To Woo Or To War - When Should An Entrepreneur Fight, Flee or Flirt?

“Fight or flight?” Nothing is more elemental to an organism’s survival than knowing when to run and when to defend itself. In which instances should a creature pick a battle and make a stand, and when should it retreat to fight another day?
Entrepreneurs often face a similar quandary, with the added wrinkle that sometimes it makes more sense to “flirt” rather than run or fight. In fact, startups, given their limited ability to effectively fight or flee, often must play nice when threatened. As such, rather than deciding between “fight or flight,” the more appropriate question for an entrepreneur is, “When should I fight, flee or flirt?”

As with most business dilemmas, there is no dogmatic response that can be uniformly applied to every situation. Each threatening instance must be evaluated in light of your resources, the criticality of the threat and the probability that you could: survive a fight, escape by flight, or establish an ally by flirting.

Fortunately, there are two excellent books that address the yin and the yang of this fundamental issue: Sun Zi’s The Art of War and G. Richard Shell and Mario Moussa’s The Art of Woo.

  The Art of War (War) and The Art of Woo (Woo) do not attempt to instruct entrepreneurs as to which business situations merit battle and which are better addressed diplomatically. However, each book does provide effective strategies for each approach, once you decide whether to fight, flee or flirt. When read in tandem, these works are particularly informative, as they highlight that, just as good management and effective negotiating skills are highly situational, so is the decision of how to best respond when threatened.

The Art of War Redux

War was written during the 6th century BC by Sun Zi (also spelled “Tzu”), a legendary general and philosopher. Like many effective tools, War has been over-applied to too many disparate business issues. Its most ardent champions notwithstanding, War is no panacea. Even so, despite its overexposure at most business schools and within Big Dumb Companies (BDCs), War does offer entrepreneurs a number of effective negotiation, corporate strategy and leadership lessons.

At the risk of oversimplifying Mr. Zi’s overall message, a few of the book’s most entrepreneurially relevant points include:

Victory Without Battle - “Those who render others’ armies helpless without fighting are the best of all.”

As described in Competing From The Fringe, there is no reason to alert a BDC that you are at war with them. The more subtle and humble your engagement, the longer it will take for the BDC to react. If executed properly, the war will be won before the BDC fires a shot in your direction.

Deception and Concealment - “A good merchant hides his treasures and appears to have nothing.”

As discussed in Corporate Creed, entrepreneurs are well served to always conduct themselves in a forthright and honest manner. The one exception is with respect to your interactions with competitors – retain your honesty but drop your forthrightness. Just as a quarterback attempts to thwart the opposing team with a fake handoff before throwing a pass, you should keep your competitors guessing about your future plans and true intentions.

Flee To Fight Another Day - “If your enemy has superior strength, evade him.” Ensure your survival by directly engaging your enemy only when victory is assured. If you have any doubts about your ability to win a battle, you should,"... prevent the enemy from engaging … (you by) throwing something odd and unaccountable in his way.”

This could be in the form of a new go-to-market strategy, an alliance with a large partner or some other strategic move, which might divert your enemy’s attention and prevent him or her from attacking you head-on.

There is no excuse to not read War, as it is brief, easily digested and available for free at Unfortunately for Zi’s heirs, War fell out of copyright protection over 2,500 years ago.

Woo Is Me

Woo was written as an explicit contrast to the venerable War. Over the course of the book, the authors describe six distinct channels of persuasion and five persuasion styles. Each persuasion style is portrayed by recounting the exploits of a successful tactician of the style.

The authors also discuss two additional factors that characterize an individual’s persuasion style: (i) the “volume” or aggressiveness by which ideas are put forth, and (ii) their proclivity to be self-oriented or service-oriented toward others.

Rather than just passively reading about these various styles, the Woo authors also give you the opportunity to determine your persuasion style, by completing a series of straightforward surveys.

I found the survey results enlightening. As you can see from the following schematic, my non-scientific, inherently self-serving survey responses placed me between “Driver” and “Promoter” status. Before I began the survey, I had assumed I would be solidly classified as a “Driver,” a decisive style that is well-suited to the startup world – just ask Andy Grove.

I challenge you to also take the Woo survey and see where you reside on the continuum of persuasion styles.

Compare And Contrast

Surprisingly, a number of similarities become evident when War and Woo are compared, including the following lessons applicable to entrepreneurs:

  1. Know yourself, your audience/enemy and your terrain
  2. Evaluate relationships before engaging with friends or foes
  3. Align soldiers’/colleagues’ interests with your own
  4. Wield the authority ceded to you
  5. Secure your commitments
  6. Win without fighting

Despite the books’ common messages, they also offer the reader strikingly different advice with respect to several key points, as shown in the following table.

