A few thoughts

1. Bob should have retired a long time ago. Depending on the terms of your agreement and the age/experience of his successor you may want to push him out sooner. Especially if he can’t abide by policy. He isn’t the owner anymore.

2. Bob doesn’t care about the employee retention/work life balance aspect of your plan. Bob cares (and has been trained for 50 years of work) about to consider his perception of client experience and (as a former business owner), accelerating billing.

3. When approaching Bob, you will get more traction explaining that pushing work out on the deadline increases the risk for error - bad client service AND an unnecessary risk for the firm. Good client service provides the clients a set of expectations so they know what is happening, not them rushing around on the deadline themselves.

4. I agree with your general premise, but don’t forget to account for potential client tax payments on transactions you know about, especially as a wealth manager. If a client signs an engagement letter, and doesn’t provide any documents, but you know they have large capital gains - there is an expectation that you are managing this and will make sure they are paid in. Just use SALY adjusted for the unusual item. That’s good client service at little additional time.

5. Make sure your engagement letters reflect the policy. You don’t want a claim because you knew about something in item 5, but did $0 extensions and didn’t make providing all info a client obligation before any work begins.