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The 10 Greatest Questions to Ask Consulting Prospects

You’re a consultant. You solve problems and give advice. Your wisdom and sagacity determine your value to clients, and you are literally paid to announce your well-reasoned thoughts. And yet, in the pursuit of new clients, your most profitable course is to learn rather than to inform.

Your genius is revealed by your questions, not your assertions.

With that thought in mind, this morning I compiled a list of my favorite questions… then threw it out, since they all involved chocolate in one form or another.

If you’re an avid reader, you know I frequently suggest lines of inquiry that will help you win more clients and enjoy higher profits. For instance, 9 Whys Every Consultant Must Master, and 7 Questions that Will Multiply Your Consulting Firm Revenue & Margin.

What, though are the very best questions for winning new consulting business? After discarding my chocolate-laden list, I quickly jotted down over 50 outstanding questions to ask while you’re in the hunt to win a consulting project. (There’s probably another 50 to ask after you win the business, but that’s for a different article.)

Fifty is too many, though. It’s challenging to remember 50 questions when you’re facing a client. Ten, on the other hand, you could commit to memory. After all, you remember the 10 commandments, right? (Okay, maybe that’s a bad example.)

Below are nine of my all-time favorite questions to ask prospects when I’m pursuing a consulting project, and an open space for you to add yours.

The 10 Greatest Questions to Ask Consulting Prospects

Why now?

Sometimes this is phrased as “What’s changed?” Either way, this question probes for the urgency necessary to drive a prospect to sign on the dotted line.

Why bother?

When your client reveals the meaningful impact your project will have on his business, his customers, his employees and, most importantly, himself, you’ve discovered the emotional juice you need to close the project.

What fee would give you a heart attack?

This astounding question simultaneously establishes and raises your prospect’s reference point for your project’s fees. It also injects levity when a dose of laughter is often needed.

What else?

Persistence and patience will reward you with your prospects deepest motivations, concerns, hopes and expectations. Their initial answers are shallow. Frequent application of “What else?” forces deeper contemplation.

What’s your process?

A closed-ended question such as, “Are you the decision maker?” often yields a misleading answer. However, when you ask, “What’s your process for hiring a consultant on this project?” you’ll learn the whole story—including the critical stakeholders.

Why not do this yourself?

Few exchanges are more fun than when a client explains all the reasons he needs you.

How would you handle that in a way that’s fair?

Consultants often feel they have to meet disagreements head on. You don’t. During negotiations, ask your prospects to solve their own objections—they’ll often come up with more favorable solutions than you would have suggested.

What’s a base hit and what’s a home run?

When your client concretely differentiates between good and great outcomes, he’s divulging how to efficiently delight him.

Is it okay if I…?

Prospects will grant you virtually unlimited leeway, as long as you ask for permission first and your request is centered on them. That includes asking personal questions, pushing back, speaking bluntly, requesting access… you name it.

<this space is for YOUR favorite question>

What do you think should be on the list of the 10 Greatest Questions to Ask Consulting Prospects? Add your suggestion in the comment box, below.


  1. Jonathan Verney
    March 7, 2018 at 7:57 am Reply

    Good one David! I like to ask my author-client prospects three questions: Why this book? Why you? Why now? It usually floors them, in a good way. They want to write a book and need help doing it, which is why they’ve reached out to me. But often they haven’t really figured out what they want to accomplish. These three questions (which publishers are known to ask, by the way) really help them start to focus–and help build trust.

    • David A. Fields
      March 7, 2018 at 8:51 am Reply

      Prospects so often reach out on impulse, which is why we consultants so often feel jerked around by prospects who are all excited about a project then disappear without a trace. Your questions are excellent for breaking that cycle, Jonathan. (They’re also a great tip for any readers who are thinking of writing a book!) Perfect additions to the list.

  2. Mark Vieno
    March 7, 2018 at 8:16 am Reply

    David, I can already see a higher win ratio on our accounting system configurations. I am using your context discussion when a prospect requests a quote. I am also using your proposal format. The context discussion helps me qualify prospects, which is important because your proposal format requires more time because it is customized for the client, and I don’t want to waste time doing proposals for clients that do not have an urgent need with a budget to afford our services. I’ve seen my win ratio climb from 25% to over 50% in just the last month since I have been doing this. I have been using the heart attack question after going over the value of the project, and when I reveal the price during the call after the heart attack question (we have unpublished fixed pricing), it seems to always be within their budget! I’ll incorporate these additional question on my “cheat sheet” that I use during the initial call. Thanks! Reading your book a second time and taking notes!

    • David A. Fields
      March 7, 2018 at 8:58 am Reply

      Hooray!! Congratulations on the terrific results, Mark. It’s your implementation of the techniques and approaches that are making the difference in your practice. Doubling your close rate is a quick path to doubling your business. Add to that the higher fees you command when you employ the heart attack question and you’re on your way to serious growth!

      (Quick shout out to Dan Markovitz, who commented on last week’s article that he was looking for a case study of someone using the heart attack question. Mark’s got it nailed.)

  3. Derek Fields
    March 7, 2018 at 8:18 am Reply

    Near the end of every discussion with a client, I ask “What are your concerned about, what about this project is your biggest fear?” I find that this helps to surface the land-mines and the hidden agendas. It also projects the veneer of empathy – whether you care or not.

    • David A. Fields
      March 7, 2018 at 9:01 am Reply

      “What are your concerns” is definitely on the top 10 list. It’s the fourth topic in the Context Discussion and adding that question to your discovery process is, I believe, one of the most powerful steps you can take to improve your close rate. Thanks for highlighting that question, Derek.

  4. Ken Steiger
    March 7, 2018 at 8:23 am Reply

    I like your list and what they get to: (as Sandler says) Pain, Money, Decision. I have a couple of others that keep things moving forward and keep me out of voicemail jail.

    “What would you like me to do next?” or its variants “What do you see as the next step/s” gets the prospect to continue to move the project forward and gets to the next level of commitment.

    Oh, and another: “So when I do (get you information, schedule, etc.), you’ll be able to commit to (decision)” when the prospect asks for “one more thing.”

    • David A. Fields
      March 7, 2018 at 9:04 am Reply

      Your questions maintain momentum, which is critical in the pursuit of new business. Agreeing to concrete steps and specific due dates (or next-step dates) with your prospects is the easiest way to significantly increase your close rates. Absolutely outstanding addition to the list, Ken.

  5. Susan Pierson-Brown
    March 7, 2018 at 12:16 pm Reply

    My favorite to use in the context discussion is a ‘time machine’ question, where I ask the prospect “if you and I were to get into a time machine and travel one year (or six months, or two years…) into the future, and our work together has been wildly successful, what does that look like? What’s different for you and your business? This accomplishes two things – it helps me understand their expectations, and it also takes them to very happy mental place where they are visualizing crazy success, and I’m in that picture with them.

    • David A. Fields
      March 7, 2018 at 1:11 pm Reply

      Absolutely fabulous question, Susan. A slight variation on your question that I also like starts with the time machine opening, and ends, “What would have had to have happened for you to be absolutely delighted?” You’re right on the mark about creating a concrete, positive association with you and their possible future. Terrific question for the list.

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