Reboot IT - Nonprofit and Association Technology Conversations for All

Dave wraps Season 7 of Reboot IT with Gretchen Steenstra, VP, Client Strategy at DelCor, and a discussion on how organizations can get unstuck and find success with their technology initiatives. Gretchen shares insights from her experience working across multiple organizations, exploring the balance between strategy and execution, the importance of adoption and change management, and how CEOs, CIOs, and business leaders each contribute to achieving success. 

Themes and Topics:

The Balance Between Strategy and Execution

• Organizations often lean too heavily toward either visionary strategy or detailed execution; success requires both.
• Strategy sets direction, but execution delivers results and the two must continuously inform each other.
• Periodic “zoom out” moments are essential to ensure execution is still aligned with strategic goals.

Alignment Across the Organization

• Technology is no longer separate. IT plans must align directly with organizational strategy.
• CIOs play a critical role in connecting leadership vision with operational reality.
• Alignment requires continuous communication between leadership, staff, and partners.

The Role of the CEO and Leadership

• CEOs should connect high-level vision to day-to-day operations without getting lost in the details. 
• Leadership can remove blockers, balance priorities, and champion initiatives effectively. 
• Leadership alignment helps teams understand how their work contributes to the organizational mission.

The CIO as a Translator and Negotiator

• CIOs act as intermediaries between business needs, technology teams, vendors, and security requirements.
• They must balance usability and security, often negotiating trade-offs between the two.
• CIOs also serve as escalation points when projects stall or teams hit roadblocks.

Adoption and Change Management

• The real work begins after launch. Long-term adoption determines success.
• Organizations often underinvest in post-launch behaviors and process changes.
• Preventing “backslide” requires ongoing reinforcement and attention to how people actually work.

Building Tech Literacy and Cross-Functional Collaboration

• Business leaders must develop a baseline understanding of how systems connect and interact.
• Cross-functional planning (marketing, finance, IT, membership) helps surface risks early.
• Mapping the full customer journey, from awareness to transaction to delivery, improves outcomes.

In this episode of Reboot IT, host Dave Coriale sits down with Vinnu Deshetty, Product Manager at the American Chemical Society, Event ROI Coach, and longtime PCMA instructor, to discuss the evolving role of technology in events. They explore how AI is reshaping planning and analytics, how associations can better serve exhibitors and attendees, and why intentional innovation matters more than ever. Vinnu shares practical insights on avoiding “shiny tech syndrome,” aligning tech with business goals, and using data to drive meaningful outcomes. The conversation highlights the importance of purpose-driven decisions in delivering real value from events. 

Themes and Topics: 

The Current State of Event Technology 

• Events are operating “between four and five” in tech adoption, reflecting strong progress with room for improvement. 
• Associations are balancing traditional goals like attendance with new expectations for engagement and personalization. 
• AI is accelerating innovation while increasing complexity in tool selection. 

Purpose-Built Event Tech (Not One-Size-Fits-All) 

• Technology is now tailored to planners, attendees, and exhibitors instead of being one broad solution. 
• Vendors are solving specific pain points like workflows, engagement, and lead generation. 
• Comparing solutions is more complex because platforms are no longer “apples to apples.” 

AI’s Growing Impact on Event Operations 

• AI is reducing manual work, like building session schedules.  
• Systems can learn from past data such as session ratings and attendance trends.  
• Predictive analytics and real-time insights are becoming more common in decision-making.  

Data Strategy: Start with Intent 

• Organizations often collect too much data without a clear purpose. 
• Defining the questions upfront is critical to making data actionable. 
• Focusing on a few key goals prevents teams from trying to “boil the ocean.” 

Exhibitor Expectations and ROI Pressure 

• Exhibitors are asking sharper questions about ROI and measurable outcomes. 
• Associations compete with alternative marketing channels for sponsor dollars. 
• Integrated systems now provide better insights into lead generation and attendee behavior. 

Change Management and Innovation Mindset 

• Innovation requires intentional planning, not just adopting “shiny” tools. 
• Pilot programs and incremental changes help reduce risk. 
• Understanding stakeholder impact is essential before rolling out new technology. 

