Most MSPs don’t “get stuck” because the owner lacks intelligence or ambition—they get stuck because the business is still wired to treat the owner as the final processor of everything that matters. The moment your profitability depends on your personal conviction, your capacity becomes the company’s ceiling. That’s why the first real unlock isn’t another tool, another hire, or another workshop. It’s learning to translate intent into a system—one that can be owned by other people without collapsing when you’re tired, busy, or skeptical. If you want a practical way to structure that translation, start with a real plan (not a list) and anchor it to execution discipline: build your priorities into a Master Project Plan, use a simple planning framework that forces trade-offs, and normalize the behaviors that protect margin—like time-entry compliance. When those pieces exist inside an operating cadence—and not inside the owner’s head—you can finally shift the business from founder-dependence to team-dependence, which is the only kind of dependence that scales. (And if you want to see what that operating cadence looks like when it’s systematized, start here: Vision.)
This roundtable episode is a study in a pattern we see constantly: a capable owner reaches the “pain threshold” where brute force no longer buys progress. Policies get drafted, meetings happen, and nothing sticks—because the real issue isn’t whether the policy is correct. The issue is whether the organization is designed to absorb change without turning every new standard into a personal referendum on the owner. When that design is missing, the team’s feedback feels like sabotage, non-billable “projects” feel like betrayal, and the owner’s effort becomes a tax instead of leverage. The leadership move is to stop asking, “How do I get them to comply?” and start asking, “What structure would make compliance the natural outcome?” Once you can answer that, you can delegate ownership instead of delegating tasks, create buy-in without surrendering direction, and build a business that doesn’t require you to be the enforcer, the implementer, and the emotional shock absorber—all at once.
When an owner says, “I feel like I have to do everything,” the industry’s default response is usually motivational: hire better people, delegate more, stop micromanaging. But most of the time, that advice misses the structural reality. The owner is not simply “doing too much.” The company is designed so that decisions, enforcement, and standards require the owner’s presence to become real. That’s why the owner can craft a policy with a consultant, bring it to the team, and immediately feel their conviction crumble when it gets questioned. The policy wasn’t anchored to a shared outcome, a shared definition of success, or a shared method of measurement. It was anchored to the owner’s willpower.
There’s a difference between delegation and abdication, and many MSP owners oscillate between both without noticing. Delegation is transferring ownership with clarity: what success looks like, what constraints exist, and how progress will be reviewed. Abdication is transferring pain: “Here, take this, and don’t bother me.” The episode surfaces a more sustainable approach: give the team the outcome, assign a capable owner, and require a plan—not your plan, their plan—so the policy becomes something they helped build and can therefore defend.
Most owners underestimate how destabilizing change feels from the employee side. When a shop has run on informal norms for years, a sudden shift into “process mode” can look arbitrary—even if the change is correct. The team doesn’t resist because they hate improvement; they resist because they can’t see the chain from the new behavior to the business outcome. That’s where the “why” becomes non-negotiable. If you can’t explain why a new standard matters—profitability, billing accuracy, capacity planning, client experience—then the team is right to treat it as noise. And if you can explain it, you’ve just created a basis for aligned disagreement: they can challenge the method without questioning the goal.
One of the most damaging founder habits in MSPs is confusing internal novelty with business progress. Technicians love solving problems. Owners love believing those solutions will create future leverage. The result is a quiet margin leak: non-billable work that feels “important” but isn’t tied to a plan, a budget, or a measurable return. The answer isn’t to eliminate internal work; it’s to put it under governance. If an internal project doesn’t map to an initiative, doesn’t have an hour budget, and doesn’t have a defined outcome, then it’s not an initiative—it’s entertainment funded by your P&L.
Gary Boyle is an MSP operator and entrepreneur with deep experience building service businesses grounded in repeatable process and financial discipline. In this roundtable, Gary brings a pragmatic owner’s lens to delegation, initiative prioritization, and the hard trade-offs required to move from founder-dependence to scalable execution.
Ryan Alter is a former MSP owner and operator with a sharp operational focus on utilization, profitability, and execution discipline. Ryan’s perspective reflects years of navigating the tension between technical creativity and commercial reality—bringing clarity to how internal projects, incentives, and accountability systems either protect or erode margin.
Connect with Ryan Alter on LinkedIn →Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast, where he and his guests explore the leadership, execution, and financial discipline required to build enduring MSP businesses.
Connect with Josh Peterson on LinkedIn →
Because the company is often structured so that standards only “become real” when the owner personally implements or enforces them. Without clear ownership, outcomes, and review cadence, policies remain suggestions—and the owner becomes the system.
Separate direction from design. The owner sets the outcome and constraints (what must be true), then assigns a capable leader to propose the policy and implementation plan. You review against outcomes, not against personal preference.
Delegation transfers ownership with clarity: success metrics, boundaries, and review rhythm. Abdication transfers responsibility without support or measurement, which creates confusion and resentment—and usually returns the work back to the owner later.
Internal work must be governed like client work: tied to a plan, given an hour budget, scheduled intentionally, and measured for ROI. Without those constraints, “important” internal projects become margin leaks and a hiding place from accountability.
Most small to mid-sized MSPs should run one to two true initiatives per quarter—especially if they’re still building planning discipline. If you’re carrying 20–30 “initiatives,” you don’t have priorities; you have noise.
If you’re running an MSP and feel like everything still routes back through you, that’s not a character flaw—it’s a design flaw. The fix starts by choosing fewer priorities, naming the outcomes, assigning real ownership, and building the cadence that makes execution normal. If you want to share what you’re working through (or want a sharper operating lens on where the system is breaking), we’d love to hear from you.
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