A 10-minute leadership exercise

Know what your club still needs to decide before approving AI.

Twenty questions help the leadership team decide who owns AI decisions, which tools staff may use, what information stays out, who reviews the work and what the club should consider first.

20 questions10-minute exerciseComplimentary PDF

Five questions leadership should answer before the club goes further.

The checklist is designed for discussion, not to produce a certification score or replace legal, privacy, security or technical advice.

01

Who owns the decisions

Who leads the work, who approves new uses and where staff go when something is unclear.

02

Which tools staff may use

Which accounts and features are approved and how a new tool is considered.

03

What information stays out

What staff may enter, what must never be shared and when specialist advice is needed.

04

Who reviews the work

Who checks AI-assisted work, corrects mistakes and remains responsible for the final result.

05

What the club should try first

One useful task, allowed information, a person responsible and a clear comparison with today.

Bring it to one leadership conversation.

Work through the twenty questions with the leadership team. Mark each item as clear, partly clear or not yet decided. The pattern matters more than the total score.

  1. 01
    Answer honestly.

    Use the club’s current practices—not the policy leadership hopes to create later.

  2. 02
    Focus on what blocks the next decision.

    Start with unclear responsibilities, unapproved tools or sensitive information before asking staff to try more.

  3. 03
    Choose the next decision.

    The right result may be a policy review, a tool decision, staff training, one practical trial—or no expansion yet.

This is a leadership aid, not a certification.

The checklist supports operating decisions and productive conversations. It does not provide legal advice, cybersecurity certification, privacy assurance or a guarantee that a use case is compliant or risk-free.

Final policies, contracts, technical controls and regulated decisions require review by the club’s counsel and relevant specialists.

Private-club experience behind the checklist.

Evan founded House & Roster after more than 20 years in private-club leadership. The checklist reflects the realities of board oversight, lean teams, member trust and putting practical policy into day-to-day operations.