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Using Strategy Overview

A complete guide to the platform: Modules, Reports, Assessments, IT Plans, and presenting TSMs to clients.

Updated in the last hour

If you're new to Strategy Overview, this guide walks you through the platform from start to finish. Each section has a short video followed by supporting text. You can read, watch, or both.
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What is Strategy Overview?

Strategy Overview is a platform for running strategic IT meetings. It's built for:

  • vCIOs and MSPs
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  • Fractional CIOs
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  • Internal IT departments

It gives you a structured way to:

  • Assess client technology environments
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  • Standardize your technology stack across all clients
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  • Build roadmaps and budgets
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  • Run a full Technology Strategy Meeting from prep through presentation

Why "TSM" instead of "QBR"?

We use Technology Strategy Meeting (TSM) because not every strategic meeting happens quarterly. Some clients benefit from monthly check-ins, others from semi-annual deep dives. TSM describes what the meeting actually is: a structured conversation about your client's technology strategy.
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If your team uses QBR, TBR, or something else, the process and tools are the same.
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Platform Orientation

This section covers the different Modules and what they're for, how Reports and templates work, and the different modes you'll use depending on what type of work you're doing. Keep in mind that you may see slightly different things in your own tenant depending on how you've been set up and what Modules are enabled.
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First things first - User Settings

Get into your settings and find your user information. Set up a profile picture (it shows up in several areas of the platform and possibly on your Reports), fill out your name and contact info, and turn on two-factor authentication.
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Modules

Down the left side of the platform you'll see Modules.

  • Companies Module shows all companies in the platform that you have access to. This may or may not be every company in your account, depending on how permissions and groups are set up. Each company shows an assigned vCIO, widgets with basic info, their market or vertical, website, logo, and client start date.
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  • Strategy Module is where most of your work happens. This is your main workspace for creating and managing Reports for each client. You'll see your client list here, and each client can have one or more Reports. We'll go deeper on this one below.
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  • Plan Module is where you manage IT Plans and strategic initiatives across clients. Plans get added as Parts of your Reports.
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  • Technology Module shows all client technology data across your entire client base: assets, Configurations, and Flexible Items synced from your PSA, IT Glue, and other integrations. Inside a Report, you'll see the same data filtered to that one client.
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  • Schedule Module lets you track your TSM cadence, assign vCIOs to companies, and set target meeting frequency for each client.
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  • Stack Module gives you a cross-client view of your technology stack, showing what's standardized and where there are gaps or non-standard items across your client base.

Your account may also have additional Modules depending on your integrations and configuration. Modules can be added, removed, and relabeled in Settings.
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You'll also find Settings in the left navigation. That's where integrations, branding, templates, and user access are configured.
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The Strategy Module, Reports, and Templates

The Strategy Module is where you'll spend most of your time. Every Report is generated from a Template.
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The default "Strategy Overview" template:

  • Comes pre-loaded with 190+ Assessment Items covering best practices from thousands of client meetings
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  • Works well for most clients out of the box
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  • Is meant to be customized for your MSP over time

You can also build from scratch, but most MSPs get more value from starting with the default and adjusting it.
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The template controls what Parts appear in a Report, what Assessment Items are included, what columns are visible, and default content for text sections.
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Most MSPs maintain one primary template.

Creating a Report:

  • Find your client in the Strategy Module and click the new file icon

  • Create a new Report for every engagement
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  • Set the Report Date to when the meeting is scheduled (approximate is fine)
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  • Leave the "carry content over from previous Report" option checked (it's preselected). Assessment entries, Plan items, and text carry forward, and the previous Report is marked complete automatically.

Parts

The Report is made up of Parts, which appear as tabs across the top. You can think of them like sections. Everything comes from the template, though you can make customizations on a client-by-client basis if you don't want to follow the template exactly. Part types include:

  • Cover Page: rich text with template macros that auto-fill the client's company name, Report date, and prepared-by name
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  • Executive Summary: freeform text for the overall state of the client's IT and strategic direction
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  • Dashboard: customizable widgets showing Health Scores, progress charts, and data visualizations
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  • Assessment: the core evaluation with items, groups, grades, and budgets
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  • Technology (Flexible Items): assets from your PSA and other integrations, organized by group
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  • Plan: embeds a live Plan from the Plan Module (commonly used for IT Plans)
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  • Office 365: Microsoft 365 users, MFA status, licensing
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  • Contacts: contacts from your PSA
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  • Roadmap and Budget: where all budgeted items from the Assessment, Technology, and Plan roll up
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  • Embed: for external widgets like BrightGauge dashboards
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  • External Content: links to external documentation
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  • Text: additional freeform text sections (meeting agendas, internal notes, custom content)

