During your initial sessions, you should see that outside counsel understands your goals and priorities. Since such things change from time to time, you should make sure that outside counsel stays current in where you are going and why. If it is more important not to go over budget than to win a case, tell counsel. If there is a personal aspect, e.g., the CEO is really committed on this one, again counsel needs to know. If the case rests on testimony of someone who may be demoted, passed over dismissed, your lawyer cannot give you decent advise without knowing such information.
Every firm has strengths, has a culture unique to it.
If your own firm's culture is one of long hours and hard work, you may well find yourself uncomfortable with a firm that keeps bankers' hours. If your sales tactics are aggressive and your marketing program is the heart of who you are as an institution, then a firm that merely advises, is never proactive, will be an uncomfortable fit. The more you know about the firm you are considering retaining, the better chance there is that you will retain one that feels right down the line as your counsel. You may have many lawyers who work on your matters, but you need one to whom you look for ultimate responsibility for matters dealing with your company. That attorney needs to be compatible with your particular needs.