4 Dynamics of Strategic Enterprising


Strategic Enterprising is the practice of the entrepreneurial adventurer engaging in a new undertaking or enterprise. It is not a new concept by any means but the regular exercise of investing in big ideas by venture capitalists, entrepreneurs, and Fortune 500 corporations endeavoring to endow the latest ideas and emerging trends in the marketplace. The word “enterprise” simply means, “to undertake or take in hand.” The abstract meaning of the same word is the “readiness to undertake challenges, or the “spirit of daring.”[i] When a person is referred to as “an enterprising young man,” it conveys a person’s resourcefulness or initiative to undertake a grand project. For example, contemporary enterprisers are people like Mark Zuckerburg, the founder of Facebook, Jack Dorsey, the co-founder of Twitter or Andrew Mason, the creator of Groupon. However, you don’t’ have to be world renown to become an enterprising person. It starts by taking a simple idea and turning it into a tangible product or service used and enjoyed by many. Anyone can become an enterprising individual; you just need to have a unique idea or talent that can be advanced with an effective strategy.

Strategy, for instance, was originally branded in the year 1810 as the “Art of a General.” Some background of the word “strategy” would help at this point. Before a General engaged an enemy in battle he would take a position on high ground overlooking the theater of battle to observe the arrangement of the opposing side and to dictate his stratagem to his Lieutenants. From his vantage point the General could see the opposing army’s tactics and maneuvers in real time so he could counter their whit with his own ingenuity. Viewing the battlefield and sourcing it from the high ground was a way to gather data, better known today as ‘intelligence gathering’, which enhanced decision-making and outcomes. These tactics, along with one’s knowledge from previous engagements, and taking calculated risks were some of the critical elements of the “art of a General”.

In today’s world, in the realm of business and commerce, strategic enterprisers are like the Generals on the battlefield, which require different strategic objectives and tactics more conducive to the marketplace. I refer to them as The Four Dynamics of Strategic Enterprising:

1. Strategic Thinking – Optimizing acumen while assessing your assets
Acumen and assessing your assets are the first two priorities of Strategic Thinking. Let’s start with acumen. Acumen is the intelligence shaped by three elements, your:
a. Hindsight – the knowledge, understanding and wisdom acquired through your past experiences.
b. Insight – attending to your intuition (promptings, feeling, spirit-sense, sixth-sense, hunch, instincts, inner-voice, etc.) at the present moment.
c. And, fostering skills in strategic foresight, or what you perceive in your immediate environment, and how you interpret this incoming stimuli in your environment to gain certain advantages.

Cultivating personal acumen is fundamental during the initial phases of strategic thinking. A better way to gain acumen is to tap into the accumulative intelligence of many advisors, a concept better known as collaboration. King Solomon, the wisest of all men, once quipped, “Surely you need guidance to wage war, and victory is won through many advisers.”[ii] Acumen is improved through the collective intelligence of a team, for the purpose of defining, honing and solidifying a winning strategy. A masterful leader exerts influence for the purpose of transformation through collaborative effort.

A second aspect of strategic thinking is assessing your assets. Your assets will consist of your talent pool and the available resources or ‘tools’ to get the job done. First, a strategist must consider their collective team’s talent, which is essential in this initial phase. In this phase you must assess the strengths and weaknesses of your team, and rearrange your team members in a way to acquire optimum results; perhaps sifting or shifting staff from one department to another. Second, you should procure the necessary resources to make your plan a success. Just before entering the Promised Land, Joshua commanded his people, “Prepare provisions for yourselves, for within three days you will cross over this Jordan.” Honing acumen through collaborative effort, assessing your talent pool and resources are fundamental practices of Strategic Thinkers.

