20 Questions You Should Ask Current and Prospective Clients

by William J. Flannery, Jr.

You've been representing your client for a time. He is aware of your expertise. He has seen your firm's brochures, attended the firm's seminar last month and received the firm's newsletter. You think there is potential for more business. You've invited the CEO or general counsel to lunch, presumably to develop more business by trying to cross-sell the rest of your firm.

You may have invited a partner from your firm to go along. The partner's role may be that of a potential new practice area opportunist or as a sympathizer if the "cross-selling" lunch craters. Now the real challenge begins: What are you going to say at lunch?

Here's where rainmaking often turns into drought. Here, lawyers inexperienced in marketing often make the crucial mistake of assuming that they're the ones who are supposed to do all the talking. For lack of anything better to do, they start their sales pitch. Or they try to convince clients that the firm has a number of good lawyers who can help them. Or more likely, they start with a small talk as a way of building rapport. The first 45 minutes of the lunch focuses on the U.S. Open, the Dallas Cowboys or subject matter that borders on the trivial. But clients don't want a sales pitch, and they don't need to be told about your lawyering skills. They probably assume you're good at what you do, or you wouldn't have gotten this far. And they certainly don't want small talk. They're as busy as you are.

What they want is to feel comfortable with you as a professional, and to see where you and your firm might fit in with their business objectives. To make them comfortable, get them to talk about themselves or their business objectives. Your marketing efforts should focus on listening to their responses. The more they talk, the more you'll learn. And the more you learn, the more natural the marketing process becomes. In client development, information is always power - because it means knowing what the client needs.

If marketing is what lawyers do to develop business, then knowing more about the client's business is what marketing is all about. Knowing what to ask and how to ask is an art and a science. As a basic introduction, I have selected 20 questions broad enough to apply to most types of clients - both current and prospective - yet specific enough to elicit the concrete information essential for the selling and delivery of legal services. Many of our questions seem to target new clients. But it is surprising how much lawyers don't know about the clients they've been serving for years. If those lawyers took the time to learn, they'd find there's substantial business going elsewhere which, with a little effort, could be kept in the family.

Asking clients about themselves will uncover opportunities that require not just your expertise, but your partners' as well. Such cross-selling is the highest form of marketing. It means long-term client relationships and long-term revenue development - not just one job today that won't pay any bills tomorrow.

Long-term is the key. When clients hear you asking about their plans three to five years hence, they begin to think of you as a 30-year friend. Don't worry about asking new clients direct questions. This is information they tell their brokers, their PR staffs, their friends. And they certainly want to tell you, because they want to trust their lawyers. They have a business need to share with their lawyers information they don't necessarily need to tell their insurance brokers or financial representatives.
Likewise, old clients will appreciate your interest. They may even realize that such expert listening is the crux, not only of selling, but of quality legal service. This article assumes that these meetings are with the client's decision-makers, including business executives, general counsel or the legal department.

First, here are a few basic rules:

You cannot sell legal services to unwilling buyers. You should not try to close the business at the first available lull in the conversation. Avoid the "sales pitch," as the client may not be in the "catching" mode.

Never put clients on the defensive. Don't use the same style of questioning you'd use in a deposition or while cross-examining a hostile witness. This is win-win. The better they feel about talking now, the better they'll feel about hiring you later. Let them be the ones to bring up sensitive or painful matters. Try to avoid the "why" questions, which are likely to carry a judgmental tone. It's empathy and rapport that you're after.

Make all your questions as open-ended as possible. A "yes" or "no" answer will seldom do you any good. Phrase questions in such a way as to give clients the opportunity to supply as much information as possible.

Don't feel you need to respond to everything clients tell you. Selling is interactive, and you want to respond intelligently to what you, the seller, are hearing. But much of what clients say should be filed away, for future use at a more appropriate moment. Silence can help build informational savings accounts.

