Smartsheet Training: How to Train Your Team on Smartsheet

Smartsheet training is one of those things that sounds simple until you actually try to do it. The platform can do almost anything -- and that's exactly the problem.

It's a spreadsheet. A Gantt chart. An automation engine. A dashboard builder. A forms tool. A reporting platform. A resource management system. Every team uses it differently, and every team's setup is a snowflake. So when someone new joins and you say "here, learn Smartsheet," what you're really telling them is "here, figure out the specific way we've configured this infinitely flexible tool over the past three years."

I'm Yuval, founder of Glitter AI. Through building a tool that helps teams create training guides from screen recordings, I've talked to dozens of Smartsheet teams who all describe the same problem. The question of how to use Smartsheet effectively isn't really about Smartsheet's features. It's about capturing how your team actually uses those features before that knowledge vanishes.

Why Smartsheet Training Is Harder Than Most Software

This is what makes learning how to use Smartsheet for project management so much harder than training on most tools.

With something like email, everyone's workflow is roughly the same. Smartsheet? One team uses it to track construction projects with 47 columns, custom conditional formatting rules, and automated alerts tied to date changes. Another uses it as a lightweight CRM with forms feeding into sheets that trigger approval workflows. A third has built an entire resource allocation system with cross-sheet references, dashboards, and weekly roll-up reports.

None of those teams can point a new hire at Smartsheet's help docs and say "figure it out." The docs explain what a Gantt chart is. They don't explain why your team uses a specific color-coding system for project phases, or that the "Status" column needs to be updated before 10am every Monday because it feeds into a dashboard the VP checks at 10:15.

This is tribal knowledge at its most dangerous. Not because anyone's hoarding information on purpose, but because the knowledge is so specific to your setup that it never occurs to anyone to write it down. It just lives in the heads of the people who built it.

When those people leave? Their custom sheets, automations, and reports become mysteries. I've heard from teams who spent weeks reverse-engineering a former employee's Smartsheet setup because nobody understood the formulas, the automation triggers, or why certain columns existed in the first place.

The hidden cost of undocumented processes hits especially hard with flexible tools like Smartsheet. The more powerful the tool, the more custom the setup, and the more devastating the knowledge loss when someone walks out the door.

Why Traditional Smartsheet Training Fails for Flexible Tools

Most teams default to one of these approaches. None of them work particularly well for something as configurable as Smartsheet.

The Live Walkthrough

You sit with the new person for an hour and click through everything. "This sheet tracks active projects. This column auto-fills from that formula. Don't touch this row, it's a template." They nod along, scribble a few notes, and forget 80% of it by tomorrow.

Their memory isn't the problem. Smartsheet has too many moving parts to absorb in a single session. Views, filters, automations, conditional formatting, cross-sheet references, dashboards -- that's a lot to process while also trying to remember where things live in the interface.

The Written SOP

Someone gets assigned to document the team's Smartsheet processes in a Google Doc or Confluence page. They write "Step 1: Open the Project Tracker sheet. Step 2: Add a new row. Step 3: Fill in the project name." But the moment they try to explain how to set up a conditional automation or modify a Gantt dependency, they're stuck trying to describe visual, interactive processes with text alone.

Written steps without screenshots are like giving someone driving directions without a map. Technically accurate, practically useless. I've written about this problem more broadly in my guide on training documentation.

The "Ask Sarah" Method

There's always one person on the team who built the Smartsheet setup and knows how everything works. New hires get told to "just ask Sarah if you get stuck." Sarah becomes a full-time help desk on top of her actual job. She resents it. New hires feel like a burden. Nobody wins.

A Better Approach: Record It Once, Use It Forever

Here's what actually works.

Instead of writing documentation or scheduling training sessions, just do the thing. Open Smartsheet, start a Glitter recording, and walk through the process while talking out loud. Explain what you're clicking and why. Mention the gotchas. Point out what tends to trip people up.

