Avoiding Expensive Mistakes: A CFO’s Guide to Software Selection (Part 1)

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.

Before engaging vendors, start with an internal technology assessment:

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

This should be a deliberate, problem-solving exercise that assesses effectiveness, criticality to the business, opportunities for automation, and vendor support of existing systems.

Gather & Prioritize Requirements

Once needs are identified, gather business and technical requirements.

  • Involve every department affected by the technology — finance, HR, preconstruction, project management, field teams, and IT.
  • Organize requirements into “must-have” and “nice-to-have” categories.
  • Use this list as your software specification and even reference it in your subscription agreement to hold vendors accountable.

Scout Vendors Carefully

Avoid limiting your search to just a few known companies.

  • Use industry associations, peer recommendations, and independent consultants to surface stronger contenders.

Take a Structured Approach to Demos

Demos are often designed to impress. To evaluate properly:

  • Use a standardized evaluation form comparing functionality, usability, and integration.
  • Schedule demos close together for easier comparisons.
  • Request sandbox environments for real-world testing.

Scrutinize Contracts

Don’t stop at features — review:

  • Hidden fees, licensing, and maintenance costs.
  • Service-level agreements.
  • Scheduled price increases.

A “cheap” solution can quickly become a budget-busting nightmare if overlooked.

The Right Players in the Selection Process

Don’t Make This an IT-Only Project

This is a business-wide initiative. Relying only on IT or executives risks blind spots.

Key Roles

  • CFO – ensures financial viability, budget alignment, and business impact.
  • Technology Leaders (IT Director/CTO) – evaluate performance, security, scalability, and integration.
  • Operations Leaders & Field Supervisors – provide day-to-day perspective.
  • Procurement & Legal – review contracts and protect from costly missteps.
  • End Users – their input drives adoption and prevents resistance.

A cross-functional team ensures the chosen system is both functional and user-friendly.

How to Avoid Being Sold To

Sales Pitches

Sales reps are trained to make solutions sound perfect. Stay focused on your requirements.

Know Who You’re Dealing With

  • Many “consultants” are actually resellers earning commissions.
  • Always ask about affiliations or financial arrangements.

Demand Real Data

  • Request case studies with measurable results.
  • Conduct reference calls with current users.
  • Ask about challenges during implementation and adoption.

Test in Your World

  • Request a customized demo aligned to your needs.
  • Use a sandbox environment to test functionality in real scenarios.

Making the Final Call

Go Beyond Features & Cost

The best solutions are scalable, supported, and future-proof.

Key Questions Before Committing

  • Can the software integrate and scale with your systems?
  • Are there hidden costs (training, customization, licenses)?
  • Is the vendor stable and financially sound?

The Cost of Overlooking the Details

Skipping these questions can lead to expensive failures, frustrated staff, and stalled operations.

Conclusion

Choosing new technology isn’t just a software decision — it’s a high-stakes business investment.

The right system will improve efficiency, control costs, and create long-term advantages. The wrong one will waste money, frustrate teams, and damage adoption efforts.

By following a disciplined vetting process, engaging stakeholders, and cutting through sales pitches to focus on fit and functionality, CFOs can transform technology selection into a competitive advantage — not a costly mistake.

Stay tuned for Part 2, where we’ll dive into negotiating software contracts and subscription terms to protect your investment.


Copyright © 2025 by the Construction Financial Management Association (CFMA). All rights reserved. This article first appeared in CFMA Building Profits (a member-only benefit) and is reprinted with permission.

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