Do your preliminary research. Clients want to tell you about themselves, but they'll also appreciate the respect you show when you take the trouble to learn as much about them as you can. Use public data bases, newspaper articles and the client's own publications as sources. Give those stockbrokers that call you daily some homework; and ask them to do research.

The selling process follows its own course and cannot be rigidly encapsulated. Ideally, you may want to start by asking general questions about the client's business: what they manufacture, sell and to whom. There's nothing they'd rather talk about. Then explore how they've structured their organizations. Finally, zero in on their legal needs: how they've met those needs in the past and intend to do so in the future.

Here are the questions:

1. What do you want your organization to look like in one year, two years or five years?

This question is a good opener, because it allows clients to begin talking about any aspect of their business they choose. But you also have your own tactical reason for asking it, which is to determine if they've formulated a strategic plan and, if so, what that plan involves.

Now is the time to listen and learn, not promote. But if the client mentions, for instance, international growth as a part of the strategy, you may have spotted a great cross-selling opportunity right off the bat, assuming your firm has expertise in that area.

Asking about strategic planning tells you something else as well. It tells you what kind of self-knowledge clients have. Do they have a specific vision of what they want for themselves, or are they playing the field, reacting to events and market developments as they happen? Getting a feel for clients in this way may tell you volumes about how they deal with every other aspect of their business, including hiring lawyers. How long has the client been in business? It's an obvious question, but don't forget to ask it if you don't already know. Mature businesses often have more experience with outside counsel, and many of their legal problems have already been resolved. With start-ups, the selling process has a completely different texture. You may need to explore fundamental questions, like setting up ESOPs or going public, that the client may not have thought through yet. In some ways, you're establishing a partnership when you sell to start-ups.

2. Do your plans involve new offices or plants in new locations?

This seemingly innocuous question is more than just a further refinement of the strategic planning issue. It will help you focus on a whole range of possible legal services, from real estate and lease negotiations to benefits planning for new staffs. In addition, it's information that will give you a real sense of just how aggressive and confident the client is. It's one thing to talk about a strategic plan. It's another thing to state boldly, "We intend to open 10 new branches in the next two years."

3. Will you be developing important new products, services or making major changes in your offerings?

What if a retailer decides he wants to offer a discount brokerage service? Suddenly there's a whole range of legal expertise that your firm may have, but that you had no idea this particular client ever would need. And the client may have no idea you feature a securities practice. Here, the opportunity for cross-selling, as well as getting a jump on the competition, speaks for itself - thunderously.

4. What kind of research and development do you see as necessary for you to meet your strategic objectives?

Legal counsel is itself a form of R&D, particularly where the client will be breaking new ground. As clients talk more about their plans - how much they plan to invest, and the kind of research they'll be doing - you may even get a glimpse of your own future: the practice areas you'll need to develop to be at the cutting edge five or 10 years down the road.

5. Could you profile your typical customer?

Getting a sense of who clients' customers are may help you determine how they themselves behave as customers. Are their buyers highly sophisticated and demanding? If so, they may want to see some evidence that you also treat your clients as peers.

Understanding how they market their products or services will naturally give you some clues as to how you should be marketing to them. If they de-emphasize the direct pitch, maybe you should, too. But, there's another reason to explore their marketing approach. How they structure their sales force, whether it's decentralized or pyramidal, and the quota pressures under which those salespeople operate, will give you crucial insights into their culture. Is it a pressure-cooker, or is their customer base solid enough to permit a more relaxed environment? What the company expects from its district managers, it may also expect from you.

6. What are your employee relations concerns?

How clients manage their sales force leads to a broader issue: how they manage their entire work force. This line of inquiry will strengthen your sense of the client's culture and its impact on the client's legal needs. Is it a paternalistic milieu, or a demanding and confrontational one?

Querying clients' concerns here also will help accomplish two other basic objectives. First, it will indicate current or future labor/employee problems: collective bargaining, wrongful discharge, benefits planning, etc. Second, it will increase the client's comfort level with you. Whether clients are closely-held businesses or Fortune 500 giants, there's nothing they fret about more, and nothing they'd rather talk over with a lawyer.

