In 2013, Apple could have bought Tesla for a rounding error on its balance sheet. Microsoft had a genuine shot at Google and passed. Blockbuster (bless them) had Netflix walk through their front door looking for a deal and showed them the exit. These are not obscure cautionary tales from companies that lacked information or intelligence. They are well-documented, much-studied failures from organizations that had every advantage except one. A fresh strategy.

The problem is almost never a shortage of intelligence. It's a shortage of freshness.

Anyone who has worked in strategy knows it feels like living in an earthquake. You have no idea which portion of the ground will fall out from under you, or what part of the roof is coming down next. Refining yesterday's strategy in that environment is like polishing a stone mid-tremor. Sure, that stone might get shiny. It won't help you dodge the cracks opening up in the pavement around you. When we focus entirely on perfecting what we already have, we blindfold ourselves to the opportunities forming in the chaos we're ignoring.

Part of the problem is that we confuse strategy with planning. A plan is like that overly optimistic friend who swears, "Follow this recipe exactly, and your soufflé will rise." Spoiler: it won't. A strategy is something else: more honest, more open about the odds. It doesn't promise a destination. It creates the right conditions for the best options to surface. That distinction sounds subtle. Organizations that miss it tend to end up writing very interesting bankruptcy filings.

The Questions Worth Asking

Roger Martin, one of the most influential strategists of the last fifty years, would tell you that strategy is really just a series of interrelated design questions. Answered well, they compel a specific behavior. They tend to sound deceptively simple: Where are we now? What are we genuinely good at? Where do we want to be? Leaders who ask those questions rigorously, and sit with the discomfort of honest answers, are the ones running the companies their competitors are writing case studies about.

The most important question of all is about the customer. Seth Godin, marketing thinker and author, put it plainly: choose your customer, choose your future. It sounds obvious. It isn't. Most organizations define their customer so broadly it means almost nothing, then wonder why their strategy resonates with no one in particular. The firms that consistently outperform tend to have made a deliberate, sometimes uncomfortable call about exactly who they're building for, and then designed everything else around that answer.

The same logic applies to the team. In most organizations, talent management is really just hiring. A position opens, you fill it, you move on. But who you put in the room shapes what ideas can even exist in that room. Treat it like a staffing problem and you will get a staffing-problem company.

Baby Steps and the Cost of Being New

Jeff Bezos left Wall Street in 1994 with two data points: internet usage was growing at 2,300% per year, and there were over 200,000 books in print at any given time. From that, he built Cadabra, Inc. (later Amazon.com) out of a garage in Bellevue, Washington, packing boxes himself and driving them to the post office in his own car.

That story is easy to romanticize in hindsight. At the time, it looked like a man who left a perfectly good job to sell books on the internet. Nobody thought it was the beginning of something. That's almost always how the beginning of something looks.

Doing something new is not efficient. Prototyping, failing, iterating, starting over: none of it looks good on a quarterly report, and your best people may appear to be spinning their wheels for months on end. Innovation always has a cost, and it is never zero. I spent 26 years in aviation, one of the most compliance-driven industries that exists, and even there, the organizations that carved out genuine space for experimentation consistently outperformed those that optimized purely for efficiency. It's a pattern you see everywhere, once you've watched long enough.

Michael Porter said that effective strategy is deciding what not to do. The flip side is equally true: good strategy requires accepting what you will do badly for a while, in service of what you're actually trying to build. That's not a flaw in the process. That is the process.

Strategy is not for the faint of heart or the short of patience. It demands courage, discipline, and a willingness to stay uncomfortable long enough to find out what you're capable of. And above all, it demands freshness: a regular return to the hard questions before the ground shifts again.

What part of your current strategy have you stopped questioning? That, probably, is where the next Blockbuster moment is quietly taking shape.