9: How to Find the Right Project Management Tool with Cadri Cunningham

How can you find the right project management tool for your business? What should you look for? What questions do you need to ask before investing money and time into a system? How does the way you think impact the tool you need?

In this episode, certified DOO and founder of Simplified Ops Collective Cadri Cunningham and I talk through what a project management system is, why you need one, and how to pick the right one for you. We share our favorite tools and break down the pros and cons of the top four options in the marketplace.

What is a Project Management Tool?

A project management tool helps you create accountability for yourself, oversight for your projects and tasks, and show you the accomplishments you’ve had in your business.

Project management tools differ from note-taking tools. With a note-taking tool like a Google Doc or Evernote, you can’t track, be held accountable, or share tasks with a team.

Why These Tools are Important

These tools allow you to:

1. Track deadlines
2. Connect daily actions to your vision
3. Provide understanding of all the steps in your project
4. Outline who owns each task

A system needs to work for those who use it. Don’t go with the shiny new tool. Use what works for you or else it’s ineffective.

Questions to Help You Choose the Right Tool for You Questions a DOO Will Ask

1. Which project management tool do you use?
2. Do you really use it?
3. Who keeps up with the information in the tool? In other words, who “owns” the tool?
4. Why do you use it?

Questions to Ask Yourself

1. Is your current tool working for you? Do you check it everyday?
2. If it doesn’t work for you, what features are missing? What is complicated about your current system?
   • To-do list people are often linear thinkers.
   • Board view people are often visual thinkers.
   • If you’re unsure where you land, ask yourself how you plan your child’s birthday party. Whatever process you use in “real life” will be similar to how you think about your business.
3. Do you prefer a to-do list or board view?
4. Do you like a calendar view for tasks?
5. Do you like a simple system or a more involved system?
6. Is there a specific project management tool designed for your industry? (Interior designers, attorneys, and home-schoolers have their own tools.)
7. What document storage program tool do you use and does it integrate with your project management tool?
8. Do you use a lot of processes and workflows? Do you like your tasks to move from left to right (visual thinker) or top to bottom (linear thinker)?
9. Do you have a lot of repeated tasks? Does the project management tool allow for that?
10. Do you need a tool with automation features?
11. What does your budget look like for systems and tools?

Questions to Ask if You Work with a Team

1. How many people do you need to communicate with?
2. Do you need to be able to track time within the project management tool?
3. How much are you doing together within the tool?

Project Management Tool Options

There are a variety of options for project management tools. We share some of our favorites and the pros and cons of various tools.

Natalie and Cadri’s Top Picks

I default to Trello because I’ve used it for so long. However, I’m also interested in Teamwork because of the messaging capability and task management features. It also has a CRM. ClickUp also has my interest because it can show you all your projects at one time.

Cadri prefers Asana because she loves to-do lists and the clean interface. She can also organize by task and it offers a calendar view. She also loves SubCast because of the to-do list capability.

Pros and Cons of the Top Project Management Tools Trello

• It’s good when you have just a few projects, and it allows you to track workflows.
• It’s visually stimulating, you can get lost if you don’t set it up well, and there’s no calendar piece.

Asana

• It offers a clean interface, to-do list and board views, and the free version is perfect for most organizations.
• You can only have a limited number of people on your team and you can’t see timelines.

Teamwork

• It allows client and team communication.
• It can get pricey an...