How to Audit Your ConnectWise Setup in an Afternoon

You don't need to hire a consultant to figure out if your ConnectWise setup has problems. You can identify most of the major issues yourself in a few hours if you know what to look for.

Now, fixing those issues is a different conversation — some of them are quick, some require careful planning. But the audit itself? That's an afternoon. Grab some coffee, block your calendar, and work through this checklist. By the end, you'll have a clear picture of where your PSA is helping you and where it's quietly holding you back.

Hour 1: Service boards and ticket flow

Open your service boards list. Count them. If you've got more than 8 boards for a team under 30 people, you probably have boards that should be consolidated. Look for boards with fewer than 5 tickets per month — those are candidates for merging.

Now pick your busiest board and look at the status list. Count the statuses. If there are more than 10, you've got status bloat. Check whether each status answers the question "what's happening with this ticket right now?" If two statuses mean essentially the same thing with a subtle distinction your team ignores in practice, consolidate them.

Check your ticket types on that same board. Are they specific enough to be useful for routing and reporting, but not so granular that techs can't figure out which one to pick? "Network Issue" is useful. "Network - Switch - VLAN - Configuration - Minor" is not.

Pull up the last 50 closed tickets. Look at the time between creation and first response. Look at the time between creation and closure. Are there outliers that sat for days without being touched? Those indicate routing or assignment gaps.

Hour 2: Agreements and billing

This is where the money hides.

Pull up your agreement list. Sort by oldest. Open the five oldest active agreements. For each one, check: does the agreement type match how you actually deliver and bill the service? Are the additions current — do the line items and quantities match what the client actually has deployed? When was the last time someone reviewed this agreement?

Now do the same for your five largest agreements by revenue. Same questions. If any of those agreements haven't been reviewed in the past six months, there's almost certainly a gap between what you're delivering and what you're billing.

Check for agreement additions tied to M365, Azure, or security tools. Pull the current license or agent count from the vendor console and compare against what's in the agreement addition. Write down the discrepancy. That number, multiplied by your per-seat rate, is money you're not collecting.

I've never done this exercise with an MSP and found zero discrepancies. Not once.

Hour 3: Workflow rules and automation

Open your workflow rules list. Sort by board. For each board, read through every active rule and ask three questions:

Does this rule still serve a current business process? If the rule references a team member who left a year ago, a board that was renamed, or a status that no longer exists, it's stale.

Can I explain what this rule does without reading the detailed configuration? If not, it's poorly documented and probably fragile.

Does this rule conflict with any other rule on the same board? Look for multiple rules that trigger on the same event (ticket creation, status change) with overlapping conditions. Those are time bombs.

Count your active rules. Count the ones you're confident are working correctly. The gap between those two numbers tells you how much automation debt you're carrying.

If you have zero workflow rules — and a surprising number of MSPs don't — write that down as your single highest-impact improvement area. Even three or four basic rules (auto-routing, SLA escalation, stale ticket alerts) will save hours every week.

Hour 4: Integrations and data hygiene

Check each integration you're running. Open the integration settings for your RMM, accounting platform, and documentation tool. Look for sync errors, failed connection logs, or items in an error queue. I guarantee at least one integration has been silently failing for weeks.

Then look at your configurations (the asset/CI list). Filter for configurations with a status of "Active." Scan for machines or devices you know have been decommissioned. Every stale configuration in an active state is potentially skewing your per-device billing and your reporting numbers.

Finally, look at your member list. Check for inactive members who still show as resources in scheduling or dispatch. Check for API member accounts tied to integrations — are they clearly labeled? Does anyone know which integration uses which API key?

What to do with what you found

You'll probably come away from this audit with 10–20 findings across four categories. Don't try to fix everything at once. Instead, prioritize ruthlessly:

Fix this week: Anything directly causing incorrect billing — stale agreement additions, missing billing line items, broken accounting sync.

Fix this month: Stale workflow rules, board consolidation, status cleanup.

Fix this quarter: Integration health, configuration cleanup, reporting improvements.

The findings from this afternoon audit are essentially the same things a professional PSA health check would identify. The difference is that a consultant would also tell you exactly how to fix each one and how to prioritize by business impact. But knowing where the problems are is more than half the battle.

---

Want a deeper audit with a fix plan? Book a discovery call and I'll walk through your ConnectWise setup with you.