You've set up Strategy Overview, built your first Report, added your team, and branded the platform. Now it's time to sit down with a client and have a real conversation.
Your first TSM doesn't need to be a polished production. It needs to be a focused, strategic conversation where your client walks away feeling like someone is looking out for their technology interests. Everything you've set up so far gives you the tools to do that.
Pick the right client for your first one
Choose a client where you have a good relationship and some room to learn. Avoid your most demanding client or your newest one. You want someone who will give you honest feedback and appreciate that you're bringing more structure to the strategic conversation.
Ideal first TSM clients tend to be mid-size accounts where you already know the technology environment reasonably well. You're not trying to impress them with the tool, you're trying to have a better conversation than you've had before.
What to have ready
Before the meeting, make sure your Report has these basics covered:
Executive Summary with 2 to 4 sentences about the state of their IT
Assessment with at least the Fundamentals items graded
IT Plan with a handful of strategic items laid out by quarter
Technology filtered to show active assets grouped by type
That's enough. You don't need a perfect Assessment, a fully budgeted Roadmap, or every column customized. Those things come with time.
Running the meeting
A great TSM is a conversation first. The Report is there to support your advice, not replace it. You could walk into a meeting with a strong Executive Summary, a solid IT Plan, and a few good questions and have an excellent strategic conversation. Not every part of the Report needs to be shown to the client, and not every part needs to be discussed. Use what serves the conversation and skip what doesn't.
Open your Report in Presentation Mode and let the conversation guide what you show. Here's a flow that works well for a first TSM:
Start with the Executive Summary. This sets the tone. Keep it brief and conversational, not a script. Something like: "Here's where I see things today, and here's what I think we should focus on."
Use Technology data to ground the conversation. If you have technology data connected, this is your credibility builder. Real data about their environment, pulled from tools you already use, presented in a way they can understand. Point out aging assets, upcoming warranty expirations, and anything that connects to your recommendations. You don't have to walk through every device, just highlight what matters for this client.
Reference the Assessment where it adds value. The Assessment is your preparation tool. It helps you think through the client's environment and identify what needs attention. You may want to show specific items during the meeting to support a point, or you may not show it at all. Not every client needs to see grades and risk levels. Use the Assessment to inform your advice, and show it when it strengthens the conversation.
Walk through the IT Plan. This is often where the best conversations happen. Show them what you're recommending, when it should happen, and roughly what it costs. Clients engage when they can see a clear path forward. Be ready for them to reprioritize items or add new ones. That's a good thing, it means they're invested.
If you have a Roadmap, use it to talk about Budget. If you've filled in budget columns on your Plan and Assessment items, the Roadmap gives you a visual timeline of projected spend. If you don't have Budget data yet, skip the Roadmap for this meeting and add it next time.
After the meeting
Take five minutes right after the meeting while it's fresh:
Update any Assessment items based on what you discussed
Adjust IT Plan priorities or timelines based on client feedback
Mark the Report as Complete (click "Open" and toggle to "Complete")
Optionally save to PDF from Display Mode and email it to your client as a follow-up
If you use a PSA for ticketing, create any follow-up tickets or project entries while the conversation is still fresh. The TSM is only as valuable as the action that follows it.
What to expect
Your first TSM may feel a little rough. That's normal. Here's what most vCIOs experience:
You'll show too much or too little. That's fine. Each meeting teaches you what this client cares about and what you can skip next time.
Clients ask questions you don't have answers for. Write it down and follow up. It shows you're listening, not performing.
The meeting runs longer or shorter than planned. You'll calibrate your pacing over 2 to 3 meetings.
You'll want to go back and change things in the Report. Good. Do it. The platform is built for iteration.
The goal isn't perfection. The goal is to start having strategic conversations with your clients that are structured, repeatable, and grounded in real data. Everything improves from here.