ArticlesOctober 20, 20266 min read

Betting big on construction technology: Why contractors need to get comfortable with failure

Two interior designers and African American manual worker.

Key takeaways
  • Construction companies that want outsized returns from technology need to create room for calculated experiments that may not succeed.
  • Evaluate potential investments based on their impact on employee experience, data and AI readiness, process development and their potential to generate valuable lessons.
  • Build a culture that supports calculated risk-taking. Leaders should avoid penalizing responsible experimentation when an initiative falls short.
  • Treat technology investments as a portfolio. Rather than expecting every initiative to deliver immediate ROI, focus on testing, learning and adapting while keeping experimentation from putting active projects or core operations at risk.

Construction companies that want to make big bets on construction technology need to accept one uncomfortable truth: some of those bets are going to fail. That’s not a flaw in the strategy. It’s something you need to lean into.

Risk management is fundamental to construction. It protects margins, keeps projects on track and keeps the business healthy. But when risk aversion governs every technology decision, it can quietly kill your upside.

Why avoiding technology risks holds you back

Most construction leaders want evidence before committing to a new platform or initiative. They want to understand the return, minimize employee disruption and avoid investing in something that doesn’t deliver. That’s reasonable, but it limits opportunities to win big.

A mentality that’s overly focused on mitigating risk makes companies reluctant to pursue anything with an uncertain outcome. And the opportunities with the greatest potential are often the ones that can’t guarantee an upfront return.

Here’s a contradiction worth pondering: many of the same owners running conservative internal technology budgets are actively seeking venture investments and alternative private opportunities outside the business. They’re looking at deals with real upside and real risk, such as startups and private companies. Some owners with meaningful annual income are talking to their money managers about getting beyond typical index funds and getting into alternative investment vehicles — like investing in the next hot startup.

If they’re comfortable taking bigger swings outside of the firm, why not within it?

What it really means to bet big

Is your firm willing to make a big bet? Venture investing means accepting that some investments will crash and burn. By definition, venture is about taking swings big enough that you’ll fail as often as you succeed, if not more. The strategy can work because the investments that do succeed hit big.

A true big-bet mentality requires accepting uncertainty. For construction companies, that means giving technology and operations leaders room to experiment with initiatives that might fail while staying focused on identifying those capable of creating outsized value.

Betting big on construction technology doesn’t mean taking risks with live projects or threatening core operations. It means carving out space for deliberate experimentation. Approach technology and AI initiatives as a portfolio rather than expecting each one to succeed.

When an initiative doesn’t work, there’s still value in learning what doesn’t fit your organization. You’ll make a more informed call on the next investment.

Which construction technology bets are worth making?

Accepting more uncertainty doesn’t mean making random investments. Construction leaders can develop a clear lens for deciding which opportunities are worth betting on by considering these four criteria when assessing technologies:

  • Employee experience: Could it improve how your people work or strengthen your ability to attract and retain talent? Labor is one of construction’s most persistent challenges; solving for it has ripple effects. If you’re focused on improving talent attraction and retention, you’re mitigating challenges that would have otherwise surfaced later.
  • Data and AI readiness: What are you doing to connect your systems or improve the data foundation that makes it easier for AI to work for you? A data warehouse like Snowflake is one example of a technology initiative that strengthens that foundation.
  • Skills and process development: Not every investment has to be software. Business process mapping and SOP development tend to have outsized benefits. You want to be consistent and give AI a better understanding of what’s unique about how you operate.
  • Learning potential: Even if the initiative doesn’t succeed, could the effort teach you something that makes the next decision sharper?

The objective isn’t to remove uncertainty. It’s to take purposeful risks rather than random ones.

Does your culture match your tech strategy?

Commit to a culture that enables innovation and doesn’t penalize the first person whose experiment doesn’t work.

Picture a technology leader at a firm who spends a year testing three new initiatives that are backed by leadership. Two show promise. One falls flat. At the annual review, that failure is a mark against their performance. The message lands clearly: experimentation is only welcome when it succeeds. This will stifle a culture of innovation.

If calculated risk-taking is genuinely part of your strategy, it’s important that your job descriptions, hiring criteria and performance management reflect that. A responsible experiment that doesn’t succeed can’t be treated the same as poor performance.

Learn from technology failures

This requires a real shift in how you define success.

Not every experiment will scale across the company, and not every initiative will result in an immediate productivity boost. There’s value in learning from those outcomes and building a culture that’s resilient to software and other tech launches that don’t go as planned.

A disappointing rollout shouldn’t set back your technology strategy for years. If you treat it as part of an ongoing process of testing, learning and adapting, it’s a source of data.

To keep failure survivable, experimentation shouldn’t put active projects at risk. The goal is a deliberate process that lets you test ideas in a way that’s safe to learn from.

What success looks like

Success isn’t batting a thousand on your technology experiments.

Success is pivoting your organization from one averse to technology and change to one with an innovative culture that is open to trying new things. Even if initiatives aren’t guaranteed to produce financial returns, the whole organization understands you’re capable of thinking big.

Make room for bigger swings

Technology and AI are opening new possibilities for how construction companies operate. But not every new tool comes with guaranteed returns. Companies that demand certainty from every experiment may be the ones standing still when a competitor’s bigger bet pays off.

Build experimentation into the strategy while maintaining a clear line between the risks you need to control and the risks worth taking. Strengthen your data and technology foundation to improve the odds of success. Choose purposeful bets and give your people room to try things. Focus on extracting lessons from projects that don’t work.

Remember, if your big bets are never allowed to fail, are they even bets?

Watch our construction technology webinar

Watch our webinar, What’s worth the risk? Driving ROI with construction technology, for a deeper dive into technology decisions. You will learn from Wipfli’s construction and technology leaders about:

  • What’s real and what’s hype in construction technology
  • The risks leaders should be willing to take
  • Why technology initiatives succeed or fail
  • How to avoid chasing every shiny new tool
  • When to invest and when to optimize
  • How waiting for ROI could limit your innovation

Read more

Whether you’re building out your data foundation, selecting and implementing new platforms or developing the processes that help AI work for your business, Wipfli helps construction organizations make technology investments that move the business forward. If you’re ready to take big bets with technology, we can help. Start thinking big with technology.