Raise your hand if you’ve ever been dropped out of an email thread because a recipient forgot to reply all.


While there are many project management tools out there, a lot of projects are run by using documents and spreadsheets, with the communication for said project spread out over messy email threads.

Many of these common tools are included in the software that companies provide employees, thus most people are familiar with using them. So when it comes to tools that teams “have always used,” proposing a new option can feel like a major disruption to their day-to-day workflow.

I know because I’ve been there. Luckily, I’ve seen some success getting teams to slowly but surely add Trello into their process. Here are a few onboarding tips I’ve learned along the way:

Spreadsheets, Documents, and Email Threads… Oh My!

Spreadsheets to Trello

Managing projects requires more flexibility than a document or spreadsheet can provide. For example, updating the status of the project can be difficult to do in the word document or spreadsheet format. Often it’s left to the project manager (and their available bandwidth) to make updates, causing a string of other issues:

  • If team members don’t have authority or access to update the master project document or spreadsheet, and the project manager isn’t able to share constant updates, the team can become out of the loop on its status.
  • Most updates are made by either adding a comment or creating a separate page or tab for notes. This separates the project updates from the project work items. Plus, these updates don’t always provide notifications to the relevant people of the change.
  • Conversations about the project often happen via email, and it’s nearly impossible to link those conversations to the document or spreadsheet. So, the latest information about the project often forks into multiple inboxes.

As you can already tell, this process becomes a jumbled mess and confusion ensues for everyone involved.

Given the difficulties of using these tools and software to manage projects, one of the first things I do when taking over a project is move it to Trello. Trello offers a visual way to understand all aspects of a project, from tasks and who’s responsible for them, to the current state and stage of each work item.

To your team’s spreadsheet sympathizers, you could say it’s a project management option that has the usability of documents and spreadsheets with additional power and flexibility. Plus, spreadsheets and longform documents are easy to link to Trello cards, thus giving them more context as to where they are in the process.


Easily attach entire folders comprised of your team’s beloved word documents and spreadsheets to Trello cards, thus giving these items more context. 

Slow and Steady Wins the Adoption Race

Sounds great, right? Not so fast.

It’s important to remember that one does not simply walk a team into Trello as if it was a Sunday stroll. While I have used Trello for years, I’ve stopped being surprised by those who have never heard of it.

“Why don’t we try Trello?”


“No, Trello.”


“Actually, that’s closer than you realize, but, no. Trello. Nevermind for now. Can you just walk me through this document?”

It’s important not to move too quickly when you want to introduce a new productivity tool to an existing project. Run the project using the current system for a couple of weeks. This shows the project team that you respect the system that they’ve already established. It also lets the team know that you can competently use the existing system, and that you’re not just changing to a new management tool because you can’t use the current one.

Introducing change without understanding the current state is a recipe for resistance. You’ll want to slowly recommend and integrate the change to the team, then drop the training wheels at the right moment.

Keep Onboarding Objective (With Handy References)

As you manage the project using the existing system, objectively point out the drawbacks. But whatever you do, don’t slam the tool! Just point out that it’s difficult for team members to provide updates without the system becoming messy. Or, show that discussion is often split between the tool and multiple email threads, which leads to essential team members (including you and me) missing crucial updates.

“When did we decide to change this requirement?”

“Weren’t you included on the email thread?”

It’s tough to manage projects by email, and it’s even more challenging to manage a project in multiple email threads.

As you run through status meetings using the current spreadsheet or master document, you’ll discover that information is often out of date because tasks have been handed off to be completed by someone else, but that person wasn’t instructed to give an update to the team.

As you update the document, point out (in another email to the team) that keeping the information up-to-date is important. Meanwhile, register a Trello account for your organization.

The Trello Maneuver

Onboarding teams to Trello

After a couple of weeks using the existing tool, make a suggestion to the team to try Trello. I have often found it useful to present Trello as an experiment with defined start and end dates.

Then I convert everything from the current system to Trello. I usually do this conversion on a quiet Friday afternoon. I’ve found it’s easier to get a team excited about a new approach while they have a fresh mind and a hot cup of coffee in hand.

It’s important that you include everything from the project in the conversion because team members will view missing information with suspicion. You’ll improve the chance of successfully transitioning to Trello if you show that it’s the same information with a better interface and more context.

Let The Tool Shine

As you start using Trello with the team, just let its natural strengths shine. The ideal end result is for the team to keep Trello updated, but you’ll need to do the heavy lifting in the beginning. Here are some tips:

  • Show how simple it is to display all work items and the current state of each one based on each card’s position between lists on the board.
  • As work flows between team members, assign the cards to the appropriate team members to present a picture of who is doing what. Show off your shortcut ninja skills by hovering over cards and using a number key to quickly assign a label or pressing the “m” key to assign team members.
  • Training on how to use Trello is crucial at this stage to guarantee adoption. Share this guide with your team so they can learn how to setup and customize their Trello boards and notifications.

You can gradually show them a few advanced aspects of Trello:

  • Describe how each card has an email address. The email-to-board feature means users can forward messages to cards when project discussions diverge into emails. These email threads become part of the history of the card and a true picture of the ongoing discussions about a project.
  • While most projects focus on deliverables, a project is really an ongoing conversation between the various people on the team. Centralizing this conversation in a Trello card chat will keep everyone in the loop.

You’ll eventually get to the point where you can unveil Trello’s secret sauce: Power-Ups. Trello integrates with the applications that most organizations use, so you’ll likely find a Power-Up for your company’s app stack (documentation, ticket tracking, sales, messaging, etc.). Enable the appropriate Power-Ups, and you’ll soon have Trello acting as the Single Source of Truth for your project team. Goodbye to the tedious task of switching between applications!

The Grass Is Really Greener On The Trello Side

“So, as I said a couple of weeks ago, I recommended using Trello on a trial basis. Does anyone want to go back to the document we previously used?”

“No way!”

After I convert a project to Trello, I always give my teams the option to revert to the old way of doing things. My management style is to regularly check to make sure that my teams agree to the tools we use to do our work.

The thing is, I’ve never seen a team want to leave Trello once they’ve experienced its power.

How to bring your spreadsheet-loving team into Trello