Flanking Challenges with Strategy

A general once said, “The direct path is rarely the safest one.” Now jump into a tense boardroom: a small startup stares down a giant rival. Instead of copying features, they quietly win over a narrow, overlooked group of customers—and the giant never sees it coming.

McKinsey estimates that “side-door” entrants into a market can outpace direct attackers in revenue growth—precisely because they break the expected pattern of attack. The same logic shows up in neuroscience: Bowden and Jung-Beeman’s work on insight problems suggests our brains literally light up differently when we stop hammering straight at a question and approach it from an oblique angle. In practice, that might look like targeting an unserved use-case instead of a dominant customer segment, or reframing a personal roadblock as a design constraint rather than a dead end. When entrenched forces—whether budgets, habits, or competitors—hold the center, strategy shifts from “How do I break this wall?” to “Where is the seam no one is guarding?” That simple shift is where flanking begins.

So how do you actually spot a flanking move in real life, outside of case studies and war games? Start by noticing where energy is being wasted: meetings that go in circles, product features nobody uses, arguments that repeat weekly. Those are often signs you’re attacking the “front” of a problem. Then look for edges—adjacent users, neighboring processes, or small rules everyone obeys but nobody remembers agreeing to. In many companies, a single outdated approval step or reporting ritual quietly blocks progress more than any official “roadblock” ever could. That is often your real opening.