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Industry Insights

A Subcontractor’s Guide to Implementing Software

Construction companies are leveraging software to combat a number of issues plaguing the industry today. From solving workforce challenges and managing job costs to reducing supply chain issues and streamlining pay apps, there is no shortage of tools that promise to make everyone’s lives easier. However, introducing new software to your team can be stressful because a) implementation rarely goes as planned, and b) it almost always takes longer than expected. 

To that end, implementing construction software should be managed just like any other major project—with a detailed plan, effective internal communication, and designated roles for everyone involved. Anything less can result in confusion and unsatisfactory outcomes. 

So, if your construction company has recently licensed new software (or you’re getting ready to), this article will help you:

  • Understand how and why software implementation fails  
  • Learn how to overcome implementation roadblocks
  • Identify markers of a great implementation plan
  • Gain strategies to ensure a successful software implementation
  • Be prepared to handle unexpected challenges

5 Reasons Construction Software Implementation Fails 

More than one subcontractor has shared their horror stories with us of software implementations gone wrong. And while everyone’s experience may be a little different, it always seems to boil down to a combination of these five factors.

1. No one understood why you bought new software.

Clearly communicating the "why" is paramount to successfully implementing any plan. We’ve seen cases where a client or an executive forces a field or back office team to adopt a new tool without adequately explaining the reasons for doing so (e.g., the problems it aims to solve or the benefits it offers). Without a clear and compelling reason for the change, your team will likely be confused, the chances of obtaining their buy-in are slim, and the entire implementation process will be a struggle.

2. The product wasn’t properly vetted. 

Deciding to introduce and implement a product in a vacuum is always a recipe for disaster. This is especially true if the team using the tool is left out of the selection process. Who better to raise questions about the software’s capabilities and understand whether they align with the business’s objectives and workflows? Not giving these folk a seat at the table could lead you to pay for a solution that isn’t satisfying any pain points—and may create more in the long run.

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3. No one knew their role in the rollout.

Just like in construction, there are clearly defined roles and responsibilities for everyone involved in the project. The same logic applies here.

When we work with trade contractors to implement our construction billing software, their implementation teams typically include folks from accounting, project managers, and executives. Having at least one person involved from every team that will use the tool can go a long way toward removing friction.

4. There was no clear plan or timeline. 

You wouldn't sign a construction contract without knowing the scope and timeline. Your team deserves the same consideration when introducing new software. To that end, establishing a realistic roadmap—with milestone markers and all—at the start is one of the most important things you can do to ensure a successful rollout. While the plan may change over time, it serves as a reference point for your team throughout the process, giving them information they can use to manage their workloads and their expectations.

Plus, as you continue to add more tools to your technology stack, it helps to have an overarching plan in place to ward off software fatigue. 

5. Vendors weren’t fully brought into the plan.

It's common for businesses to buy new software without realizing how much the vendor is willing to help with the rollout and adoption process. But here’s a little-known tip: Vendors are often measured on how successfully their clients utilize their software. Therefore, they are invested in helping you achieve a smooth rollout and maximizing the software’s benefits. It’s mutually beneficial for both parties to set expectations about what a successful implementation plan looks like, how long it will take, who should be involved, and how to gain adoption quickly. 

How to Overcome Implementation Roadblocks

Like they always say, an ounce of prevention is worth a pound of cure. To that end, planning ahead is the best way to prevent these common challenges from slowing your implementation down. Here’s our advice for overcoming implementation roadblocks well before you sign the purchase agreement.

Ask the right questions.

Remember, you are the client. And you should ask a lot of questions to ensure you’re not paying for a piece of software that isn’t a fit and that your team will be reluctant to use. Here are a few tips to guide your vetting process.

  • Invite key stakeholders to sit at the table when selecting new tools to broaden and diversity the questions asked.
  • Identify what problems the software will solve, what capabilities it will unlock, and who will use it. 
  • Show up to your demos with a list of questions. This accounting software buyer’s guide contains a vendor Q&A checklist to get you started. 
  • See what other subcontractors are saying about the software. You’ll likely find case studies and testimonials on the vendors’ websites. We also recommend checking third-party software review sites like G2, Capterra, and Software Advice.  

