Questions to Ask Before Switching Construction Software#

Executive Summary#

Switching construction software affects daily operations for months or years. The decision involves more than feature comparisons—implementation timelines, data migration, training, and total cost all determine whether a software change succeeds or creates new problems. This guide provides vendor-neutral questions to ask during evaluation, helping subcontractors understand what they are committing to before signing contracts.

The Context for ICI Subcontractors#

Software transitions are disruptive. During implementation, staff must learn new systems while continuing to manage ongoing operations. Data must move from old systems to new. Workflows may need adjustment. The disruption is worthwhile if the new system genuinely improves operations—but transitions that are poorly planned or based on incomplete information can create months of frustration.

Asking the right questions before committing helps subcontractors understand what they are getting into and make informed decisions.

Implementation Questions#

Timeline and Process#

What is the typical implementation timeline for contractors of our size?

Implementation timelines vary significantly. Simple tools might be operational within days. Complex enterprise platforms might require months of configuration. Understanding the expected timeline helps with planning and sets realistic expectations.

Follow-up questions:

• What factors affect implementation timeline?
• What is the fastest implementation you have completed? The longest?
• What typically causes delays?

What does the implementation process look like?

Understanding the process helps prepare for what is coming. Some implementations involve intensive configuration periods. Others follow phased approaches. Some require significant contractor involvement; others are largely vendor-managed.

Follow-up questions:

• What are the major phases or milestones?
• What decisions do we need to make during implementation?
• How much of our team's time is required during implementation?

Can implementation be phased?

For contractors who cannot afford major disruption, phased implementation may be preferable—starting with core functions and adding capabilities over time.

Follow-up questions:

• What functions should we implement first?
• How long between phases?
• Does phased implementation cost more?

Resources and Responsibilities#

What resources does the implementation require from us?

Implementation requires contractor involvement—someone to make decisions, provide information, and coordinate internal activities. Understanding the time commitment helps plan appropriately.

Follow-up questions:

• Do we need a dedicated project manager?
• How many hours per week should we expect to invest?
• What roles need to be involved?

Who from your team manages the implementation?

Understanding who you will work with—their experience, availability, and role—helps set expectations for the working relationship.

Follow-up questions:

• Is there a dedicated implementation manager?
• What is their experience with contractors like us?
• How accessible are they during implementation?

What happens if implementation takes longer than expected?

Delays happen. Understanding how vendors handle delays—additional costs, extended support, schedule adjustments—helps evaluate risk.

Follow-up questions:

• Are there additional costs for extended implementation?
• What causes most implementation delays?
• How do you handle schedule changes?

Data Migration Questions#

Scope and Process#

What data can be migrated from our existing systems?

Not all data migrates easily. Understanding what will transfer—customer lists, job histories, equipment records, financial data—helps plan for what will need to be recreated.

Follow-up questions:

• What data typically does not migrate?
• How is data mapped between systems?
• Can we see sample migrations from systems similar to ours?

What format does our data need to be in for migration?

Migration often requires data in specific formats. If current systems do not export data cleanly, preparation work may be needed.

Follow-up questions:

• Do you provide data templates?
• Can you help extract data from our current systems?
• What data cleanup is typically needed?

Who is responsible for data migration?

Some vendors handle migration as part of implementation. Others provide tools for contractors to migrate their own data. Understanding responsibilities affects planning and cost.

Follow-up questions:

• What do you handle versus what do we handle?
• Is migration included in the implementation cost?
• What support is available if we encounter problems?

Data Integrity#

How do you verify data migrated correctly?

Data errors during migration create problems that may not be discovered until months later. Understanding verification processes helps ensure data integrity.

Follow-up questions:

• What validation checks are performed?
• How do we verify migration ourselves?
• What happens if errors are discovered after migration?

What is the timeline for data migration?

Data migration timing affects when the new system can go live. Understanding the timeline helps coordinate the transition.

Follow-up questions:

• When in the implementation does migration occur?
• How long does migration typically take?
• Can we continue using old systems during migration?

Training Questions#

Initial Training#

What training is provided during implementation?

Training approaches vary widely—from self-service videos to on-site instructor-led sessions. Understanding what is provided helps assess whether it will be sufficient for your team.

Follow-up questions:

• Is training in-person, remote, or self-paced?
• How many training sessions are included?
• Is training role-specific (office staff vs. field workers)?

How is training delivered for field workers?

Field workers often need different training approaches than office staff. Understanding how field training works is important for subcontractors with distributed workforces.

Follow-up questions:

• Can training happen at jobsites?
• Is training available outside business hours?
• How long does field worker training take?

What training materials are provided?

Training materials—videos, guides, reference cards—help with ongoing learning after initial training ends.

Follow-up questions:

• Are training materials available on-demand?
• Are materials updated when the software changes?
• Can we create internal training materials using yours as a base?

Ongoing Training#

How do you train new employees after initial implementation?

Staff turnover means new employees will need training long after implementation is complete. Understanding ongoing training options is important.

Follow-up questions:

• Is training available for new hires?
• What does ongoing training cost?
• Are there self-service options?

How do you communicate new features and changes?

Software evolves. Understanding how you will learn about changes—and how to use new capabilities—helps maximize value over time.

Follow-up questions:

• How are updates announced?
• Is training provided for significant changes?
• How do we access release notes or change documentation?

Support Questions#

Support Availability#

What support is available after implementation?

