#5 – Don’t Be That Guy - ConnectWise Setup Mistakes & Fixes (Ryan Alter)

In Episode #5 of Don’t Be That Guy on the BMK Vision Podcast, Josh Peterson and Ryan Alter deliver a blunt reality check: most MSPs aren’t “bad at ConnectWise” because they lack advanced automation — they’re bad because they skip the basics that make the PSA valuable in the first place.

The irony is that the fundamentals Josh calls out — ticket hygiene, time entry discipline, accurate statuses, cost inputs, and clean agreement data — don’t magically make tickets resolve faster. Instead, they make your business measurable. And if you can’t measure it, you can’t manage it, price it, or scale it without leaking profit.

If you’ve ever proudly built workflows, templates, and integrations — only to realize your boards are chaos and your reporting is unusable — this episode will feel uncomfortably familiar (and extremely fixable).

The punchline: this isn’t about faster tickets — it’s about better data

Josh sets the tone early: the items most MSPs skip (type/subtype/item, clean boards, accurate statuses, cost inputs) rarely produce an immediate dopamine hit for a technician. But they generate the data that lets leadership answer the questions that actually matter:

• Which clients are profitable — and which are quietly draining us?
• What problems keep repeating — and what should be refreshed or replaced?
• Are we dispatching the right work to the right cost level?
• What do projects really take so we can price fixed-fee confidently?

Agreements: additions are table stakes — costs are the unlock

Most MSPs understand they should use agreement additions. But Josh calls out the deeper failure: building additions for invoicing accuracy while ignoring the cost inputs that make agreement gross profit reports meaningful.

• Use additions so the agreement reflects what’s being delivered (licenses, services, devices).
• Add cost to each addition so gross profit reporting actually works.
• Keep costs updated, especially for common licenses and recurring vendor charges.

ConnectWise + QuickBooks: stop “hand-carrying” your accounting

Josh shares one of the most common “out of the blue” calls BMK receives: a company has used ConnectWise for years — and only now decides to integrate with QuickBooks. The usual reason? A long-time bookkeeper is retiring and the manual process can’t survive the handoff.

• If you delay integration, your invoicing and data hygiene often stay artificially low.
• Manual entry is expensive, fragile, and hard to scale.
• Integrate early so ConnectWise becomes a system — not a reporting mirage.

Ticket categorization isn’t admin work — it’s evidence

Ryan explains why type/subtype/item became non-negotiable: mature clients (especially CFOs) ask for proof. When you can show ticket history tied to a device or system, the upgrade conversation stops being opinion — it becomes evidence.

• Better categorization supports client-facing justification for refresh cycles.
• It also exposes internal dispatch mismatches (expensive labor doing cheap work).
• Dispatch becomes a force multiplier when the system is measurable.

Member cost: if labor cost is missing, profit reporting is fantasy

One of the most common reporting failures is simple: labor cost isn’t set. Without member cost, you can log hours all day long and still learn nothing meaningful about profitability by client, agreement, or service line.

• Set member cost so labor becomes real in profitability reporting.
• Use a clean model: base wage plus the necessary payroll burden.
• If internal visibility is a concern, handle it with permissions — not by skipping the data.

Too many service boards is a symptom of immaturity

Josh calls it “peeking into the mind of a mad man”: board sprawl. The guidance is simple: keep boards minimal (Josh’s baseline is three) and only add boards when you truly need different workflow behavior.

• Add a board only when it requires meaningfully different SLAs or workflow rules.
• Use views to segment work without exploding complexity.
• High board count confuses technicians and blurs accountability.

Views: exception-based management for dispatch, time review, and leadership

Views aren’t just “nice filters.” Used properly, they enable exception-based management: show me what’s most likely wrong so I can fix it fast. Whether it’s time entries missing agreement linkage or tickets stuck in “New” with time attached, views let you manage by signal instead of noise.