You're not locked into the default layout. Parts you don't need can be removed. You can also add Parts: a Text Part for a running meeting agenda, an additional Plan, a custom Dashboard. Reorder them in template settings or by dragging the tabs directly on the Report.
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Three modes

Each Part can be configured for three modes:

  • Build Mode: your working view for prep and documentation. All fields, internal notes, and editing controls are visible. This is where you do your work.
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  • Presentation Mode: full-screen, one Part at a time, like slides. Optimized for screen-sharing or in-person presentations. Navigate forward and backward through the Report. Everything is still editable: just double-click.
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  • Display Mode: the clean, formatted, client-facing view. Used for PDF generation and the client portal. Editing controls are stripped out.

The checkboxes in template settings control which Parts load in each mode by default. You can always override these when you're in a given mode.
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How template changes work

There are a few different types of template changes, and they flow to Reports differently:

  • Assessment Item changes (adding items, editing options, modifying tags, changing risks and solutions) update all Reports immediately, including existing drafts.
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  • Structural changes (Parts, column layouts) apply to new Reports automatically. To push them to existing open drafts, use the Apply changes to all drafts button in template settings.
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  • Text Part content (Cover Page, Executive Summary) disconnects from the template after the first Report. Edits you make for a specific client stick. See the Cover Page and Executive Summary section below for more on how this works.

Explore Dunder Mifflin

Dunder Mifflin is a pre-built sample company. Open its Report and browse through the Parts to see what a finished Report looks like. This is what you're building toward with your own clients.
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Building Your Report

This section walks through the main Parts of a Report and how to work with each one.
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The Assessment

The Assessment is where most of the analytical work happens, and it's where the Report Health Score comes from. It's a structured list of Assessment Groups and Items covering the client's full technology environment, all driven by the template.
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Running the Assessment gives you:

  • An ongoing inventory of where things stand for each client
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  • A way to demonstrate to the client the work you're doing for them

Assessment Items
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Each Assessment Item represents a specific topic you're evaluating: backup strategy, email security, endpoint management, server hosting, and more. Click any item to open it.
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Item Description and Health Standard
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Click the gear icon on an Assessment Item to see its template-level settings. Two fields matter most:

  • Item Description: plain-language explanation of what this item evaluates
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  • Health Standard: what your MSP considers "healthy" for this item. Example: a server Health Standard might specify the server needs to be under five years old, covered under manufacturer's warranty, and running on Dell or Lenovo hardware.

Both fields are customizable per MSP. They're not just instructional for your team. Arya uses the Item Description, Health Standard, and Item Name when generating status summaries and Grades. The more specific your Health Standards, the better Arya's automated Grades.
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Each item also has a Health Weight (1-5) that reflects its importance. A backup item would typically be a 5; something smaller and less critical would be a 1. Weights affect how much each item influences the overall Health Score.
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Status, Grade, Risk, and Solution
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Each Assessment Item has four fields:

  • Status: factual description of where the client stands (e.g., "Running Exchange 2016 on-premises, end of support October 2025"). Type directly or choose from pre-selectable options at the bottom. Those options are controlled at the template level.
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  • Grade: your evaluation (Healthy, Warning, Danger, Not Applicable, etc.). Each Grade counts as healthy, unhealthy, or excluded from the Health Score. Items left with the question mark Grade are unanswered and generally excluded from the Health Score.
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  • Risk: what could go wrong if this item isn't addressed
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  • Solution: your actionable recommendation

This is a living document. If you don't know something, leave the Status as "Needs Review" or "Needs Discussion." Items that don't apply can be set to Not Applicable, or hide an entire group using the eye icon.
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Don't worry about having everything graded when you're starting out.
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Budgeting
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Each Assessment Item has budget fields:

  • One-time costs: cost, target month, target year. These flow into the Roadmap and Budget Parts.
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  • Recurring costs: recurring amount, period, quantity, effective date, cancellation date. For ongoing costs like managed services or subscriptions.