When you stop recording, Glitter automatically generates a complete training guide with:

• Video of your entire walkthrough
• Annotated screenshots of each key step
• Written instructions pulled from what you said and did
• Voiceover so people can watch and listen

One recording. Four formats. Every learning style covered.

This matters especially for Smartsheet because so much of the tool is visual. Conditional formatting rules, Gantt chart dependencies, dashboard layouts, automation logic -- these things need to be seen to make sense. A screenshot of a properly configured automation is worth a thousand words of explanation.

Having built Glitter, I've seen our best teams document 5+ different operational workflows. The ones who stick aren't creating one guide -- they're building an entire knowledge base for how their company runs.

The 8 Smartsheet Workflows You Should Document First

Start with what your team uses most. These are the workflows I see causing the most confusion and generating the most questions.

1. Updating Project Timelines

This is the daily bread-and-butter of most Smartsheet teams. Walk through how to update task dates, adjust durations, manage dependencies in the Gantt view, and handle the ripple effects when one task slips. Show how your team uses predecessors and what happens when you change a date on a task that other tasks depend on.

Pro tip: Record yourself handling a timeline change that cascades across multiple tasks. Edge cases are where people get stuck, not simple date updates.

2. Creating Automated Workflows

Smartsheet's automation engine is powerful -- and completely opaque to anyone who didn't set it up. Walk through your existing automations so the team understands what's running in the background. Then show how to create a new one: setting triggers, defining conditions, choosing actions, testing the workflow.

Cover the common ones like sending notifications when a status changes, requesting approvals when a new row is added, or moving rows between sheets when a task is marked complete.

3. Building and Editing Dashboards

Dashboards are often how leadership interacts with Smartsheet, which means getting them wrong is highly visible. Show how to add and configure widgets, pull data from specific sheets, set up charts, and arrange the layout. Explain which sheets feed each widget and what happens if source data changes.

4. Managing Resource Allocation

If your team uses Smartsheet for resource management, this is probably one of the most complex workflows to learn. Walk through how you assign people to tasks, track workload across projects, spot over-allocation, and adjust assignments. Show the Resource Management views and how they connect to your project sheets.

5. Running and Customizing Reports

Reports in Smartsheet pull data across multiple sheets, and they're only useful if they're configured correctly. Show how to create a new report, select source sheets, set criteria and filters, choose columns to display, and sort the results. Walk through the reports your team uses regularly and explain what each one shows and who relies on it.

6. Setting Up and Managing Forms

Forms are how many teams collect data from people outside of Smartsheet -- intake requests, project briefs, feedback, status updates. Show how to build a form, connect it to a sheet, configure conditional logic, and manage incoming submissions. If you have automations triggered by form submissions, show how those connect too.

7. Using Conditional Formatting

Conditional formatting is what makes your sheets scannable at a glance. Red for overdue, yellow for at-risk, green for on track. Walk through the rules your team has set up, explain the reasoning behind them, and show how to modify or add new rules. This is one of those features where a five-minute recording saves hours of confusion.

8. Managing Permissions and Sharing

Permissions in Smartsheet can get complicated -- sheet-level sharing, workspace-level access, published views, row-level locked fields. Document how your team handles access control. Who gets editor access versus viewer access? Which sheets are shared externally? What's the process when someone needs temporary access to a project?

How to Structure Your Smartsheet Onboarding

Once you've recorded the core workflows, put them in an order that makes sense for a new team member. A structured Smartsheet onboarding plan makes the difference between someone who's productive in two weeks and someone who's still confused after a month.

Week 1: Navigation and Daily Tasks

Start with the basics. How to navigate your workspace, find the right sheets, switch between Grid, Gantt, Card, and Calendar views, and update tasks. These are the things they'll do every day, so they need to become second nature fast. Send them the relevant Glitter guides and let them explore on their own.

Week 2: Reporting and Dashboards

Move into the read-only side of things. Teach them how to pull reports, read dashboards, and understand the data flowing through your Smartsheet setup. Understanding the outputs helps them see why the inputs matter.

