Why the Same Problems Keep Coming Back at Work

Editorial Note
This essay is part of the Cultivated canon — a body of work focused on understanding how systems, behaviours, and leadership choices shape the distance between idea and value. It explores a recurring theme in this library: that many persistent problems are structural, not personal.

Why the Same Problems Keep Coming Back at Work

Systemic problems have a particular feeling.

It’s the sensation of being stuck on a roundabout — going round and round, solving the same issues, hiring new people, changing roles, and yet arriving at exactly the same outcomes.

Different faces. Familiar results.

There is a reason for this. Many organisational problems are not caused by individuals. They are caused by the system those individuals are part of.

One of the most useful ideas in management thinking is the assertion that the vast majority of a business’s results are determined by its system — the structures, processes, incentives, goals, and constraints that shape everyday work. People matter, of course, but they operate inside something larger than themselves.

And yet, it is remarkably common to find managers focusing almost exclusively on people while leaving the system untouched.

This is understandable. People are visible. Systems are harder to see.

But when the same problems keep returning, the organisation is giving you a signal: stop treating symptoms and start studying structure.

Systemic problems rarely announce themselves clearly. More often, we see their effects — delays, frustration, workarounds, stress, and repeated failure. Leaders understandably want quick answers, but without taking time to understand how the system actually behaves, those answers remain superficial.

Fixing a system starts with learning to spot patterns.

Recurring bottlenecks are one such signal. When work repeatedly queues in the same place, the issue is rarely effort or intent. It is capacity, flow, or design.

Over-reliance on a small number of individuals is another. When certain people become critical to everything, the system has quietly become fragile.

Repeated mistakes, skipped processes, or rule evasion often indicate that the system is asking too much, moving too fast, or rewarding the wrong behaviour. People adapt to survive, even if that adaptation undermines the organisation.

Misaligned goals are another classic marker. When teams are measured on outcomes that compete with one another, the system produces conflict by design. No amount of goodwill can resolve that.

One of the most common responses to systemic problems is to shift the burden elsewhere. New tools are introduced. Consultants are brought in. Frameworks are adopted. Responsibility is passed sideways or downwards.

Sometimes these interventions help. Often they simply add complexity.

The most reliable indicator of a systemic issue is this: when new people, even capable and motivated ones, produce the same results as those before them. At that point, it is no longer credible to blame performance or attitude. The system is winning.

Another signal is disproportionate attention. Small problems consuming large amounts of time usually point to something deeper that is being avoided, misunderstood, or considered too difficult to tackle. Workarounds proliferate. Energy leaks away quietly.

Culture plays its part too. Phrases like “that’s just how things are done here” or “it would never work” often mask untested assumptions. Many systems persist simply because nobody feels able to challenge them.

Pressure amplifies all of this. Under stress, systems distort. Corners are cut. Decisions escalate. Short-term survival overrides long-term sense. What emerges is not bad behaviour, but predictable behaviour under constraint.

Fixing systemic problems requires a different stance from leadership.

It requires observation before action. Curiosity before certainty. A willingness to accept that the organisation is perfectly designed to produce the results it is currently getting.

Leaders hold the greatest levers for change — goals, budgets, processes, incentives, and norms. They may not have created the system deliberately, but they are responsible for shaping it now.

Even without formal authority, individuals can contribute by gathering evidence, spotting patterns, and making the system visible. Systems change begins with understanding.

There are no quick fixes here. Systemic problems demand patience, study, and intent. But the reward is significant.

Fix the system, and many people problems resolve themselves.

Ignore it, and the roundabout continues.

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Editor’s note: This essay grows from an earlier exploration in another medium. The thinking remains central, even as the format has changed.