How Simple Workflows Become Complex Nightmares (Without Anyone Noticing)

Nobody sets out to build a complicated workflow. In my experience, complexity is never the plan. It is the byproduct of success and good intentions.

I have spent the better part of three decades working in and around enterprise technology, and I can tell you that the moment a workflow starts working well is the moment it starts getting more complicated. Not because anyone is being careless, but because the business keeps evolving, and the requests that follow are always reasonable when viewed one at a time.

One More Step, One More Rule

Let me paint a picture that will be familiar to anyone who has managed SharePoint-based processes.

You build a simple approval workflow. One approver, one list, one notification. It works beautifully. Then someone in finance says they need a second approver for anything over $500. Makes sense. Then HR wants a conditional step where certain categories route to a different manager. Sure. Then legal needs rejection comments to be mandatory so there is a paper trail. Of course. Then someone points out that the workflow should handle the case where an approver is on vacation and the request just sits there.

Each of those requests is individually reasonable. None of them feel like they are adding dangerous complexity. But after four or five rounds of “just one more thing,” you have a workflow with branching logic, conditional fields, multiple approval tiers, and timeout handling that nobody fully understands.

Someone recently shared an example with me that illustrates this perfectly. Their client had a workflow with four sequential approvers. It ran fine until users started hitting the 28-day timeout in Power Automate. If any single approver took too long, the whole process had to restart from scratch. The workflow was originally designed for one approver. The business added three more over time, and nobody thought about what that would mean for the execution model.

The Hard Limits Nobody Talks About

Here is something that surprises a lot of people who are early in their automation journey. SharePoint’s built-in automation has concrete, documented limits that you will hit faster than you expect.

A single list or library supports a maximum of 15 rules and 15 quick steps. If you have a team of 30 people who all access the same list and you need individualized notification logic, you are going to run out of capacity before you run out of requirements. That is not a criticism of SharePoint. Those limits exist for good reasons. But if you do not know about them, you will hit a wall and wonder what happened.

The built-in Power Automate templates that ship with SharePoint are similarly constrained. The reminder workflow, for example, requires a custom date field and only supports advance notice. If you need to flag something as overdue (five days past due instead of five days away) you have to open Power Automate and edit the underlying flow. Jonathan wrote a blog post about this the day after the feature shipped. The fix is simple: change a 2 to a -2 in Power Automate. But the fact that you have to leave SharePoint entirely to make that change tells you something about where the boundaries are.

Why This Matters for Your Team

The reason I keep coming back to this topic is that complexity is not a technical problem. It is a governance and planning problem. And it tends to hit organizations hardest when they are feeling most confident about their automation capabilities.

I always tell the people I work with: your first workflow is never the one that causes problems. It is the fifth version of that workflow, after three rounds of business requirements changes and one personnel transition, that becomes the headache. By then, the original builder may have moved on. The documentation, if it exists, is probably outdated. And the person who inherited it does not want to be the one who breaks something that 300 people use every week.

If that sounds familiar, you are not alone. And the good news is that recognizing the pattern is the first step toward designing workflows that can actually absorb change without falling apart. That starts with understanding the limits of your current tools, being honest about when you have outgrown them, and making deliberate decisions about what comes next rather than just bolting on one more step and hoping for the best.