7. Who are your main competitors?

Here's another opportunity to get a sense of the business climate in which your clients are operating. Where there's an ongoing survival struggle with competitors, there are myriad legal issues, like commercial litigation, that the buyer may not yet be pondering but ought to. Conversely, less intense competitive environments may direct the client dialogue elsewhere.

8. What has the financial climate been like for your business?

Use care here. This is information you need to have to understand any prospective client, but the question must be presented in as non-threatening a way as possible. You don't want to put anyone on the defensive. And you certainly don't want the client thinking you're worried about who's going to pay the bill.

You're really trying to accomplish something very different. Clients in distress may want to think about spinning off a division, or even tapping your firm's bankruptcy expertise. Or perhaps you will want eventually to suggest custom-designed billing methods. You may even want to mention that your firm has helped other companies under the gun.

Once you have a sense of where your prospective clients are in the marketplace, shift the focus somewhat. Find out what makes them tick.

9. How are you organized, what does your organization chart look like, and who are the key executives?

You're really trying to gauge the client's level of complexity. Is it a flat organization or hierarchal? Are there dozens of subsidiaries, or is it a one-cell organism? You don't necessarily need the whole organization chart, just enough information to know with whom you're dealing. The names of the key executives are important at this juncture. You may never actually meet, say, the CFO, but you certainly don't want to sound ignorant later if that person's name comes up.

This is another particularly good time to think about cross-selling. You may, for example, uncover reporting relationships between clients and their divisions or subsidiaries that you never suspected.

10. How are decisions made, and who are the decision-makers?

Here, you're fleshing out the political underpinnings of the organizational setup. How bureaucratic is it? How autocratic? How many meetings will be needed before decisions, including retention decisions, are made? How efficiently are legal counsel implemented? For lawyers in particular, it's vital to know who specifically makes the decisions. Is there a general counsel? If not, it may be advisable to minimize legal jargon in the selling process.

11. What is the leadership style here?

This question will give the client an opportunity to provide a wealth of insight into the personalities of the key players. Get a sense of those people before you meet them. You may learn that the leadership style emphasizes consensus-building. That's a cue to suggest setting up other meetings with as many of those important team players as possible. Even brief introductions are useful. The more decision-makers you meet, the more opportunities for cross-selling open up.

12. Is there a legal department, and how is it organized?

Many sophisticated users of legal services have legal departments. The role of the department and its officers vary widely. Obviously, you need to know, but be careful here. The general counsel may be out of the decision-making loop altogether. Let the clients describe the role of their legal department and draw your own conclusions. But ask to meet the members of the legal department in any event. There's no point in alienating your in-house counterparts.

13. What do you see outside counsel accomplishing for you or your organization?

Again, the question is broad enough so that it's the clients who supply the essential information. Let them tell you what they want to buy, not just react to what you want to sell. They state their needs. YOU decide if you can fill them.

14. Are there any recent uncertainties affecting your business, or changes of any sort that have particularly concerned you in the last few months or so?

Most clients have something on their minds, otherwise they wouldn't be talking to a lawyer. Some of them may want to jump right in and tell you about a serious problem that's been keeping them awake at night. Others will prefer to talk about bewildering regulatory, political or market changes. But even generalities will highlight what they need from you today, as well as how you might be solving their other problems tomorrow and the day after tomorrow.

You're now on the verge of making an absolutely crucial determination: Does this client want proactive counseling or crisis management? You're not going to use the same tone of voice with a client who wants you to co-pilot long-range business strategy that you'd use for someone who needs you as a safety net. To know which tone of voice will make clients most comfortable, listen carefully to the tone they use with you.

15. What sort of legal services are you currently using, and do you expect that to change?

Perhaps they've been relying on outside counsel for, say, garden variety tax work or ERISA. If so, ask yourself why they're talking to you now. Maybe some new and critical situation is in the offing, and they feel the need to shop around. Or perhaps they're just dissatisfied with their current counsel and are looking to turn everything over to another firm.

This line of inquiry is also helpful because you'll be able to compare their current legal needs with the services they're now buying. Something may well be missing on the service end. With new or first-time buyers, there may be particularly glaring omissions. With veteran buyers, watch for certain recurring patterns. Some of them may be turning to Firm X for, say, tax work, and to Firm Y for litigation. Do they even know that many firms offer the best of both? One-stop shopping is a powerful lure for most clients.

You should have some sense at this point of the clients' legal needs. Move on and, for experienced clients, explore what sort of lawyering has made them happy or unhappy in the past. For less sophisticated clients, modify the questions. Ask them to imagine the best-case lawyer/client scenarios, as well as the worst.

16. What dissatisfies you about the level of legal services you've been getting?

Learn from your competitors' mistakes without attacking them directly. Pinpoint where they've fallen short in order to determine where you'll need to do better. It's helpful to find out who those other firms are, because they're likely to continue to compete with you for future work. The client may mention their names without your having to ask.

17. How much detail do you like to get from your lawyers?

Here is where you can get a real picture of your clients' legal environment, and how much knowledge of the law they're bringing to the table. That knowledge will have a direct impact on the selling process. Clients who aren't interested in hearing about all the details of a case aren't likely to appreciate your trying to sell yourself with dazzling displays of esoteric legalese.

By the same token, clients who say they demand line and verse on every deal may well expect to be talking shop before they hire anyone. Incidentally, clients who take pride in their legal knowledge probably have invested power in their general counsel, at least in determining which firms get what business.

18. How do you perceive our firm in particular?

You should be listening here to two things. First, what is it that has interested the client enough to consider hiring you? Is it a particular practice area or your firm's overall reputation? Define that strength and, whatever it is, reinforce it in your presentation.

But listen, too, for what even the most admiring clients are not perceiving. Remember, you're trying to build a long-term relationship. That means going beyond the one or two areas of expertise that these clients have seen fit to mention. In other words, sell everything you have.

19. What criteria do you use in selecting lawyers? What makes a good lawyer?

For clients, a good lawyer may be variously defined as someone who wins cases, returns phone calls, respects in-house counsel or keeps costs down. Sometimes these clients have no particular impression of you or your firm, one way or another. They may just be spreading their nets, talking to as many lawyers as possible. So don't guess what they're looking for. Ask them.

20. How does your budgeting for legal services compare to what you spend on other resources?

Get a sense of the cost pressures beleaguering the client. Sophisticated buyers aren't looking for bargain-basement rates, but they are attracted to lawyers who are sensitive to their need to stay within reasonable limits. Again, the main issue is the clients' comfort level. They're going to want to know that you're someone they can deal with.

At this point you probably have developed a sense of the organization's operating environment, the personalities and their decision-making styles.

Any number of things might happen next. You may meet with other key executives. Or you will now begin preparing the formal presentation, written or verbal or both. With such myriad data now in hand, you can tailor that next step to the client's unique situation. You've substantially reduced the distance between you and built or enhanced the relationship.

Many lawyers don't reach this stage in a relationship with their established clients. Such relationships are built on trust, and trust is generally built on understanding and face-to-face communication. Asking relevant questions builds trust, and people give business to people they trust. Clients learn more about trusting lawyers and law firms from face-to-face meetings than probably any other source.

Too often, lawyers inexperienced in client relationship-building and business development squander client development opportunities. The sad part is the client may become permanently turned off to his lawyer's amateurish efforts. This could result in a loss of trust in his lawyer. Clients will be reluctant to share information if they perceive that they will get a non-stop sales pitch. Avoid the premature "sales pitch," as it could have disastrous long-term implications for client relationships.

The last question you may want to ask is the one that will lead to a commitment. Building relationships is a process, and one in which the clients themselves participate. So ask your client or prospective client for help in determining what the next step might be.

This article was featured in the September 23, 1991 issue of Texas Lawyer.