In this episode of Reboot IT, host Dave Coriale, President of DelCor, sits down with fellow podcasters KiKi L’Italien (former EVP Marketing & Community), Joanna Pineda (CEO, Matrix Group), and Dave Will (Co-founder, PropFuel) to discuss why technology implementations often take longer than expected. From strategic misalignment and governance bottlenecks to emotional resistance and resource constraints, the group explores the underlying causes of slow change. 

Themes and Topics:

The Emotional Impact of Letting Go

• KiKi shares her experience stepping away from Association Chat after 16 years, describing a mix of grief and relief.
• Joanna reflects on taking a break from LinkedIn during a personal loss and the surprising sense of freedom it brought.
• The group discusses how identity and purpose are often tied to long-term projects, making change psychologically difficult.

Strategic Planning and Prioritization Gaps

• Associations often struggle to define clear strategic goals, making it hard to prioritize technology decisions.
• Lack of alignment on KPIs leads to confusion and stalled initiatives.
• Dave Will emphasizes that knowing what’s important makes change easier and faster.

Governance and Decision-Making Bottlenecks

• Too many stakeholders involved in decisions leads to paralysis and delays.
• Joanna suggests sunsetting committees when strategic plans change to realign focus and authority.
• Leadership must clarify who owns decisions and avoid retroactive interference.

Risk Aversion and Culture of Caution

• Associations operate in a highly visible environment, making them more cautious about failure.
• Fear of public scrutiny and investing too early in emerging tech (like AI) slows down innovation.
• Dave Will notes that experimentation is often discouraged, even when it could lead to valuable breakthroughs.

Leadership and Ownership 

• Leadership must define clear goals and empower teams to make decisions without fear of being second-guessed.
• Joanna highlights the importance of psychological safety and trust in project ownership.
• Late-stage leadership involvement often derails progress and undermines team autonomy.

Resource Constraints and Internal Silos

• Many associations lack internal tech expertise or project management capacity, leading to delays.
• Misunderstanding the need for internal PMs results in stalled implementations.
• Silos between departments (e.g., marketing, membership, IT) hinder collaboration and alignment.