I meet MSPs all the time, and so many of them are in the exact same place.
They’re not doing real strategic planning with their clients. Maybe they meet some of them somewhat regularly, but rarely all of them, and rarely with any real structure. It’s the thing they know they should be doing, but never quite get around to.
If that’s you, this post is for you.
Let’s start with the why, then I’ll walk you through the simplest possible way to begin.
The #1 reason: retention
Want to grow your business? The first thing you have to do is keep your clients longer.
It’s the easiest and cheapest way to grow. Acquiring new clients is expensive and slow. Keeping the ones you already have is neither. If you only take one thing from this post, let it be this: strategic planning is a retention engine, and retention is your cheapest growth lever.
The other reasons stack up fast
Once you’re meeting your clients strategically, a lot of good things start to happen.
You reconnect with the executives, the people who actually signed the contract. That relationship alone drives retention. It also gets projects approved. Those projects standardize your clients’ environments. Standardized environments are easier and cheaper to support, which means you operate a better, more profitable business.
Retention, revenue, standardization, efficiency.
Don’t go nuts, start simple
Here’s where most MSPs get stuck. They decide to “do QBRs” (a term I think is wrong, but that’s another post) and try to do everything at once: report on metrics, run audits, present audit results, talk projects, the whole thing. It’s too much. They burn out and quit before it becomes a habit.
So don’t do that. Start with what moves the needle.
Meet your clients once a year. Specifically, meet the executive, the person who signed the contract. Run a simple process with them built around two meetings.
Meeting one: understand where they’re going
The first meeting is about them, not you.
You sit down with the client and ask open-ended questions about their business. What are their goals for the next 12 months? The next 36? What’s changing in their business? What’s keeping them up at night?
That’s it. You’re listening, not pitching.
(We actually have a template for this meeting that you can download here)
Meeting two: show them the future
Then you go back and build a plan.
A three-year plan that highlights the projects you recommend, laid out as a roadmap with a budget attached. This is where you connect their business goals to a clear technology path forward.
We recommend using PropelLive to present this, because it lets you give the client a quick glance at where they are today, their current stack, their assets, and then shift the conversation to the future. We like to bring forward a few key objectives for the next three years, with a list of projects tied to each objective, all fitting inside a three-year budget and roadmap.
“But some of my clients are cheap and never buy anything”
I hear this a lot. “These clients just won’t take anything, so what’s the point?”
Here’s my argument: running this process is helping your retention even when the client doesn’t buy a single project.
Why? Because that client walks away thinking “My MSP is really on the ball. These guys are organized. They’re thinking ahead for me.” That impression alone keeps clients. You’re not just selling projects, you’re reinforcing that they made the right choice picking you.
Why the executive matters so much
If you’re not having these meetings, you’re relegated to your day-to-day point of contact: the office manager, the controller, the executive assistant, whoever that is. That person matters, but they didn’t sign your contract.
Think back to when the executive signed with you. They were excited. They were leaving a situation they didn’t like, and you sold them a picture of a better future. That excitement is what won the deal.
Your job now is to keep painting that picture. To keep showing them you’re pushing their business forward. The annual strategic meeting is the simplest, most powerful way to do exactly that.
Keep it simple
This doesn’t have to be a massive, metric-heavy production.
Show them what they have and where they’re at, simply. Then show them what you propose, aligned to their objectives, with a budget. That’s what PropelLive is built to do: help you run these meetings, impress your clients, and reinforce that they made the right choice in you.
Where to start
If you’re not doing this, this is what you need to start doing. Not everything at once, just this.
Meet the executive once a year. Two meetings: one to listen, one to show them the future. Start slow, build the other pieces later. If a client genuinely has very little going on, fine, maybe you do it every 18 months. But you need to do this, and honestly, you need to do it for every single client.
That’s how you grow your business. That’s how you keep your clients. And PropelYourMSP makes it easy to do.
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.
