A key factor in planning for your retirement (what I call your transition) is being confident that the people who will succeed you have the 'timber' (aka the ability, passion, knowledge etc.) to lead your company into the future.
Choosing and developing them is one of your challenges. It's an obligation you have to your partners, shareholders and other staff members.
If you fail, all the rest of your work in building a sustainable organization will have been wasted. You will have failed in leaving your legacy.
Many leaders and owners pick their potential successors based on erroneous assumptions about 'What it takes' to be a leader. They incorrectly assume that loyalty, longevity, good technical competence, being a family member, etc. are the best criteria to use.
That's what it takes to be a good 'Number two' - a good 'doer.' That MAY qualify then to be good managers - this is not what it takes to be a leader. There are relativly few people who can lead.
What's the difference between a good manager and a good leader? A recent article in the Wall Street Journal is a good reference.
You may have lots of good managers in your company. And you'll be lucky - or brilliant - if you have surrounded youself with several people who have leadership potential - the qualifications to lead the company after you step aside.
THE BOTTOM LINE; take a long, hard look at the people around you.
Identify those who have leadership potential and focus on grooming them. If you don't have what you need, start searching - outside your company NOW. And stop wasting your time trying to make your good managers into mediocre leaders!