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  • Dan Manning

Creating a Designed Strategy: Thinking @ the intersection of design, creativity, and opportunity

Updated: Nov 2, 2019

(This is the first of a two-part article examining strategy as a designed, decision making framework to help entrepreneurs identify and pursue opportunities that drive towards a common vision of the future.)


Do you have a strategy? More importantly, do you and other decision makers on your team use a strategy to choose which opportunities get a green light and which get a hard pass? The difference between having a strategy and using a strategy is the difference between having a map and using a map. Until you put it to use, it is just a fancy piece of paper.




Throughout my career in the military, I was frequently surprised at bad we are at strategy. When you ask two people about strategy, you get at least 3 answers. For an organization that enforces a dress code and has dozens of offices with the word "strategy" in the title, you'd expect some agreement.


The military isn’t the only organization spending time creating strategies. Corporations, non-profits, entrepreneurs, solopreneurs, sports teams, and universities spend time and resources to roll out “strategic” documents. Despite honest effort and some hard thinking, these strategies rarely live up to expectations.


What about you? Do you see any shift in your daily work when a new strategy comes out? Do you read it? Do you consider the strategy when you are choosing opportunities?


What if we designed strategy to be a useful tool for dynamic decision making to make better, more informed choices pushing the team towards a desired future.


For our purposes, let’s use the following definition of strategy first crafted by a former National Defense University professor: (NB: This definition appeared in a US Army strategy journal and caused a mini-tempest as it challenged the traditional way of thinking. If you feel strongly about another definition, please share in the comments.)


--->Strategy is an organization’s theory of success. <----



Strategic Examples


Here are three examples of strategies designed to pursue an objective while allowing users to choose opportunities. They are taken from three very different contexts…one taken from a leader whose vision included world domination, one from business, and one from a road trip.


Mongolian Empire



Genghis Khan was history’s greatest conqueror controlling an area the size of Africa spanning from the Pacific Ocean to the Danube. His conquests may have caused the deaths of 40 million people, and his impact is still visible in the faces of Central Asians. His victory in the city of Bukhara in 1220, a jewel of the Khwarezmid Empire, was so complete the neighboring city of Samarkand surrendered despite being better defended.


Genghis Khan was born into a culture defined by wars of revenge and conquest. His skill as a fighter and general fueled his rise, and he knew there would be many future opportunities to build not only his legend, but the Mongol Empire. His strategic goal was to win every battle and reap the rewards of every conquest. Many writers add “at any cost” to this aim, but his approach contained more nuance than you might expect from the leader of the Mongol hoards. He was willing to inflict any cost on the enemy, but he aimed to win every confrontation without the loss of a single Mongol warrior…an unachievable aspiration.


Despite the size of his armies, he was often outnumbered, always playing an away game, and often facing enemies entrenched inside fortress walls. How could a band of illiterate, nomadic hunters erase the most powerful empires in the world? Genghis Khan adopted a theory of success that prioritized producing overwhelming fear in his enemies. He understood the most effective way to instill fear is through surprise, so he developed capabilities allowing his armies to appear in unexpected places with unexpected instruments of war.


Mongol warriors were able to move with startling swiftness. Their protein-rich diet, 13th century horsemeat keto, enabled them to ride for days without stopping. Genghis Khan had no foot soldiers, only mounted warriors on horseback. Any dismounted manpower he needed would come from the men he captured along the way. He maintained no supply train back to Mongol territory, but instead fed on horses and looted the rest. Rather than building large, slow-moving siege engines to defeat fortresses, he captured capable engineers who could fell forests and create the catapults and siege towers he would need upon reaching the enemy’s territory.


His forces moved in winter, across deserts, learned to skate on animal bones, preserved food to be reconstituted on the move, passed orders in rhymes to overcome illiteracy, and standardized camp construction down to the arrangement of tools inside the primitive medical tents. Even more surprising, Genghis Khan’s forces may have the most prolific bridge builders in history.

This impressive array of capabilities were developed long before the exact enemy was known but could be brought to bear swiftly and with massive impact to seize whatever opportunities presented themselves.

Snack food empire

Far from the Mongolian steppe, and about 800 years later, Stacy Madison and her co-founder Mark Andrus decided to leave their sociology and psychology professions to start a business. After considering a few options and having their home-kitchen catering service shut down by the health department, they decided to purchase a food cart to sell made-to-order wraps in Boston. Named “Stacy’s D’Lites,” their theory of success included growing a profitable business selling healthy, delicious food.


Their wraps were a hit, but because they were made-to-order, lines at the food cart grew. At the same time, they always padded the order for fresh-baked pita bread—if a wrap cart is out of bread, it is out of business. Mark had the idea to slice the leftover pitas and bake them into chips at night in their home oven to serve the next day.


