Category: Leadership

digitalNow 2023 Keynote Speakers to Focus on AI and Innovation for Associations

digitalNow 2023 is just around the corner, and it’s time to introduce the lineup of super-star keynotes at this year’s conference, taking place Nov. 2-4 in Aurora, Colorado.  digitalNow, Sidecar’s annual conference for association executives, brings together forward-thinking leaders to learn about cutting-edge technology, share ideas, network, hear from industry experts, and participate in in-depth […]

Private AI Bootcamp


4 Ways to Keep Your Association Relevant and Thriving 

Associations have long been a powerful force for bringing together like-minded individuals to share ideas, best practices, and knowledge. However, in today's rapidly changing world, a pressing question arises: how can associations not only remain relevant but truly thrive?  To address this challenge, associations must be bold. They need to have a clear vision, take […]


3 Takeaways From Our Generative AI for Associations Webinar

If the last few months have taught us anything, the future of AI is developing quickly and its implication on associations cannot be understated. From new tools and applications staff can use to streamline work, to chatbots and content summarizers your members can use to interact with your organization.   And while your association doesn't need […]

Overcoming Leadership Avoidance: 5 Strategies to Embrace Responsibility

Leadership avoidance is a phenomenon in which individuals, despite having the potential to lead or the opportunity to take charge, intentionally shy away from leadership roles or responsibilities. This behavior can be driven by fear, self-doubt, or a lack of confidence in their abilities, among other factors. When leadership is avoided, it can have a […]

Volunteer or Staff Position? Determining the Right Fit for Your Organization

The good news: your Association is growing by leaps and bounds, and volunteers are flocking to your door. The bad news? These volunteers, although enthusiastic and consistent, may not be what your association needs. But how do you know when it’s time to convert the work of many volunteers into one paid staff position?  The […]

Inspiring Associations to Embrace the Possibilities of Generative AI

Despite the significant benefits of generative AI, many association leaders are telling me that they are hesitant to embrace this cutting-edge technology due to various factors – including a history of having challenges using new tech. When airplanes first took flight, some looked up in awe and were inspired to think big. Others looked away […]

Sidecar Water Cooler: Workplace Trends to Know for 2023

Have you ever heard people talking about "the future of work," particularly in the wake of the pandemic?  Well, guess what? The future has arrived, and associations need to be aware of the shifts and trends that are shaping the workplace in 2023 and for the coming years.  Welcome to the Sidecar Water Cooler Show, […]

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