2. Strategic Planning – Arranging your assets and considering your approach
If Strategic Thinking is devising strategy through the combined acumen of a team and how a person uses that information and their talent pool, then the second phase is simply designing the blueprints of the plan. Strategic Strategic-PlanningPlanning is the ability to arrange one’s assets to strengthen the plan then designing a strategic approach for winning. First and foremost, a leader must consider the arrangement of their assets. Clinical Psychologist Dr. Henry Cloud notes, “It’s about leading the ‘right people’, empowering them to find and do the ‘right things’ in the ‘right way’ at the ‘right times.’ This is what will bring a real plan to measured results.”[iii] In the classic book Good to Great, Jim Collins says, “…to build a successful organization and team you must get the right people on the bus.” His research shows that great companies and organizations do this. They get the right people and arrange them strategically in the right seats.[iv]

Another core item in Strategic Planning is considering your approach. The method is just as important as the timing of your launch. Your approach is simply creating a dynamic marketing strategy that shifts public opinion, and acquires a new consumer base, which manifests to an upswing in profit. In other words, communicate your optics effectively, and gather tangible metrics early on. Here’s an sample of what I mean:

Samsung has dethroned its California-based rival to become the world’s top Smartphone maker… Recent Smartphone launches have lost something of the glamour and excitement that surrounded the early (Apple) iPhone releases, in part because they are seen as offering incremental technology upgrades rather than breaking new ground… The S4s features include a high-definition, five-inch – 12.7-centimeter screen, enhanced picture-taking capabilities and the capacity to translate to and from nine languages… Its release has been preceded by a massive promotional campaign (a lunch strategy or approach) — from the glitzy launch in New York to lighting up the sails of Sydney’s iconic opera house on Tuesday night with images shot by ordinary Australians (Optics). Samsung — the world’s largest technology firm by value and also the top handset maker — has boasted stellar sales growth, setting new records for operating profit in every single quarter of last year (Metrics).[v] [italics mine]

Did you notice the marketing genius (the vision or optics) with tangible results in the marketplace (the metrics of Samsung’s Smart iPhone). Your approach, methods and timing, are a critical part of your launch strategy.

3. Strategic Execution – Taking action and being fully aware of oncoming stimuli
Strategic Execution is the implementation phase after you have had your strategic meetings in the ‘war room’ with your staff. In basic form, this phase of your plan is the ‘boots on the ground’, where your team members execute the plan or take action. The original meaning of the word “execution” was “an action of carrying something out.”[vi] This ‘carrying out’ brings about initial outcomes; desired or undesired. If desired outcomes are achieved you continue affirming these actions. If undesired ones emerge, you must take correction action early on to avoid mediocre results and shift toward better ones. 

Being ‘aware’ of oncoming stimuli and responding appropriately to its meaning is an art in itself but critical for capturing early momentum and strategic advantages. Where there is an action there is a reaction. Allow me to explain: Let’s take an analogy from the initial kick off of the Super Bowl to start the game. The defense is lined up ready to kick off the ball, the fans stand to their feet in great anticipation. As the kick is initiated the audience holds its breath momentarily as the ball glides in the air. The football is then caught and the offensive team engages its defensive rivals on the field. Simultaneously, the fans jeer and cheer depending on the dynamics on the field, as they respond to the clashing forces on the Gridiron. If you were to close your eyes for a moment, you can gage who is having the advantage on the field by what side of the field is getting more cheers. Is it the offensive team running the ball through a defensive wall capturing a strategic advantage, or has the runner been snubbed on the 10-yard line energizing the defensive team? Let’s continue my analogy in the next and final phase called Strategic Operations.

4. Strategic Operations – Managing awareness and making crucial adjustments
During the transition of players on the field, the special teams return to the sidelines while the regular players march onto the field to take their positions. The coaches on the sidelines are in deep communication with the coaching staff in the sky-booths above. Together they are receiving and calculating the data from the previous events on the field and adjusting their tactics. What they are doing is taking into consideration the momentum dynamics created by the initial play on the field. Momentum is crucial to have on one’s side; once lost it takes time to regain. In this phase one must manage one’s awareness then make critical adjustments to the initial strategy, which requires real time observation, quick intelligence gathering, and recalculating the next move. The objective is to stay on offense, and put points on the scoreboard; the goal is to win and win big. Strategic Operations happen in real time, which is why managing awareness and adjusting your plan are two critical elements of this phase.

