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5 Questions You’re Afraid to Ask (and It’s Costing You Projects)

In the 1936 Buster Keaton classic, The Consultant, Mr. Reginald pauses dramatically, a sudden glimmer of understanding ghosting across his face before he turns back to the prospect and delivers the line that many say won Keaton the Oscar: “Isn’t it possible you’re the problem, Slade?”

Seriously, turning the tables with a pointed probe can play an important role in your business-building routine. As consultants we’re walking, talking, perpetual inquisition machines. Our genetic makeup seems to be a strand of diagnostic curiosity inextricably entwined with SPIN-selling power questions.

And rightly so. Posing insightful queries is a necessary trait during the diagnostic and solution phases of a project. Plus, best-practice approaches to winning consulting engagements, including the Context Discussion, rest on a series of artfully designed inquiries.


Most of our questions are designed to demonstrate our perspicacity and expose the client’s need for our intervention. However, turning the tables on ourselves by openly challenging our role is a surprisingly effective technique during the selling process.

Unfortunately, these questions scare the pants off most consultants because they appear to undermine your likelihood to win the gig. Take a leap of faith. Each of the suggestions below puts you in the client’s seat, voicing their unspoken concerns.

They elicit a remarkable response: 95% percent of the time, your prospect will start selling you on why they require your services. And with that script, you’ll ride off into the sunset with a signed deal in hand.


Five Table-Turning Questions That Will Help Seal the Deal

  • Why not do this yourself? This question is actually part of my standard, Context Discussion with every prospect. Internal staff is frequently your biggest competition and this question will usually knock them out of the picture.
  • Why not just do a pilot? If the prospect seems to be wavering on a large initiative, I’ll break this out. Sometimes it will provoke an instant close on a small project that leads to a large, ongoing engagement. Other times it cements the client’s desire to take on the whole megillah.
  • Couldn’t you wait and do this later? If you push urgency, the prospect will question the need to jump into the project. Ironically, when you raise this client-centric question the prospect taps into their driving desire to move forward.
  • There’s a chance this won’t work, are you sure it’s worth the risk? You may think asking this is insane and plants seeds of doubt; however, the opposite is true. Your client is already concerned about outcome risk. This question forces the client to work through the apprehension and conclude the project makes sense.
  • Are you sure this is worth an investment of $xxx? The ultimate in table-turning queries. Rather than striving (again) to prove your value, flip the scenario upside down. Use a figure in the ballpark of your anticipated fees to test the prospect’s appetite for your project.

Are you ready to try turning the tables on your prospects? Which of these questions do you think will work best for you? Let me know by posting your thoughts below.


  1. Luda Fedoruk
    March 18, 2015 at 8:41 am Reply

    This makes total sense!

    • David A. Fields
      March 20, 2015 at 12:37 pm Reply

      I agree, Luda. Let me know how these work for you, and thanks for adding your support.

  2. R Mallory Starr
    March 18, 2015 at 9:01 am Reply

    David — this is terrific? Such questions are extremely important even as part of first interview with a prospective client decision maker and even with those in a company who are in positions to be of significant management consulting purchase influencers such as Board members and some below C level executives and managers..

    • David A. Fields
      March 20, 2015 at 12:44 pm Reply

      Right you are, Mallory. There’s a category of people I call “breakers” because they have the capability to stop a project from going forward, but they can’t make it happen. Often the most effective way to work with a breaker is to directly point out the concerns that could make them detractors from your initiative. When they work through the issue–either with you or without you– they transform from breakers to champions.

  3. Tom Morgan
    March 18, 2015 at 11:50 am Reply

    Excellent, David,. A kind of reverse psychology approach that in effect establishes the consultant as being in the position of strength. Thank you.

    • David A. Fields
      March 20, 2015 at 12:46 pm Reply

      You’re welcome, Tom. It’s judo, the force and consulting all wrapped up in one!

  4. Neil
    March 18, 2015 at 3:36 pm Reply

    As always an interesting article. Here is my issue with your questions. Since what we sell is so nebulous, one of the most important things we are selling is confidence that we can solve a prospect’s problem.

    No one would ever say that you lack confidence. You can ask these questions and not undermine a prospect’s confidence in you. However, I have observed many consultants lack your level of confidence and asking these questions can backfire. For example, if you went to a doctor for surgery and s/he seemed nervous and asked why you wanted to go through with the procedure, many potential patients would get the heck out of there. After all, if the doctor questioned whether we should do the procedure and s/he is the expert, then maybe this is too risky for me.

    In summary, if a confident/borderline arrogant consultant asked these questions, it could be seen as empathetic and caring. If a less than confident consultant asked these questions, it could raise a lot of red flags for the prospect.

    • David A. Fields
      March 20, 2015 at 12:56 pm Reply

      Neil, you make a great point about success in rainmaking requiring confidence. The reply from Thomas is right on the mark: clients have concerns about our projects that usually lurk in the shadowy background, unaddressed. These table-turning questions bring the concerns into the light of day where they can be managed. Ideally, the prospect addresses her own issues; however, occasionally prospects need some guidance from you.
      Back to your original point: check out this blog post about building confidence. Also, this short Q&A about confidence.

  5. Thomas Cox
    March 19, 2015 at 8:55 am Reply

    Neil, while I get the point you’re making, isn’t it true that just about anything a “nervous” or less than confident consultant did, might undermine the client’s confidence in him — probably justifiably? Isn’t the solution to be good enough to have true confidence?

    I take David’s questions as useful ways to help us voice the client’s thoughts and make it okay to talk and think about them in a shared way, rather than have the client think them silently, never discuss them, and “go dark” or back away.

    It’s hard to address an unspoken concern. Speak them.

    • David A. Fields
      March 20, 2015 at 12:57 pm Reply

      Amen! Perfectly said, Thomas. Thanks for posting.

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