Gain buy-in from end users. 

Involving end-users in the selection process is a great way to get buy-in from the beginning. Once you know who the software will impact most, you can invite key members from user teams to join demos. This way, they can:

  • see the software in action, 
  • think through use cases and how it will make their jobs easier, 
  • surface any questions or issues upfront so they don’t pop up later, and
  • get others excited about the change to encourage adoption later on.

Understand what support looks like.

Work with your software provider to understand what support they provide during implementation and what’s expected of your team. 

  • Do they host training sessions, or are you responsible for learning the product on your own? 
  • If it’s the latter, what type of training modules, videos, or help articles do they provide?
  • What are the fees (if any) for training support?
  • Which team members should be involved in implementation? Is it best to introduce the software to select team members in each department or roll it out to everyone at once?
  • If you’re migrating from an existing system, who is responsible for data migration, and on what timeline? Will you have both systems running for a little while during the transition?
  • What does training look like when new features are added?

Keep in mind that this isn’t an exhaustive list. We recommend brainstorming questions with your team to ensure their needs are fully addressed. 

Build a realistic timeline.

Timelines are critical, but construction companies know better than anyone that rushed timelines equal poor outcomes. So, developing a realistic timeline that works for everyone is important. 

Start by getting input from the vendor on typical implementation timelines for companies like yours. Then, sit down with your team to build a schedule they’re comfortable with and can agree to. Lastly, share this schedule internally and with your vendor so everyone can fully view the dates you’ve committed to. 

Markers of a Great Software Implementation Plan

Beyond avoiding the major roadblocks, how can you ensure smooth sailing the next time you implement new construction software?

Document timeline and goals.

Some implementations take a week. Maybe it’s a simple app for your supers to download, and training only takes a few minutes. Some implementations (think: ERPs) take a year or more before you’re fully using the product.

Regardless of whether you’re implementing a point solution or a more robust all-in-one construction software, documenting your timeline and goals is essential to success. If everyone expects the implementation to take a year, they can prepare for that. If they think it’ll take a month and it takes a year, then they won’t be prepared, they’ll get frustrated, and you likely won’t get the adoption you need to see ROI on your investment.

Some things to consider when establishing a timeline include:

  • What else is going on in the company, and how may that conflict with the rollout?
  • What are the training expectations of your team and the timing involved with that?
  • Does our schedule align with our goals?

What I’ve seen work really well for companies is to start with their end goals and then work backward to create checkpoints along the way (e.g., every end user should have their login setup by this day, X number of projects should be migrated to this new system by this day, the team will have completed X number of training modules by this day).

Establish a change management team. 

Implementing new software inevitably means change. And change is hard. So whether you’re switching from one tool to another or moving from manual processes to software for the first time, the best way to encourage adoption is by building a team of folks to champion the new solution. 

A strong change management team includes multiple stakeholders, such as: 

  • The project manager: Arguably the most important role on the change management team, this is the one person responsible for driving the change forward. At any point, other stakeholders should be able to ask them for status updates. Similarly, they will be the ones reporting progress back to the executive team. This person should be delegating tasks to other members of the implementation team along the way.
  • The champion: This is the person responsible for building excitement for the product. Usually, these folks are open to and comfortable with new technologies and have a keen understanding of what the new solution does—making it easier to convince others of its value to their roles.
  • The executive sponsor: While not typically involved in the day-to-day, the executive sponsor is the extra muscle sometimes needed to overcome particularly hairy roadblocks. They have the influence required to get the project—and the team—back on track.
  • The end users: These are the folks who will be using the product the most and, therefore, will require early access to the product and ample training.

Before assigning these roles, make sure that each person understands the expectations, timeline, and goals so that they can know whether they have the bandwidth. These can be demanding projects, especially for larger organizations. 

Furthermore, make sure to document each person’s role in the project plan. This can help others determine who to direct their questions to during the rollout (and eliminate any finger-pointing).

Define KPIs to measure success.

