When Yesterday’s Decisions Become Today’s Constraints

No organization wakes up one morning and decides to make itself harder to lead.

There is no meeting where a leadership team agrees to slow decision-making, blur accountability, or complicate execution. In fact, the opposite is usually true. The leaders involved are capable, well-intentioned, and actively trying to solve problems as they arise. And yet, over time, many organizations find themselves constrained by systems, roles, and habits that feel oddly misaligned with their original intent.

The uncomfortable truth is that most structural problems were not designed. They were accumulated.

They emerge when temporary fixes are allowed to harden into permanent features of the organization without ever being re-examined. In my experience working with both businesses and nonprofits, here’s how it happens: Over time, an initial “workaround” becomes a cemented process. A stopgap role quietly turns into a standing position. An exception made under pressure becomes an informal rule. Each of these decisions makes sense in isolation, but taken together, they form a structure no one remembers choosing.

What leaders eventually experience is not outright dysfunction, but inefficiency or friction. Things take longer than they should. Decisions require more coordination. Responsibility feels diffuse or ambiguous. Forward progress becomes costly, whether financially or time-wise. At that point, many leaders sense that something is off, even if they struggle to name it precisely.

Why smart organizations are especially vulnerable

Paradoxically, this pattern shows up most often in organizations that are doing many things right.

Think about it. Competent teams tend to move quickly and decisively. Capable leaders trust their people and don’t micromanage. Success creates momentum, and momentum inevitably reduces scrutiny. Thus, when results are generally positive, there is little incentive to pause and examine how those results are being produced. Your attention stays focused on outputs rather than on the systems quietly forming underneath them that will eventually blunt the same outputs.

In these environments—most environments, in my experience—structure tends to grow organically rather than intentionally. Competent teams solve problems as they arise, layer new initiatives on top of existing ones, expand certain roles to meet demand, and so forth. The result? Over time, the organization becomes more complex without anyone having made a clear decision that complexity was warranted.

Because everyone involved is intelligent and hardworking, the friction that emerges is often misattributed. Leaders assume the issue is at the level of communication or execution, rather than structure itself. The system remains unexamined, even as it eventually undermines outcomes.

Borrowed answers and the illusion of progress

When this “systems-friction” becomes noticeable, leaders often reach for the wrong solutions.

They might adopt a well-known planning cadence, carte blanche. They might mirror a competitor’s product strategy. Or, they might borrow and slightly adapt the messaging of an industry leader. These moves feel prudent, and they feel like a serious attempt to align with what “leading organizations” are doing.

These types of solutions rarely resolve the underlying problem.

Best practices are, by definition, context-dependent conclusions. They reflect what worked for someone else, under different conditions, with different constraints. When imported prematurely or carte blanche, they undermine sound judgment. They create the appearance of progress without requiring leaders to wrestle with the specific realities of their own organization.

This dynamic has accelerated with the growing use of AI in strategic thinking. AI is exceptionally good at synthesizing patterns and producing coherent, confident recommendations. It can tell you what usually works. What it cannot do is determine whether those patterns make sense here, now, for this organization, under these conditions.

The danger is not that these tools are wrong. It is that they are persuasive. Leaders receive polished answers before they have clarified the real question. Confidence arrives before understanding. The result is often borrowed certainty rather than earned clarity.

The compounding cost of unexamined structure

When structural issues are left unaddressed, their effects compound quietly.

Decisions slow as conversations widen to include people who were never meant to decide. Responsibility spreads thin as roles grow without being clarified. New priorities arrive before old ones are retired, and the organization begins to exhaust itself trying to honor everything at once. Over time, capable people don’t disengage because they lack talent or drive, but because they can no longer see a clear line between effort and outcome.

None of this happens overnight. That is precisely why it is so dangerous.

The business (or nonprofit) continues to function. Meetings continue to occur. Work continues to get done. But the cost of movement rises steadily, and leaders find themselves expending more energy to achieve outcomes that once came more easily. At that stage, the problem is no longer tactical. It is structural.

What a true reset actually requires

When leaders sense this accumulation, the instinct is often to “reset.” Unfortunately, reset is frequently misunderstood.

A true reset is not a reorganization for its own sake, nor is it the wholesale installation of new frameworks, tools, or processes. Those moves may follow, but they are not the starting point. When resets fail, it is usually because leaders attempted to change systems without revisiting the thinking that produced them.

A meaningful reset begins upstream, with judgment.

It requires leaders to re-establish first principles, clarify what actually matters now, and make explicit choices about what no longer fits. It involves aligning leadership priorities, strategic intent, and executional reality around a coherent set of decisions. Only then do structures begin to boost revenue, productivity, and morale rather than being a drag on those things.

This kind of work is slower and less visible than adopting “best practices.” It may not produce immediate artifacts to point to. But it is the only way to ensure that the organization’s structure reflects its current reality rather than its past urgencies.

In the end, structure is never neutral. It embodies decisions, assumptions, and tradeoffs, and it embodies those things whether it’s been examined or not. Leaders who want different outcomes must be willing to revisit the thinking that shaped the system they are now leading.

*When organizations reach this point, the work is rarely about fixing one department. It’s about re-aligning leadership, strategy, and execution as a system. That’s the kind of work my Small Business Flight Plan™ and Nonprofit Flight Plan™ engagements are designed to support.