I can hear the collective groan from your team when you tell them about your nonprofit’s new project management tool (or any software, for that matter). 

And, believe me, I get it. 

Rolling out a new tool can be overwhelming, challenging, and downright annoying, especially if you’ve tried it before without success.

To make it less annoying for you and your team, I put together four recommendations to consider before introducing a new project management software. 

Set Clear Expectations on the Size of a Task

Projects are made up of tasks – the basic building block of a project. Tasks can be broken down into subtasks, and subtasks can be broken down into sub-subtasks (and so on).

Because tasks can be broken down into smaller and smaller pieces, it’s easy to lose track of where each task is in the project. 

My recommendation: agree on what a task is – and what it isn’t. Here’s how. 

Don’t Make Tasks Too Big 

The task “Plan the Gala” is technically correct (action verb + object), but the project of planning a gala is HUGE. (See what I did there?) That’s six or more months of planning crammed into a single task. 

Tasks like this need to be broken down into smaller, manageable chunks. 

Don’t Make Tasks Too Small

Don't add tasks that take less than five minutes to complete! Just do the work and move on. In most cases, creating and completing tasks creates notifications for others, which generates noise.

For all of you who like to write things down to check them off… avoid doing that in your project management software. (I use my journal for this. So satisfying.)

Find the Sweet Spot

A good task should take between a few hours and a week to complete. For example, Request quotes from vendors for gala furniture. Anything bigger is a project. Anything smaller? Don’t bother tracking it. 

Create a Clear Definition of Done

What’s the difference between these two tasks? 

• Task 1: Figure out marketing for the gala

• Task 2: Set budget for marketing the gala

Task 2 has a clear outcome! You know when you’re done when the budget for marketing the gala is set. Task 1? That’s an unhelpful placeholder on a task that will never be “done.”

My recommendation: write constructive task titles and descriptions that clearly illustrate “done.” Here’s how.

Use Action Verbs

Start every task with a verb – “create,” “submit,” “review,” or “fix.” Follow that verb with a clear object – “plan,” “proposal,” “budget,” or “landing page.” For example, instead of: “Do budget,” try: “Complete three-month advertising budget for the gala.”

This way, everyone knows what’s been accomplished when the task is marked as “done.”

(If you have ever legitimately created a task called "do budget" and feel attacked, your feelings are correct.)

Define Success

If the task is to “Create a two-page marketing plan for the gala,” then the team knows success means that two pages of marketing strategy exists. The person responsible also knows not to write a novel. Two pages will suffice.  

Simple enough, right?

Put Someone in Charge

Remember group projects in school? (If you remember them fondly, you are the problem.)

Assigning tasks to a group is a fast track to confusion.

My recommendation: put ONE person in charge of completing a task, and let them collaborate with others. Here’s how. 

Single Owner, Collaborative Effort

Most project management softwares will only let you assign one person to a task… except ClickUp whose designers LOVED group projects in High School. 🙄

Selecting one person to be in charge of a task creates clarity. They can easily loop in other team members with comments or subtasks as needed. Most tools will let you add "followers" or "collaborators" who can follow the progress without ultimately being responsible for the work.

Be Kind With Deadlines

Avoid assigning tasks with immediate deadlines. One person can only do so much in a day. For example, when you assign Cheryl to create that two-page marketing plan for the gala, ask them when they can complete this by.

Speaking of Deadlines...

While some deadlines are non-negotiable—like the date of the gala—most are more like loose targets. Humans are terrible at estimating how much time and effort a task will take. Has anyone ever remodeled a bathroom ahead of schedule? Exactly.

My recommendation: be intentional about how you treat deadlines – or things will get messy fast. Here’s how.

Avoid Arbitrary Deadlines

If deadlines don’t matter, don’t use them! Instead, organize tasks by priority and let the work flow naturally. Save deadlines for tasks that truly need them. 

Work Will Still Get Done (I PROMISE)

Ordering tasks by priority allows your team to tackle them from the top down – from the most important to the “Eh, we’ll get around to it.” Priority drives progress and ensures people constantly work on the most important thing.

Deadlines do not. 

Every Nonprofit Should be Using Project Management Software

When done right, project management tools improve productivity and collaboration. They force people to articulate their work, moving our institutional knowledge from our "head" to our team.

But they are only helpful when used as a team. Before you roll out new software, set aside some time to clarify these expectations. 

It’ll make all the difference.