I’ve worked with teams using Asana, Monday, Trello, Jira — you name it. And across every platform, I see the same pattern.
A team picks a tool. Someone — usually one or two people who really understand the work — sets it up. And it makes sense to them. The fields capture what they track. The views show what they need. The workflow feels logical.
But then the tool gets shared with the rest of the team. And that’s where things start to fray. Other people look at the same setup and don’t see what the builder sees. They can’t tell what they’re supposed to do next. The information they need isn’t obvious. The fields that make sense to one person are confusing to another.
So they adapt. They create a separate spreadsheet because the tool’s view doesn’t give them the slice they need. They ask for status in a Slack thread because looking it up in the tool takes too long. They build a quiet shadow system that works for them — and the tool becomes just one piece of a fragmented workflow.
Eventually, someone asks: “Should we switch to something else?”
That question comes from a good place. But in my experience, it’s usually the wrong diagnosis. The tool itself almost never needs replacing. The setup does.
How do you know? Here are two signs.
1. The Tool Has More Workarounds Than Workflows
A workaround is anything your team does outside the tool because the tool doesn’t quite give them what they need. For example:
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A separate spreadsheet tracks approvals because the project view doesn’t show the right information.
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Status lives in a Slack thread instead of the tool because looking it up takes too long.
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Someone prints a manual checklist because their role in the workflow isn’t clear.
Workarounds like these usually point to one of two things.
It could be a setup issue. The tool may not be configured to match how your team actually works. The fields don’t reflect what you track. The views don’t show the information people need. The automations that could save time were never turned on. The builder understood the logic, but that logic didn’t translate to everyone else. The fix here is a better setup — one that makes each person’s role and next step obvious without explanation.
It could be an adoption issue. The tool may be set up well enough, but the team was never brought along for the ride. There was no clear adoption path and no formal training. No one was driving the rollout. The fix here isn’t reconfiguring the tool — it’s investing in how you introduce it.
The key question when you spot a workaround: Would this be unnecessary if the tool was configured differently, or is this a sign that the team never fully adopted it? Both are fixable. The answer just tells you where to focus.
2. You’re Rebuilding Repeatable Processes From Scratch
Some projects are genuinely new. They deserve fresh thinking. But many of the projects flowing through your organization aren’t unique:
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Onboarding a client.
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Running a quarterly review.
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Planning an annual event you’ve run for years.
Every time one of these repeatable processes gets built from scratch, you’re paying a hidden tax:
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Steps get forgotten or done inconsistently.
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Handoffs look different each time.
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Time is spent recreating the same project structure instead of focusing on what’s different this quarter.
A well-implemented tool gives you templates that capture the repeatable pieces so your team can focus energy on what changes. But it’s also true that sometimes the process itself could be improved. Just because something has always been done one way doesn’t mean it’s the best way. Sometimes the right move is to improve the workflow while you build the template.
And neither of those happens overnight. The best adoption path I’ve seen is gradual:
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Pilot with one team.
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Work out the kinks.
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Refine the workflow.
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Roll out to another team.
Each iteration makes the process stronger.
What These Two Signs Have in Common
Both patterns point to the same root cause: the tool and the work have drifted apart.
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Maybe the setup was never quite right.
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Maybe the work evolved and the tool didn’t keep up.
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Maybe the tool was introduced without a clear adoption plan — no formal training, no champion driving adoption, no gradual rollout.
The goal of a work management tool like Asana is simple: reduce the administrative overhead of doing the work. Give everyone insight into where things are, who’s working on what, what’s stuck, and what’s next. When you’re spending more energy managing the tool than managing the work, something needs attention.
That doesn’t always mean a full rebuild. Sometimes it means a targeted setup refresh. Sometimes it means a proper rollout with training and gradual adoption. Sometimes it means revisiting processes that have been the same for years and asking whether they still serve the team.
The important thing is recognizing the signs — and knowing the tool itself isn’t the problem.
CTA: 👉 Book a Discovery Call — Not sure if your setup is the issue or if something else is going on? I’ll take a look with you. No commitment, just a clear picture of what’s working and what isn’t.
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From the SmartWork Bulletin