In this episode of Reboot IT, host Dave Coriale, president of DelCor, sits down with Joe Carr, Vice President of Information Technology at the American Academy of Ophthalmology, who shares how “light governance” can encourage experimentation while still protecting member data and intellectual property. They also discuss IT’s evolving role as an enabler rather than a gatekeeper, the importance of data hygiene and content management, and why fostering an entrepreneurial mindset matters more than chasing the perfect AI policy. The conversation offers guidance for IT leaders and non-technical staff alike on how to safely and usefully integrate AI into daily work.

Themes and Topics:

Light AI Governance vs. Overengineering

• Keeping AI governance policies short (3–5 pages) and written in plain language.
• Establishing “rules of the road” instead of rigid, draconian controls.
• Allowing experimentation while increasing oversight for sensitive data use.

IT’s Evolving Role: From Gatekeeper to Enabler

• IT provides secure platforms, guardrails, and integration—not every AI solution.
• Encouraging staff to explore AI independently within safe environments.
• “Making the sandbox” so staff can build their own solutions.

Multiple AI Tools, One Strategy

• Supporting several leading platforms (Copilot, Claude, OpenAI, Gemini) based on use cases.
• Focusing on how tools are used, not controlling which tool is used.
• Ensuring security, legal review, and IP protection across platforms.

Data Hygiene and Content Management as AI Foundations

• Recognizing that outdated or unmanaged content can undermine AI results.
• Shifting from document retention to true knowledge management.
• Designing content and websites so AI can surface accurate, relevant information.

Encouraging AI Curiosity Through Culture

• Using non-IT staff to demonstrate real-world AI use cases.
• Hosting lunch-and-learns, showcases, and Teams channels for sharing ideas.
• Executive support as a key driver of experimentation and adoption.

Entrepreneurial Thinking and Mission Alignment

• Embracing experimentation and being willing to fail safely.
• Using AI to rethink workflows, not just automate existing tasks.
• Tying AI initiatives back to organizational mission and business goals.

In this episode of Reboot IT, host Dave Coriale, president of DelCor, sits down with Kelly Henseler, Marketing and Communications Director at INCOSE, to discuss how associations are actually using AI, and where they’re struggling. Kelly shares what she’s seeing across the community, from rapid adoption by individual contributors to the lag in executive-level strategy and guardrails. 

The conversation explores member trust, disclosure, brand integrity, ROI-driven adoption, and how associations can avoid blending into the growing “sea of sameness.” This episode offers practical, grounded advice for marketing and communications professionals navigating AI from both the bottom up and the top down.

Themes and Topics:

AI Adoption in the Association Community

•  Individual contributors are adopting AI quickly, especially for content creation.
• According to ASAE’s State of Associations, 87.5% of associations are using AI for content creation.
• Executive teams often lag behind in setting strategy, policies, and guardrails.

Executive Strategy vs. Individual Use

• Organizations need to decide whether they’re encouraging adoption or putting guardrails in place.
• Conversations with leadership should start by understanding where the organization already is.
• Bringing concrete use cases and benchmarking data helps move executives forward.

Guardrails Beyond Data Privacy

• Guardrails aren’t just about PII and intellectual property. 
• AI tools can blur role boundaries, especially in design and brand ownership. 
• Access to tools like Canva AI should align with staff roles and responsibilities.

Trust, Transparency, and Disclosure

• Member trust can erode even when AI use is disclosed.
• Members want reassurance there are still humans behind the organization.
• Disclosure practices are evolving and require thoughtful, consistent approaches.

Avoiding the “Sea of Sameness”

• AI-generated content often looks and sounds the same across organizations.
• Prompt writing and human editing are critical differentiators.
• Associations must protect and reinforce their unique brand voice.

ROI, Upskilling, and Practical Wins

• ROI is the most effective entry point for AI conversations with leadership.
• AI can dramatically speed up content repurposing across channels.
• Upskilling staff and creating brand and editorial guidelines are essential first steps.

In this episode of Reboot IT, host Dave Coriale, President of DelCor, sits down with Katherine Bayless, Senior Director of Data and Analytics at the Consumer Technology Association, to discuss how associations are evolving in their use of data amid rapid advances in AI. Katherine shares candid insights on data governance, trust, hygiene, and why “fast crawling” with data is becoming more effective than rigid crawl-walk-run models. Together, they explore how AI is reshaping data-driven decision-making, shifting the focus from literacy to fluency, and why curiosity is now the most critical skill for association professionals. This conversation offers practical guidance for both staff leaders and executives navigating data maturity in an AI-driven future.