Week 3: Automations and Forms

Now they're ready for the behind-the-scenes stuff. Walk them through your automation rules, show them how forms feed into sheets, and explain the logic that keeps everything connected. This is where they start understanding the system rather than just individual sheets.

Week 4: Advanced Configuration

Conditional formatting, cross-sheet references, formulas, permissions. These are the power-user features that take your Smartsheet setup from a collection of spreadsheets to an integrated project management platform. By week four, they have enough context to understand why these features exist and how they fit together. This is also when they start to truly understand how to use Smartsheet for project management the way your team has designed it.

For a broader look at structuring training programs, see my post on employee training best practices.

Tips for Recording Better Smartsheet Guides

The best training recordings I've seen share a few things in common.

Talk Through Your Reasoning

Don't just show what you click. Explain why. "I'm setting this predecessor as a finish-to-start dependency because the design phase has to be completely done before development can begin. If I used a start-to-start, development could kick off too early and we'd have rework." That context is what turns a screen recording into actual training.

Show the Gotchas

Every Smartsheet setup has them. The column that looks editable but is actually a formula. The automation that fires if you change a status before filling in the required fields. The dashboard widget that breaks if you rename a sheet. Record these warnings alongside the normal workflow -- they'll save your team hours of debugging.

Keep Guides Focused

One workflow per guide. "How to update project timelines" is a guide. "Everything about our Smartsheet setup" is a novel nobody will read. Short, focused guides are easier to record, easier to update, and easier to find when someone needs them. I've written about this approach in my post on how to train employees faster with documentation.

Name Them Clearly

"Smartsheet - Updating Project Timelines" is a good title. "Training Video 3" is not. When someone's stuck and needs help at 4:47 PM, they need to find the right guide in seconds.

Re-Record When Things Change

Smartsheet updates its interface, and your own processes evolve. When they do, re-record the affected guides. With Glitter, it takes a few minutes. Outdated training guides are worse than no guides at all because they create false confidence.

Why Video Plus Screenshots Plus Written Steps Beats Any Single Format

Let me be direct about this. A written document alone won't cut it for Smartsheet training. Neither will a raw screen recording. Here's why the combination matters.

Video captures the flow. People see how you navigate between views, how quickly you move through certain steps, where you pause to think, and the overall rhythm of a workflow. It's the closest thing to sitting next to an expert.

Screenshots capture the details. When someone's configuring an automation and needs to verify they're looking at the right dialog box, they don't want to scrub through a video. They want to glance at a screenshot and confirm they're in the right place.

Written steps capture the logic. Why you chose that dependency type. What the conditional formatting rules mean. When to use a report versus a dashboard. Text is searchable, scannable, and easy to reference.

Voiceover captures the context. The spoken explanation carries nuance that written text often misses -- the "don't forget this part" warnings, the "this is important because" reasoning, the "I learned this the hard way" stories.

When all four formats come from a single recording, they stay perfectly in sync. That consistency is what makes training stick. For a deeper look at why this multi-format approach works, check out my post on operations documentation best practices.

Getting Started Today

You don't need to document everything at once. Here's what I'd do this week.

1. Identify the workflow that generates the most questions. For most teams, it's either updating project timelines or understanding the automation rules.
2. Open Smartsheet, start a Glitter recording, and just do the task. Talk through what you're doing and why. Don't rehearse. Don't script it. Just be natural.
3. Review the generated guide. Make any quick edits to the written steps if needed.
4. Share it with your team. Next time someone asks how to do that thing, send them the guide instead of walking them through it again.
5. Record one more guide next week. Then another the week after. In two months, you'll have a complete Smartsheet training library.

The teams that get the most value from their documentation aren't the ones with the most polished guides. They're the ones who actually have guides at all. Start messy. Start today. Your future self -- and every future hire -- will thank you.

Frequently Asked Questions

How long does Smartsheet training take for a new hire?

