On Plans and Planning Back to Journal →

Sunday, April 21, 2024

Winston Churchill knew a thing or two about the paradoxes of leadership. His aphorism, “Plans are of little importance, but planning is essential,” is one of those gnomic utterances that sounds like a Zen koan but actually brims with practical wisdom. Let’s delve into this seeming contradiction and how it plays out in the corporate world, where PowerPoints and strategy documents multiply like rabbits on espresso.

First, let’s get this out of the way: Plans are a bit like New Year’s resolutions. They look great on paper and inspire a fleeting sense of control and optimism. You know the type—promising to hit the gym thrice weekly, eliminate carbs, or—if you’re a company—dominate the market by Q3 with a revolutionary app that combines Tinder, Uber, and a life coach. But much like those gym visits dwindle to zero by February, most business plans don’t survive first contact with reality.

Take Kodak, for instance. Once the behemoth of the photography world, they had a plan: keep selling film. They even had the digital camera technology but shelved it to avoid cannibalizing their film sales. Spoiler: the digital wave drowned them anyway. Their meticulously crafted plans were rendered obsolete by the relentless march of technology. It wasn’t the plan that mattered; it was the lack of adaptive planning that led to their downfall.

Now, let’s talk about planning, the verb. Planning is the process, the mental calisthenics that prepare you for the unexpected. It’s the difference between having a map and learning to navigate. A map shows you a predetermined route; navigation skills let you adapt when a hurricane has turned your highway into a waterway.

Consider a tech startup launching a new product. The initial plan might lay out a clear path: develop MVP, beta test, market launch, iterate based on feedback. But then, the real world intrudes: a key developer quits, a competitor releases a similar feature, or a pandemic disrupts supply chains. This is where the act of planning shines. The team’s ongoing planning sessions, their constant re-evaluation of resources, timelines, and goals, allow them to pivot, to re-route, to transform obstacles into opportunities.

Remember Agile methodologies? That’s planning personified. In an Agile framework, the emphasis is on iterative progress and constant feedback. Teams don’t cling to a rigid blueprint; they adapt and evolve. Each sprint reflects a microcosm of Churchill’s wisdom—plans may change, but the discipline of planning ensures continuous improvement and responsiveness.

Finally, Churchill’s insight encapsulates a vital truth for businesses: the static nature of plans can become a liability in a dynamic world. What truly matters is the continuous process of planning—an activity that fosters agility, resilience, and creativity. Embrace the irony that your plans will likely falter, but your commitment to planning can transform chaos into opportunity.

Note: I’m pushing myself to write with greater depth and intention when I connect with a topic. Writing like this in public will help me become a better writer.