A Strategic Enterpriser understands the four dynamics of Strategic Enterprising. Each phase provides a crucial element for the overall strategy to take hold and achieve its desired results. The first two phases are about weaving your thoughts into a winning plan. The final two phases are about executing and moving operations forward in real time. A Strategic Enterpriser has each phase in mind all the time, and makes the necessary adjustments to the plan to achieve his or her intended outcome.


[i] Etymology Online Dictionary: Enterprise.  http://www.etymonline.com/index.php?allowed_in_frame=0&search=enterprise&searchmode=none, accessed on 4-16-13.

[ii] Proverbs 24:6 (NIV)

[iii] Cloud, Dr. Henry (2013), Boundaries for Leaders. HarperCollins, New York, NY., pg. 3.

[iv] Get the Right People on the Bus by John Gordon; http://www.jongordon.com/article-gettherightpeople.html, accessed April 24, 2013.

[v] Samsungs Galaxy S4 to Bite Fresh Chunk from Apple Market Share. Mybroadband; Tech News. http://mybroadband.co.za/news/smartphones/76370-samsung-galaxy-s4-to-bite-fresh-chunk-from-apple-market-share.html , accessed on April 24, 2013.

[vi] Etymology Online Dictionary: Execution. http://www.etymonline.com/index.php?allowed_in_frame=0&search=enterprise&searchmode=none, accessed on 4-24-13.

Circle and Dot Training: Enlarging Your Awareness Capacity


A “dot” is a person/employee with a very limited awareness capacity.

A “circle” is a person/employee who is fully aware of his or her working environment, and covers more ground within their scope of awareness.

During a road trip to Los Angeles I witnessed a “dot” in action. I stopped at a nationally known coffee house for a cup of joe. Instead of going through the drive-thru I decided to stretch out my legs a little, so I went inside. As I walked across the parking lot I noticed an employee sitting outside perhaps on his fifteen-minute break. Next to him I noticed two garbage cans filled beyond capacity, overflowing with garbage. The area around him was littered with trash. It was so bad I had to step around, and over some of the garbage to get into the store. I almost said something to the young man about the litter around him but I kept it to myself, only to see what he would do. I wanted to see what type of employee he was; a dot or circle. Was he really aware of his surroundings. After I purchased my drink I sat down keeping a watchful eye to see how he would respond to his environment. After his break he got up, and went behind the counter to assist the customers waiting in line, which is commendable and perhaps company protocol, which probably states something like, “After your break you must go back to work.” On my way out the door I made a comment about the garbage overflowing outside and continued on my journey. My point about this story is simple; the employee was totally unaware to the garbage scattered all around him or was he? I thought to myself, “Now there’s a dot!” Someone who does only what is required in his job description, instead of going above and beyond the call of duty.

A Bourne Example

A great example of a circle is found in the movie Bourne Identity starring actor Matt Damon, who plays CIA Agent Jason Bourne. Jason Bourne is very much aware of his surroundings since he was trained to “think and act” like a circle during his initial training as a CIA agent. There is a part in this movie where he is sitting in a restaurant with his gypsy female counterpart trying to make sense of his life, after a lapse of memory during a secret mission. At the restaurant he is somewhat confused and does not seem to remember who he is at the moment, somehow he is extremely aware of his surroundings. For some reason he seemed to know:

  • The license numbers of all six cars parked outside the café.

  • The waitress is left handed.

  • The guy sitting at the counter weighs 215 lbs. and knows how to handle himself.

  • The a gun may exist in the cab of the grey truck parked car outside the restaurant.

  • And, that he could run for so many miles in the high, cold altitude before his hands started to shake.

At the moment Bourne seems confused and doesn’t seem to know why he knows these things. What he does not know at the moment is the training he received as a CIA agent made it possible for him to possess such extraordinary awareness. In sum, he is operating like a circle – he is aware of many details in his environment that the common person would not know or care about knowing.

