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.
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Topics
Assessments Cloud Services Cybersecurity Data Governance Digital Workspace Fractional CIO Leadership Managed Services Project Management System Selection
Dave and the Collabocasters discuss:
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.