Obtain a valuation of your business
This is something that should be done just about every year regardless of whether you are close to a transition. The number doesn't have to be exact, but should be a good representation of what your business is worth.
The sooner you start preparing for a transition, the better. It gives you time to iron out any wrinkles and allows for you to think through all parts of the process. It will also allow for more time to get input from others concerned.
It's important to enlist people such as accountants, lawyers, and business consultants. Three or four people who understand the legal and financial aspects of a transition can provide insights and advice.
It's vital that all sides of an ownership transfer are on the same page regarding what is expected after a transition and what the process will entail. Having expectations and not communicating them early on can cause huge headaches later.
Prepare for the future
Some lives end much earlier than expected and not all marriages last. With that in mind, be prepared for anything the future may hold. As part of the transition process, it's a good idea to have an operating plan in case of a sudden death or if there's a messy divorce. Succession plans and pre-nuptial agreements are ways to deal with these issues.
Accept who's in charge
Many times, the hardest part for someone handing over the reins of a business is coming to grips with no longer being the head honcho. Good business owners understand that those taking over will do things differently and they must be given the freedom to do so. If you plan in advance and have confidence in the new boss, this should be less of a factor.