Understanding Assessments

The Assessment is the core of every TSM. It's where you evaluate and grade different areas of your client's IT environment, from backup strategy and email security to endpoint management and server hosting. A well-run Assessment gives your client a clear picture of where they stand and what needs attention.

Each Assessment contains a list of items: topics you're evaluating for the client. Items are organized into groups (logical categories like Security, Infrastructure, Business Continuity, etc.). For each item, you grade how the client is doing, note the current status, identify risks, and recommend solutions.

The Assessment connects to the rest of your TSM in several ways:

Each Assessment item has several fields you fill out as part of your evaluation:

You don't need to fill in every field for every item right away. Start with grades and a few key items where you have strong recommendations, then build out more detail over time.

You don't have to go back to template settings to adjust Assessment items. Open any draft Report in Build Mode and click the gear icon on an individual Assessment item to edit its settings — name, weight, tags, default values, and more. Changes made here update the template, so they apply across all Reports using that template.

This is a practical way to make small, iterative adjustments as you go. After running a few TSMs, you'll notice items that need a different weight, a better description, or a tag change. Editing from the Report lets you refine on the fly without interrupting your workflow.
​

Grades are the ratings you assign to each Assessment item. Your template defines what grades are available and how they're used.
​

Go to Settings > Templates > [Your Template] > Parts > Assessment > Grades to configure your grading system. Each grade has two important settings:

Health Scores use a weighted average. Each Assessment item has a weight (0-5) that you set at the template level.

The calculation works like this:

Health Scores appear in several places: next to the company name in the companies list, next to Reports in the Reports list, for item groups within the Assessment tab, and in widgets (Last Report Health and Progress Chart) based on tag filters.

Tags are labels you can attach to Assessment items to organize and filter them. You can filter your Assessment view by tag, which makes it easy to focus on a specific subset of items without hiding or removing anything permanently.

Strategy Overview's standard Assessment template comes with a set of tags already built in. These are designed to help you scale your Assessment process progressively:

Additional category tags (Efficiency, Security, Prospect, Vertical) help you filter items by topic area.

These are a starting point. You can create your own tags, rename existing ones, or build a tagging system that fits how your team works. Tags are managed at the template level under Settings > Templates > [Your Template] > Parts > Assessment > Tags.

Start with Fundamentals for your first several TSMs. Expand to Operating and Scaling as your process matures and as you learn what your clients need.
​

Not every Assessment item is relevant to every client. You have two ways to hide content from Display, Presentation, and Print modes while keeping it available in Build Mode:
​

Click the eye icon next to the group name in Build Mode. The icon changes to a crossed-out eye, and the entire group with all its items is hidden from client-facing views.
​

Important: If items in a hidden group have Budget values, those items will still appear in the Roadmap and Budget sections even though the group is hidden from the Assessment view.
​

Set up "hidden" grades, grades with Display Mode unchecked in your template's grade settings. When you assign a hidden grade to an item, it won't appear in Display or Presentation Mode.
​

To configure hidden grades: Settings > Templates > [Your Template] > Parts > Assessment > Grades. Uncheck "Display Mode" for any grade you want to use for hiding items.
​

Important: Like hidden groups, items with Budget values will still appear in Roadmap and Budget sections regardless of their grade visibility setting.
​

One of the most powerful features in Strategy Overview is relating Flexible Item groups to Assessment items. When you do this, the actual technology data appears right alongside the Assessment item, so when you're grading "Server Host," you can see the client's actual server list with age, warranty, and OS information.
​

This feature also enables Arya AI to give better recommendations because it has real client data to work with.
​

For setup instructions, see Tailoring Your Assessment in the Going Deeper collection.
​

The standard template gives you a comprehensive set of items and groups to start with, but you're not limited to what's there. You can add your own items, create new groups, and customize the Assessment to match how your team works.

To add items or groups that appear in every new Report:
​

Add a new item: In your template's Assessment settings (Settings > Templates > [Your Template] > Parts > Assessment), click Add Item within an existing group. Give it a name, set a default grade and weight, and configure any tags. This is useful when your team evaluates something specific that isn't in the standard template — like a vertical-specific compliance item or a tool your MSP standardizes on.
​

Add a new group: Click Add Group to create a new category. Groups let you organize items logically (Security, Infrastructure, Business Continuity, etc.) and they get their own Health Score rollup in your Reports.

You can also add items, groups, or duplicates directly from within a client's Report in Build Mode. This is useful when a specific client has a unique need that doesn't apply to your other clients.
​

Important: Items and groups added from within a Report only exist on that client's Report going forward. They are not added to your template and won't appear in other clients' Reports. If you want the change to apply everywhere, make it from the template settings instead.
​

You can duplicate existing items and groups when you need variations:

Copy a single item: Open the Assessment in Build Mode, click the ... menu on the item, and choose Duplicate. The system creates a copy right after the source item.
​

Copy a group: Hover over the group name, click the group's ... menu, and choose Duplicate group. A "Copy of..." group appears. Note that group duplication copies the group structure and settings but items within are copied as well with all their values.
​

Copies made from within a Report follow the same rule — they only exist on that client's Report. To add a copy to the template for all clients, duplicate from the template settings.
​

You need Edit permission (Admin, Manager, or Editor role) to add or copy items.

The Clear button on an Assessment item (available only in draft Reports) resets the item to its default state:

This is useful when you want to start fresh on an item without deleting and re-adding it.
​

If Assessment items have recurring expenses (like annual software licenses or monthly service costs), you can track them directly in the Assessment and have them flow into your Roadmap and Budget.
​

For each item with recurring costs, you can set:

Date behavior: The effective date determines when recurring costs start appearing. If you set a cancellation date in the middle of a period, that period is excluded. If the cancellation falls on the last day of a period, that period is included.
​

Recurring costs from Assessment items flow automatically into your Flexible Roadmap and Flexible Budget parts.

Arya can help you fill out Assessments faster by analyzing your connected data and suggesting grades, statuses, risks, and solutions. For the full guide on using Arya with Assessments, see Arya AI Assessment Assistant in the Arya AI collection.

Key points: