Like a visit to the dentist, litigation is often necessary but seldom fun. It takes time, interferes with your business, disrupts your life, and can exact a substantial monetary and emotional toll. So if you have to go down the litigation road, choosing your travel guide is one of the most important decisions you will make. In a very real sense, your legal counsel will lead you on this journey. Therefore, you need someone who is not only skilled but also compatible with you and right for the case.

Despite the stereotypes, attorneys are as diverse as any group of people can be, each with a different approach and level of knowledge and experience. Most of us, however, do share one characteristic: we strive zealously to represent the interests of our clients.

Within that context, how can you determine which attorney is best for you? Although there are no guarantees (and if a lawyer tells you differently, immediately start looking for someone else), here are 10 questions you can ask to determine if an attorney is right for your matter.

Question 1: Why Should I Retain You or Your Firm?

Attorneys are not one-size-fits-all. You need a lawyer with whom you are comfortable, who also has the knowledge and skills necessary to represent you well and can differentiate himself or herself from other lawyers. To use a cliché, you need someone who can add value. After all, adding value for our clients is what lawyering is all about.

Although attorneys approach this challenge in many ways, generally it all comes down to one thing: helping you solve your problem in the most efficient and cost-effective way possible. This is especially true in litigation, where the emotional cost often exceeds the financial one. Thus, it is vitally important to discuss up front your attorney's perspective and strategy. How will he or she proceed in order to accomplish your goals? Of course, that presupposes that you have already established those goals, which brings us to the next question.

Question 2: How Strong Is My Case?

This is perhaps the most obvious and most important question to ask. It's also what you want to know more than anything else, with the possible exception of Question 4. This is your opportunity to learn exactly what your lawyer believes about your case, which can be quite revealing in other ways. For example, if a lawyer tells you that you have a "slam dunk," pick up your things and leave. There are no slam dunks! Why? Because there is no certainty whatsoever when a case goes before a judge, a jury, an arbitrator or any other third party.

Question 3: What Are the Weaknesses?

Here is the flip side to Question 2, and it is just as important. What you want from your attorney is an honest assessment of the strengths and weaknesses of your position—not only why you are likely to prevail but also why you might lose. As human beings, we tend to view everything through a self-serving filter. Your lawyer, however, should strive to see beyond that filter in order to accurately evaluate your case.

Question 4: How Much Will It Cost?

When you embark on litigation, it is important to decide whether it makes economic sense to fight to the end or settle as quickly as possible. In other words, if you have a $50,000 dispute, you need to know if it's going to cost you $5,000, $15,000 or $40,000 to resolve it.

In a litigated matter, your lawyers might not be able to provide much certainty with respect to cost. But they can share their billing rates and estimate how much time they expect to devote to the case. This information will help you make an informed decision about how to proceed. If you are considering a lawyer who is not willing to give you an estimate or budget, find someone else who will.

Question 5: Will You Consider Alternative-Fee Arrangements?

Although lawyers generally charge by the hour and that traditional approach works for many clients, there are other methods of billing. For example, many attorneys are willing to handle certain matters on a blended-rate, flat-fee or contingent basis. Others might be willing to discuss an arrangement based on the result achieved.

Question 6: How Much Relevant Experience Does Your Lawyer Have?

You need to feel confident that your lawyer has the skills and knowledge to effectively represent you in the matter at hand. Likewise, your lawyer should want you to feel comfortable with his or her ability to represent you effectively. Therefore, don't be shy about asking your attorney how much experience he or she has related to your particular dispute.

Question 7: Who Will Handle My Matter?

Let's say you've met with a lawyer, were impressed with her capabilities and retained her to represent you. Will it really be that lawyer who acts on your behalf, or will your matter be relegated to a less experienced associate or maybe even a paralegal? You can't know for sure unless you ask. Of course, when you select an attorney from a firm like Much Shelist, you are really hiring a team of lawyers at different billing rates, which may be advantageous on multiple levels. Research, for example, can often be done better and less expensively by associates or younger partners. If, however, you want a particular lawyer to handle everything, you should make that clear up front.

Question 8: Where Is the Engagement Letter?

Once you have decided to retain a lawyer, make sure there is an engagement letter signed by both you and the attorney. An engagement letter protects the client as much as, if not more than, the attorney. It should set forth the fee structure, the scope of the engagement, any requirement for an up-front retainer (including the amount), how out-of-pocket costs will be handled, what other charges are involved and so on. If there is anything in the letter that you do not understand, make sure the attorney explains it to you. Most importantly, your lawyer should never dismiss the engagement letter as "just boilerplate." If he or she does, then you should seriously consider getting another lawyer. Ultimately, the engagement letter constitutes a contract between you and your attorney and is invaluable in establishing the parameters of the relationship.

Question 9: What Charges Should I Expect to See on My Bill?

This may seem like an obvious question, but in many respects, it is not. Generally, if you phone your attorney, you are going to be billed for that call. If your attorney has a substantive discussion about your matter with someone else in his or her office, you will usually be billed for that conference. If an associate does research on your file, you will likely be billed for that work. If a paralegal reviews documents or organizes a file, you will probably be billed for his or her time. There is nothing particularly surprising about these examples, but what about charges for electronic research like Westlaw? How about faxes or photocopies? All of these billing issues should be addressed in the engagement letter. And if it includes something you do not like, discuss it with your attorney before you sign on the dotted line.

Question 10: What Is the Likely Outcome?

Although your attorney will not be able to answer this final question with certainty—especially during the initial stages of the matter—it is important to discuss the issue right away. As I've said before, there are no guarantees, but experienced counsel should be able to give you an idea of what might take place down the road. Ultimately, there is no benefit to you or your relationship with your lawyer to have unrealistic expectations.

This list of questions is by no means exhaustive, and that's a good thing. You should never hesitate to ask your lawyer anything, no matter how big or small. We are here to help, so ask away!