Themes and Topics:

Where Associations Really Are with Data

• Data maturity across the community averages around a “two-and-a-half.”
• Governance has value but can become a “weaponized stall tactic” if it blocks action.

Trust, Hygiene, and the Reality of Imperfect Data

• Trust in organizational data often skews low, even when data exists.
• “All data is wrong. Some data is useful,” depending on how it’s applied.

Rethinking Crawl, Walk, Run in an AI World

• Many organizations never truly reach the “run” stage.
• AI enables a faster, messier crawl that delivers value sooner and sparks curiosity.

 AI as a Catalyst for Better Questions

• AI shifts teams from deterministic questions to probabilistic “what if” thinking.
• Execution is now cheap, making experimentation and iteration easier than ever.

From Data Literacy to Data Fluency

• The goal is fluency—using data naturally as part of everyday work.
• Data teams must move from being interpreters to capability builders.

Culture, Curiosity, and Organizational Enablement

• Curiosity is now “the currency of the moment.”
• HR, IT, and leadership must partner to create space for experimentation, not just training.

In this special guest‑hosted episode of Reboot IT, KiKi L’Italien takes the reins and chats with Trevor Mitchell (President and CEO, IAVM) and Dave Coriale (President, DelCor Technology Solutions) to explore why associations struggle with tech decisions and how decision discipline can change everything. They dig into readiness, risk, AI pressure, and the myths leaders tell themselves when urgency takes over. Whether you're facing shiny objects, data distrust, or board confusion, this candid conversation shows how to make clearer, more confident choices that actually move your mission forward. 

Themes and Topics: 

The Tension Behind Tech Spend 

• Leaders face simultaneous pressure: money, risk, staffing capacity, and board expectations. 
• Urgency leads to chasing trends instead of linking choices to business objectives. 
• “Tech spend” triggers spiraling questions, often without shared understanding. 

Readiness as a Cultural Indicator 

• Readiness isn’t about money; it’s about the capacity to adopt change and adjust processes.  
• Associations overestimate their ability to implement and manage change.  
• Leaders who frame technology as strategic (not operational) increase alignment and reduce risk. 

Maturity Models and Shared Language 

• The 501(c) IT Maturity Model™ gives leaders a common vocabulary to make decisions. 
• Assessment creates clarity: “What’s real?” instead of “What we assume.” 
• The alignment portfolio becomes a roadmap, not a report card. 

AI Pressure and the Myth of “We Need This Now” 

• Boards and members introduce AI ideas before assessing readiness. 
• Smart leaders pause to ask whether AI aligns with strategic direction. 
• Buying prematurely creates more problems than it solves. 

The Most Common Decision Mistakes 

• Believing a new system will “solve everything.” 
• Relying on vocal minority feedback when making tech decisions. 
• Letting minutiae, or fear of user reaction, delay well‑planned initiatives. 

What Improves Decision Quality in the Next 90 Days 

• Create a repeatable decision-making framework for all major tech choices. 
• Move from data-driven to data-informed decisions. 
• Operationalize assessment findings inside everyday project management tools. 

In this episode of Reboot IT, host Dave Coriale, President of DelCor, sits down with Andrew Leggett, Director of Cybersecurity at DelCor, and Chris Ecker, Chief Technology Officer at DelCor, to unpack two critical cybersecurity topics every association and nonprofit should be thinking about right now: phishing‑resistant MFA and preparing your Microsoft 365 environment for Copilot. They discuss why passkeys truly improve the user experience, how oversharing in Microsoft 365 creates risk, and what steps organizations must take before deploying AI tools. This conversation is packed with practical guidance leaders can act on immediately.

Themes and Topics:

Why It’s Time to Level Up Your MFA

• Traditional MFA isn't enough anymore with modern phishing attacks. 
• FIDO2 passkeys make logging in easier for your staff, not harder.

Passkeys Are Way Simpler Than Passwords (Really!)