When you were vetting the software, you should have identified the potential benefits that drove your final decision. Use these benefits to establish the key performance indicators (KPIs) to measure your implementation success. This might include things like time savings, cost savings, reduced errors, or increased collaboration. 

Some of the KPIs trade contractors measure when implementing Siteline are:

  • How much faster they get paid (reducing invoice aging)
  • How much time their PMs and accounting teams save on billing
  • How many fewer pay apps get kicked back by GCs 

Once you’ve established your KPIs, circulate them among your teams to ensure everyone involved understands what they’re working toward and how it enhances business outcomes.

Build a training and adoption plan.

Understand the training offered by the software provider (using some of the tips provided above) and customize their training program to fit your company’s needs. Depending on how complicated the software is, you may want to break training up into multiple sessions and include a refresher course after everyone’s used the tool for a while. 

Create a schedule that’s aligned with your goals and is considerate of your team’s current workload. The last thing you want to do is force software training on everyone during a time when they have several major project deadlines looming over their heads. 

Offering incentives to encourage your team to attend training sessions is always a smart move (and nothing to be ashamed of). For instance, a vendor I've collaborated with in the past would provide a monthly pizza party alongside their demonstrations during lunch hours. This approach ensured a high attendance rate and minimized the impact on work hours, which is particularly beneficial to industries (like construction) where overtime is common.

Consider a pilot test.

Depending on the size of your company, how many projects you’re running at one time, and how complicated the new software is, you may want to consider pilot testing before full-scale implementation. 

To run a pilot test, start by identifying a group for testing. This could be one department or office or projects under one project manager. Characteristics you may want to consider for this group include individuals who: 

  • are familiar with technology, 
  • excited to test new tools, 
  • have some bandwidth to take this on, 
  • are a reliable bellwether, and/or 
  • are currently running projects that are a good fit for the tool.

Then, build a smaller-scale implementation plan that you can later replicate across the entire company. Use the pilot phase as an opportunity to gather feedback, address issues, and fine-tune the software before rolling out company-wide.

Prepare for data migration and integrations.

It’s wise to determine at the outset what existing systems your new software needs to connect with and understand how these systems talk to each other. Ensure you have the right people (internally or externally) to manage, maintain, and troubleshoot the integration as needed. 

The biggest thing to note is that not all integrations are equal. Some are file-based, some are pre-built, and some require customization. Get details on the integrations offered and understand your responsibilities versus the vendor’s. Some helpful questions along this front include:

  • What other platforms does the software integrate with?
  • What information actually flows from one software to the next?
  • When will the data flow, and is it a batch process? 
  • How often is the system pulling the data over if it flows automatically?
  • How does it move from one system to another?

If you have an IT team, this would be the time to bring them in to help you understand whether the integration does everything you intend for it to do.

Monitoring Software Adoption and Measuring Success

Even the best-laid plans can go astray. Preparing for the unknown and monitoring progress along the way will help keep your implementation on track, regardless of what comes up. 

  • Prepare the team for possible roadblocks. Chances are new users will run into some issues along the way. Establish channels for users to report problems and receive assistance. And make sure everyone has the contact information of support.
  • Monitor progress toward goals. If you set a goal for the entire accounting team to start using the new billing software or for all projects to be built out in the new PM software, schedule periodic check-ins along the way. Communicate status updates and be ready to make changes to the plan if needed. 
  • Measure ROI. Base success on the KPIs you established prior to implementation. Measure your return on investment in terms of time saved, money saved, mistakes eliminated, etc. Report success back to stakeholders, illustrating the before and after scenarios using data and visuals.

The moral of the story is this: You’d never buy new construction equipment without ensuring your team knows how to use it. So why not put that same effort into new software tools? Even better, choose a software partner, like Siteline, that makes implementation easy and is committed to your success well after onboarding. We’re here to help you streamline your pay application process so you can get paid up to three weeks faster. If you're interested, schedule a no-obligation demo of Siteline today and witness our commitment to helping you eliminate payment delays once and for all.

Co-Founder · Head of Construction Solutions
@ Siteline

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