The Art of War

The Art of Woo

Rely on force Rely on influence and persuasion
Do not repeat tactics which resulted in past victories Be consistent
Deceive your enemy Persuade your enemy through open and honest communications
Make decisions in an authoritative manner Make decisions based upon the input and approval of multiple stakeholders

Life During Wartime

Can Woo and War strategies simultaneously coexist? Certainly. Trade Associations are routinely comprised of ardent competitors who combine forces to thwart a common, external threat, such as adverse legislation, onerous regulations or a market incursion from an emerging technology.

A more dramatic example of Woo and War cohabiting occurred during the trench warfare of World War I. The Allies, led by the United States, had far more soldiers, equipment and other lethal resources than their German enemy. As such, the Allies’ War strategy was simple - engage the enemy daily and slowly win by attrition. This was a sound strategy for the Allied Generals, but a lousy one for the foot soldiers vested with its execution.

Rather than engage in daily pitched battles, the Allied soldiers and their German counterparts developed a Woo strategy that ensured their mutual survival. The first concession on the road to Woo was the agreement that neither side fire at the other during breakfast. This unofficial ceasefire was later expanded to include all meals and then further extended to whenever mail was delivered.

The next step in the soldiers’ collective Woo strategy was the demarcation of “no fire zones.” These safety zones allowed the soldiers to leave their trenches without fear of being fired upon. This Woo strategy was so effective that full-fledged cooperation broke out and fighting ground to a halt.

A British staff officer, after touring the trenches, remarked that he was:

“… astonished to observe German soldiers walking about within rifle range behind their own line. Our men appeared to take no notice; such things should not be allowed. These people evidently did not know there was a war on. Both sides apparently believed in the policy of "live and let live." (Dugdale 1932, p. 94)

Once the Allied Generals became aware of the unofficial ceasefire, they changed the rules of engagement and required that artifacts, such as guns, ammunition and other equipment be periodically shipped to headquarters as evidence of the Allied troops’ daily encounters with the enemy.

Rather than thwarting the Woo accord, this edict simply provoked the German soldiers to deposit broken guns, used artillery shells and other debris on the battlefield nightly so they could be dutifully picked up by the Allied soldiers the following day, as a means of satisfying the Allied General’s edict.

Eventually, the Generals realized that the only effective way to overcome the incongruity between the Army’s overall goal of winning the war and the soldiers’ goal of preserving their lives was to periodically rotate career Officers among the ground troops to avoid the Officers from becoming too aligned with any particular group of soldiers. This approach eliminated the tendency for the Offices to go native and sympathize with the foot soldiers’ goals, rather than those of the overall organization.

In this instance, War and Woo strategies were at odds. Neither strategy could ultimately be effective without the elimination the other. Unfortunately for the ground troops, Zi’s tactics won the day.

War Woop

Ohhh. Great warrior. Wars not make one great.”

–Yoda, Jedi Master

If you are unable to win by deploying a Woo strategy and you have the resources and bandwidth to win a sustained battle, then War might make sense. However, in most cases, startups do not have the wherewithal to execute a business plan while simultaneously fighting a protracted battle. As such, only deploy a War strategy as a last resort.

One venture that I helped foster from inception through its initial public offering allowed the heat of battle to adversely impact its judgement. Frustrated by its primary competitor’s market success, the company decided to sue its larger, more financially sound, competitor for patent infringement.

Although I had moved onto my next adVenture at the time the company declared war on its chief rival, I can appreciate why management reacted so irrationally. After years of being the market leader and defining a new industry, it was frustrating to see a clever, fast follower erode the company’s leadership position.

However, even though it might be satisfying in the short-term to rush into battle, deciding between Woo and War also involves evaluating the long-term consequences. Although viscerally pleasing, it was unreasonable for my former colleagues to declare War when a strategy of Woo would have been far more effective. Fortunately, cooler heads eventually prevailed and the company was able to broker a sale to its larger rivals despite the bad blood that arose from its declaration of War. Even so, the legal battle had significantly defocused my former company and cost it millions in legal fees, which caused the resulting sale to be far less advantageous than it might otherwise have been.

As noted in Roping In The Legal Eagles, it is almost never a sound strategy for a startup to attempt to sue its way to victory. Courts should be viewed as a battleground in which to make a final stand, not a venue for launching a pre-emptive strike.

Take These Broken Wings And Learn To Fly

You must continually evaluate the fundamental fight, flight or flirt dilemma as you grow your nascent organization into a thriving, self-sustaining entity. If, after reading War and Woo, you are still unable to determine whether to fight or flirt, consider fleeing into the comforting arms of a BDC where your wage-slave status will preclude you from ever again contemplating such elemental survival conundrums.

This article was inspired by and portions were drawn from a presentation created by two of my more talented graduate students, Lonya Breitel and Nick Cunningham.  

Copyright © 2008 by J. Meredith Publishing. All rights reserved.


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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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