There is a subtle but pervasive affliction that affects many organizations, from startups to mature enterprises. It’s a condition I call “Should” Sickness. Its primary symptom is the constant use of the word “should” to justify strategic decisions and resource allocation. The word feels authoritative, but it often serves to mask a lack of rigorous, independent thought. It allows unexamined assumptions to masquerade as strategic imperatives.
You can hear it in boardrooms and planning sessions everywhere. “We should expand into the European market this year.” “We should be spending more on AI research.” “We should have a bigger presence at the annual industry conference.” Each of these statements may or may not be true, but the word “should” short-circuits the necessary inquiry. It implies an external, objective standard that we are failing to meet, creating a sense of pressure and anxiety.
A strategic leader’s job is to act as an immunologist, identifying and challenging these “should” statements. When you hear one, the immediate question must be: “According to whom? And why?” Where does this pressure originate? Is it coming from a board member’s anecdotal observation? Is it a reaction to a competitor’s press release? Is it driven by a desire to simply look like a more “serious” company? Or, most dangerously, is it driven by the ego of a single leader?
By consciously replacing “should” with a more precise line of questioning, we restore strategic discipline. Instead of “We should expand to Europe,” we ask, “What is the specific business case for European expansion at this time? What is the estimated cost, the potential return, and how does it rank against our other strategic priorities?” This simple linguistic shift moves the conversation from the realm of vague, external pressure to the domain of disciplined, internal choice. It ensures that the company’s strategy is being built from a foundation of its own objectives and resources, not from a reactive fear of what others think it “should” be doing.
Freeing your company from the tyranny of what it “should” be doing allows you to build a strategy based on what is actually right for you. I act as a strategic partner to challenge these assumptions—as a coach questioning the narrative and as a CFO demanding the business case. If your strategy feels like it’s being driven by external pressure rather than internal conviction, I’d be happy to discuss how to reclaim control.