Asking the Right Questions: What you Need to Know to Sell your Legal Services

Research shows that the most successful business generators ask a lot of questions, particularly at the beginning of the sales or business development cycle.  Good questions build rapport and help to determine a prospect’s needs, problems, motivations, rationale, choices, and objectives. Plus, successful business generators tend to ask questions in particular sequence. This sounds fairly simple, but it takes consistent work and strong skills to become effective at using this approach to successfully generate new business.


Background Questions are used to establish the facts about the prospect’s situation. They are the first level of questions that you ask.  They are important, but you want to limit them, particularly with more senior level prospects.  Research shows that the higher up your prospect is in the organization, the less likely he/she will like answering Background Questions. Their time is very valuable, so the more information you can gather prior to the meeting, the better.  Look to annual reports and articles, and try to find out what other public and relevant information that you can about the company and prospect. Background Questions can lead smoothly and naturally to a discussion of potential problems.

When asking Background Questions, you will want to listen for implied or explicit needs. Implied needs are statements about a prospect’s problems, difficulties and dissatisfactions. A typical example of an implied need may start with “I’m unhappy with…” or “I’m worried that…”. On the other hand, explicit needs state the prospect’s wishes. For instance, “I am looking for a full-service firm.” Explicit needs are the key drivers of purchasing decisions.

Sample Background Questions:

  • What are the biggest challenges that you face?
  • How do you feel the recession has impacted your business?
  • Who is your typical customer/client?
  • How is your legal department organized?
  • What type of legal work do you use outside counsel for?
  • What are the current trends in your market/industry?
  • How long have you been in business?
  • What is happening in your market/industry?
  • What are your top priorities over the next six months?
  • Describe your experience working with outside counsel.
  • What has worked well? What has been a challenge?


Problem-Solving Questions are used to explore problems, difficulties, and dissatisfactions with an existing situation. These questions are asked after you have asked your Background Questions. Listen for implied or explicit needs.

Sample Problem-Solving Questions:

  • How would you like to see your current counsel improved?
  • Where do you anticipate your current counsel will not be able to meet your needs as your business grows?
  • It sounds like you’re concerned about [problem].
  • Could you please tell me more about…?
  • How important is it to solve this problem and by when?
  • What is happening in your business that necessities that expertise?


Consequence Questions take a prospect’s problems (i.e., a need that is not being satisfied) and explore their implications or effects. These questions are especially effective when you are selling to a decision maker whose success in his/her organization depends upon his/her ability to see beyond the immediate problem and to comprehend its eventual consequences. Consequence Questions help the prospect understand a problem’s seriousness or urgency so that it becomes large enough to justify an immediate and significant action (such as retention of outside counsel or making a firm change) or help the prospect see a link to another potential problem. Consequence Questions create a stronger sense of need before you introduce a possible solution. These questions can transform implicit needs into explicit needs. A prospect may be engaging in denial or avoidance behavior. These questions force the prospect to acknowledge pain and, therefore, to appreciate the need for treatment.

Sample Consequence Questions:

  • How often does that cause…?
  • What does that result in…?
  • Does that ever lead to…?
  • What effect does that have on…?
  • What have you done so far to protect your position?
  • It sounds like you do not feel like you are getting the best terms. How has that translated into lost dollars, lost opportunities…?
  • How is this problem affecting your organization and you personally?
  • If you did nothing, how would that impact your organization and you personally?


Outcome Questions try to get at what outcomes the prospect would find acceptable. They get the prospect to tell you the benefit that your solution could offer rather than your being forced to explain it.  Selling is not about convincing a prospect but, rather, about creating the right conditions for the prospect to talk him/herself into acceptance.  Outcome Questions also reduce objections. Consequence Questions are often the mirror image of Outcome Questions.

Sample Scenario and Outcome Questions:

You are an experienced entertainment attorney. You are speaking to a prospect who is a famous pop singer. The pop singer feels that her current attorney may not be getting her the most favorable terms in her contracts, but she does not know what those are because the terms in artists’ contracts are not publicly reported and are subject to confidentiality requirements. On the other hand, your firm may have represented those companies or peer artists in similar contracts and, therefore, know what terms they have agreed to. Without breaching confidentiality, the entertainment company and you know what those terms are so the companies could not reject a position you have gotten on the basis that is not “market.” One way to explore the problem would be to ask as a Consequence Question like: “Do you feel that your current attorney is knowledgeable about the terms your peer singers are getting in their contracts?” or “Which of your peers has your current attorney represented in similar negotiations?” An Outcome Question may sound like, “How could our deep experience working with the big entertainment companies (or peer artists) help you to achieve more favorable terms?”


In summary, excellent questions asked at the appropriate times build rapport and help you to focus your solution. They also help you to keep your prospect involved in the business development process. Try some of these techniques at your next business development meeting and see what results they yield.

Written by Sheryl A. Odentz. Sheryl  is the president of Progress in Work LLC, a career management firm for attorneys. She can be reached at or  This article was published in the April 2013 issue of LJN (Law Journal Newsletter) an ALM Publication.