I see clients -- both individuals and companies -- trying to decide if/when to retain their own counsel.  Often, the chief consideration is cost. However, I find, too, that some clients simply are unaware when they are in a dispute (or potential dispute) that requires counsel. 

Here are some considerations: 

1) Does any other party have a lawyer in the current dispute/issue?; 

2) Has any one asked you to review legal douments that you are unsure you understand completely?;

3) Has any one asked you to sign a release?; and

4) Is there a possibility that you could either be sued or pursue a claim regarding the current dispute/issue?

If the answer to any of the foregoing questions is "Yes", then I would recommend you consult with counsel.  Even if not free of charge, the initial consultation will still likely be inexpensive relative to cost of the overall dispute. 

I have seen homeowners, in particular, get themselves, into jams when thinking a builder/contractor that is represented by counsel is pursuing their interests.  If they have a lawyer, you almost certainly at least need to talk to a lawyer. 

Also, I have seen defendants in negligence claims create sticky situations in discovery later (and inadvertently create leverage for the claimaint) by failing to hire counsel early to provide advice in coordinating a claim investigation.  Again, if you have a good idea a lawsuit is coming it is better to prepare accordingly.  To do otherwise may save pennies now but cost many more dollars later.  

Good lawyers are expensive.  Failing to hire a good lawyer when you need one is really expensive.