Association AI Leadership: The Four Stages of Readiness
A Conversation with Rich Vallaster and Mary Connor
Webinar Recap | May 2025 | Featuring Rich Vallaster (Personify) and Mary Connor (SMG)
Rich Vallaster: Welcome! Today, we’re digging into how associations can better prepare for AI — not in some vague, futuristic sense, but practically, starting now. I'm here with the incredible Mary Connor, President of SMG Association Consulting and VP of Client Relations at Stringfellow Management Group. And we’ve got a lot to unpack!
Mary Connor: Thanks, Rich. I'm excited because AI isn’t just for tech companies. It’s here for associations too, and the real question is: how do we lead through this shift, not just react to it?
Why AI Matters Now for Associations
Mary: Let’s be honest — this train has left the station. Whether you're ready or not, AI is being used by your staff and members. In fact, in our internal survey at SMG, 73% of our staff said they are already using generative AI — ChatGPT, Claude, Copilot, Gemini — mostly for content generation but for many other applications. And that’s just the start.
Rich: That’s huge. Associations are notoriously time-strapped. We hear it all the time: “Do more with less.” AI is an actual, tangible way to do that — not theoretical. It’s already automating email writing, member support, content summaries, even travel plans. (Mary used it to plan her whole Yellowstone vacation, which I’m still jealous of.)
Mary: What excites me most is member value. We sit on mountains of industry knowledge, but we’re not delivering it the way our members need. AI can enable 24/7 access, personalization, and real-time support. That’s not just cool — it’s strategic.
The Four Stages of AI Readiness
Rich: To make this actionable, we shared Grammarly’s AI adoption model, adapted for associations. It breaks down into four stages:
1. Awareness
Mary: You’re here if you’re reading about AI, sharing articles, maybe trying ChatGPT personally. There’s curiosity — but no formal strategy yet. This is where most folks start, and that’s OK.
2. Experimentation
Rich: Many associations are here now. You’re testing tools like Claude or ChatGPT for newsletters or session descriptions. It’s ad hoc, often one team or individual trying things out. It’s low-risk, high-learning.
Mary: This is also where you start noticing real value: automating meeting notes, summarizing survey results, writing social posts. Once you’ve done that a few times, the lightbulb goes off.
3. Optimization
Mary: Now, AI gets embedded in workflows. You’re using prompts consistently. Teams are aligning on best practices. You’ve got internal training and maybe even started building custom GPTs or automations with Zapier or other tools.
Rich: We saw that only about 12% of attendees in our poll are here — but they’re laying the foundation for huge gains.
4. Transformation
Mary: This is the strategic level. AI isn’t a tool here — it’s a partner in decision-making. It’s helping you predict trends, develop new services, and innovate. Few are here yet, but it’s coming fast.
Guardrails, Policies & Culture
Rich: Let’s talk about something most orgs don’t have: AI policies. If your team is using AI and you don’t have a policy, that’s a risk.
Mary: Absolutely. You need to define what’s okay: what counts as proprietary? What’s off-limits? What is PII? Spell it out. And then go a step further — talk to your insurance broker. AI touches liability and cybersecurity.
Rich: Culture plays a role too. Your team needs to feel safe asking questions. And leaders need to address the elephant in the room: job fears. The truth is, AI won’t replace people — but people using AI might.
Mary: We’re already seeing companies like Duolingo and Shopify use AI-first approaches. That’s not a scare tactic — it’s a wake-up call. Upskilling your team is non-negotiable.
Ethics, Equity, and Upskilling
Mary: We also need to be thoughtful about ethical use. What biases are built into the tools? How transparent are our processes? And are we giving everyone on staff — not just leadership — access and training? That’s why I recommend programs like Sidecar’s Association AI Certificate.
Rich: It’s built for our world, not the tech sector. And there’s so much free training too — YouTube, LinkedIn Learning, webinars like this.
What the Audience Told Us
During the webinar, we polled attendees:
- 16% were still in the Awareness phase
- 69% said they were actively Experimenting
- 12% in Optimization
- A few are beginning to Standardize
- Just 1 brave soul marked “Transforming”
What Should You Do Next?
- Create or update your AI policy – Especially around data, ethics, and IP.
- Audit your usage – Ask your team who’s using AI and how.
- Invest in training – From entry-level prompts to strategic forecasting. (Training Resources List)
- Map your workflows – Identify where AI could save time now.
- Start small, but think big – Don’t wait for perfection.
Final Thoughts: Lead the Way
Rich: At the end of the day, this isn’t about tools. It’s about leadership. Your members expect fast, personalized, seamless experiences. AI is how you deliver that.
Mary: We’re here to guide you forward. Associations are in a unique position to model ethical, human-centered AI adoption. But it starts with being brave enough to try — and smart enough to plan.
Rich: Stay tuned — we’ll be back with more sessions, more demos, and even more real-life examples. In the meantime, let’s all keep climbing the ladder of readiness — together.