Recurring columns are off by default. Turn them on at Settings > Templates > [Your Template] > Parts > Assessment > Columns.
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You don't need to budget everything. Focus on items that need work and have a realistic cost estimate.
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Flexible Item Groups
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Assessment Items can link to technology data from your integrations. Each item supports one related Flexible Item Group (e.g., "Managed Workstations" or "Firewalls"):

  • Configure the relationship at the template level: open the template, find the Assessment Item, select a Flexible Item Group
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  • Actual devices and assets from your PSA or IT Glue then pull in directly below the Assessment Item when you open it
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  • Gives you real data to reference while grading

Tags and Filtering
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Each Assessment Item has one or more tags. Use the tag filter in the toolbar to narrow the list:

  • "1. Fundamentals": core items; a good starting point
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  • "2. Operating": additional depth as your practice matures
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  • "3. Scaling": deeper items for larger or more mature clients

You can also use mass maintenance (filters and multi-select) to apply Grades or Statuses across multiple items at once.
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Manual Groups and Items
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Need to track something for a specific client that isn't in the template? In Build Mode, use:

  • + Manual Group in the Assessment toolbar
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  • + Manual Item in the Assessment toolbar

Manual entries only exist on that client's Report. They aren't added to the template.
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Arya
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Arya can help you fill out Assessment Items faster by generating status summaries and Grades from your data. See Arya AI Assessment Assistant for how to use her effectively.
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For deeper configuration, see Customizing Your Assessment and Health Score Logic.
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The Cover Page and Executive Summary

Cover Page
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Take some time with your Cover Page. It sets the tone and signals quality.

  • Uses template macros to auto-fill company name, Report date, and prepared-by name
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  • Additional macros available for MSP logo or client logo
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  • You can paste images directly
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  • Test it in all three modes to see how it looks

Executive Summary
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Keep it short. A CEO or CFO should be able to read it and get a snapshot without diving into details.
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What to include:

  • Current state of the client's IT
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  • Their strategic objectives
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  • What's been accomplished since the last meeting
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  • What's in progress

A custom GPT or Claude project is a good workflow for filling these out consistently. MSPs use the Executive Summary in different ways, so experiment with what works for you.
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How Text Parts behave
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Both of these are Text Parts, and Text Parts disconnect from the template after the first Report. That's intentional: you don't want your Executive Summary overwritten every time you update the template.

  • Changes for a specific client stick and carry forward
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  • To sync with an updated template later, use Reset Content from Template or Append Content from Template on the Part toolbar

Technology

The Technology Part shows assets from your integrations, organized into Flexible Item Groups: user technology, infrastructure, network, and others. Rearrange groups by dragging them.
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Working with assets:

  • Filter to Active items only and group by Type
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  • Grade assets like Assessment Items: click the Grade field and pick from the color-coded options
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  • Use filters and multi-select to apply Grades or budgets across a group at once

Budgeting asset replacements:

  • Assign a budget value to any Flexible Item with a target year (and optionally a quarter)
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  • Budgeted items appear automatically in the Roadmap and Budget Parts
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  • For recurring items (like managed service contracts), enable recurring columns in your template. They display differently than one-time budget columns.

Note: Column configuration for Flexible Item Groups is set account-wide at Settings > Flexible Items Settings > Columns. This is typically handled by an admin and applies to all users, all companies, and all Reports.
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For a deeper dive, see Configuring Your Technology Module.
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Office 365

The Office 365 Part pulls in Microsoft 365 users with MFA status, licensing, and other details. Group by license to see how many users are on each license type for a client. That's a useful view for license review conversations and for spotting mismatches or overprovisioning. Filter out free licenses (like Fabric or Power Automate Free) that add noise.
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The IT Plan

The IT Plan is where you manage project-level work: initiatives, projects, and recommendations organized by timeline. Items live in a year-and-quarter view, with a backlog for work that isn't scheduled yet.
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Adding a Plan to a Report:

  • Click Settings at the top of the Report, then Add Part
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  • Set the type to "Plan"
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  • Select an existing Plan or create a new one from the IT Plan template

If you don't see a template, check the Marketplace.
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Each Plan item has:

  • Status: Open, In Progress, Decision Needed, Future, or Completed
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  • Explanation / Risk: why you're recommending this and what's at risk (client-facing)
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  • Next Steps: what needs to happen before the next meeting
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  • Estimated Budget$: ballpark for planning conversations. Does not flow to the Roadmap.
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  • Confirmed Budget$, Year, Month: committed project budget. Does flow to the Roadmap and Budget Parts.

