Onboarding and training new users is essential to the success of any software implementation, even for the most intuitive or easy-to-use project management software. These 4 tips will help you have a successful and stress-free onboarding.

Set up your tool before providing broad access

While it’s tempting to purchase a software and release it to the whole team the next day to use, it’ll make your life a lot easier if you spend a little time getting the tool set up for all the different types of users that will access it. Consider building these structures before giving access to the tool:

  • Workflows: Remember back when you were planning your purchase, and you took stock of the most important workflows that departments used in their tools? Time to dust those off and building automations. This has a two-fold benefit: your team will be impressed that their most-used processes are already set up and work like magic, and you’ll get a chance to practice building several workflows before you’re asked to train anyone on the process.
  • User access: Whether you work for a large organization or a small business, you’ll likely need to restrict access to certain projects, reports, or files. When you build accounts for the teams, take advantage of a tool’s built-in user access restrictions to ensure everyone can see what they need, and no one has access to data they don’t need. If you’re unsure about which employees should get what kind of access, consult departmental or team managers.
  • Departmental rooms/ boards/ projects: You already know which departments or teams will be using your new project management software, so why not make a home for them to navigate to when they first get into the tool? If available, think about setting up user access directly to their department’s boards or projects. The best project management software will let teams add outside users as needed.

Provide a ride-along training session where you walk through major features

Let your new users learn by doing by providing a step by step walkthrough of the major features of the project management tool. Take the time to explain what the features do, how they work, and any little tips or tricks you’ve found along the way.


This is a good time to take advantage of your power users — those employees you’ve given trial access to — as deputy trainers. Have them review the tool with their peers during the session and encourage them to help with quick issues and broadcast any tough questions to the larger group.

At the end of the session, show employees where the vendor’s help documentation lives. Encourage individuals to check the support documentation and self-serve for answers. After your session is over, provide vendor help videos, walkthroughs, documentation, and access to the vendor’s support team.

Follow-up in a week

Whew! Your training is finished, every user has access to your project management software, and now your job is done. Celebrate!

And then follow up in a week. Don’t let too much time go by before checking in with your users to ensure that they’re using the tool regularly and are finding answers to their questions. Solicit feedback on the parts of the tool that pose difficulties and provide support documents for common problems. In addition to getting the tool set up, it’s your responsibility to ensure widespread adoption.

The best project management software will let you check tool engagement stats for that first week and beyond. Use these metrics to understand where you might need to retrain some users:

  • How many users log in each day?
  • Which features do users get the most use of?
  • How many new projects and tasks are opened each day?
  • How many reports are run or dashboards viewed every week? This metric may take longer than a week to mature, but keep an eye on it either way.

Make a plan to retrain stragglers

With any new software implementation, you’re going to have stragglers that are reluctant or outright refuse to use the new software. Short of cutting off access to the old tool (which you should do) or firing employees for using their old systems (which you should NOT do), your best bet is retraining those reluctant adopters.

Here are some tips on how to do that with sensitivity:

  1. Listen to them: these folks likely have very good reasons for not wanting to move over to the new system. It’s scary to learn a new tool, and those employees with long-standing, complicated project systems may be the hardest to convince. Ensure that they know their voices are being heard, and that you want to help make their lives easier.
  2. Make a joint plan: Plan with the employee how training will go. Maybe they need a hand setting up a complicated workflow, or they need 1:1 attention to learn the tools.
  3. Let the employee drive: Ever sit through a software training where the instructor quickly clicked through step after step and completed tasks at lightning speed, and then said “it’s that easy!” Yeah, it’s easy for them because they know the tool and where to click for each feature. By handing over the mouse and keyboard to the learner, they are more likely to get a clear sense of the software’s layout.

Taking the time to train (and retrain) your team on your new project management software purchase will set you up for success. It’s almost as important as finding the best project management software for your company’s needs. As you look for your new project management software, don’t forget to gather reviews, recommendations, and resources from TechnologyAdvice.com, or to call us directly for a 5-minute consultation at 877.702.2082.