Why Your Best Workflow Is Probably Your Biggest Risk

I have been in and around the Microsoft ecosystem for over 25 years, and I have watched more workflow projects succeed than I can count. I have also watched a troubling number of those same projects quietly fall apart six months later. Not because the technology failed. Not because the team lacked skills. But because the workflow worked exactly as designed, attracted attention, and then buckled under the weight of its own success.

This is a pattern I see constantly when talking with customers and partners, and it is one of the least discussed risks in enterprise automation.

The Success Trap

Here is what typically happens: Someone on the team identifies a painful manual process. Maybe it is an approval chain that lives in email. Maybe it is a document routing process that depends on someone remembering to forward a file. They build a workflow in SharePoint or Power Automate, and it works. The team is thrilled. Management notices. Other departments want the same thing.

And that is where the trouble begins.

The original workflow was built to solve one specific problem for one specific team. It was not designed to handle three additional approval levels, conditional routing based on dollar thresholds, mandatory rejection comments, and an exception for the finance department. But each of those requests arrives individually, and each one seems reasonable. So the workflow grows. And grows. And what was once a clean, simple solution becomes something nobody wants to touch.

Following a webinar earlier this year, I was chatting with fellow MVP Jonathan Weaver (@j_weaver74) from Smarter Consulting, who builds these kinds of solutions every day. He put it simply: teams routinely underestimate how complex these things become over time. He told me about getting a message that very morning from a former client whose users were hitting the 28-day timeout on a multi-level approval flow. Four approvers in sequence, and if any one of them takes too long, the entire request has to start over from scratch. That workflow worked perfectly when it had one approver. It became a liability after the business added three more.

Complexity Does Not Announce Itself

What makes this pattern so dangerous is that it is invisible until it is not. Nobody wakes up one morning and decides to build a fragile workflow. Complexity accumulates through a series of perfectly reasonable decisions. Each small change is justified. Each one responds to a real business need. But the cumulative effect is a solution that only its creator fully understands, and even they might be nervous about modifying it.

Shai Petel, the Head of Engineering at SnapOn Software, described this perfectly during that webinar. He said that workflows become so complex that even the person who created them is scared to make a change because they do not know what is going to happen. When the builder is afraid to touch it, you know you have crossed a line.

The Question Nobody Asks Early Enough

In my experience, most organizations ask the right first question: Can we build this? And the answer is almost always yes. The Microsoft platform gives you incredible building blocks. SharePoint, Power Apps, Power Automate, Copilot. You can build almost anything.

But the question that gets skipped is whether the team can sustain what they build at scale. Can they maintain it? Can someone else take it over? Can it adapt to new requirements without breaking? Those are fundamentally different questions, and they require different thinking than the initial design.

What I Tell Customers

I am not a developer. I am a strategy and marketing person who has spent 35 years watching technology projects succeed and fail, and the pattern is remarkably consistent. The projects that struggle are rarely the ones that failed technically. They are the ones that succeeded technically and then outgrew their operational support model.

If you are building workflows today, here is my advice: celebrate the win, but start planning immediately for what happens when someone asks you to add just one more step. Because they will. And the decision you make at that moment will determine whether your workflow scales gracefully or becomes the thing everybody is afraid to touch.

That is not a technology problem. It is a leadership problem. And it is one that more organizations need to talk about openly.