A client of mine hired a part-time executive assistant. The role was supposed to free her up. Instead, she was busier than ever.
She was working nights and weekends just to keep up with her own strategic work, the work only she could do. When we dug into where her time was actually going, the answer surprised her. She was spending hours every week managing around her assistant’s gaps. Writing out extra-detailed instructions because the assistant struggled with problem-solving. Building templates because the assistant needed more structure than a normal handoff would require. Reviewing and re-reviewing assignments because the work rarely came back right the first time. Fixing mistakes quietly so nothing fell through the cracks.
None of this looked like a problem day-to-day. It looked like being a good manager. Patient. Supportive. Willing to invest in someone.
But she wasn’t managing an assistant anymore. She was managing a workaround, and it was costing her the very thing she’d hired help to protect: her time for the strategic work that actually moved her organization forward.
She eventually made a change. Her new assistant is more productive, more accurate, and proactive in a way the role had needed from day one. The relief was immediate. But what stuck with her wasn’t the relief. It was realizing how long she’d spent treating the symptom instead of naming the actual problem.
This is exactly what happens with culture
Organizations do this constantly. Something isn’t working, so a policy gets written, a new approval step gets added, and a manager starts double-checking work that shouldn’t need double-checking. None of these moves is wrong in the moment. They’re often the responsible thing to do under pressure.
A workaround built to manage a symptom doesn’t fix the underlying cause. It just makes the symptom more bearable. What makes a workaround dangerous is that it rarely stands alone.
One workaround creates the need for another. The extra approval step slows things down, so someone builds a workaround to speed things back up. Unclear expectations cause a mistake, so a new check is added, which creates friction elsewhere, so another fix goes in to manage it. Each fix is reasonable on its own. But stacked together, they start to take on a life of their own.
Given enough time, the workarounds aren’t workarounds anymore. They’re just how things are done here. They become culture, the same culture you were trying to avoid creating, and the cost of untangling them only grows. What started as one quiet patch is now load-bearing. Pull on it, and other things shift.
Why this is so easy to miss
The hardest part of this pattern is that it doesn’t feel like a problem while it’s happening. It feels like support. Like care. Like doing your job well under difficult circumstances.
That’s exactly why it goes unaddressed for so long. Leaders who absorb the cost of a workaround often see themselves as the solution rather than as evidence of a problem. My client thought she was being a good manager. Plenty of leaders think the same thing about absorbing tension between two team members, smoothing over a process that doesn’t really work, or quietly redoing work rather than addressing why it needed to be redone.
The question worth asking isn’t “how do I make this workaround easier to manage?” It’s “what is this workaround actually a symptom of, and what would it take to address that instead.”
What this costs you
The real cost isn’t just time, although time is real and it adds up fast. The deeper cost is what doesn’t get done because the workaround is consuming the bandwidth that should be going toward the work that matters. Strategic thinking. Real conversations. The kind of leadership that actually moves an organization forward.
The longer the workaround runs, the more expensive it becomes to address. Early on, the fix is usually simple: a conversation, a clarified expectation, a role correction. Wait long enough, and you’re not untangling one issue anymore. You’re untangling a structure that grew up around the original problem and now has its own dependencies.
Naming it is the first step
If you’re reading this and recognizing your own version of the executive assistant story, the goal isn’t to feel bad about the workarounds you’ve built. Most of them came from good instincts: a desire to keep things moving, to support your people, and to avoid unnecessary conflict.
The goal is to get curious about what they’re keeping you from seeing. What pattern has become so normal that you stopped questioning it? Where have you built a structure to manage a symptom rather than name the cause?
That’s the work I do with leaders through the Culture Threads Assessment. It’s built to help you see the patterns that have become invisible simply because they’ve been there so long, and to give you a clear, honest picture of what’s actually driving the symptoms you’ve been managing around.
If you’re ready to peek beneath your own layers of workarounds and symptoms, let’s talk about what we could bring to the surface for your organization.
