challenges of today but pioneering the solutions of tomorrow. In a world of uncertainty, that makes you not just a problem-solver but a pathfinder — a true leader in a world that desperately needs them.

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Todd McLees
Todd McLees

Written by Todd McLees

humanskills.ai Founder | Bridging Humans & AI in Higher Ed & Enterprise | Creator of AI Agility | HBR Contributor | Global Speaker | Future of Work & Learning

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