Here’s a pattern I see at almost every MSP, including ours for years.
You sign a new client. The CEO is in the room. You sold them a vision of the future: better technology, fewer problems, IT that supports where the business is going. They’re excited. They sign.
And then you hardly ever see them again.
You get handed off to an office manager, an executive assistant, or a controller. Someone whose job is to “manage IT.” They’re good to work with, but they’re not the person who bought the vision. And year after year, the relationship drifts further from the decider.
That’s a problem. Because the vision you sold on day one? You need to resell it every single year. And you must do that with the decider.
The fix: one meeting a year
The way to get executives re-engaged is a Strategic Alignment Session. Once a year, held before you present the annual IT plan.
The format is simple: you ask open-ended questions about their business, and then you shut up and listen. The client should do 95% of the talking.
That’s it. Just questions about their business.
And here’s the thing: executives love this meeting. People love talking about their business. I had one of these meetings with the CEO of a company doing over $300M in revenue. He talked for basically the entire meeting. At the end, he told us it was the best meeting he’d ever had with us.
We barely said anything. We just asked good questions and let him go.
Why this works
It gets the executive back in the room. When you invite a CEO to a meeting about their business, not about IT, they show up. And once they’ve spent an hour telling you where the company is headed, they come back for the IT plan presentation too. Because now it’s their plan. They’re invested. You’ve reconnected the person who bought the vision with the people delivering it.
Your team learns the business. Your vCIOs and account managers sit in that room and absorb more about the client in one hour than they would in a year of QBRs. New departments, new service lines, new offices, growth targets, what’s keeping the CEO up at night. That context changes everything about the recommendations they make.
Your IT plan actually addresses the business. When you build the roadmap and budget right after this session, recommendations tie back to something the client told you. You’re not guessing at priorities. They handed them to you.
What to ask
The goal is to understand what’s really going on inside the business. Some of the questions we use:
- What are your goals for the next 6–12 months? The next 3 years?
- What’s changing? New departments, new lines of service, new markets, new offices?
- What are the biggest pain points in the business right now?
- Where is the team losing time or getting frustrated?
- How are your current tools and applications helping, or getting in the way?
Then two rules:
- Never interrupt. The more they talk, the better. Take notes and keep them going.
- Don’t sell. This meeting is about them. The selling happens naturally later, when your IT plan reflects everything they just told you.
We’ve built a full Strategic Alignment Cheatsheet with the complete question set if you want a ready-made guide.
What it did for us
We implemented this at our MSP across all our clients, and it completely changed the relationships. We’re closer to our clients. They see us as more proactive. And our vCIOs and account managers simply know the businesses better, which shows up in every roadmap.
One meeting a year. Open-ended questions. Let them talk.
If you’re only going to add one thing to your vCIO process this year, make it this!
Simon is the President of S3 Technologies, a leading Canadian MSP he co-founded in 2003. He built and scaled the vCIO team which eventually lead to him co-founding Propel Your MSP in 2018 to help MSPs with their vCIO services.
