The Small Business IT Briefing

Episode: How to Actually Work Well With Your MSP (The Executive Alignment Conversation)

John Huston:

Welcome back to The Small Business IT Briefing. I’m John Huston.

Adam Butler:

And I’m Adam Butler.

John:

Today we’re diving into something that honestly might be one of the most important conversations we have on this podcast. How to actually work well with your Managed Service Provider. This isn’t a sales conversation. This is a reality conversation. Because we’ve seen relationships where the MSP becomes a strategic growth lever… And we’ve seen relationships where both sides are frustrated. The difference usually isn’t technical skill. It’s alignment.

Most businesses think hiring an MSP solves IT. And technically — it does. But operationally? It introduces a partnership dynamic. IT is no longer the person down the hall. It’s now a third party that needs direction, authority, communication structure, budget clarity, and risk tolerance defined. Without those things, even a great MSP will struggle.

Let’s make this practical. A company hires us. We assess the environment. We identify risks. We recommend MFA enforcement, device standardization, removing local admin, replacing aging infrastructure, lifecycle planning. Department heads agree. Operations says yes. HR says okay. Finance says we’ll review. But no one makes the final decision. So tasks sit. They go into what I call the Pending Bucket.

Adam:

What exactly sits in that bucket?

John:

Everything important. Security improvements. Lifecycle upgrades. Policy approvals. Compliance changes. Access controls. Vendor consolidation. These are structural improvements. They stall because ownership is too busy, delegating without empowering, or unaware decisions are waiting.

Then ownership gets looped in weeks later. They approve fifteen things in twenty minutes. Suddenly we’re executing everything at once. It feels chaotic — but it’s compressed decision-making.

Adam:

Let’s talk about something uncomfortable — how MSPs make money.

John:

Most MSPs operate on per-user or per-device recurring agreements with defined scope. Monthly agreements cover helpdesk, patching, monitoring, security stack, and standard administration. They usually do not cover major migrations, vendor troubleshooting, custom integrations, compliance audits, or architectural redesigns. Just because something touches software doesn’t mean it’s included. If that isn’t clearly understood, tension builds and trust erodes.

Let me tell you a story where alignment worked. We recommended MFA enforcement. Before rollout, the CEO sent an internal email: “Starting next month, MFA will be required. This is our security standard. IT will assist.” No drama. Minimal pushback. Smooth rollout. That alignment saved hours of support and reinforced authority.

Now let’s flip it. Leadership says go ahead — but doesn’t communicate internally. We enforce MFA. Tickets flood in. Employees are angry. Managers escalate concerns. Now we’re defending security instead of implementing it. That doubles the workload and creates unnecessary friction. All of it could have been avoided with a two-minute leadership communication.

An MSP cannot make policy for your company. We can draft it, recommend it, design it. But someone internally must say yes. Security requires leadership sponsorship.

Business owners have two options: Stay engaged. Or delegate clearly and empower someone qualified. What doesn’t work is being too busy to engage while refusing to empower anyone else.

Let’s talk communication structure. If employees contact IT via text, email, Teams, portal, or personal cell phones without structure, fragmentation occurs. Choose one primary intake channel and reinforce it internally. Structure equals efficiency.

Executives sometimes say, “I don’t know what my MSP is doing.” Ask directly: Where are we on lifecycle upgrades? What is our risk posture? What projects are pending? What compliance gaps exist? Clarity reduces noise.

When alignment is strong: Lifecycle planning is predictable. Security investments are intentional. Budgets stabilize. Compliance improves.

When alignment is weak: Hardware ages. Emergency purchases spike. Risk increases. Insurance premiums rise.

Here’s the rule we’ve learned: Twenty minutes of real executive alignment doubles productivity. Without it, we spin. With it, we execute.

Adam:

So ultimately, this isn’t about technology.

John:

It’s about alignment. Technology amplifies structure. If structure is strong, IT becomes leverage. If structure is weak, IT becomes friction. Your MSP cannot replace leadership. But with leadership alignment, they can multiply it.

Thanks for listening to The Small Business IT Briefing. Alignment is a competitive advantage. We’ll see you next time.