The great organisational workaround – and how to prevent it

When my daughter asks me for something she wants, I’ll often check whether she has already made the same request to my wife. Sometimes she has and sometimes she has already received a thoughtful, considered “no”.

That doesn’t always stop her. Instead, she tests the waters with dad, just in case the answer may shift.

This is entirely predictable and normal behaviour. Children quickly learn to scan for inconsistencies between authority figures. Once they find them, they adjust accordingly, gravitating toward the person most likely to deliver the outcome they want. In that moment, they’ve discovered a workaround.

This dynamic doesn’t disappear when we grow up. It simply becomes more sophisticated. Workaround culture within organisations is alive and well, and it often stems from misalignment within leadership teams. Employees learn quickly who to approach for flexibility on deadlines, who is more open to remote work, who bends the rules and who enforces them rigidly. Over time, they navigate these differences to their advantage, working around formal structures and reporting lines to get what they need.

It’s worth noting that the term ‘workaround culture’ is being used in a slightly different way to how it traditionally has been. In general, the term has been applied to policy workarounds, health and safety workarounds, employees bypassing systems and procedures to get the job done. In that sense, it can even be seen as adaptive or resourceful but, of course, there is a very real danger to this behaviour, especially in high-risk environments such as mining or healthcare.

But relational workaround culture is dangerous in a different way and the consequences are far-reaching. Subcultures begin to form around individual leaders, each with their own unwritten rules and expectations. The organisation’s stated values start to lose meaning, overridden by the personal values of those in positions of authority. Accountability weakens, particularly when certain individuals become ‘protected’ by specific leaders. Silos deepen, collaboration suffers and well-meaning employees grow increasingly disengaged as they observe the daily inconsistencies playing out around them.

Clarity begins to blur. People find themselves caught between competing instructions, responding to one leader’s priorities at the expense of another. In time, a group of ‘untouchables’ often emerges: individuals aligned with the most powerful voices in the organisation, operating with a perceived immunity that sends a clear signal to others. Even strategy starts to fragment, with different leaders pulling in different directions rather than moving together along a shared path.

So how do we mitigate this?

Imagine a group of leaders standing scattered across a large field. It’s easy for someone to walk around one and head toward another. Now imagine those same leaders standing shoulder-to-shoulder in a tight formation. Suddenly, the gaps close and the ability to work around them disappears. This is what alignment looks like in practice.

Leadership teams that are genuinely aligned around vision, strategy and values, with clear and measurable behaviours attached, create an environment where workaround culture struggles to take hold.

But alignment alone isn’t enough. There is a deeper requirement: mutual respect. When leaders respect one another’s roles, differences and authority, they reinforce each other rather than undermine. They close ranks, not in a defensive way, but in a way that provides clarity and consistency to the organisation. Just as a strong organisational culture is built on a strong leadership culture, workaround culture is incubated in disconnected leadership environments.

Ironically, organisations led by dynamic, visionary individuals can be particularly vulnerable. Casting a compelling vision is one thing, but aligning a leadership team to deliver on it is another. It only takes one or two leaders acting independently, or out of sync, for cracks to appear. Those cracks quickly become pathways that others learn to navigate.

Mitigating workaround culture becomes less about policies and more about disciplined leadership practice. It requires regular, honest strategic conversations where alignment is actively built, not assumed. It demands robust debate – the kind that surfaces differences and resolves them, rather than allowing them to linger beneath the surface. It calls for values to be translated into specific, observable behaviours that become part of an organisations performance management system, so that they are lived daily rather than remaining as words on the wall.

It also requires leaders to hold the line. When employees attempt to bypass structures to get what they want, it needs to be addressed – not harshly, but clearly. Accessible leadership is important, but so is integrity of process. People should feel heard, but they should also experience consistency.

Finally, leaders themselves need to be equipped and willing to have the difficult conversations that alignment demands. Upholding boundaries, addressing inconsistencies and challenging one another constructively are not optional extras; they are central to preventing the slow drift into workaround culture.

The most effective organisations are those where people work in ways that serve the whole, not just themselves. When workaround culture takes root, it is often a sign that self-interest and siloed thinking are beginning to dominate. Left unchecked, it leads to frustration, disengagement and stalled progress.

The good news is that it is entirely preventable. But it requires intention, discipline and, above all, a leadership team willing to stand together.

Travis Gale

Founder & Managing Director

Appletree Group