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How to Convince Your Boss To Buy Project Management Software

How to Convince Your Boss To Buy Project Management Software

You‘ve found this amazing new project management tool.

It’s way better than what your team is using now.

You know that this tool will make your team more productive – greater clarity, better teamwork, less frustration, and fewer delays.

But there’s a problem.

How do you convince everyone else to switch to the new app?

Especially those who love their existing project management software?

It’s Easier Than it Sounds to Convince Your Boss

Convincing people to switch will be child’s play, if you know how.

In this article, I will show you a simple three-step process to get your boss and other people on board with the new project management software.

Your boss will be willing to make the switch if he’s confident about three things:

  1. The new tool has indisputable advantages over the existing one
  2. The benefits of switching will be greater than the pain of the transition
  3. There are enough people who are keen to try out the new tool

This process will help you check all three boxes.

The process is based on the work of two of the world’s preeminent leadership experts:

  1. Dr. John Kotter – New York Times bestselling author, Harvard professor, Chairman at Kotter Intl., consultant to Fortune 500s, and considered to be the world’s leading authority on change management.
  2. Dr. Robert Cialdini – New York Times bestselling author, advisor to Warren Buffet, and considered to be the world’s leading expert on the science of persuasion.

Bottom line – it works!

A Feather in Your Cap

The good news is, if you succeed in getting the tool adopted, there are huge rewards in store.

The guy who introduced a project management tool that shot up the company’s productivity – that’s the sort of employee your top bosses are actively seeking to groom. This could be just the thing you need to bag that promotion!

So, let’s get to it.

Note: Need proof that project management is the right step for you? Check out all these benefits! 

Step 1: Compare Project Management Tools

What’s important to you?

What’s important to your team?

What’s important to your boss?

Keeping these three things in balance will help you make the right choice.

  • If you already have a tool, take careful notes about what the team likes and doesn’t like. Do they want custom statuses? To assign multiple people to one task? Need a board view or scrum story points?
  • Make a list of these priorities, and survey your team to rank their “must-haves” versus “nice-to-haves.”
  • Once you have your rankings, compare project management software options to see who has what.

Here’s a great list of free project management software to begin your search, but then you can expand to sites like Capterra and Task Reports to see a full picture of reviews and feedback.

As you’ll soon notice, there are hundreds to choose from. Knowing your needs and priorities before selecting will help you narrow each one down. Once you settle on three, then try each tool with a free sign-up, trial or demo.

If you are already using a tool, you know what you like and don’t like. In that case, check out how the alternatives stack up to the tool you’re considering. Here are a few popular comparisons to get you started:

Step 2: Know the Project Management Software

“What’s the big deal about this new tool?”

That’s the question that everyone’s going to ask. And you need to be ready with answers.

The only way to be ready is to use the tool yourself. Your research from Step 1 will help you, too. 

Because you should know the use cases you’re trying to work through. If you’re a marketing team, you’ll have different needs than the dev or product teams. Some tools (like ClickUp!) are flexible enough to handle any type of team, it just depends on how you set it up. Other tools are meant for one purpose. Be aware of that before introducing the tool your boss or team.

Apply It

Going through the tool’s features pages isn’t going to cut it. You need to apply it to your own work. Here’s what you need to do.

Transfer one or two of your ongoing projects to the new tool. If you plan to use ClickUp, you can automatically import tasks from several project management tools like Asana, Todoist, Trello, Jira and more. Or if you use another tool, you can download a CSV file and import that file right into ClickUp. If you need more help importing, here’s a video that explains it all. 

Use both tools simultaneously for a week or so. That experience will give you a crystal-clear picture of the advantages of using the new platform.

If ClickUp is your new choice for productivity software and project management, you can add unlimited tasks and users from the beginning and use every feature, because it’s completely free! We found that most free versions are limited by users, features, and/or tasks – we can’t get behind that business model.

Team Up

Want to build an even more solid case?

Don’t do this alone. Bring in two or three people to use the new collaboration tool as a team.

Why is this important?

Shared group experience is crucial because the real test of a good project management tool is how well it improves team productivity. It’s not only a personal to-do list.

For example, ClickUp has an Assign Comments feature, which can turn a comment to a task with a couple of clicks. This feature helps tasks from being forgotten.

The only way to test this feature is by roping in another person.


