Organizations Struggle with Digital Strategy and Technology, but an Innovation Mindset can help you thrive in the new AI Era.
- Brad Caldana
- May 1
- 9 min read
Updated: Nov 7
While digital strategy, engagement, and technology continue to pose challenges for most organizations, embracing an innovation mindset can equip your organization not just to survive but to thrive in the new AI era, unlocking new opportunities and driving growth.

TLDR: An Innovation mindset isn’t about constantly trying to innovate and do something new for the sake of doing something new or novelty.
An innovation mindset is a framework and a culture shift that enables an organization to leverage new processes, ideas, methods, and tools, thereby creating a greater impact on its organizational goals.
From this definition of Innovation: the process of successfully introducing a new and valuable idea, method, or product into a specific context, often to address a problem or improve a situation.
Now, here is the long of it and why an innovation mindset matters in the wake of the digital disruptions of the last five years and the face of even more disruptions from AI.
By 2023, we had transitioned into what I termed as Digital Strategy 2.0. The digital landscape had undergone significant shifts, disrupting traditional digital strategies from the late 2010s to the early 2020s.
Email has gotten more complex and more critical than ever. Email acquisition costs increased, deliverability became more challenging, inboxes were more crowded, and fundraising declined after a pandemic surge.
Websites were an afterthought. Chasing social media, lack of strategic vision, and the advanced mobile web were leaving websites behind.
Social Media is not at all what it was three years ago. (Now 5)It’s more decentralized than ever before; the Facebook and Twitter duo is nothing like it was before. First-person video is front and center.
Digital Advertising shifted/ is shifting. Conversion costs are on the rise, ad networks and audiences are becoming more decentralized, and many organizations continue to lack robust strategic budgets.
Text Messaging, it is critical, and most organizations are still sleeping on it over a decade later.
AI, yes, it’s real. It was here, and folks needed to start planning.
And here we are.
Over the past decade or two, nearly every organization has grappled with the complexities of Digital Strategy. The rise of AI only adds to these challenges, making it more crucial than ever to adopt an innovation mindset.
For almost two decades, I’ve been in conversation after conversation about organizational leadership not understanding digital strategy. It’s a fundamental problem that has plagued leadership and digital staff alike. Organizational leaders struggle with understanding what to realistically expect from the broad set of creative and technical roles that fall under digital. Digital staff are burning out from unrealistic expectations and a lack of mentorship that hinders their advancement into leadership roles. The conversation has spun in my mind so many times and lacks many things you can’t see until you change your vantage point. I’ve been flummoxed until now, unable to see a possible sector-wide shift that is needed for digital and technology to make its full positive impact.
We’ve been missing an innovation mindset.
When I say this to others, it’s an ‘aha’ moment.
Organizations have struggled with “digital transformation”. The phrase “digital transformation” is a challenging one to apply neatly to organizations. In the for-profit sector, it has often been about shifting to online purchasing, modernizing logistics software, and enhancing data infrastructure to remain viable in a new economy. For nonprofits, digital transformation is often applied to modernizing customer relationship management systems (CRMs), updating websites, or IT projects.
Many digital evangelists have sung from the streets: ‘You need to be digital first. However, they wouldn’t always describe it well. But if you are a service-based nonprofit or build physical things, what exactly would ‘digital first’ mean to you? Some meant digital at the leadership table, but some meant all things should happen through digital means first.

Be a modern organization. Not digital-first, but also not digital as an afterthought or add-on. At this point, organizations that should be digital-first already are. Being a modern organization in 2025 means fully adopting digital engagement, marketing, strategy, and technology into your organization. A modern organization is adopting digital and technology in the appropriate places and at the proper proportions.
An Innovation mindset is a framework and a culture shift that enables an organization to leverage new processes, ideas, methods, and tools, thereby creating a greater impact on its organizational goals.
The three traps of externalized digital, deprioritized digital, and attempting to run digital as an add-on to what we did before.
Let’s break down these three traps and how an innovation mindset helps the organization break through.
1) Externalized digital
Externalized digital can mean two things. First, purely externalizing to an outside source, assuming they have the best strategy and skills to meet your organization’s needs. On the face of it, it makes sense. Secondly, and it often goes hand in hand with the first, Externalizing digital as something someone else does. The latter makes sense; digital and technology are a sprawling and frequently overwhelming set of skills, strategies, and tools.
We are three decades into websites as the standard for organizations. Indeed, two decades into email as a critical strategy and platform for engagement and fundraising. And almost two decades into social media as an integral part of our social communication. Externalizing as someone else’s thing isn’t leadership anymore.
The innovation mindset is critical. It is about setting a tone as leadership that we will truly invest in new processes, ideas, methods, and tools, creating a greater impact on organizational goals.
Leaders must truly lead here. Most likely, they are stepping out of their comfort zone and are willing to learn and adapt their mindset and processes. Until leaders step up to that challenge, their digital strategy and implementation will suffer. Resources will go underutilized, organizations will squander capacity, and staff will most likely burnt out.
Trust me, if you aren’t hearing it indirectly, there is a conversation about how leadership just doesn’t get it. I hear it echoed again and again by folks in digital and tech who are inside organizations, at agencies, and with the people running platforms. “Leadership just doesn’t get it.” or “They just aren’t investing enough.”
The hour is too late, and the problems are too significant not to get it.
2) Deprioritized Digital
If you don’t get it, it’s hard to imagine it will be the proper level or priority. At the same time, I’m on board with not being a digital-first approach. Digital is truly at the center of what every organization does. Digital at the center means that everything is run through digital technology. Digital at the center applies to both the concept of a modern organization and a digital-first approach. Let’s say you provide services in person. There are still tech platforms for managing human capacity, documenting services, and communications. If you do outreach services, you should have a website ready to meet people where they are and text messaging capabilities to manage real engagement.