• Create views that surface the most common hygiene failures.
• Give each role a default view (tech, dispatcher, service manager).
• Let the system show problems automatically instead of relying on tribal memory.

Statuses: if they aren’t accurate, you lose the “A” in PSA

Josh makes a strong claim: inaccurate statuses break the automation engine — SLA timers, workflow triggers, and leadership visibility. Ryan agrees in principle and adds realism: the goal is operational consistency, not perfection every second. But the standard still matters because everything downstream depends on it.

• Status accuracy drives SLA performance tracking.
• Status changes trigger workflow rules and customer communication.
• Dispatch cannot load-balance if the system lies about reality.

Budget hours + due dates: better dispatch, better estimating, better sales

The budget and due date fields are an underused lever for MSP maturity. They enable real planning: workload vs. time window, technician load balancing, and accurate feedback loops for sales and fixed-fee pricing. Ryan shares a practical insight: technicians tend to consume whatever budget exists — so MSPs must use budgeting thoughtfully and consistently.

• Budget hours create a learning loop for estimating and fixed-fee confidence.
• Due dates prevent tickets from aging into “163-day mysteries.”
• Sales gets real feedback when estimates are validated against ticket reality.

Episode highlights

• 00:01:54 – The punchline: none of this is “faster tickets” — it’s about the data you can extract.
• 00:03:54 – Using ticket data to justify upgrades (especially to CFOs).
• 00:06:51 – Agreement additions are table stakes — costs are what make gross profit real.
• 00:09:00 – Why ConnectWise + QuickBooks integration still gets delayed for years.
• 00:13:54 – Why member cost matters — and the internal objections MSPs raise.
• 00:18:58 – Too many service boards: why it happens and how to test whether you need them.
• 00:22:56 – Views as the path out of board sprawl and into exception-based management.
• 00:30:36 – Status discipline: the foundation for automation, SLAs, and visibility.
• 00:34:50 – Budget hours + due dates: planning, dispatch clarity, and sales feedback loops.
• 00:41:14 – The leadership truth: none of this matters if you don’t care about the numbers.

About the guest: Ryan Alter

Ryan Alter is a former MSP owner who grew a one-man shop into a 25-person operation before selling the business. He brings an operator’s perspective to PSA discipline — especially around dispatch structure, budgeting, and the reporting hygiene required to price confidently and scale profitably.

🌐 Connect with Ryan Alter on LinkedIn →

About the host: Josh Peterson

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through Don’t Be That Guy, Josh helps MSP owners identify operational leaks, improve PSA discipline, and build systems that scale without relying on heroics.

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Frequently asked questions

Why do MSPs build advanced automation but still “fail” at ConnectWise?
Because workflows and templates don’t compensate for messy boards, bad time entry, missing costs, and inconsistent statuses — and those fundamentals are what make reporting actionable.

What’s the fastest ConnectWise fix that improves profitability insight?
Set labor cost (member cost), ensure agreement additions include costs, and enforce status + time discipline so the system stops lying about reality.

Do we really need type/subtype/item?
If you want evidence for refresh cycles, client spend conversations, agreement profitability insight, and dispatch optimization, yes. If you don’t care about reporting, it will feel like pointless admin.

How many service boards should an MSP have?
Keep it minimal. Add boards only when you truly need different SLAs or workflow behavior. Use views to segment work without multiplying complexity.

What do budget hours and due dates actually do for us?
They enable workload planning, improve dispatch decisions, and create feedback loops that make estimating and fixed-fee pricing more accurate over time.

Related resources from Bering McKinley

• Recurring Revenue in ConnectWise: How to Set Up Agreements That Don’t Break Later
• Dispatchers Keep Your Support Team Accountable
• BMK Vision Podcast main page →

Want to continue the conversation?

If you’re ready to stop “ConnectWising wrong” and start using your PSA as an actual operating system — not a glorified ticketing tool — explore Vision or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision