Posts Tagged ‘Sherry Connects’
Interim Isn’t a Gap. It’s a Gift.
Why the organizations that use interim talent strategically outperform the ones that don’t. When a key leader leaves an organization, the first instinct is usually to fill the seat as fast as possible. That urgency is understandable. A vacant role feels like a liability. Boards get nervous. Staff wonder what it means. The pressure to “solve” the problem by…
Read MoreYour Retreat Produced a Beautiful Document. Now What?
The difference between a facilitation that feels productive and one that actually is. I want to tell you about a pattern I see at least a dozen times a year. An organization invests two days and significant resources into an off-site retreat. A skilled facilitator leads the group through a well-designed agenda. Energy is high. The…
Read MoreThe Upskilling Gap: Why Some People Jump into AI and Others Freeze
Upskilling has always mattered. But right now, with AI evolving faster than most organizations can update job descriptions, a clear AI upskilling plan has become a survival skill, not a bonus. Here’s the part leaders rarely say out loud: AI is exposing the gap between people who learn by exploring and people who learn by being told what to do. And that…
Read MoreDigital Culture Isn’t Optional—It’s Your Competitive Advantage
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…
Read MoreThe Myth of Member Loyalty—and What Actually Drives Retention in 2026
Spoiler: It’s not your dues discount or annual meeting Let’s get real about something we don’t talk about enough in the association space: Member loyalty isn’t what it used to be. And pretending it is? That’s costing you relevance—and revenue. For decades, associations have relied on an assumption: “If we offer enough value, members will stay.” But here’s the truth: Value isn’t the issue. The real issue is that value has been redefined. …
Read MoreDigital Dexterity: The Skill Your Association Can’t Ignore
You invested in the platform. You launched the tools. You checked the “digital transformation” box. But something’s still off. Systems don’t talk to each other. Staff rely on workarounds. Member experiences feel… clunky. Sound familiar? The problem might not be your tech stack. It might be your team’s digital dexterity. What Is Digital Dexterity? Digital dexterity isn’t about coding or mastering AI. It’s your organization’s ability to adapt, adopt, and apply digital tools—across…
Read MoreStop Chasing Trends. Start Solving Problems.
There’s a new tool. A new platform. A new webinar on “emerging tech” almost every week. The noise is loud. And if you’re like most association leaders, you’ve probably asked: Here’s the truth no one wants to say out loud: Chasing digital trends is easy. Solving real member problems is harder. But that’s where the real value is—and that’s where your strategy needs to live. The Cost of Chasing Digital Trends It’s tempting to…
Read MoreAI Won’t Replace You. But It Will Replace What You Ignore.
It’s tempting to treat AI like a buzzword. Something big… but also vague. Fascinating… but not quite urgent. Maybe useful—eventually. But AI adoption in associations is already happening. While many organizations are still forming task forces or “monitoring the landscape,” your members are already living in an AI-shaped world. And some of your competitors? They’ve stopped waiting and started building. AI won’t replace…
Read MoreAI is Reshaping Associations—Are You Ready to Reskill Your Workforce?
Artificial intelligence is no longer optional. It’s not just a tool—it’s the force reshaping how we operate, deliver value, and remain relevant. For associations, the real risk isn’t that AI will eliminate jobs. It’s that your team won’t be prepared for the new ones unless you begin reskilling your workforce to meet the demands of a rapidly changing digital era. To thrive in the era of Association…
Read MoreWhy a Technology Assessment Is the First Step to Your Future-Ready Roadmap
For many associations, it feels like a never-ending checklist: new AMS? Check. Website redesign? Check. Virtual conference platform? Check. But here’s the uncomfortable truth: having tools is not the same as having a strategy. The first real step toward clarity is a future ready technology assessment — a process that uncovers what’s working, what’s outdated,…
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