Why your tech investments won’t matter if your mindset is stuck in 2009 

You can buy every tool on the market. You can implement the best AMS, CRM, LMS, CMS—and throw in a chatbot, too. But if your culture is still operating like it’s 2009? None of it will matter. 

Let’s be honest. Digital transformation isn’t failing in associations because of bad tech. It’s failing because we’ve made culture an afterthought. 

The most successful associations we work with at .orgSource? They don’t just do digital. They think digitally—every day, in every department, across every decision. 

So what exactly is digital culture?  

It’s not about ping pong tables or unlimited Zoom licenses. Digital culture is the collective behavior, values, and mindset that support using technology to solve problems, make decisions, and serve members better. 

When your culture is digital: 

  • You use data to drive decisions—not opinions or politics 
  • Your team experiments, iterates, and moves quickly 
  • Innovation isn’t a side hustle—it’s how you operate 
  • Technology is a tool for achieving your mission—not a barrier to it 

It’s not about being perfect. It’s about being adaptable, curious, and courageous. And right now? Too many organizations are still leading with fear, control, and nostalgia. 

You can’t fake culture—and you can’t delegate it 

If your board says they “believe in digital,” but won’t fund strategic tech investments… 
If your executive team buys new tools but keeps outdated workflows… 
If your staff uses AI tools but leadership doesn’t know what ChatGPT is… 

You don’t have a digital culture. You have a disconnect. 

Culture doesn’t live in your mission statement—it lives in what your team does when no one’s watching. It lives in the decisions you make under pressure. It shows up in how you treat experimentation, failure, and learning. And it starts at the top. Digital leadership isn’t an IT responsibility—it’s a CEO mandate. 

Here’s how you know your culture is not digital: 

  • You still have silos that kill collaboration 
  • People wait for permission to innovate 
  • Strategy lives in a binder—not in your daily behavior 
  • Change feels scary instead of exciting 
  • Metrics are built around outputs, not outcomes 
  • The phrase “We’ve always done it this way” still shows up in meetings 

Sound familiar? Then it’s time to shift—not just your tools, but your thinking

What does a high-functioning digital culture look like? 

Let’s break it down: 

 Cross-functional collaboration is the norm 

Silos don’t survive here. Teams co-create solutions. 
Data, ideas, and ownership flow across departments. 

 Tech is aligned to strategy 

Every tool has a purpose—and that purpose is tied to mission, member experience, and results. 
No more random software purchases because “someone liked a demo.” 

 Leadership walks the talk 

Digital strategy isn’t delegated. It’s lived. 
Executives model curiosity, agility, and learning. They make room for iteration—and lead with vision, not fear. 

 Failure is part of the process 

Innovation is messy. In digital cultures, failure isn’t punished—it’s analyzed, learned from, and used to improve the next iteration. 

 Everyone is digitally literate—and continuously learning 

From the front desk to the C-suite, your team understands digital tools and how they connect to their work. 
Professional development isn’t “extra”—it’s essential. 

Digital culture is your advantage—especially in tough times 

Let’s be clear: We are not going back to “normal.” The members, the workforce, the tools, the environment—all of it has changed. Associations with strong digital cultures adapt faster. They innovate under pressure. They recover quicker. And they serve members with relevance and agility—no matter the challenge. 

As we saw in the pandemic, resilience isn’t built during a crisis. It’s built before one. 

Ready to change the culture? Here’s where to start: 

  1. Audit your leadership behavior 
    Are you reinforcing curiosity, speed, and transparency—or bottlenecks and hierarchy? 
  1. Reward innovation 
    Recognize and elevate teams that test, learn, and improve—not just those who check boxes. 
  1. Invest in professional development 
    Train your staff to lead in digital-first environments. Skill-building is retention—and growth. 
  1. Kill your silos 
    Create cross-functional teams for strategic initiatives. Make collaboration the default setting. 
  1. Tie tech to mission 
    Stop buying tools in isolation. Build a roadmap that connects systems to strategic outcomes. 

Don’t let your technology outpace your people 

Digital culture isn’t a “nice to have.” It’s the difference between thriving and becoming irrelevant. 

If your tools are modern but your mindset is stuck in analog… 
If your staff is working around your systems instead of with them… 
If change always feels like an emergency… 

It’s time for a reset. 

At .orgSource, we help associations build the culture that supports the strategy, that drives the tech, that delivers the value. Because transformation doesn’t start with technology—it starts with thinking differently. 

📩 Want help building a digital culture that’s built to last? Let’s talk. Your culture may be your biggest barrier—or your biggest asset. 

📧 sherry@orgsource.com 
🌐 orgsource.com