Library/Leading with Strategic Thinking
Leading with Strategic Thinking book cover - Leapahead summary
Listen to Key Point 1
0:000:00

Leading with Strategic Thinking

Aaron K. Olson and B. Keith Simerson

Duration43 min
Key Points9 Key Points
Rating4.8 Rate

What's inside?

Discover the art of strategic leadership and learn how to make better decisions, manage risk, and lead your team to success.

You'll learn

Learn1. What's your leadership style and when to use it?
Learn2. Wanna make smarter choices? Think strategically!
Learn3. Learn the tricks to create and use killer strategies.
Learn4. Leading a team to hit big goals - here's how.
Learn5. Why being adaptable and tough matters in leadership.
Learn6. Use your leadership style to boost your company's success.

Key points

01Why Strategy Is Everyone's Daily Business

Are you tired of hearing the word "strategy" thrown around in meetings like a buzzword that nobody actually understands? We often treat strategy as if it is a mystical document, drafted once a year during an expensive executive retreat, only to be shoved into a desk drawer and entirely forgotten by February. Olson and Simerson open their book by challenging this frustrating reality head-on. They argue that strategic leadership is not a job title, a yearly event, or a static document. Rather, it is an active, continuous process that every single professional must engage in daily. The authors beautifully demystify the concept by splitting it into two distinct but deeply interconnected halves: the cognitive process of strategic thinking and the behavioral process of strategic leadership. Understanding this vital distinction is the very first step to transforming how you operate in your career. Let us break down what that actually means in the real world. The cognitive side is all about what happens inside your head. It involves how you gather information, how you recognize hidden patterns in a sea of data, and how you mentally frame complex problems. On the other hand, the behavioral side is what the rest of the world sees. It is how you communicate those brilliant ideas, how you influence your peers to buy into your vision, and how you actually execute the plan. You can be an absolute genius at the cognitive part, dreaming up the most innovative business models the world has ever seen, but if you lack the behavioral leadership skills to inspire a team to build it, your brilliant strategy is nothing more than a daydream. Conversely, if you are a charismatic leader who executes flawlessly but lacks deep strategic thought, you might just be leading your team incredibly efficiently off a cliff. The magic happens when you combine both. Consider a typical mid-level manager working in a bustling marketing department. She spends her days approving budgets, mediating minor team conflicts, and ensuring that weekly email campaigns go out on time. She is undeniably busy, but is she being strategic? The authors would argue that unless she is actively connecting those daily tasks to the broader, long-term goals of the organization, she is merely stuck in an operational grind. Operational management is about ensuring things are done right; strategic leadership is about ensuring the right things are being done. When you begin to ask yourself "why" we are doing this campaign instead of just "when" it is due, you are taking your first steps into strategic thinking. You stop being a passive recipient of orders and start becoming an active architect of your organization's future. The book introduces a powerful realization: the environment we work in today is vastly different from the one our grandparents navigated. We operate in a world defined by volatility, uncertainty, complexity, and ambiguity. In the past, a company could coast on a single good strategy for a decade. Today, a strategy might be obsolete in six months due to a new technological disruption or a sudden shift in global markets. Because the pace of change is so incredibly rapid, organizations can no longer afford to have only a handful of senior executives doing all the thinking. They desperately need people at every single level of the company to act as strategic sensors, picking up on weak signals in the market and adjusting their daily workflows accordingly. To truly embrace this mindset, you have to let go of the limiting belief that you do not have enough authority to be strategic. You do not need a C-suite title to initiate a strategic shift. You simply need the courage to look beyond your immediate silo. When you start observing how your specific department interacts with sales, how sales impacts customer service, and how customer service drives product development, your perspective widens dramatically. You begin to see the invisible threads that hold the entire business together. This wider perspective allows you to anticipate problems before they occur and propose solutions that benefit the entire ecosystem, rather than just optimizing your tiny corner of the world. Olson and Simerson emphasize that stepping into this role requires a fundamental shift in your professional identity. You must transition from being a mere problem solver to becoming a problem finder. Anyone can put out a fire once it is blazing, but a strategic leader walks around smelling for smoke. They actively seek out inefficiencies, question outdated legacy processes, and constantly ask if there is a better way to deliver value. As we dive deeper into the specific frameworks provided in the book, keep this foundational idea in mind: strategy is not something that happens to you. It is something you do, every single day, through the choices you make, the questions you ask, and the connections you build.

