An agency’s success — and sanity — comes down almost entirely to workflow. Choosing project management software over the traditional scattershot collection of emails, Word documents and phone calls removes confusion by offering  a systematic way to track projects and centralize communication with clients across your team. Without this essential tool, you’re wasting time chasing details, putting a strain on your client relationships and your project deadlines.

Clients won’t pick up your project management software on their own, however.  If you don’t take the time to carefully and intentionally onboard them, you put your client relationship into jeopardy. Include them from the beginning by taking a proactive approach to teaching them your system. Here’s how to onboard your clients to your project management software effectively so both your agency and your clients come out on top.

1. Set up the ground rules

Maintaining excellent client relationships comes down to reliability, according to the expert consultants and authors of the book The Trusted Advisor. Consistency and ability to meet agreed-upon deadlines play a huge part in creating trust, but meeting your client’s anticipated needs is even more important. This is how they put it:

“The more a provider can do to understand and relate to the usually unconscious norms of the client, the more the client will feel at ease and experience a sense of reliability.” In order to work well with your clients, you need to know how they work or their “unconscious norms.” To do this, outline the desired outcomes of your project together. Lincoln Murphy at Sixteen Ventures calls this “defining success,” which means that you determine what qualifies as success for both you and your clients before the project launches. Everyone needs to know what the final product should look like before you start working on it.

When you set explicit expectations around the project parameters  how your project management software will be used, and what the finished result will look like, you’re charting the course ahead. Everyone is clear on what part they’ll play, and you get a close look at the work style of the other party involved. Understanding how your clients think and what they need from you will help you both work better together.

Email your clients a questionnaire

Before you start planning a project for a client, you’ll want specific information about their needs and expectations. Don’t make assumptions about what you think your clients want to accomplish — ask them.

Pull together a list of questions for them to answer via email. This gives them the chance to articulate their definitions of success in their own words, and you’ll have a reference guide to guide the project and future conversations. Use these questions to get started:

  1. What results do they want to see? How will they measure these results?

  2. What does successful execution look like to them? What does it look like for their boss?

  3. What customers are they looking to engage with this project? Who is their ideal customer?

  4. What platforms or channels will they use once the project is finished to disseminate it?

Their answers will give you a clear idea of what they expect to receive from you. With these answers in hand, you can show your clients what you need from them in return.

Pick up the phone and talk it through

As you create a better sense of performance and expectations from the client, you can provide a clear picture of the project scope and responsibilities from your side. In addition, you can make it clear what they shouldn’t expect from you. Feel free to set boundaries on issues like too-frequent update requests, last minute revisions, or other tasks that could jam up your workflow. Whether you talk to clients over the phone or discuss it in a document, make sure you explain these issues:

  1. The type of project management software you use and why

  2. How tasks get completed in the software,

  3. How products get shipped and when, and

  4. Resolve any questions they have about the process

Also send your clients guides, outlines, and examples showing how this software has been effective for past projects. These may look like screenshots of your project management software and an explanation of how tasks within your project might move through it. Often, short videos can make onboarding simple and provide an excellent troubleshooting tool that doesn’t require a staffed help desk. Make it clear how you will deliver on their project goals and how they can expect your software will be used to track all of the project landmarks. Project management templates are great for that. This reinforces trusts every step of the way.

2. Train your clients on your software

If you want to support your clients, your team, your goals and your deadline, then help your clients get comfortable with your project management software right away. If you just toss clients straight into the software without making certain that they are secure in the basic functions they need,  those confused clients will create more work for you. If new clients find the software intimidating, they’ll design their own avenues outside your workflow to get the answers they need. They’ll badger you with emails asking for updates or phone calls that waste time and can’t be tracked later. Invest in training right away, because–if they don’t trust it, they won’t trust you. To onboard your clients to your project management software:

  • Set up their personal account within the software.

  • Make it clear what areas they need to be active in: the comments section, where they’re tagged, etc.

  • Show them what the value of each action within the software is: moving a card shows that the task is completed, check-ins mean these team members are working on it, etc.

  • Demonstrate how the team works to complete a task within the software.

  • Show them where they can get an overview of project.

  • Introduce them to the in-house language your team uses in the software.

Note: If you have a client that’s difficult to onboard, use the Rule of 3. Show them how to do 3 tasks they need to know, and once they’ve mastered those, show them another 3, and so on. Breaking down the process into manageable steps removes a lot of fear and overwhelm. That’s right — training is imperative. According to a study from Survey Monkey, a third of respondents said they don’t have the time to learn a new tool, so you need to overcome that barrier and make onboarding simple for them.

3. Accommodate your clients in your workflow

After the initial training is over, remember that your clients may still need help integrating the project management software into their daily routine. It may take some time before they understand how useful its tools can be for day-to-day communication, organizing key documents, and monitoring progress.   Here’s how to maintain a seamless workflow for you and your client that builds trust and nails deadlines:

  1. Have short regular, scheduled check-ins about progress. This quick, simple meeting leaves the door open so uncomfortable questions or issues can be addressed before they become full-blown problems. This can happen through the project management software.

  2. Look for patterns. Do your clients seem to be confused about a certain process or notification in the software? Are you assuming that they understand your workflow? Are they ignoring your requests for important information? Find these patterns and solve the underlying problem — a misunderstanding,  lack of training, etc.

  3. Find places within your workflow to accommodate their comfort level. This may mean providing more training or using Google Calendar instead of Microsoft Outlook temporarily until they gain more confidence with your platform.

While this may sound like a lot of work, keeping tabs on your clients’ preferences and work style are simply part of a healthy high-value relationship.


Providing your clients with the necessary onboarding to have a friction-free start with your project management software will give you more peace of mind, fewer headaches, and more on-time projects.

Even better, when your software takes care of the details, your clients will think you’re a genius.