Red Flag: Why Leadership Buy-In in Software Selection Is Costing Your Association Millions

Depicts why without active leadership involvement, 55-75% of software projects fail.

When the American Institute of Certified Public Accountants selected its new AMS system in 2019, they didn't just gather requirements from its IT department. Their Executive Director personally attended vendor demonstrations, their CFO participated in budget discussions, and their Chief Member Experience Officer helped evaluate workflows.

The result? A successful implementation that modernized operations for their 400,000+ members. Compare that to a mid-sized professional association that delegated its entire software selection to a junior IT manager while leadership "stayed out of the technical details." Two years and $300,000 later, they're still struggling with adoption rates below 40% and considering starting over.

The difference between these outcomes? Active leadership involvement from day one.

Why Leadership Buy-In Matters More Than the Software Selection Itself

Here's an uncomfortable truth that bears repeating: between 55% and 75% of enterprise software projects fail to meet their objectives, according to research from the ERP implementation industry. A Delphi study examining critical success factors found that top management support and commitment ranked as the highest-priority factor for successful implementations—above technical fit, above user training, above everything else.

Think about what that means for your association's software selection process. You could select the most feature-rich, technically perfect AMS on the market, but without genuine leadership engagement, you're statistically more likely to fail than succeed.

Why? Because software selection isn't just a technology project—it's a strategic initiative that touches every aspect of how your association serves members, generates revenue, and delivers on its mission. When leadership treats it as merely an IT decision, they signal to the entire organization that it doesn't warrant serious attention. Staff adoption suffers. Change management fails. The project drifts. Without leadership buy-in from the start, even the best software selection process is doomed.

The Hidden Costs When Leadership Buy-In Is Missing from Software Selection

The financial impact of failed software implementations extends far beyond the software license fees. Research from the Consortium for Information and Software Quality found that poor software quality and unsuccessful projects cost organizations approximately $2.08 trillion annually. For associations specifically, failed AMS implementations typically consume 2% to 6% of the annual operating budget in the first year alone—and that's just the beginning.

Think about the consequences when leadership is not engaged: Your membership director participates in some demos but lacks the power to make decisions. Your events team provides a wish list that no one prioritizes. Your finance department realizes halfway through implementation that the system can't manage your intricate dues structures. Every delay incurs real costs. According to IBM's research, resolving software problems post-implementation is 100 times more expensive than fixing them during the design stage.

A national trade association learned this lesson the expensive way. Their executive director delegated the AMS selection to a committee that met sporadically over 18 months. By the time they finally selected a vendor, staff turnover meant that three of the five committee members had left the organization. The new system launched with minimal executive oversight—and failed within six months. The association spent another $200,000 reverting to their old system while simultaneously hemorrhaging membership revenue from poor service during the transition.

However, financial costs are just one aspect of the issue. In the late 1990s, Hershey's faced a disastrous ERP implementation, leading to $100 million in lost sales due to inventory mismanagement during the crucial Halloween season. Similarly, in 2004, HP encountered a system failure that prevented 20% of orders from being processed, resulting in $160 million in lost sales and long-term harm to customer relationships. For associations, such disruptions can result in missed event registrations, failed membership renewals, and an inability to access member data, which are essential for the organization's operations.

What Active Leadership Buy-In Looks Like in Software Selection

Active involvement doesn't mean your Executive Director needs to become a software expert or sit through every technical specification meeting. It means establishing clear ownership, accountability, and strategic alignment from the C-suite down. Leadership buy-in in software selection is about presence, not technical expertise.

When Cisco Systems effectively rolled out their ERP, Enterprise Resource Planning, system, it credited its success to the "steadfast support and active involvement of executives." In practice, this meant that executives took part in planning sessions, were accessible for crucial decisions, consistently communicated the importance of the change, and allocated resources, including staff time, to guarantee success. Crucially, they did not pass strategic decisions down to tactical teams.

For associations, active leadership involvement includes several non-negotiable elements. Your Executive Director should personally approve the project charter and participate in vendor selection—not just sign off on recommendations but actually understand the strategic implications. Your CFO needs involvement beyond budget approval, ensuring the selected solution aligns with your financial systems and revenue tracking needs. Your senior membership and events leaders must help define success metrics tied to member experience and revenue generation.

Here's how that rhythm might appear: Leadership is present at the initial vendor demonstrations for the top three finalists. They engage in a half-day workshop to align software capabilities with strategic priorities. They receive updates every two weeks during implementation and actively remove obstacles when staff encounter barriers. They promote the change in meetings with all staff and during board presentations.

How Leadership Buy-In Prevents AMS Implementation Failure and Revenue Loss

Let's connect this directly to what likely keeps many association executives up at night: revenue. Your AMS touches every revenue stream—dues collection, event registrations, certification fees, sponsorships, and non-dues revenue from education. Leadership buy-in in software selection directly impacts your ability to protect and grow these revenue sources. A 2019 study found that 49% of businesses see major improvements after implementing enterprise systems, while another study showed organizations with strong leadership backing achieved 25% productivity increases and 25% cost reductions.

