In his book, The Innovator’s Dilemma, author Clayton Christensen writes that big companies fail to innovate not because of a lack of resources but because the processes and values that helped them scale are not designed for disruptive innovation.

Lately, I’ve been noticing a trend I call “the implementer’s dilemma,” which follows similar logic to explain why leading companies find themselves woefully stuck in outdated implementations of their software. Like the innovator’s dilemma, the implementer’s dilemma is a product of how enterprises function: Enterprises tend to approach software implementation with how to fix today’s problems, not weighing the future needs of the business.

Enterprises invest by customizing the software to meet their very specific current needs. Organizations might even coax the software vendor to add new features, fields, or functionality to meet specific needs. Then lay out extensive, exhaustive governance around how their teams will use the software and build processes around that specific version of the software.

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Unfortunately, it does not take long for this custom-implemented software to become outdated. The problem is compounded when new employees, many of whom may be digital natives, join the enterprise and are pigeonholed into what may be an increasingly clunky, archaic system.

So, how do you avoid or escape the implementer’s dilemma? Here are three bits of wisdom I’ve learned from experience and from talking to customers and partners:

1. Don’t stop learning

Technology leaders must keep up with the market and trends, or they may need to catch up. It is important to keep on trend with best practices and recognize that best practices evolve.

Working with outdated practices and software will impact the employee experience. As younger generations enter the workforce, the tolerance for inefficient software and extensive governance continues to decline.

Digital natives expect their work software to perform at the same level of sophistication and usability as the consumer apps they use daily. Asking them to do their best work using tools that slow them down is a losing proposition that could lead to recruitment issues and high turnover.

Read the latest industry news, talk with peers, and attend third-party events to ensure your company is not stuck in the past.

2. Engage with internal business users

The company’s internal business users are a vital resource and should be treated as such. Keep an ear close to internal business users – the ones using the software and following its governance daily. Understand their expectations and pain points.

If these users are not providing feedback, it could signal that they do not care enough and may have found another internal or external approach or partner to meet their needs, which could spell bad news for IT leaders who may end up serving the old needs rather than the new ones.

[ Related read: Open source communities: How CIOs can leverage their power ]

Be diligent about checking in with constituents and talking with software vendors. Maintain your focus on having a solution that serves its intended business purpose and satisfies the latest needs of internal business users.

3. Maintain humility

Leaders often fear admitting we’ve fallen behind or drifted off course. It requires humility to acknowledge that decisions we made 18 or 24 months ago might require updating.

I find it helpful to think of leadership like gardening: The goal of any garden is for it to grow. But vibrant and healthy growth may require regular pruning. Just as pruning plants encourages the right kind of growth, analyzing our software needs regularly helps ensure our teams are growing in the right direction.

I often use humility in my approach to corporate strategy. It requires humility from an executive team to say: Although we feel confident in the strategy we have set forth today, we recognize it will likely change over time and will need calibration.

We must have the same humility in managing our software implementations unless we want to risk falling victim to the implementer’s dilemma.

[ Learn the non-negotiable skills, technologies, and processes CIOs are leaning on to build resilience and agility in this HBR Analytic Services report: Pillars of resilient digital transformation: How CIOs are driving organizational agility. ]