Deprioritized digital can look like not having the capacity to:
Modernize and continually refine the website and user experiences.
Create rich and engaging social media content.
Content across your properties is not created for distinct audiences.
Produce consistent videos that engage audiences.
Maintain data structures that inform decisions and strategy.
Run digital advertising programs.
The twins of digital downfalls — Uninvested and underinvested digital projects and properties, and improperly invested digital projects.
Uninvested and underinvested digital projects and properties. Mediocre brochure-style websites for nonprofits litter the internet. They fail to reach their target audiences and are left to run as is because that is deemed good enough. Sparingly updated social media accounts, with no investment in audiences or content, join the mediocre, brochure-style websites.
Paired, unfortunately, well with digital projects that spent money on the wrong project or without realistic timelines. In improper investments, some individuals are spending significant sums of money without understanding the potential outcomes. But more often, it’s just spending on the wrong elements of digital to meet the goals.
3) Digital as an add-on
After the plans have been created, budgets set, and meetings held, someone realizes this should be online, too. As if we were in the early 2000s, and we were still collectively figuring out how to use the internet.
Digital, as an add-on, clearly doesn’t put it at the center; it often places it near the end. If you create a plan without digital at its center, you are making an outdated plan.
There are farmers currently asking AI questions to receive better answers on updating the software in their tractors. Those farmers are planning their planting dates with updated data modeling and weather forecasts.
Creating a plan and just shoehorning digital isn’t strategic. Thinking of email, websites, text messaging, audiences, and analytics as a thing you do later isn’t a good way to create meaningful engagement and impact.
An innovation mindset changes the inputs and outputs.
Digital channels, platforms, strategy, and technology are not static. Everything is changing at an increasingly rapid pace.
Let’s break it down: An innovation mindset is a framework and a culture shift that enables an organization to leverage new processes, ideas, methods, and tools, thereby creating a greater impact on its organizational goals.
First, at a leadership level, the organization is committed to becoming a truly modern organization with digital at its center. Leaders themselves must be ready to learn and adapt. Adapting once is not a reality, and that mindset is what left many organizations still struggling after a transformation. Leading with an Innovation Mindset is understanding that everything undergirding what we call digital is fluid. Best practices, platforms, and technology evolve from year to year, and in this new AI era, some of these changes occur more frequently every month.
To leverage new processes and ideas, leaders and staff must understand that adoption and adaptation take time. Parts of new processes can be as simple as adding the task of updating a specific piece of content on the website to keep it fresh for users. However, implementing the update will require time for the staff member to adopt it. In six months, how might this change, and what is the adaptation and adoption time of the new process?
Every new tool or platform I have used to save me time has a learning curve. A learning curve is often an initial loss of time. Leaders should incorporate this into their organizational planning and expectations surrounding individual and organizational goals.
New ideas, potential platforms, and tools will emerge. Innovation within an organization involves the ability to try out new ideas and determine what can be adopted. But also the space to fail. Innovation comes with failures.
Minor innovation failures occur all the time, such as when people have been “Slacked to death.” The expectation is that they’ll be available in a constant stream of consciousness in an organization. Any missed information might be on them, as a sudden shift away from including longer information in emails. An innovative mindset isn’t just about trying new things but also about refining or letting go of what isn’t working. In this Slack example, we are revising how an organization defines the use of various communication channels and sets expectations.
Making a strategic decision to start that podcast finally might be a great innovation. You might also realize, after producing five episodes, that you haven’t reached the audience you planned for. And the project isn’t fully invested in the capacity to have an impact on your goals. With an innovative mindset and strategy, you can pause and ask, ‘Can we invest in a way that makes this work, or do you wrap this up in a well-communicated way?
Innovation Mindset, Change Management, and Building a Modern Organization
An innovation mindset is a framework and a culture shift that enables an organization to leverage new processes, ideas, methods, and tools, thereby creating a greater impact on its organizational goals.
We often hear change management tossed around with varying degrees of what that means to team members.
Change management is a structured process that helps organizations navigate and adapt to changes in their goals, processes, technologies, or organizational structure. It focuses on the human side of change, ensuring individuals and teams can successfully adopt and use new approaches. — A blended AI definition.
Harvard Business School outlines these 5 Steps in the Change Management Process.
Prepare the Organization for Change
Craft a Vision and Plan for Change
Implement the Changes
Embed Changes Within Company Culture and Practices
Review Progress and Analyze Results
The Innovation Mindset and Change Management go hand in hand. Innovation is the willingness to open and remain adaptable. Change Management is the operationalization of new adaptations or the adoption process for the innovations.
Across the nonprofit and advocacy spectrum, organizations have struggled to integrate robust digital strategies and engagement into their operations fully. It is common for organizations to bring elements into their work but struggle with full adoption. AI is only further highlighting the struggles many organizations face in becoming truly modern organizations.
This new, chaotic era of AI presents an opportunity for organizations to reset and prepare for the future. Pivoting to an Innovation Mindset prepares an organization to identify its current gaps and blind spots in digital and technology. To become a truly modern organization, here are a few things organizations can do now to prepare themselves:
Review current processes for digital marketing, engagement, and fundraising. AI will augment these processes.
Understand the various organizational approaches to technology and data currently in use. AI will change these approaches, but you need your new foundation to pivot from.
Ask the hard questions of how much leadership and non-digital or tech staff understand about digital and tech.
Create an outline of how various roles interact or should interact with digital and tech.
The new AI era can be one of thriving in new ways for every organization. Leading with an Innovation Mindset is the right way to help you thrive as a modern organization.
