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Luck, Serendipity, and the Contextual Strategist

by Mike Rollings  |  December 27, 2011  |  Comments Off on Luck, Serendipity, and the Contextual Strategist

Recently, @davegray @tetradian @nickmalik and I (@mikerollings) had a brief twitter exchange about the role of luck in strategy. What is luck anyway? Isn’t it just a happy accident, an unexpected happening, a simple explanation for the unexpected, a serendipitous association that leaves us in awe of the randomness of life?

In that context, strategy has everything to do with luck.

Strategy’s biggest problem is that it has lost its co-creative link to execution. Look at your own organization. Has the relationship between strategy, planning and execution become so skewed toward planning that the organization feels mechanistic and lacking innovative improvisation? If so, luck may be exactly what you need.

Strategy has lost the ability to be informed and reformed by all the insights found in doing. Strategy’s context guides doing, and doing reshapes strategy. You cannot learn without doing, and strategy is an experimenting and learning exercise. Just try to make strategy concrete without doing. Just try to finally discover the way to operationalize an idea without learning from doing. I don’t believe it can be done, do you? If you do believe it can be done, just look at how you learned key insights into your strategy, it had to come from some form of doing.

But, in order for all of us who are involved in execution to make mindful choices, we must understand the context for a strategy as it traverses the layers of an organization. How does it apply to my circumstances? Do we actually know if it applies? Are we just testing a hypothesis, or have we really figured out a way forward?

In order to do that well, we must all become contextual strategists.

A contextual strategist is anyone, without regard to title or position, who actively manages and operates with a firm understanding of the strategic context for his or her actions. Leaders understand that it is more important to understand and convey the context of a decision than it is to manage activities. When you have a leadership ecosystem that communicates and grooms context, then┬áthe entire organization has the ability to autonomously operate within a strategic context. It releases the ability to be surprised by the unexpected. It makes you ‘lucky’.

Anybody out there have good stories about releasing luck? If so, please share.

For Gartner IT1 clients, the document “Becoming a Contextual Strategist” helps managers and staff understand and reshape the work practices and human behaviors that cause a disconnect between execution and strategy. Instead of focusing on new processes and disciplines, its purpose is to help organizations and individuals become less operationally rigid and instead become more experimental, co-creative, forgiving of error, and responsive. Its purpose is to help your organization become ‘lucky’.

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Category: altered-states  contextual-strategist  human-behavior  management  strategic-planning  transformation  

Tags: behavior  business-outcome-mindset  empathy  innovation  insight  production-mindset  taylorism  transformation  uncertainty  

Mike Rollings
Research VP
5 years at Gartner
28 years IT industry

Mike Rollings is VP of Gartner Research within the Professional Effectiveness team. His research discusses what IT professionals need to know about transformation, innovation, human behavior, contextual strategy, collaborative organizational change, communication and influence, and cross-discipline effectiveness . His research can be read by IT professionals with access to Gartner for Technical Professionals (GTP) research. Read Full Bio

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