Short case of leadership

I have a friend who has a position of authority in an organization.  My friend, I'll call him Jesse, is responsible for development and training.  He oversees the leadership team that develops training activities, collects data on participation and engagement, and executes continuing development.

This role may sound familiar to you--perhaps one that you fill.  The organization depends not only on the leader for direction, but also on the performance and participation of members.

I watched Jesse as he worked with different members of his team.  He was decisive, thoughtful, and kind.  However, over time, he became frustrated with members of his leadership team, and then became prescriptive in his direction, developing a reputation as somewhat of a micromanager.

Meanwhile, Jesse's leadership team members were developing patterns of behavior in response to his demands.  Where they had once approached projects with energy, they began approaching new projects with hesitancy.  When developing training events, they would frequently postpone not only important decisions, but also trivial decisions about elements of the presentations and activities.  Where plans had been innovative and bold, they became plain as the team members waited to act until they received Jesse's specific direction.  When working with outside vendors, negotiations became protracted as team members went back and forth, seeking Jesse's approval for every element of a vendor's agreement.

Jesse felt that each progressive project and training session became less effective, felt less enthusiastic about participating himself, and less confident in his leadership team.  He felt like he was losing steam.  What had gone wrong?

Jesse had effectively become a de-energizer in his organization.  After interactions with him, and in anticipating interactions with him, others felt less empowered to do their jobs, less motivated to invest creative thinking, and less important to the success of the organization.

How would you respond if Jesse asked you for some suggestions?