They gave away the chips to their customers to make waiting in line more tolerable. Soon, their chips became as popular as the wraps. As the Boston weather began to turn from summer into a wicked winter, food cart sales were less appealing. Commercial real estate near their existing customer base was in high demand and costly. Rather than continuing with their wrap business, they saw opportunity in pita chips. After all, their theory of success wasn’t exclusively tied to wrapped sandwiches.


One of their fellow vendors, the pretzel cart lady, offered access to her larger oven and allowed Stacy and Mark to begin to scale their chip making. After a loan, they were able to automate their packaging. As sales increased, they leveraged their demand to get more loans to continue to scale production. Sales to health-conscious stores boosted their revenue and required even larger ovens and factory floor space. In a span of about 10 years, Stacy and Mark grew from a wrap cart named Stacy’s D’Lites to Stacy’s Pita Chips with revenue of $65M per year when it was acquired by PepsiCo.


When their business started, their intent was simply to grow a business. When they started the pita chip business, they aspired to become a quality regional brand. But, at each step, they were on the lookout for opportunities to scale inside a framework prioritizing quality ingredients and healthy food options.


Road Trip

In the summer of 2018, my wife, son, and I made an epic road trip along the Pacific Coast Highway from San Francisco to Seattle. We had airline tickets departing from Seattle on a specific day, but otherwise we had no hotel reservations and no real agenda. Each day we set out driving towards the Emerald City, but we were on the lookout for opportunities.



We used an app called Roadside America to let us know about kitschy roadside attractions and pieces of Americana along the way. Because of the app, we saw a 20-foot tall wooden Sasquatch in Northern California and visited sea lion caves in Oregon. In Washington, we learned about Albert C. Mason, the 1880’s super salesman of Tacoma who, in a rarely matched feat of divergent thinking, came up with 100 promotional slogans to attract new citizens to the growing city (“Neither tornadoes nor hurricanes,” “Lowest Death Rate in the US”). All the while we drew closer and closer to our end goal, and we evaluated sightseeing opportunities based on how far off the direct route they were and the app’s recommendation.


Good strategies should also give a framework to guide decision making. They should be designed to transition from the present to a desirable future condition within a certain timeframe.


The Art and Science of Strategy

Formulating strategy requires both art and science, but current thinking tends to emphasize the analytical over the artistic. As NYU Stern School professor Adam Brandenburger writes in a recent article in the Harvard Business Review, “Strategy professors typically teach students to think about strategy problems by introducing them to rigorous analytical tools—assessing the five forces, drawing a value net, plotting competitive positions.” These tools are common because they are concrete, easy to teach, and lead to objective conclusions. In other words, these tools are the science of strategy.


Conclusions born from this analysis, however, are generally unsatisfying. Brandenburger continues, “Game-changing strategies are born of creative thinking: a spark of intuition, a connection between different ways of thinking, a leap into the unexpected…If we want to teach students—and executives—how to generate groundbreaking strategies, we must give them tools explicitly designed to foster creativity.” In contrast to science, creativity is often assumed to be an inherently subjective, abstract, unteachable talent—everything science isn’t. Strategy-making is a creative act, and design thinking tools are the key to enabling the art of strategy.


Jeanne Liedtka, a Darden School of Business professor, strategist, and design thinker, has explored the intersection of strategy and design for over two decades. Her article, “In Defense of Strategy as Design,” is a powerful examination of the intersection of design and strategy. Despite frequent critiques, there have been few happy marriages of design and strategy.


So, what is design? Finding a unified definition of design is even more difficult than finding consensus on the definition of strategy. In short…design solves problems, but not just. A product, idea, building, or meal that is well designed addresses problems that are not immediately visible. It works within constraints to produce something not only useful, but elegantly tuned to the need and the user. (NB: For a well-designed examination of the subject of design, see this 5 min video of Q&As about design with industrial, and furniture, designer Charles Eames.)


The Nest thermostat is an example of great design. I haven’t touched mine in over a year. It looks great, and it solved problems I didn’t know I had. It learned my family’s temperature preferences and uses a sensor to know when we are home. When we aren’t, it lets the temperature stray to a more energy efficient setting, but it snaps back in time to welcome us home after work. “Unboxing” the Nest was a memorable experience, and I still have the thoughtfully included, perfectly shaped screwdriver. The Nest thermostat also signals to others that I appreciate cool, well-designed products and gives me silent satisfaction when I see it in the background of my favorite television shows. What more could I ask for in a temperature control device?


What is a designed strategy?


