Avoiding Expensive Mistakes: A CFO’s Guide to Software Selection

Technology implementations often sound great on paper — better data, streamlined processes, and improved efficiency — but too often, companies end up with blown budgets, frustrated teams, and systems that don’t deliver.

For CFOs, the stakes are even higher as they balance cost, long-term viability, and integration across the business while avoiding disruption.

With technology investment surging across the construction industry, making smart, informed decisions is more critical than ever — and far more complicated.

This four-part series aims to guide CFOs and IT leaders through each stage of the technology adoption process, from evaluation to negotiation, implementation, and long-term support. In this first installment, we’ll focus on how to properly vet potential software solutions — helping you avoid common missteps, build the right team, and set the foundation for a successful technology investment.

The Right Way to Vet New Technology

Start With an Internal Assessment

Selecting new technology isn’t about chasing the latest software — it’s about solving real business problems. Yet many companies dive into the search without first evaluating what they have and what they actually need.

Before engaging vendors, start with an internal technology assessment.

Ask yourself:

  • What operational pain points are we trying to solve?
  • What inefficiencies are costing the most?
  • What specific functionality is missing from the current systems?

Too often, companies pursue new technology because a competitor upgraded or a vendor made a convincing pitch. Instead, this should be a deliberate, problem-solving exercise that assesses each solution’s effectiveness, its criticality to the business, opportunities for automation and integration, and vendor support of existing systems.

Gather & Prioritize Requirements

Once you’ve prioritized needs, gather business and technical requirements for your software initiative. This is where many companies falter — collecting limited detail or failing to engage the right stakeholders.

Every department affected by the technology should have a voice, from finance, human resources, and preconstruction to project management, field teams, and IT.

Organizing requirements into “must-have” and “nice-to-have” categories keeps you focused on what truly matters. This requirements list becomes your software specification, guiding vendor discussions and providing a framework for evaluating fit and functionality. When done right, this document should even be referenced in your software subscription agreement to hold vendors accountable.

Scout Vendors Carefully

With your requirements in hand, move into scouting, vendor research, and product demonstrations. It’s tempting to reach out to the first few companies you know, but poor scouting limits your options — and risks overlooking better-fitting vendors.

Industry associations, peer recommendations, and independent (non-reseller) consultants can help surface strong contenders.

Take a Structured Approach to Demos

Evaluating demos is another area where things often go wrong. Demos are carefully designed to showcase the most impressive features, which is why you need a structured process.

Use a standardized evaluation form that compares each system’s functionality against your requirements, ease of use, and integration potential. Schedule demos close together to keep details fresh. When possible, request access to sandbox testing environments so your team can gain hands-on experience before making a decision.

Scrutinize Contracts

Finally, decision-making goes beyond the features. Now is the time to scrutinize contracts, terms, service-level agreements, long-term costs, and the vendor’s approach to implementation. Hidden fees, licensing structures, maintenance costs, and scheduled price increases can quickly turn a seemingly affordable solution into a budget-busting nightmare.

The Right Players

Don’t Make This an IT-Only Project

The technology vetting process isn’t just an IT project — it’s a business-wide initiative.

One of the most common mistakes is allowing IT or a small group of executives to drive selection without broader input. The most successful technology selections happen when a cross-functional team is involved from the beginning.

Key Roles in the Selection Process

At the center of the company’s team is the CFO, who ensures the financial viability of the technology investment, alignment with budgets, and anticipated business or operational impacts.

Technology leaders, such as an IT director or chief technology officer, evaluate technical performance, security, integration, and scalability.

Operations leadership, project managers, and field supervisors provide frontline insight into how well the technology will support day-to-day construction operations.

End Users Involvement

In larger organizations, procurement and legal teams review contracts, negotiate terms, and protect the company from costly missteps. Just as critical are the end users — both office and field staff — who will interact with the system every day.

Engaging end users early and keeping them informed helps secure buy-in. Without it, adoption suffers, effort stalls, and future technology initiatives face even greater resistance.

Build a Team That Prevents Blind Spots

A well-rounded selection committee prevents blind spots and ensures the new system is not only functional, but also operationally viable and user-friendly.

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