Here's the flip side: lacking leadership support can jeopardize the systems essential for generating revenue. Consider the chaos if your annual conference registration system fails during the early bird pricing period. Envision your automated dues renewal process sending incorrect invoices to 5,000 members. Imagine your sponsorship team being unable to access prospect data for six months. These aren't just theoretical situations—they're actual outcomes of poorly managed implementations where leadership wasn't sufficiently involved to guarantee business continuity.

The National Society of Professional Engineers offers a successful example. Their CEO took charge of a cross-functional steering committee that convened monthly when choosing a new AMS. They pinpointed their three key revenue periods—annual conference, certification exam registration, and dues renewal season—and planned implementation milestones to steer clear of these times. Instead of adding the project to regular duties, they dedicated 15% of staff capacity to it. The outcome? They not only prevented revenue disruption but also boosted renewal rates by 8% in the first year due to an enhanced member experience.

The Opportunity Cost of Delayed Software Selection Without Leadership Buy-In

Beyond immediate revenue risks lies something even more insidious: opportunity cost. Every month your association operates on outdated systems represents missed chances to serve members better, generate new revenue streams, or reduce operational costs. Lack of leadership buy-in in software selection often leads to analysis paralysis—endless evaluation cycles that cost more than any single implementation ever could.

A regional medical association took three years to assess AMS systems due to its executive director's repeated delays, citing the need for "more information." During this period, they were unable to launch an online community platform that their members were eager for. They also couldn't implement tiered membership structures that would have appealed to younger professionals. Additionally, they were unable to automate their certification tracking, requiring staff to handle spreadsheets manually. When they eventually calculated the costs, they discovered that the delay resulted in approximately $400,000 in lost membership revenue and consumed 2,000 staff hours in manual workaround efforts.

According to research by the Project Management Institute, just 6% of projects in mature, efficiently managed organizations are considered failures. This indicates that organizations with robust leadership and project governance achieve success at significantly higher rates. Conversely, the lack of executive involvement in other organizations leads to wasted resources, not only on unsuccessful projects but also due to the stagnation caused by continuous evaluation cycles.

How to Secure Leadership Buy-In for Your Software Selection Process

If you're an Executive Director reading this and recognizing that your organization's software selection process lacks adequate leadership involvement, here's your path forward. Start by acknowledging that securing leadership buy-in for software selection is a strategic priority worthy of executive time—not a technical detail to delegate and forget.

Create a steering committee that includes your senior leadership team, not just IT and operations staff. Establish clear decision-making authority and timelines. Most critically, commit to regular engagement throughout the process. That might mean blocking two hours monthly in your calendar during vendor evaluation and selection, then weekly touchpoints during implementation.

For membership directors and CTOs who see the danger but aren't in the executive seat, you have a crucial role in surfacing this issue. Build a business case that connects software capabilities to strategic objectives your leadership cares about. Frame the discussion around member experience, revenue protection, and mission delivery rather than technical features. Use data: cite that 67% of organizations with engaged leadership report project success, while those without face failure rates approaching 75%.

If you're on an association board, consider whether you're providing adequate oversight. Does your board receive regular updates on major technology initiatives? Have you ensured the executive team has both the authority and accountability to make these decisions effectively? Remember that failed software implementations don't just waste money—they can fundamentally disrupt your association's ability to serve members and fulfill your mission.

The Bottom Line on Leadership Buy-In in Software Selection

Leadership buy-in isn't a "nice to have" in software selection—it's the single most important success factor. The research is unequivocal: projects with active executive involvement succeed at rates up to 88%, while those without face failure rates of 55% to 75%. For associations, where technology directly enables member service, event management, education delivery, and revenue generation, the stakes are even higher.

The cost of passive leadership extends beyond wasted budget dollars. It shows up in staff frustration, member dissatisfaction, missed revenue opportunities, and strategic drift. It manifests as systems that don't meet needs, implementations that drag on for years, and organizations that can't execute on their strategic plans because their technology won't support them.

The good news? Leadership buy-in in software selection is a choice, not a constraint. It requires acknowledging that software selection is strategic work, committing real time and attention, and maintaining engagement from vendor selection through go-live and beyond.

Your association deserves better than delegated decisions and crossed fingers. Your members deserve technology that enhances their experience rather than creating barriers. Your staff deserves systems that support their work rather than making it harder. And your mission deserves the full commitment of leadership to ensure your technology enables rather than hinders your impact.

The question isn't whether you can afford to invest leadership time in software selection. It's whether you can afford not to. Without leadership buy-in, you're not just risking a failed project—you're jeopardizing your association's ability to serve members effectively and fulfill your mission.

Need help ensuring your software selection has the right leadership involvement from day one?

SmartThoughts specializes in guiding associations through strategic software decisions with proven methodologies that engage leadership effectively and avoid costly mistakes. Our 25+ years of experience has taught us that successful implementations start with the right people at the table—not just the right technology. Schedule a consultation to discuss how we can help your association make this critical decision with confidence.