Support needs do not end when implementation finishes. Understanding ongoing support options helps assess whether help will be available when problems arise.

Follow-up questions:

• What are support hours?
• What channels are available (phone, email, chat)?
• What is typical response time?

Is support included or does it cost extra?

Some vendors include support in subscription pricing. Others charge separately. Understanding the support cost model affects total cost of ownership.

Follow-up questions:

• What support is included in the subscription?
• What costs extra?
• Are there different support tiers?

Support Quality#

Can we speak with current customers about their support experience?

References provide insight into how vendors actually deliver support—not just what they promise.

Follow-up questions:

• Can you provide references from contractors similar to us?
• What questions should we ask them?
• Are there any contractors who left? Can we understand why?

What is your process for handling critical issues?

Understanding how urgent problems are handled—system outages, data problems, issues affecting payroll or billing—helps assess risk.

Follow-up questions:

• How do you define critical issues?
• What is the escalation process?
• What are your SLA commitments?

Integration Questions#

Accounting Integration#

How does the system integrate with QuickBooks Online (or other accounting software)?

Most subcontractors use accounting software. Understanding integration capabilities helps assess whether systems will work together smoothly.

Follow-up questions:

• What data syncs between systems?
• Is sync one-way or bidirectional?
• How often does sync occur?
• What happens when sync errors occur?

Other Integrations#

What other systems does the platform integrate with?

Beyond accounting, contractors may need integrations with payroll services, equipment vendors, or other tools.

Follow-up questions:

• Do you have an API for custom integrations?
• What integrations do contractors like us typically use?
• Are integrations included or do they cost extra?

Cost Questions#

Pricing Structure#

How is pricing structured?

Pricing models vary—per user, per project, flat fee, tiered pricing. Understanding the model helps calculate costs accurately.

Follow-up questions:

• Is pricing per user? How are users counted?
• Are there different pricing tiers? What differs between them?
• Are there minimum commitments?

What is included in the subscription price?

Understanding what is included—and what costs extra—prevents surprises.

Follow-up questions:

• What modules or features are included?
• What costs extra?
• Is support included?
• Is training included?

Total Cost of Ownership#

What costs should we expect beyond the subscription?

Total cost includes more than subscription fees—implementation, training, integrations, support, and internal time all contribute.

Follow-up questions:

• What does implementation cost?
• What do integrations cost?
• What are typical annual costs beyond subscription?

What happens to pricing after the initial contract term?

Understanding how pricing may change at renewal helps plan for long-term costs.

Follow-up questions:

• How often does pricing change?
• What limits exist on price increases?
• What is your pricing history?

Contract Questions#

Terms and Flexibility#

What are the contract terms?

Understanding contract length, renewal terms, and commitments helps assess flexibility.

Follow-up questions:

• What is the minimum contract length?
• How does renewal work?
• Can we add or remove users during the term?

What happens if we need to cancel?

Understanding exit options—even if you do not plan to use them—helps assess risk.

Follow-up questions:

• What is the cancellation process?
• Are there cancellation fees?
• What notice is required?

Data Ownership#

Who owns our data?

Data ownership matters—both during the relationship and if it ends.

Follow-up questions:

• Can we export our data at any time?
• What format is exported data in?
• What happens to our data if we leave?

How is our data protected?

Understanding data security helps assess risk, especially for sensitive information like payroll data.

Follow-up questions:

• Where is data stored?
• What security certifications do you have?
• How is data backed up?

Reference Questions#

Customer Verification#

Can you provide references from contractors similar to us?

References from contractors of similar size, trade, and geography provide the most relevant perspective.

Follow-up questions:

• How long have they been customers?
• What was their implementation experience?
• What challenges have they encountered?

What do your most successful customers have in common?

Understanding success patterns helps assess whether your organization is positioned to succeed with this platform.

Follow-up questions:

• What characteristics lead to successful implementations?
• What do struggling customers have in common?
• What advice do you give new customers?

Making the Decision#

These questions generate information, but the decision requires judgment. Consider:

Does the vendor understand your business? Vendors who ask thoughtful questions about your operations demonstrate understanding that translates to better fit and support.

Are answers clear and direct? Vague or evasive answers suggest problems the vendor does not want to discuss.

Do references confirm vendor claims? Reference conversations should validate what the vendor told you—or reveal discrepancies worth investigating.

Can you picture your team using this daily? Beyond features, consider whether the system fits how your team actually works.

What does your gut say? After thorough evaluation, intuition often captures factors that are difficult to articulate.

How Appello Approaches These Questions#

Appello welcomes these questions from prospective customers. The platform is designed specifically for ICI subcontractors, with implementation approaches and pricing structured for the subcontractor market. Appello can provide references from mechanical insulation, sheet metal, and HVAC contractors who have implemented the platform.

Prospective customers are encouraged to ask these questions—and others—during evaluation. Informed customers make better decisions, and better decisions lead to successful implementations.

Conclusion#

Switching construction software is a significant decision that affects operations for years. Asking thorough questions during evaluation—about implementation, data migration, training, support, integration, cost, and contract terms—helps subcontractors understand what they are committing to and make informed decisions.

The questions in this guide are vendor-neutral by design. They apply whether evaluating Appello or any other platform. The goal is not to favor any particular vendor but to help subcontractors gather the information needed to make good decisions for their businesses.

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Related Reading:

• What to Look for in Construction Software as an ICI Subcontractor
• The Difference Between GC Software and Subcontractor Software