Keep Notes

Don’t expect to remember stuff!

Jot down every single advantage that you found over your existing tool on a Google doc or Evernote.

You will need these notes when you present your case to your boss.

You could also take screenshots of the two tools comparing how the new one is better in different situations.

For example, if you are planning to switch from Asana to ClickUp, keep side by side screenshots of project views in ClickUp vs. Asana. ClickUp allows you to switch between Agile and List views, but Asana does not.

After you have used this for a week, you will have enough confidence and data to back up why your company should use it.

Back Up Your Reasons

Create a list of why the tool you’ve chosen is better than the others and the one you’re currently doing. For instance, here’s why many users choose ClickUp over other similar tools:

1) People know what they need to work on. The hierarchy, multiple views and “Team” vs “Me” tasks filter provide clear direction and details.
2) Everything is in one place. Files, attachments, and integrations all happen in ClickUp. You can even import over from other tools.
3) Know what people are doing. Collaboration detection, multiple assignees and statuses help teams collaborate and see the progress they’ve made.
4) See how much has been done.  Advanced reporting features helps you see which tasks have been completed and what deadlines have been met.
5) Ultimate organization and prioritization. Between the custom fields, views and filters, ClickUp makes it simple to organize and prioritize every element of your work.

1) More productive.
2) Much more efficient and working on the “right” things
3) People have fun using it
4) Turn like 5 apps into one with its multiple integrations.

Step 3: Build Consensus

Here’s a fact about your boss.

He or she will never make a unilateral decision on adopting a new tool.

(Unless, of course, your boss is the CEO and majority shareholder!)

Every other boss will want to make sure that there are a number of people on board with the idea. According to Dr. Cialdini, we are easily persuaded by arguments backed by ‘social proof’ or ‘consensus’ – essentially, the wisdom of the masses.

Besides, your boss will also need at least a cursory sign off from his/her superior.

Therefore, don’t go to your boss alone.

Get a few influencers in the company to support your idea. They could be colleagues who manage teams of their own, or top performers who might not be managers, but are well-respected in the company.

Begin by gaining the support of 3 to 4 influencers who are frustrated with the existing tool. Go to these folks and show them the new software. They will be delighted when you demonstrate your experiences with it and the advantages you‘ve found.

Don’t just stop there.

Also go to people who are sort of “ok” with the existing tool. Ask them what they think about the new software. What do they like/ dislike? What reservations would they have about the new tool?

Only when you know what people’s objections are, will you be able to respond to them.

Many of them will be excited by the new software. And several people will be glad that you spoke to them. Even if they don’t actively support you, they won’t get in your way either!

Step 4: Present your Idea

If you want your boss to make the switch, you need to make it easy for him to take a decision. Try to prepare a presentation that makes the new software look like a no-brainer with all of the advantages of having project management software and productivity software

Here’s what you need to cover in your presentation.

Have a group meeting

Rather than go alone, take a few people with you to a meeting with your boss. They should be the managers and influencers who you spoke to in Step 2.

Highlight challenges

Explain the limitations of the existing tool and all potential impacts of those limitations. For instance, if project delays are commonplace in your company, show how your team became x% more productive by using the new tool.

Talk about ROI

If your new tool is less expensive than the existing one, than this part should be easy. If not, highlight how the productivity gains will easily make up for the extra that you will pay.

ClickUp, for example, has a forever free version with all features. No ROI debate there!

Soft Switch

Don’t ask for the tool to get adopted across every single team. Rather, propose to start using it in just the 3-4 teams who have already said that they want to try it out (In step 2).

Easy Transition

This is one of the greatest reasons why companies hang on to outdated tools. The prospect of learning a new software is naturally intimidating and the process of moving projects to a new tool can be exhausting.

Make sure you explain how these two factors will not get in the way.

For example, if you use a tool like ClickUp, you can automatically import projects and tasks from several tools such as Asana, Jira, etc. And there are several helpful videos that make every feature extremely easy to understand.

At ClickUp, our customer success team will also help you set up the tool, transfer your projects and show you how to use it.

Can anything be easier?!

Go For It!

Follow these tried and tested steps and you will have your colleagues convinced about the tool in no time! And getting a new project management tool adopted will be a fantastic addition to your resume.  

All of these benefits begin with trying out the tool yourself. Sign up for a webinar or a free demo of ClickUp!


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