Dave wraps Season 7 of Reboot IT with Gretchen Steenstra, VP, Client Strategy at DelCor, and a discussion on how organizations can get unstuck and find success with their technology initiatives. Gretchen shares insights from her experience working across multiple organizations, exploring the balance between strategy and execution, the importance of adoption and change management, and how CEOs, CIOs, and business leaders each contribute to achieving success. 

Themes and Topics:

The Balance Between Strategy and Execution

• Organizations often lean too heavily toward either visionary strategy or detailed execution; success requires both.
• Strategy sets direction, but execution delivers results and the two must continuously inform each other.
• Periodic “zoom out” moments are essential to ensure execution is still aligned with strategic goals.

Alignment Across the Organization

• Technology is no longer separate. IT plans must align directly with organizational strategy.
• CIOs play a critical role in connecting leadership vision with operational reality.
• Alignment requires continuous communication between leadership, staff, and partners.

The Role of the CEO and Leadership

• CEOs should connect high-level vision to day-to-day operations without getting lost in the details. 
• Leadership can remove blockers, balance priorities, and champion initiatives effectively. 
• Leadership alignment helps teams understand how their work contributes to the organizational mission.

The CIO as a Translator and Negotiator

• CIOs act as intermediaries between business needs, technology teams, vendors, and security requirements.
• They must balance usability and security, often negotiating trade-offs between the two.
• CIOs also serve as escalation points when projects stall or teams hit roadblocks.

Adoption and Change Management

• The real work begins after launch. Long-term adoption determines success.
• Organizations often underinvest in post-launch behaviors and process changes.
• Preventing “backslide” requires ongoing reinforcement and attention to how people actually work.

Building Tech Literacy and Cross-Functional Collaboration

• Business leaders must develop a baseline understanding of how systems connect and interact.
• Cross-functional planning (marketing, finance, IT, membership) helps surface risks early.
• Mapping the full customer journey, from awareness to transaction to delivery, improves outcomes.