Overcoming challenges when moving to a new project management tool

Switching to a new project management tool can be a huge leap. It means you’re setting out to change how your team thinks, communicates, and tackles their work daily. That’s no small feat! So, why do companies make the switch? Often, it’s because the old tools:

    Can’t keep up with the growth and changes of the business.
    Lack features that are now essential,
    Don’t integrate well with other tools you’ve started using.


Or perhaps it’s just about seeking better efficiency and more insightful data to drive your projects forward. Whatever the reason, making the jump to a new system is both exciting and a bit daunting! Think about it. You’re not just dealing with software here but with people. Everyone on your team has their habits and preferences. Some might welcome the change with open arms, excited by new features and smoother workflows. But others? They might be more set in their ways, comfortable with the old system, and wary of the learning curve they face.

    What if this transition were smoother than you expected? 
    What if everyone could adapt and become more collaborative, proactive, and aligned with your business goals?


That’s the promise of moving to a powerful, well-chosen new project management tool. But to get there, you need a really good plan! You need to understand the capabilities of the new tool as well as the needs and dynamics of your team.

    How do they work?
    What challenges do they face with the current tool?
    What do they wish they could do that they currently can’t?


Here’s where you step in with leadership and vision. Your role is to guide your team through the transition, reassuring them, training them, and showing them how this change will improve their work life, not make it more complicated. Sure, it’ll take some effort. Yes, there will be a learning curve. But remember, every successful change begins with a single step. And who knows? This new tool might propel your projects and team to new heights.


Challenge #1: Resistance to change

Have you noticed how the announcement of a new project management tool can get mixed reactions? It’s not just you. It happens in almost every MSP! You might see a spark in some eyes, but others might look like you just told them their favorite tool is going extinct. That resistance to change is one of the biggest hurdles you’ll encounter.

Why the resistance, though? It usually comes down to comfort and uncertainty. People get used to their routines. They know the ins and outs of the current tool, and now, suddenly, they need to learn something new. The thought alone can be overwhelming. Plus, there’s always that nagging question: “Will this make things better or just different?”

And here’s another twist: your team—engineers, helpdesk staff, dispatchers—rely heavily on these tools for their day-to-day tasks. Any disruption might make them worry about dropped tasks or missed deadlines.


How to overcome this challenge

Start talking about the change well before it happens. Give everyone a heads-up about what’s coming, why it’s happening, and, most importantly, how it will benefit them. Yes, focus on the benefits!

    Will it make their work easier? Faster?
    Will it help them meet their targets or reduce the daily grind? Spell it out!


Next, involve them in the process. Ask for their input.

    What features do they love in the current tool?
    What frustrations do they hope the new tool will solve?


When they feel like they’re part of the decision-making process, resistance often turns into support. Training is key. Don’t just offer a single crash course and call it a day. Offer multiple training sessions—some basics to get started and more advanced workshops down the line. And make sure these are interactive. Let everyone play with the new tool, click, and make mistakes in a safe environment. 

Set up a dedicated helpline or chat channel for any questions or issues. Recognize that the learning doesn’t stop after the first week; keep the support ongoing. Celebrate the wins, no matter how small.

    Did someone figure out a quicker way to log tickets? Share that victory!
    Did the new tool play a role in solving a complex issue? Highlight it!

Celebrating these moments reinforces the new tool’s positive impact and helps everyone see the value in the change.


Challenge #2: Data migration

Moving all your project data, client details, and backlogged tickets from one system to another is no small feat. The fear of losing critical data or facing days of cleanup after a messy transfer can keep even the most seasoned service manager up at night.

Your MSP relies on historical data for insights and ongoing projects for revenue. Any glitch in migration could mean lost history, confused ticket statuses, or even billing errors. And let’s not forget how important this data is for your daily operations—dispatchers managing schedules, technicians tracking tasks, and helpdesk personnel resolving client issues.


How to overcome this challenge

Start by clearly cataloging what needs to be migrated. Not everything might need to move, and some data could be archived instead. Involve all stakeholders in this phase—managers, techs, and helpdesk teams can provide invaluable insights into what’s essential.

