There's a bad old list of topics that we prefer not to discuss, for a variety of reasons. Personally, we're not all that wild about talking about and planning around death, lest talking about it bring it on too soon. Social taboos tell us not to discuss politics (ha!) or religion if we want to keep our relationships intact and positive. In business, the topic is succession - often pushed and pushed on behalf of more urgent issues - until it becomes the urgent issue. Lack of a succession plan is a risk to your business.
Why haven't we done it already?
Maybe you don't want to think about the day that the venture around which you have organized your life is no longer your central purpose. Maybe you know deep down that your team is not equipped to operate successfully without you, and you prefer to close your eyes and get on with your daily routine. Maybe you're worried about handing off the business in its current state, when there are problems that you want to resolve and tie with a bow first. After all, you know best, right?
What's your plan for the business?
Your plan creates the context for your continuity thinking. If you are in growth mode, the seats on the bus (structure) might need to change. Some people might need to develop, switch seats, and step up. Moreover, the team that took you to this stage might not have all of the resources you need to take you to the next level.
If you're planning to cash out, you might be assuming that the buyer will run it, and he or she might. OR you could increase the salability of the business if the depth of the team makes it turnkey for a prospective buyer. If you are selling to your employees, they need to know about how to execute your role. And succession/continuity is not only about you. There might be one or two key positions in your company that, were they disrupted, would negatively impact your results. And eat your personal life until you've resolved things.
Start with a Team Assessment
You have opinions about each of your employees, but let's organize them. Let's evaluate each person by 1) alignment with your company values and 2) productivity. Your A players are high scorers in both areas. Your B and B+ players have values alignment, but might need training to reach their full potential in productivity. C players may or may not be productive, but they may not see the world through the same lens that you need them to use. A highly functional individual can still be a risk to a business if they are toxic with the rest of the team, unresponsive to customers, etc.
Evaluate the Functions
There are a lot of ways for functions to be distributed and fulfilled. You might determine that some are better redistributed to even out the work flow. You might choose to outsource some of it. Someone might be wearing too many hats right now to properly manage what they already have on their plate. And an up-and-comer that you really want to retain in your company might be looking for a juicy opportunity to stretch and demonstrate what more they can do.
Develop and Implement Your Game Plan
This process doesn't happen overnight, and it isn't a once-and-done venture. Your team members might not be ready yet to change and grow - they may need training, or opportunities for small test projects in new areas. But you can't wait until you need your bench if you want your transition to move smoothly. Think of some redundancy in your business as a valuable measure against risk. And leverage the full strength of your team.
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