• A short PIN or FaceID is more secure than a long, complex password.
• Your device’s TPM chip keeps those credentials locked down safely.

How Modern Phishing Tricks Users, and What Stops It

• Attackers now steal MFA approvals and ride along on active sessions. 
• Phishing-resistant MFA shuts the door on those token-harvesting scams.

Before You Turn on Copilot, Fix How Your Association Shares Files

• Years of sharing files without guidelines or guardrails can create hidden risks.
• Copilot can surface any file users have access to, even old oversharing.

Why 365 Sharing Settings Matter More Than Ever

• Users must run their own OneDrive reports (admins can’t see it all).
• SharePoint tools help find where HR, finance, or executive docs may be exposed.

Leadership Buy‑In Makes or Breaks These Upgrades

• Change management matters, especially if the C‑suite wants exceptions. 
• Passkeys also offer a chance to simplify tools and retire extras like Duo.

In this episode of Reboot IT, host Dave Coriale, President of DelCor, sits down with David Stephenson, SVP of Technology at Entrepreneurs’ Organization, to unpack what true collaboration really means in associations and nonprofits. Together, they explore the difference between transactional vendor relationships and deep strategic partnerships, how to build psychological safety within project teams, and why honest dialogue is essential for successful outcomes. David also shares practical tactics for selecting partners, navigating conflict, and reducing organizational risk through collaborative practices.

Themes and Topics:

What Collaboration Really Is (and Isn’t)

• Collaboration isn’t about being nice or making sure “everyone’s at the table.” It’s about having the right mix of people with different perspectives.
• When everyone thinks the same and has the same motivations, you end up with polite agreement, not real progress.
• There’s a big difference between just enlarging a meeting and actually collaborating with intention.

Getting the Right Mix: Staff, Members, Vendors, and Partners

• Associations juggle vendors, partners, staff, and members, each with different levels of involvement and motivation.
• David distinguishes between people who are in the weeds with you (like design and development partners) and those who play a key but more behind‑the‑scenes role (like hosting providers).
• Upfront, he works to get everyone on the same page: What problem are we solving? What role do you play? What’s your motive (and recognizing that everyone has one, and that’s okay)?

Vendors vs. Partners: Building the Right Kind of Relationship

• In his head, David does see a spectrum: some are more transactional services (SaaS products, integration tools), while others are strategic partners who need to understand mission, business objectives, and strategy.
• He tries not to use the word vendor in conversation and instead works to make everyone feel like a partner, even if their role is more narrow.
• When negotiating, he looks for a fair outcome on both sides — if a partner walks away with “really thin margins,” you end up with constant “change order” moments and a strained dynamic from day one.

Honest Dialogue, Healthy Friction, and Psychological Safety

• David values partners who can say things like “That’s just not possible,” or “That doesn’t align with the strategy you described,” instead of always saying yes.
• He expects and welcomes friction and hard conversations around timelines, costs, and expectations. If there’s zero friction, something’s probably off.
• Psychological safety is key: people need to feel they can disagree, say “I don’t think this is working,” or ask tough questions without fearing for their job, contract, or relationship.

Doing the Work: Projects, Postmortems, and “Disagree but Commit”

• David admits he hasn’t “cracked the code” on postmortems, but he knows they only work if people feel safe enough to speak up during the project, not just after.
• When collaboration is done well, it may feel slow at the beginning, but it ultimately makes the work go faster and smoother than siloed, go-it-alone approaches.
• He likes setting expectations from the start: speak up when it’s “cheap to disagree,” and embrace the idea of “disagree, but commit” so the team can move forward with one voice.

Collaboration as Risk Reduction for the Future

• David sees collaboration as a way to de‑risk his future; the stronger his network and partnerships, the better prepared he is for what’s coming.
• Staying insular and only looking inside your own team or organization raises your risk, especially in fast-changing areas like technology and AI.
• By collaborating widely and intentionally, associati

In this episode of Reboot IT, host Dave Coriale sits down with David Cade, CEO of the American Health Law Association, to explore how AHLA moved from talking about AI to actually using it. David shares how the organization developed policies, balanced innovation with risk, and empowered employees to experiment responsibly. He also breaks down the “triangle” of business units, IT, and leadership, and why leaders can’t afford to guide their organizations from a place of fear.

