Hey Wranglers,
At 20 people, the workaround is fine.
Something slips through your ticketing system, someone sends a Slack DM, and it gets handled. No big deal.
But at 100 people, that same workaround is costing you real money and real time.
The difference is that at 20, you notice everything. At 100, you cannot.
This is the messy middle: the stage between startup scrappiness and enterprise structure, where you are too big for informal systems but not yet organized enough to replace them. And almost every internal process problem I see is a messy middle problem.
Key Takeaways
The messy middle is not a performance problem. Your team is not underperforming. The work is just invisible.
Most of the work happening around your systems is invisible. Your team is not underperforming. You just cannot see what they are actually doing.
When someone who ran everything informally leaves, they take the institutional memory with them. There is no record of what was decided or why.
Big-bang replacements almost never work. The companies that navigate this well add structure around how people already work - they don't try to redirect them somewhere new.
The Gap You Can't See
I often see IT leads or ops managers spend real time rolling out a ticketing platform. It looks exactly like the kind of thing that should work.
What they find instead is a split world:
The official system: the portal, the ticket count, the reports.
The real system: the DMs, the channel threads, the shoulder taps that moved from the hallway into Slack.
From a management perspective, this is invisible. You look at your ticketing platform: not many tickets, team looks fine. But underneath, hundreds of conversations are happening in DMs that never show up anywhere.
One of the most consistent things we hear when companies start using Wrangle is surprise. Not at what the product does, but at what was already happening without anyone knowing.
An IT team thought they were handling a manageable ticket volume. When we surfaced what was actually moving through Slack, the real volume was two to three times what the portal showed.
The team was not underperforming. They were handling an enormous amount of work that was completely invisible.
That cuts in two directions:
For the person doing the work, it is demoralizing. You spend your whole day responding to DMs, triaging requests, answering the same questions over and over, and none of it shows up anywhere.
For the person managing the team, it is a blind spot that compounds. Decisions about headcount, process, and investment get made on data that does not reflect what is actually happening.
The invisible workload problem is painful in the moment. But there is a slower, quieter version of the same problem that only surfaces when someone puts in their notice.
At one of my previous companies, we had a deal desk process that ran across sales, engineering, and the CX team. Multiple approvals, multiple systems, multiple teams.
What we found was that the real decisions - the exceptions, the approvals, the context behind why something was handled a certain way - were all happening in DMs.
When you asked someone how a decision was made, the answer was always: "So-and-so messaged me in Slack."
And then, the employee left, taking with them every bit of institutional knowledge that had been living in their DMs.
It is not just the workload that is invisible. It is the reasoning:
Why was this exception approved
Why did that process change six months ago?
Who decided that this team handles this type of request and not the other one?
If those conversations happened in DMs and the person who had them is gone, the organization has no way to answer those questions.
The longer informal systems run, the more knowledge concentrates in specific people. They bear the load without anyone fully realizing it.
When they leave, you don't just lose a person - you lose the undocumented system they were running.
Why the Obvious Fix Fails
The instinct when you recognize this problem is: we need to force people into the right system.
For a couple of months, there is compliance. Then people slide back.
You cannot force people off the shortest path. If your team is in Slack, asking them to open a portal every time they need to raise a request adds friction. It is small per instance, but enormous across a hundred instances a day.
The workaround persists not because people are difficult, but because it is simply faster.
Big-bang replacements have the same problem. New systems require behavior change. Behavior change requires sustained effort. Sustained effort dies the moment something urgent comes up, which in ops work is approximately every twenty minutes.
What Actually Works: Structure Around the Existing Path
We have a customer who started with one team, tracking bug reports and feature requests in a single Slack channel. It worked.
Other teams saw it and wanted the same thing. Six months later, they were using it across twelve departments.
No implementation project. No change management kickoff. Just structure layered on top of conversations that were already happening.
That is the difference between a transitional system and a replacement system. You are not trying to redirect how people work. You are making visible what they are already doing.
Three Questions That Tell You Where You Stand
Answer these three questions, and you'll know if you're in the messy middle:
Does your ticket volume look manageable, but your team says they are overwhelmed? If both are true, you are missing tickets.
When something falls through the cracks, is the answer always a DM? That means Slack is your real ticketing system. It is just not set up to be one.
If a key person on your team left tomorrow, would their replacement know why decisions were made the way they were? If the answer is no, your system of record is not a system. It is a person.
If any of these are true, the gap between your official process and your real process is already costing you.
You just cannot see it yet.
The companies that navigate the messy middle best do not wait for the big fix. They start with one team, one type of request, and make it visible. The volume that surfaces usually makes the case for everything else.
Thanks for reading,
Adam Smith
CEO & Founder, Wrangle
PS - What internal process has your team quietly worked around for so long that it just feels normal now?