02Thinking in Systems to See the Whole

Have you ever tried to fix a frustrating problem at work, only to realize that your brilliant solution accidentally created three brand new problems somewhere else? This incredibly common workplace phenomenon happens because we are culturally conditioned to think in straight, linear lines. We see a direct cause and a direct effect. However, business organizations are not simple machines; they are complex, living ecosystems. To lead strategically, Olson and Simerson insist that you must completely upgrade your cognitive operating system to embrace what is known as systems thinking. This chapter is all about moving your perspective from the isolated trees to the massive, interconnected forest. Systems thinking is the profound ability to understand how different parts of a whole interact with, influence, and depend on one another. When a traditional thinker looks at an organization, they see separate departments: marketing, finance, human resources, and operations. When a systems thinker looks at that exact same organization, they do not see departments at all; they see flowing streams of information, interconnected feedback loops, and complex relationships. They understand that cutting the budget in the training department today will inevitably lead to a higher rate of customer complaints in the sales department six months from now. Everything is connected, and treating any single part of the organization in total isolation is a recipe for strategic disaster. To truly grasp this, we must explore the concept of mental models, which the authors highlight as the invisible lenses through which we view the world. Your mental models are built from your past experiences, your education, and your biases. They act as cognitive shortcuts, helping you process massive amounts of daily information quickly. However, these models can also become dangerous blinders. If you grew up in a strict, top-down corporate culture, your mental model of leadership might be heavily authoritarian. If you transition to an agile tech startup, that old mental model will cause you to misinterpret situations and make terrible strategic choices. The best strategic thinkers are intensely aware of their own mental models. They regularly pause to ask themselves, "Why do I believe this is the right approach? What assumptions am I making that might be entirely wrong?" Let us look at a practical, everyday example to cement this idea. Think about a software development company that is suddenly facing a severe drop in customer renewals. The linear thinker immediately blames the sales team for not pushing hard enough and demands that they increase their daily cold calls. The systems thinker, however, steps back and looks at the entire board. They notice that the engineering team was recently incentivized to release software updates faster. By digging deeper, they discover that this push for speed caused a massive increase in software bugs. The customer service team was subsequently overwhelmed and unable to respond to complaints quickly, which made the customers furious and caused them to cancel their subscriptions. The root cause of the sales problem was actually an engineering policy. If the company had just punished the sales team, the problem would have only gotten worse. Olson and Simerson provide brilliant guidance on how to develop this holistic vision. One of the most effective techniques is to actively seek out diverse perspectives. You cannot see the entire system if you only ever talk to people who do the exact same job as you. You need to intentionally build relationships across different departments and different levels of seniority. Go have coffee with the folks in accounting. Ask the frontline customer support agents what their biggest daily headache is. When you gather these diverse puzzle pieces, the grand picture of the system begins to reveal itself to you. Another crucial element of cognitive strategy discussed in the book is the ability to recognize patterns over time. Short-term thinkers react to isolated events. A bad quarter is just a bad quarter to them. Strategic thinkers, however, look for trends. They analyze data over years, not just months. They ask themselves if this current crisis is a freak anomaly or part of a larger, recurring cycle. By identifying these long-term patterns, you can move from a state of constant reaction to a state of calm anticipation. You begin to skate to where the puck is going to be, rather than chasing it where it currently is. Developing systems thinking takes deliberate practice and immense patience. It requires you to slow down your natural impulse to jump immediately to a solution. You must learn to sit comfortably in the uncomfortable space of ambiguity, exploring the varied nuances of a problem before deciding on a course of action. When you master this cognitive skill, you become an incredibly powerful force in your organization. You stop fighting the symptoms and start curing the disease. You become the person who can step into a chaotic, confusing situation, clearly identify the hidden levers of power, and calmly confidently point the way forward.

Leading with Strategic Thinking book cover - Leapahead summary

Continue reading with LeapAhead app

Full summary is waiting for you in the app

03Leading Strategic Execution with Precision

04The Hidden Power of Strategic Influence

05Navigating Chaos Through Strategic Adaptation

06Igniting Growth Through Strategic Innovation

07Developing Your Personal Strategy Toolkit

08Conclusion

About Aaron K. Olson and B. Keith Simerson

Aaron K. Olson is a global leadership and talent management expert, currently the Chief Talent Officer at Aon. B. Keith Simerson is a management consultant and author, specializing in leadership development and organizational effectiveness. Both have extensive experience in executive education and consulting.