Above all, a designed strategy is useful. It unifies action as it establishes a common objective, sets priorities, and guides decision making in an unknowable future. The core of design thinking, and a designed strategy, is the user…in this case, the decision makers who drive the organization forward.

Most strategies, however, are built to serve the needs of the creators, the most senior levels of an organization rather than the people who are the users of strategy, those who make the hundreds or thousands of daily decisions moving the organization in some direction. In large organizations, a designed strategy gives employees the information they need to make the choices the C-suite would make…without giving the CEO the impossible task of predicting the future.


Genghis Khan led enormous armies with up to a hundred thousand warriors on a campaign. Knowing no one leader could command such a force, he divided the army in a decimal system. Ten subdivisions had ten smaller units, and so on, down to each warrior managing a staff of 10 captives. Each of these leaders and subunits had to understand the overall objective, Mongol values, and operational constraints. In short, they had to understand Genghis Khan’s theory of success. Given his brutal legacy, you might imagine he would have been a horrible boss, but history shows while he demanded immediate obedience in battle, he developed empathy with even the most junior troops when developing his strategies and tactics.

Designed strategy guides large organizations, but it is important for small ones as well. As an organization grows, its number of possible futures narrows. Google is unlikely to move into the vegan pet food market, and Ford Motor Company will probably not start building houses. Conversely, Stacy’s Pita Chips was the third incarnation of Stacy and Mark’s entrepreneurial adventure. What started as a personal-sized catering company turned into a sandwich cart, then a privately held pita chip company, and now is part of a multi-national conglomerate.



Entrepreneurs need a designed strategy to discipline alignment towards their desirable future. Stacy and Mark focused on growth and valued high-quality food. Their opportunity selection stayed true to these aims. When the theory of success lacks clarity, businesses stumble. When this goes really wrong, you end up with businesses like Dehart’s Bible and Tire in Morehead, Kentucky.


Creating a Designed Strategy

When employees and team members are a part of strategy making rather than simply an audience for the stone tablets, they are more likely to become “users” rather than “havers.” Liedtka encourages strategy makers to aim for a spirit of “commitment rather than compliance.” As I have mentioned in several other articles, tapping into a person’s intrinsic motivation opens creativity and increases resilience in the face of challenges. When a teammate is committed to a strategy, you get the benefit of their intrinsic motivation.


Opening space for employees to have a voice in strategy design also makes good fiscal sense. In a tight labor market where good employees can quickly find a job with equal pay, employees value more than a paycheck. Max DePree, author of Leadership is an Art, and former CEO of Herman Miller Company, writes:


Contractual relationships cover such things as expectations, objectives, compensation, working conditions,…etc. These are all a part of normal life and need to be there. But more is needed—particularly today when the majority of us who work can properly be classified as volunteers. The best people working in organizations are like volunteers. Since they could probably find good jobs in any number of groups, they choose to work somewhere for reasons less tangible than salary or position. Volunteers do not need contracts, they need covenants.

As DePree also points out, team members are entitled to “a voice, not a vote.” Whether in the military or a business, the authority for a decision can be delegated, but the responsibility is not. Employees expect leaders to make decisions about the future of the organization. Having their voice heard and respected, however, is a reasonable expectation contributing to an environment that encourages (and receives) commitment. If Genghis Khan can connect with the junior ranks, surely you can too.



Finally, the value of strategy-making extends beyond production of a document. Liedtka illuminated the idea of intelligent opportunism, the identification and pursuit of opportunities furthering the intended strategy despite not being a part of (or even envisioned in) the strategy document itself. The process of strategy-making should enable leaders and team members to understand the desired direction of travel while leaving specific route selection to those best positioned to evaluate the bridges when they are reached. Forecasts frequently fail to correspond to reality. Useful strategies bake-in flexibility allowing decisions to be aligned with principles, values, and desired end states without requiring inhuman foresight from the leader.


When strategy becomes real and useful, organizations can debrief decision making against the expectations set in the strategy. Red teams can use it as a standard against which to sharpen specific action plans. Supervisors can provide feedback and mentorship by comparing performance to the expectations and direction of the strategy. In short, a useful strategy is one that is unfolded across the organization revealing increasing levels of detail, nuance, and opportunity. (Thanks again to Jeanne Liedtka for this metaphor.)


When a strategy is intentionally designed, it serves its users with elegance and efficiency. It addresses problems before they are encountered, and its striking clarity blasts away the fluff too often found in foundational strategic documents. As a result, strategy becomes a signpost pointing toward a desired destination rather than a shelved study of one hopeful route to an indefinite future.


A practical guide to designing strategy according to these principles follows in the second part of this series.


Contact me to start designing your strategy today.


Download the PDF for reading offline.




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