Philosophy of Strategic Time

A few weeks ago, I wrote about an agile approach to strategy.  

Since then, I’ve had conversations with leaders that have almost sounded like a philosophy seminar on the concept of time:

“How do you define ‘year’?”

“What does time really mean to you?”

“What’s the value of time?”

All of those conversations originated from: If a 5-year strategic plan is too long, what is the right cadence? 

Some ideas:

First, there are limiting factors on both ends of the planning spectrum. 

Leaders can’t change strategy every single day. Or at least, one cannot effectively communicate a strategy change and get a group of people to change their focus every day. That’s a recipe for disaster. 

On the other end of the spectrum, one needs to live within the constraints of his commitments. For example, in my annual strategy retreat, I don’t ask myself “Do I still want kids?” (That’s more of a minute-by-minute assessment, based on their behavior.)

Second, there are real-world events that define time. Policy organizations live on budget cycles and legislature session timing; education organizations have the school year. For them, annual planning as the basic template makes sense.  

But what about everything that falls in the middle? Once an organization has a good enough strategy, how often should it revisit the strategy? 

A helpful framework for that decision: the OODA Loop. 

OODA stands for Observation, Orientation, Decision, Action. From the U.S. Marine Corps doctrinal publication on tactics: “As our enemy observes and orients on our initial action, we must be observing, orienting, deciding, and acting upon our second action. As we enact our third, fourth, and fifth move, the time gap between our actions and our enemy’s reactions increasingly widens.”

The OODA Loop was developed by U.S. Air Force Col. John Boyd, based on an observation that when smaller forces won battles and wars over larger forces, it was typically driven by their agility.

Or put another way: One wins by having the fastest cycle of observing the changing environment, getting the organization ready to react (orienting), and taking action. 

Outside of the military context, the first question for organizational leaders is: Once we set a strategy, how soon might there be a change in the environment that might cause the strategy to be wrong?  

That’s an indicator of how frequent strategy review cycles need to be. 

But just as important, leaders should ask: How effective are our systems for collecting and synthesizing data on and feedback from stakeholders—customers, suppliers, funders, competitors, employees? And is that data relevant to the core assumptions of the strategy?

The answers to those questions are what makes the difference between (a) an organization whose strategy check-ins are simply project updates or filled with subjective decision-making and (b) a learning organization that can actually use those strategy check-ins to make grounded decisions about the best way to make progress.