Engage, Experience and Expand Your Awareness

I first learned to think like a circle in a part time job that I held during my college years as a Loss Prevention Agent for a large merchandise chain. This occurred before retail stores installed the cameras you see in many stores today. In this job I learned to develop and use my skills of observation, intuition and follow-through. During my training I learned to read my environment, enlarge my scope of vision and look for certain traits of a typical shoplifter. Over time I gained more experience by discerning with a high level of accuracy a shoplifter’s shopping patterns and behavioral profile. I learned “the way of a circle” and how to expand my awareness zones. I got so good at detecting shoplifters I soon started to locate professional shoplifters. These professional shoplifters were really crafty. They are swift and make themselves undetectable by dressing, acting and blending in as clean cut citizens. They think and act very much like a circle themselves. This is why they get away with so much merchandise because they take the time to study and observe their environment. They will often come in to scope out an area of the store and buy something at a low price. During this time they are checking out the weak areas of the system by examining employee working patterns, mainly those employees who think and act like dots. After the experienced shoplifter has scoped out the land he or she will return within a few days. When they return they know exactly what they want ahead of time (they are not impulse shoplifters). They have a plan and execute it very well, right up until they meet someone who thinks more like a circle.

Many years after working in Loss Prevention I was at a nationally recognized bookstore sipping on some coffee and enjoying a conversation with my friends. As we sat at the coffee shop I noticed a young man at the magazine rack. He looked suspicious so I kept a watchful eye on him without alerting any of my friends. All of the sudden he turned his back toward the coffee shop where I was sitting. He looked around to see if anyone was watching, and stuffed a magazine down the front of his pants and covered the merchandise over with his shirt. Since he was already near the exit door it took just a few steps and he was out the door. I told my friends what just took place, and asked one of them to accompany me outside. Once outside I called out to the young man and asked him to give me the magazine that he had hidden underneath his shirt and pants. At first he denied it but when I told him that I was just interested in retrieving the magazine he relented, and took the concealed item in his clothing and handed it to me. As an experienced Loss Prevention Agent I was trained to look beyond my immediate surroundings to the larger area around me (circle thinking). I was trained to think and act like a circle, therefore, I became one.

What will it take for you to grow your awareness in the workplace? Can you sense things in your environment before anyone else does? What do you do with this information?

Are you a “dot” or a “circle”?

Organizational Intelligence: Stay Connected to Your Business Web


Part III of III

Stay Connected to Your Business Web

Your business operates among a web of networks within and without the organization. Your internal web consists of various departments, a system of reporting and accountability, and employees with varying degrees of experience, knowledge and education. Your external web is made up of vendors, shareholders and consumers who also may interact with your competitors and other related enterprises. As you become more intimate and connected to the entire web you begin to sense the slightest changes within your field of relationships. According to author Mary Beth O’Neil,

When anything comes in contact with a spider web, anywhere on its surface, the whole web moves… so it is with an interactional force field established between two or more people. It has its own anchor points, resiliency, and breaking point, and it is most often invisible to the members within it. When anyone in the field moves, all members feel the effect, though differently based on their positions.”[1]

When you become more familiar with your internal and external business webs you become more sensitive to slight movements, and their effects upon your business.

In the opening story in this article at what point should Bob have felt change in his environment? Could it have been the moment he sensed the missing river? Remember he had been there several times before with his father. At this point he should have stopped and asked himself, “Something isn’t right here. Let’s regroup.”

Back to Bob

If Bob had detected and thought through the changes in his environment early and learned to use this information, he probably would have made better decisions and avoided an embarrassing trip. Some environments do not stay the same within time; they change, while others stay the same. Therefore, we must remain on constant vigil or else learn life’s lessons the hard way. What could Bob and his companions have done differently? It’s easier to gain insight from hindsight but it’s even better to develop foresight; insight fostered by perception and knowledge. Therefore, learning how to learn is the key to increasing intelligence capacity, which must become a priority for every organization. A “winging it” approach simply won’t help you survive through the unexpected changes in your business environment.

What can you learn about Bob’s story? Go to link>>> (See Part I of III)

The better question is – Are you Bob?


[1] O’Neil, Mary Beth. Executive Coaching with Backbone and Heart. John Wiley & Sons; San Francisco, CA. 2007, pg. 49.