AI strategy for MSPs isn’t about using AI – it’s about proving ROI fast without creating security risk.
This is Part 2 of my conversation with Darryl Cresswell, and I’m excited to get back into it because this is where the conversation moves from “AI curiosity” to real operational truth.
Darryl isn’t theorizing about what MSPs should do. He’s actively implementing AI and automation, and he has clients lined up right now waiting to have conversations about it.
But what stood out most wasn’t the tools.
It was the discipline.
Because the MSPs who win in 2026 won’t be the ones who adopt the most AI platforms.
They’ll be the ones who build AI capability with focus – quick wins, connected systems, and security-first governance.
Here’s the framework that ties it all together:
What Is the One AI Insight MSP Leaders Keep Missing Right Now?
Here’s the core idea from this episode:
AI becomes transformational when it creates visibility you didn’t have before; not when it just automates what you already see.
Most AI conversations in our industry revolve around speed.
Faster tickets.
Faster responses.
Faster reporting.
But Darryl described the most exciting AI wins differently.
He talked about integrating systems that were completely separated and using AI plus API connectivity to make them talk to each other. Then taking that information and presenting it in a way that fits how the business actually works.
That’s not just automation.
That’s operational intelligence.
And once you get that kind of visibility, something interesting happens.
You start discovering gaps you didn’t know existed:
- systems that aren’t aligned
- workflows that look fine on paper but break in reality
- reporting that hides problems instead of surfacing them
- manual audits that are so painful nobody does them
This is why Darryl said it’s a game changer.
And I agree.
The next wave of MSP differentiation won’t come from “AI features.”
It’ll come from using AI to eliminate blind spots.
Why Are MSP Clients Demanding AI Implementation So Fast in 2026?
One of the strongest signals Darryl shared is the demand curve.
He has a long list of clients already waiting to talk about implementing AI – and what’s driving that demand isn’t curiosity.
It’s fear.
They believe their competitors are already doing this.
They feel outpaced.
Outworked.
Outperformed.
They don’t want to lose ground, but most of them don’t know where to start.
And that’s where MSP leadership becomes the difference.
Because clients aren’t really asking for “AI.”
They’re asking for:
- automation that reduces overhead
- integrations that eliminate double entry
- better workflows
- better insight
- competitive advantage
AI is just the layer that makes those outcomes possible.
How Do MSPs Actually Get 5X ROI From AI and Automation?
Darryl wasn’t talking about small ROI.
He was talking about 5X ROI right out of the gate.
And the strategy behind it is simple:
Get quick wins early.
Quick wins don’t just create savings.
They create belief.
Darryl described something I’ve seen repeatedly too: once you successfully help a client put in one automation, one meaningful quick win: their mindset changes immediately.
Their brain starts firing:
“What if we did this in operations?”
“What if we did this in finance?”
“What if we connected this system to that system?”
“Can you help with this too?”
And the answer is almost always yes.
That’s how AI adoption compounds.
Not through hype.
Not through education alone.
Through proof.
Why Not Everything Should Be Automated (And Why That’s the Real Strategy)
This was one of the most important parts of the episode, because it’s where a lot of MSPs get distracted.
Darryl said something that should be a rule, not an opinion:
Not everything needs to be automated.
He gave a simple filter that every MSP leader should adopt.
If you’re saving three hours a month, it’s probably not worth automating.
That’s not leverage.
But if you’re saving four hours a week across five or six people, now you have a real business case.
That distinction is the difference between:
- AI activity (busy work)
and
- AI capability (repeatable leverage)
The goal isn’t to automate more.
The goal is to remove constraints.
What Happens When AI Fits Your Workflow Instead of Forcing You Into Software?
Darryl described something I’ve seen across high-performing operators: the power of making systems work the way you work.
Most MSPs have spent years helping clients adapt to off-the-shelf software. That’s always been the model.
But AI flips the opportunity.
Now you can:
- integrate systems through APIs
- pull data across disconnected platforms
- build workflow-native dashboards and insights
- reduce learning curves
- increase adoption
Darryl talked about how much insight they gained internally once they did this, and how they found things that weren’t working the way they thought they were.
That’s the point.
AI isn’t just about efficiency.
It’s about clarity.
Why AI Governance and Cybersecurity Must Come First for MSPs
This episode wasn’t just about ROI.
It was about risk.
Darryl said something that I want MSP leaders to take seriously:
AI implementation without strategy is a disaster waiting to happen.
And the next layer is even more important:
AI implementation without security is dangerous.
Cybersecurity hasn’t changed because AI arrived.
If anything, it has become more important: because now we’re integrating third-party AI applications into Microsoft 365, CRMs, ERPs, and internal business systems.
Without boundaries, controls, and governance, you can leak sensitive information faster than most organizations realize.
And the risk isn’t just from outsiders.
AI introduces two categories that many businesses still aren’t thinking about clearly.
What Is Shadow AI and Why Is It Already a Problem?
Shadow AI is the same concept as shadow IT; but faster.
Employees inside organizations are using AI tools that leadership doesn’t know about.
Free ChatGPT accounts.
Browser copilots.
Random AI plugins connected to email.
Many people don’t realize what data they’re sharing or where it goes.
That’s exposure.
And if MSPs don’t create guardrails, clients will learn the hard way.
How Do Insider Threats Change When AI Has Too Much Access?
Darryl also made a point that most security conversations miss.
When AI has too much access, insider risk changes.
A junior employee can unintentionally access payroll, financial records, or sensitive internal information, not because they’re malicious, but because governance wasn’t built first.
This is why Darryl believes (and I agree) we’ll see compromises in 2026 tied directly to failed AI implementations.
Not because AI is “bad.”
Because access was sloppy.
Leadership Takeaway: What This Means for MSP Leaders
If you’re leading an MSP right now, the goal is not to “sell AI.”
The goal is to build repeatable, secure outcomes.
This episode reinforced a few non-negotiables for me:
- Start with ROI discipline, not shiny tools
- Prioritize quick wins that build trust
- Use AI to create visibility, not just automation
- Integrate systems through APIs to remove blind spots
- Make governance and security the foundation
- Treat shadow AI as a current risk, not a future one
Anchor Quote
“AI implementation without strategy is a disaster waiting to happen.”
That line frames the entire market.
Because AI is not forgiving.
If you deploy it with no plan, you don’t just waste time.
You create shelfware, confusion, and risk.
Practical Application: One Action You Can Take This Month
Run an AI + Automation Quick Win Assessment with a security lens.
Ask three questions:
- Where are we losing four or more hours per week across multiple people?
- Which systems are disconnected and hiding operational truth?
- What guardrails must exist before AI touches sensitive data?
That’s enough to create a real roadmap.
One Memorable Takeaway
AI capability isn’t built by automating more.
It’s built by automating what matters and securing it before it scales.
That’s how MSPs become trusted advisors in the AI era.
And that’s exactly why AI By Design exists.
Stay tuned for more. Until next time.
