Rollercoaster: Navigating Access, Accountability, & Alignment with Your Executive

​Executive partnership is often described in ideal terms, but real conditions are messier. Leaders cancel 1:1 meetings, resist structure or consistent communication, and sometimes have never worked with a Chief of Staff before.

​This session centers on operating under real constraints: limited access, inconsistent rhythms, resistance to process, and the emotional strain that can build inside the partnership itself.

​Here are some real practitioner questions/challenges we will explore together:

• ​How do I work with a leader who’s never had a CoS? "Something heavy on my mind is training a CEO who’s never had a Chief of Staff before, especially figuring out how to get them into a regular operating rhythm instead of working independently."

• ​What do I do when I can’t get time with my leader? "I’ve been struggling to get consistent access to my leader—there are no standing 1:1s, and even ad hoc meetings often get canceled."

• ​How do I add structure without triggering resistance? "I’m trying to introduce some structure to help my principal achieve what they want, but they’re deeply afraid of anything that feels like bureaucracy."

• ​Is this executive partnership sustainable? "I’m starting to question the sustainability of the executive relationship itself, because it’s become mentally exhausting and confidentiality makes it hard to process openly."