The Secret to Picking the Perfect Project Management Software

Asana. Trello. ClickUp. Monday. Airtable. Notion. Basecamp. Hive. Smartsheet. Keap… OH MY!

Are you thinking about any of these project management softwares?

It can feel so overwhelming to pick the perfect project management software and I’ve seen so many business owners sign up for tons of free trials, never to log into the software again.

And worse, I’ve seen business owners PAYING for project management software subscriptions – only to manage their tasks through their emails and Google Docs.

If this feels familiar and you’re struggling to pick or use your project management software, it all comes down to 1 problem… and it’s NOT the software.

The problem is a lack of clarity around your process.

Because your project management software is a direct reflection of the clarity and organization you have about how you work.

And the software doesn’t matter when you don’t know the process it’s supporting.

This might be blowing your mind when you just wanted me to tell you what project management tool is the best, but I’ll give you something better…

I’ll tell you how to pick the perfect project management software for you.

1️⃣ Define what features you need so you can cut through the noise and only look at the software that will actually work for you. There are endless options when it comes to project management softwares and the one you pick should work for YOU. Start by asking yourself:

Do I like lists, spreadsheets, Kanban boards, or free-flowing mind maps? How do I like to see work laid out?
Do I work on the go/on my phone so the software needs to have a great mobile app?
How many people will use the software with me?
Will I use it just with my team or will I also share info with clients?

Focusing on these questions will help guarantee that you actually use the software.

For me, I like spreadsheet layouts with a strong mobile app for 3 – 5 users to manage internal work only. Knowing this, Asana, Trello, Basecamp, Notion, ClickUp, Keap were all off the list and I don’t have to worry if I’m “missing out” by not testing the other tools.

Figure out your preferences and you’ll save time by only looking at the tools that will work for you.


2️⃣ Outline your task management structure. Step 1 was all about picking the right software, but that’s only half the battle. You can pick a software, never use it and be right back in indecision. To make sure you pick a tool and use it, set it up for your workflow.

The easiest way to do this is to brain dump every task, to-do, follow up, idea, voice note, and email you sent to yourself in the last few weeks.

Once you have it on paper, it will be easier to organize and group your work. These groupings will be the first level of organization in your project management software. The tasks that fall into each grouping category are the second level of organization.

🎊 Congratulations, you just created your basic task management structure! 🎊

You can stop here and your project management software will work… or if you’re like me, you can let your OCD run wild and break it down even further by defining the work to complete the level 2 tasks. 😂


3️⃣ Outline your work phases. With structure to organize your work, now you can think about the workflow aka how you’ll use the project management tool. This means to answer the question:

What happens on the way to finishing a task?

Do I finish everything in one shot and cross it off the list? Do some tasks take a few days or weeks before they’re finished? Do I follow up? Do I review or proofread work before it’s complete? Does my VA need to check in with me before marking a task done?

The steps on the way to finishing the task are your statuses and this is how you’ll move your tasks through the project management tool. This is how you’ll know what to work on now, what to follow up on, and whether you need to review work from your team.

On my team, our basic work phases are Open → In process → Follow Up → Approval → Hold → Closed. What does yours look like?


4️⃣ Testing. This is the step that I’m sure you’re the most familiar with. You probably skip straight to this step whenever you sign up for a free trial…

And it might have led to frustration because how many project management software trials have you signed up for and had no idea how to get started?

Now, you have a better way.

If you finish steps 1 – 3, the testing is a breeze. You can set up your basic structure, your work phases and test the software to see if it is actually a fit for you.

This is how you pick the perfect project management software. By knowing how you organize your tasks and how you work on them until they’re done so test and make your decision based on facts.

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