Sirens, Scylla, & Charybdis: Why Your Strategy Needs an Experienced Captain & Crew

Don’t let your strategy end up shipwrecked.

In Greek mythology, ship captains had to safely pass the Sirens “whose sweet singing” lured sailors to their doom; Scylla, a devouring six-headed monster (the rock) on one side of a narrow passageway; and Charybdis, a swirling, un-navigable whirlpool (the hard place) on the other. Not much different than the challenges of leading a major strategic effort in business today.


These creatures of mythology frequently contribute to the high failure rate of major strategic efforts. There are different ways to battle these challenges and improve the success rate but one of the most effective is to establish a strategic management rhythm. This should include weekly and/or monthly as well as quarterly meetings to mitigate the risks, keep strategies on course, and navigate the rocky shoals that will sink even the best of efforts. Here are three reasons why you need to establish a strategic management rhythm with an experienced captain at the helm.


Dealing with the Sirens – When strategies get underway, there are many voices; each singing the sweet benefits of why you should change the objectives or make adjustments to something to accommodate them. It takes an experienced captain not beholding to the Sirens to know when to “plug the ears of their sailors” and “lash themselves to the mast” to keep the ship on course.


Managing Scylla – Most strategy leaders would consider it a blessing to deal with only a six-headed monster. Realistically, strategic efforts will impact more than just a few department heads, each capable of devouring a sailor or two for lunch. It takes a skilled, experienced captain to navigate all those hungry heads and keep the casualties, and damage to the strategy to a minimum.


Avoiding Charybdis –Though the captain may deal with the Sirens and successfully manage the six-headed monsters, there’s still Charybdis; the unseen force that can suck your strategy down and destroy it. An experienced leader knows how to keep the strategy afloat in the swirling caldron of organizational firefighting, habits and attention spans and avoid getting bogged down or sunk by bureaucracy or the culture.


Many major strategic efforts flounder and fail to meet objectives. Establishing a separate strategic management rhythm is essential. With an experienced captain at the helm, businesses can successfully navigate the Sirens, Scylla, and Charybdis.



(We work with our clients to set up a simple system for strategic management. We do this at the end of our strategy workshop. Contact us to learn more.)