Use Estimated for early conversations, then move the number to Confirmed once the client agrees and you want it on the Roadmap.
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Working with Plan items:

  • Drag items between quarters
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  • Replace quarters with months or years if that fits your workflow
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  • Anything you're not sure when to schedule goes in the backlog

Bundle projects together rather than listing every task as a separate item. One item per initiative, with scope in the notes field. Example: instead of separate items for DMARC, email security training, and phishing protection, create one "Email Security Overhaul" item and list the scope in the notes. This keeps the Plan strategic and client-readable.
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Start with 5-10 items for a first TSM. Add more as you learn what the client needs.

A workflow that works well: use the Assessment and Technology parts for your analysis and grading, and drive the client conversation through the Plan. Keep the Plan focused on what you're actually going to discuss.

For a deeper dive, see Building and Managing an IT Plan.
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Roadmap and Budget

Budget data from the Assessment, Technology, and IT Plan rolls up into two Parts:

  • Roadmap: timeline view of projects and replacements organized by year and quarter. Focuses on one-time costs. Items with only recurring costs won't appear here.
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  • Budget: complete financial picture including both one-time and recurring costs across all sources.

Which to use when:

  • Budget gives the more complete picture for most clients
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  • Roadmap is useful for visualizing the project timeline when presenting to the client

For your first Report, both are optional. If you have budget estimates in your Plan and Assessment, they build themselves. If not, skip them and focus on the Executive Summary, Assessment, IT Plan, and Technology. Add Roadmap and Budget once you have more financial data.
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For details on how items flow into these Parts, see Turning Recommendations into a Roadmap and Budget.
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Presenting to a Client

Before the meeting

Make sure your Report has these basics covered:

  • Executive Summary with a few sentences about the state of their IT
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  • Assessment with at least the Fundamentals items graded
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  • IT Plan with a handful of strategic items laid out by quarter
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  • 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.
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Pick the right client for your first TSM:

  • Someone you have a good relationship with
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  • Not your most demanding client or your newest one
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  • Someone who'll give honest feedback and appreciate more structure in the conversation

You're not trying to impress them with the tool. You're trying to have a better conversation than you've had before.
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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.
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Click the mode toggle at the top of the Report and switch to Presentation Mode. The view changes to full-screen with one Part at a time, like slides. Navigate forward and backward through the Report. If there are Parts you don't want to show, click Parts and deselect them. Apply a filter to hide unanswered or hidden items.
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Not every Part 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. Everything is still fully editable in Presentation Mode: just double-click.
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Here's a flow that works well:

  • Start with the Executive Summary. This sets the tone. Keep it brief and conversational, not a script.
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  • Use Technology data to ground the conversation. Real data about their environment is your credibility builder. Point out aging assets, warranty expirations, anything that connects to your recommendations. You don't have to walk through every device.
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  • 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. Not every client needs to see Grades and risk levels. Use it to inform your advice, and show it when it strengthens the conversation.
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  • Walk through the IT Plan. This is where the best conversations happen. Show what you're recommending, when it should happen, and roughly what it costs. Be ready for clients to reprioritize items or add new ones. That's a good thing: it means they're invested.
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  • If you have a Roadmap, use it to talk about budget. If you don't have budget data yet, skip it 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
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  • Adjust IT Plan priorities or timelines based on client feedback
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  • Create any follow-up tickets or project entries in your PSA
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  • Mark the Report as Complete (click the status indicator at the top and toggle from "Open" to "Complete")
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  • To send the client something to take away, switch to Display Mode and print to PDF (Ctrl+P, select "Save as PDF"). Or better yet, invite clients into the portal as external users so they can access the Report directly.

What to expect

Your first TSM may feel a little rough. That's normal.

  • You'll show too much or too little. Each meeting teaches you what this client cares about and what you can skip next time.
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  • Clients ask questions you don't have answers for. Write it down and follow up. It shows you're listening, not performing.
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  • The meeting runs longer or shorter than planned. You'll calibrate your pacing over 2-3 meetings.
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  • 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.
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What's Next

Related Articles
Deliver Your First TSM
Understanding Technology Data in Strategy Overview
Turning Recommendations into a Roadmap and Budget
Report Parts Overview
The Strategy Module
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