Most teams need 2-4 weeks of Smartsheet training to get a new hire comfortable with core tasks like updating project timelines, reading dashboards, and running reports. With documented training guides that combine video, screenshots, and written steps, you can cut that timeline significantly because new team members can learn at their own pace and revisit guides whenever they get stuck. The exact timeline depends on how complex your Smartsheet setup is and how many custom automations and workflows your team relies on.

What Smartsheet features should I train my team on first?

Start with daily tasks: navigating your workspace, switching between Grid, Gantt, Card, and Calendar views, and updating task statuses and dates. Then move to reports and dashboards so they understand how data flows through your setup. Save advanced features like automations, conditional formatting, cross-sheet references, and permissions management for after they are comfortable with the basics. Prioritize the workflows that generate the most questions from your current team.

Can I use Smartsheet's built-in help documentation for Smartsheet onboarding?

Smartsheet's help documentation is useful for learning general features, but it cannot cover your specific setup. Your team needs to learn your project tracking conventions, your automation rules, your dashboard layouts, and your reporting workflows. Generic docs can supplement Smartsheet training, but they should never replace guides that show exactly how your company uses the platform. Every team's configuration is unique, and that uniqueness is what makes internal documentation essential for proper Smartsheet onboarding.

How do I handle Smartsheet training for remote employees?

Screen-recorded training guides are ideal for remote Smartsheet onboarding because they can be accessed from anywhere at any time. Record yourself walking through each Smartsheet workflow with narration explaining what you are doing and why. Tools like Glitter automatically generate video, screenshots, and written steps from a single recording. Remote employees can learn how to use Smartsheet at their own pace without scheduling live training sessions across time zones.

What is the biggest mistake teams make when training on Smartsheet?

The biggest mistake is relying entirely on live one-on-one training with no documentation. When training happens only through verbal explanation, knowledge disappears the moment the trainer is unavailable. The second biggest mistake is pointing new hires to generic Smartsheet tutorials that do not reflect your specific setup. Your team's sheets, automations, dashboards, and workflows are custom to your organization, and training needs to reflect that.

How often should I update my Smartsheet training guides?

Update your guides whenever Smartsheet releases interface changes that affect your workflows, whenever your internal processes change such as new automation rules or modified dashboard layouts, and do a general review at least quarterly. If you use a tool like Glitter, re-recording a workflow takes just a few minutes, which makes regular updates practical rather than painful.

How do I document Smartsheet automations for my team?

Start by recording a walkthrough of each existing automation. Open the automation panel, show the trigger, the conditions, and the actions. Explain in plain language what the automation does and why it exists. Then record a separate guide showing how to create a new automation from scratch. Cover common patterns like status change notifications, approval requests, row-moving rules, and reminder alerts. Visual guides with screenshots of each configuration step are far more effective than written descriptions alone.

How many Smartsheet training guides does a typical team need?

Most teams need between 8 and 15 core guides to cover their essential Smartsheet workflows. This typically includes guides for updating project timelines, managing automations, building dashboards, running reports, using forms, applying conditional formatting, handling permissions, and any workflows specific to your industry or department. Start with the 5 workflows your team uses most frequently and expand from there.

Should I create separate Smartsheet training for different roles on my team?

Yes, different roles typically interact with Smartsheet in different ways. A project coordinator updating task statuses daily needs different training than a department head who mainly views dashboards and reports. Create a core set of guides that everyone needs, then add role-specific guides for specialized workflows. This keeps training relevant and prevents people from being overwhelmed with information they will never use.

How do I handle Smartsheet training when the person who built our setup has already left?

Start by doing a systematic audit of your Smartsheet workspace. Open each sheet and document what it contains, what automations are attached, what formulas are in use, and how sheets connect to each other through cross-sheet references and reports. Record yourself exploring and explaining each component as you figure it out. This reverse-engineering process, captured on video, becomes your training documentation. It is harder than documenting a setup you built yourself, but the alternative is letting the mystery compound over time.