We tax lawyers like to talk about all the creative ways our clients can transfer wealth and save millions in taxes.  For transfers of operating businesses (including a real estate portfolio), there are a number of often overlooked business issues. 

For example, does the next generation have the management capability to run the business?  How will new lines of authority be established?  (You can’t have three CEO’s).  Does the next generation have the desire to manage the business?  What about all the interpersonal dynamics—sibling rivalry, spouses, etc.—that can affect business operations after the founder is gone? 

There are also external business issues.  How will key customers react if the founder of the business is no longer around?  What will the reaction of key employees be?  Has the next generation had a chance to establish independent relationships with key employees, or are those personal to the founder?  What will the impact of successor management’s relationships with banks and key vendors...

 Wall Street Journal, Family Businesses Catch a Big Break, by Anne Tergesen: