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5 Ways To Convince Your Boss To Say Yes To A Project Management Tool

As a project manager, you oversee projects from start to finish, taking responsibility for the timeline, the quality of deliverables, and everything in between. It's not an easy job, and project management software can make life so much easier. But how do you get your manager to approve such a tool when all they see is the added costs?

5 Ways To Convince Your Boss To Say Yes To A Project Management Tool

Project managers are used to keeping several balls up in the air. They have to make sure goals and objectives are met, stakeholders are happy, and all the members of their team are on the same page. Every project manager deserves a project management tool, as it does so much of the tedious and time-consuming work for you. However, it’s your boss who pays the bill, and they might not understand the return on investment. In this blog, we tell you exactly how you can build your case, to convince your boss to say “yes” to a project management tool!

Table of Contents:

1. Make problems and challenges known
2. List the benefits of the tool
3. Pinpoint the concerns
4. Get the whole team on board
5. Create an implementation plan
6. Conclusion

#1 Make problems and challenges known

This should go without saying really. In any company, your manager should always know which type of challenges you and your team are facing. 

When you propose to buy a project management tool, the first thing your manager will ask is why you need it. If your plea is full of assertions about issues they have never heard about before, they won’t be convinced.

Whether you want to start using a PM tool for the first time or want to switch to a better one, convincing your boss will be a piece of cake if it sounds like a solution to problems they have been hearing about for a while.

If you already have a specific PM tool on your mind, you can also wait a bit before bringing it up. Over the course of a couple of weeks, you casually and strategically mention some issues it helps to solve. 

For example: “Oh how I wish we had a PM tool that automatically sends recurring invoices with our company’s layout and logo on them…” Then a few weeks later you show your boss Rodeo, which does exactly that. It’s a bit cheeky, but for a good cause.

#2 List the benefits of the tool

Whether you are contemplating to change careers, divorce your spouse, or switch project management software, writing up a good old pros and cons list is a great idea.

It gives you an overview of what you might be losing versus what you gain, and how this balances out in the end. So if you want to replace a PM tool, list all of the benefits of the new tool and pit them against the flaws of the current tool.

If you aren’t currently using a tool but want to introduce one, you can just focus on listing all the benefits. However, make sure you do this by highlighting exactly how certain features can improve the workflow for your team, but also how they help your company’s bottom line. 

The tool will seem much more appealing to your boss if you can relate it to their concerns too. So really do your research, and try to frame the benefits in a way he/she cares about. 

Don’t just say: 

This tool has a time tracker, so I will be able to track how much time my team spends on projects.

Be more thorough in how each feature benefits the whole company, listing all the advantages.

The time tracker of this tool will help us:

- find out how many hours staff put into projects

- gain insight into employee productivity

- estimate how long a project will take

- estimate how much a project will cost

- keep project costs under budget

- increase project profitability

- speed up the invoicing process

- etc…

Don’t forget to have this list ready before you talk to your boss about implementing a tool, so you will be better prepared for questions.

5 ways to convince your boss to say yes to a project management tool

#3 Pinpoint the concerns

During this first talk, really gauge your managers’ reaction and carefully listen to the way they formulate questions. Their concerns are reflected in the questions they ask. 

Making a decision about a PM tool takes time, so you will not be getting an answer straight after the first conversation on the topic.

Use this time to prepare yourself properly for the follow-up meeting, by pinpointing what their concerns seem to be and how you will address them.

For example, if you remember your boss asking how much time the onboarding process will take, it’s pretty clear they are worried that it’s going to be a hassle. 

Do your research again, and figure out exactly what the onboarding process will look like and how your team can prepare for it. 

At Rodeo, our experts completely guide you through the onboarding process after learning everything they need to know about your workflows. This really smoothens the process.

#4 Get the whole team on board

A PM tool might have a brilliant marketing strategy, promising amazing results. Don’t simply look at the features and take their word for it, put it to the test!

You don’t want to convince your boss and team to buy a certain tool, only to find out later that it doesn’t deliver on its promise. 

Most project management tools offer a free trial period or some type of demo. Use this opportunity to really find out what it will be like for your team to use it. Listen to their feedback and make sure they are just as convinced that it’s the right fit.

You need a group of allies to convince your boss that you need this specific tool. It would be the ultimate persuasion technique if you can say the team has tested it and unanimously agrees that it’s a game-changer.

How to convince your boss to say yes to a project management tool

#5 Create an implementation plan

A lot of managers think switching or implementing new software is time-consuming, involving a high level of technical expertise. Moreover, just the thought of files and documents getting lost or processes coming to a halt sends shivers down their spine!

Creating an implementation plan that shows exactly how and when the tool will be implemented, and who will help with what, will give them so much peace. 

Determine beforehand how files will be transferred, and how you can make sure the workflow won’t be disturbed for example. 

If everybody knows what to do to make the onboarding as swift as possible, and all your boss needs to do is say “yes”, this might turn out to be the last little nudge they needed.


As it turns out, it shouldn’t be that hard to get your boss to say “yes” if you present your case in a convincing way. It all comes down to how well you are able to answer the “why?”.

Don’t forget that there are thousands of apps, tools and solutions out there that claim to be quintessential to business organisations. 

Your boss probably receives daily emails from salespeople promoting their product. He/she is rightly skeptical about why the one you found is really the best.

If you do your research, you’ll be able to explain exactly how the tool can make a difference for your team, while adding value to the whole company. 

Once your team is completely on board and you have a detailed implementation plan ready, your boss will be as convinced as everybody else is. 

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