There's a report your leadership team plans around each month, and it might not come from any system you own. It comes from a spreadsheet one person rebuilds by hand, pulling from a few places and cleaning it up in ways others can't quite follow. It works. It's usually on time. You probably don't think of it as a risk, because for years it hasn't been one.

You tend to find out how much you depend on that report the first month the person who builds it is out. The number your board sees, the number sales forecasts against, the number that anchors the quarter, turns out to live in one person's process rather than in anything the company actually built. That's not a reporting quirk. That's shadow work, and many revenue engines are running on more of it than their leaders realize.

Shadow work doesn't come from people cutting corners. It comes from capable people solving a real problem the official system left open. The CRM can't show what the team needs to see, so someone builds the spreadsheet that can. The process doesn't cover the messy seam between two tools, so someone reconciles them by hand each week. The onboarding that would take a new rep from lost to productive isn't written down anywhere, so the knowledge lives in whoever's been there longest.

In each case the person is doing exactly what you'd want. They saw a gap between what the system produces and what the business needs, and they closed it themselves. The workaround is a rational response to a design that asks for something it wasn't built to deliver.

This is why telling people to stop using their workarounds rarely works, and usually makes things worse. The workaround isn't the problem, it's the evidence of one. Take it away without changing what created it, and you've pulled out the thing holding the number together while leaving the gap wide open. Your team understands this even when leadership doesn't, which is why the spreadsheet quietly comes back a month after someone bans it.

The real cost of shadow work starts long before anyone leaves. It's what the workaround hides while it's still running.

When effort quietly fills a gap, the gap stops showing up in your metrics. The number comes in, the report gets delivered, the quarter closes. From where leadership sits, the operating model looks like it's working, because the output looks fine. What you can't see is how much of that output depends on a few people doing by hand what the system was supposed to do on its own.

So you plan against a picture that's more fragile than it looks. Forecasts get built on data that one person cleans up manually, which makes the forecast only as reliable as that person's time and attention. Decisions get made on a view of the pipeline that lives in a side thread rather than a system, so leadership is trusting a number it can't actually audit. The stability everyone's relying on is real in the moment and borrowed against the future, and the size of that loan goes untracked.

This is what makes shadow work more than a staffing risk. It isn't only that a person might leave. It's that while they're here, they're masking the true state of the operating model, and you're making real decisions on the masked version.

Then someone does leave, or go on leave, or move into a new role, and the bill arrives all at once.

The workaround goes with the person, because it lived in their process and their head, not in your systems. The report stops getting built, and it can't be rebuilt cleanly from what's left behind, because the cleanup steps were judgment calls that stayed in their head. The deals that moved because that person knew who to call stall, because the relationship and the timing went with them. The manual reconciliation stops, and two tools that didn't quite agree are suddenly out of sync in front of everyone.

The cost lands on both sides of the house. If you run sales, you lose the pipeline visibility and the side channels that were quietly carrying deals, usually in the middle of a quarter you've already committed to. If you run marketing, you lose the routing or the reporting that one person maintained by hand, right before the review where you have to defend the number. Neither of you saw it coming, because a workaround that's performing is hard to tell apart from a process that works.

Each month the workaround succeeds is a month the underlying gap goes unaddressed, because the number keeps coming in and nothing forces the question. The better your people are at covering for the system, the longer its real condition stays hidden, and the larger the eventual bill.

You don't need to fix anything this week, and you shouldn't try to. You need to see clearly what you're actually running on, which many leaders haven't looked at directly.

For one cycle, watch for four things:

Then ask your team one question, and ask it plainly. What would break next week if you were out? People will tell you the truth, because they've been carrying these workarounds and they know which ones are load-bearing. Their answers are a map of where your operating model depends on effort you can't see.

When you raise this upward, frame it carefully, because the wrong framing gets your best people punished for holding the company together. This isn't a case for cross-training a couple of individuals or writing more documentation. It's evidence that the system is leaning on people to cover gaps it should be closing itself. That's a different conversation with a CEO, and a more honest one, because it points at the design instead of the people who've been quietly covering for it.

Seeing the shadow work is the whole task for now. What it tells you about the system underneath is worth sitting with before you touch a thing.

If this was useful, forward it to a colleague who would benefit from rethinking how sales and marketing align to drive sustainable growth.

Until next week,

Jeff

RevEngine™ | Built for Revenue Leaders Driving Alignment and Growth — Together.