Ensure the new project management tool offers robust data import capabilities that match your data structure. If it doesn’t, you might need custom solutions or middleware. Don’t shy away from investing in professional services if that means a smoother transition. Before going all in, run a pilot migration. Select a subset of your data and see how it transfers. This trial run will help you identify any tweaks needed in your process and avoid a full-scale disaster.

Once the data is migrated, don’t assume everyone will know where to find what. Offer specific training sessions that focus on navigating the new system. Highlight where common data points are now and how to access historical information.






Challenge #3: Integration complexity

When MSPs transition to a new project management tool, integrating it seamlessly with existing systems—like CRM, time tracking, or billing software—can be a major hurdle. The complexity of ensuring these integrations are smooth and functional is a critical challenge. Without proper integration, teams might juggle multiple systems that should ideally work as one, leading to inefficiencies and errors. Concerns such as,

    “Will the new tool work with our existing software?”
    “How do we avoid disruption in daily operations?”

are typical during this phase.

How to overcome this challenge

Before finalizing the new tool, verify its compatibility with your existing systems. Check if the tool offers native integrations or needs third-party solutions to bridge gaps. If direct integrations are unavailable, consider middleware solutions that can connect disparate systems without extensive custom coding. Run a pilot test involving the new tool and your existing systems to see how they interact. Identify any issues and address them before a full-scale rollout. Ensure your vendor provides ongoing support for integration issues.  


Challenge #4: Support and maintenance  

Ongoing support and maintenance can often become a significant challenge when implementing a new project management tool. This aspect is important because the initial setup is just the beginning. The real test comes when the tool is used regularly and requires continuous updates, bug fixes, and system optimizations to maintain efficiency. For MSPs, whose daily operations heavily depend on the reliability of their project management software, insufficient support can lead to operational disruptions and decreased customer satisfaction.


How to overcome this challenge

    Assess the vendor’s support structure before finalizing your tool. Opt for a vendor that provides comprehensive support through various channels like live chat, phone, and email. Check for 24/7 support availability, especially if your MSP operates around the clock.

    Ensure the tool receives updates that improve its functionality and security. Subscribe to update notifications and schedule regular sessions to implement these updates. This keeps the software running smoothly and secures against emerging threats.

    Invest in training your IT staff to handle basic troubleshooting and maintenance tasks. This empowers them to manage minor issues promptly without waiting for external help, ensuring little to no downtime.

    Set up a routine checkup schedule for the tool to review its performance, update needs, and integration points with other systems. Regular audits help catch issues before they escalate into bigger problems.

    Create a feedback loop with users to continuously gather insights about the tool’s performance and areas needing improvement. This feedback should be regularly reviewed and acted upon to enhance tool functionality and user satisfaction.

Solve your project management challenges with TopLeft

TopLeft is designed to integrate seamlessly with major Professional Services Automation (PSA) tools like ConnectWise Manage and Datto Autotask. This integration simplifies the data synchronization process, ensuring that all your existing data in these systems can be effortlessly transferred to and utilized within TopLeft without causing disruptions or data integrity issues.  

Every MSP operates differently, so TopLeft allows for highly customizable workflows. You can tailor the system to mirror your existing processes, reducing the learning curve and helping your team feel more comfortable with the new tool. This customization extends to views, filters, and boards, all designed to match your team’s and projects’ specific needs.

Understanding that adopting a new tool can be daunting, TopLeft provides extensive training resources and customer support. From detailed tutorials and webinars to responsive customer service, TopLeft ensures your team can utilize all features effectively. Additionally, TopLeft offers a dedicated customer success manager to help ensure seamless onboarding and help your team every step of the way. This educational support helps mitigate the anxiety around using new software and accelerates the adoption process. So, why start today and see how TopLeft can transform your project management experience? 

And the best part? It all happens within the tools your team already uses every day. Ready to see how it works in action?

Request a demo. 


PS: Get the Agile Project Management Certification Course designed specifically for professionals seeking to master Agile methodologies in managing MSP projects. This course covers everything from integrating Agile with Waterwater approaches to mastering budgeting differences and developing an Agile mindset. Whether you’re a project manager, team leader, or executive, this course will equip you with the skills to drive operational efficiency and enhance service delivery. Don’t miss out—only 30 seats available! Click here to register.


Ready to streamline your project’s workflow and see real results?

Contact us now to schedule a demo.