Themes and Topics:

Moving From Fear to Experimentation

• David emphasizes that leaders “can’t lead from a position of fear” when it comes to AI. 
• Fear of getting it wrong is holding some organizations in the 0–3 adoption range, which risks their relevance to members. 
• Instead, leaders should test, learn, monitor impact, and be willing to expand or abandon initiatives based on results.

The AI Governance Triangle: Business Units, IT, and Leadership

• AI adoption at AHLA was driven roughly 70% by business units and 30% by IT. 
• Dave and David describe a triangle model: 
• Business units: define needs and use cases.
• IT: handles security, integration, licensing, and scalability.
• Leadership/CEO: sets culture, protects IP, and champions smart change.
• When one side dominates (IT control, business “run amok,” or absent leadership), AI efforts become lopsided and less effective.

Real AI Use Cases at AHLA

• AHLA uses AI to generate a weekly podcast from existing content—no human host needed—creating new value from existing assets. 
• AI tools support marketing content creation, improving speed and clarity without eliminating positions. 
• AHLA explored using AI to unlock a decades‑deep archive for members, learning where cost, scale, and accuracy become limiting factors for smaller associations.

Staff Enablement, Training, and Culture

• AHLA discovered both extremes: some staff moving too fast with unvetted tools, others refusing to use AI at all. 
• They created a tool inventory, embraced specific platforms, and pulled hesitant staff in with the clear message: these tools are part of doing your job well. 
• Internal lunch‑and‑learns and “each one teach one” sessions help reduce fear, demystify tools, and showcase how AI can accelerate everyday work.

Legal, Ethical, and Accuracy Considerations

• In the legal community, bars and courts are requiring disclosure when AI is used in client work or court filings. 
• David draws a line between tools like spellcheck (enhancing what you wrote) and having AI generate entire arguments or articles that aren't truly “yours.” 
• He stresses that AI outputs must be reviewed, adopted, and owned by humans, especially given risks like hallucinated cases, outdated standards, and embedded bias.

Where Associations Are on the AI Adoption Curve

• David sees most associations in the 6–8 range of AI adoption, with a few early lightning rods in the 9–10 space. 
• A minority remain in 0–3, often due to fear or misunderstanding, which he believes will make them less relevant to members over time. 
• Members are already using AI themselves—associations that don’t keep up with how their communities work risk falling behind their own audiences.

In this episode of Reboot IT, host Dave Coriale sits down with Colleen Gallagher, President & CEO of Onward and Upward, to talk about how associations are using AI as more than just a tool—they’re treating it like a thought partner. Colleen shares real-world examples of AI helping with PR strategy, repurposing research, and freeing up time for small-staff associations. They also dig into why authenticity matters, how to set guardrails, and what it takes to make AI work without losing your human touch.

Themes and Topics:

AI in PR, Communications, and Research

• A national IT and workforce association used a custom GPT trained on PR strategy to brainstorm ideas and create strategic plans.
• AI helped identify targeted journalists and outlets for a research report, saving days of manual research and landing coverage that previously seemed impossible.
• AI transformed 100-page technical reports into member-friendly summaries, increasing engagement without replacing original research.

Small Associations Leveraging AI

• A small-staff association implemented an AI policy early, focusing on transparency and data protection.
• Weekly meetings encouraged staff to share AI use cases, leading to automation of job aids, survey analysis, and content repurposing.

Efficiency vs. Authenticity

• AI accelerates workflows, but human editing and fact-checking remain essential, especially in technical fields.
• Associations intentionally keep a “human roughness” in writing to avoid robotic tone and maintain authenticity.

Disclosure and Transparency

• Best practice: note when AI supports content creation (e.g., “This article was assisted by AI and edited by a human”).
• Transparency builds trust, even if disclosure norms evolve over time.

Infrastructure and Security

• Before implementing tools like Copilot, associations must secure their infrastructure and protect intellectual property.
• Data fencing and cybersecurity measures prevent unintended exposure of sensitive information.

AI as Amplification, Not Replacement

• AI should enhance human creativity and capacity, not erase it.
• The real win is amplification—doing more with the same resources while maintaining trust and authenticity.