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Be a Better Consulting Rainmaker: The One Question that Precedes All Others

Unless you’ve limited your practice to responding to RFPs, winning new consulting projects involves asking questions. Many questions. Like, “What are your objectives?” “By when does this need to be completed?” “How many Navy Seals will I have to train?” and, “Can I negotiate free access to the ice cream machine in your cafeteria?”

Some inquiries are uncomfortable, and for them you need a particular “pre-question” which I’ll explain in a moment. 

We’re told we “should” be able to ask about anything, even the most sensitive information. In fact, I’m guilty of instructing the consultants I work with to “Just ask!” How do you know the prospect’s budget? Just ask. How do you find out their personal gains from a project? Just ask. How do you find out who the decision maker is? Just ask. Yeah, right.


If it were that easy, you would have asked already. Clearly there are daunting, internal impediments preventing us from blurting out all our questions. Some part of the resistance is fear that our prospect will be offended or taken aback by our request. That we will be perceived as rude, uncouth, insensitive and not worthy of a project.

That’s a legitimate concern. Were we to blithely fire off whatever questions flit through our mind, unfiltered and unfettered, we could irreparably harm the relationship and eliminate any chance of winning the consulting gig.

The risk of offending a prospect with questions that are deemed inappropriate is particularly high in some Asian cultures; however, even in the brash U.S. of A., it’s  doggone easy to pull the plug on your Likeability with a misplaced question.


It turns out there’s a very easy solution to this problem: first, ask for permission.

No matter how difficult, uncomfortable, awkward or sensitive the information is you’re seeking, if you ask for permission and give (or are assumed to have) a good reason, you’re likely to get it. Some variation of “May I…” or “Do you mind if…” is the question that can precede any inquiry.

Asking for permission demonstrates that you’re thinking Right-Side Up. That you’re putting your prospect’s interests first. It doesn’t always work, of course. For instance, a privately-held company may be unwilling to reveal their financial details, no matter what.

However, even if permission isn’t immediately granted, this simple pre-question opens the door for deep, trust-laden communication, and long-lasting consulting relationships.

Below are a few examples of asking for permission that I often use with prospects:

  • Are you open to a separate discussion?
  • May I ask a delicate question?
  • I have to share some results today that are not altogether favorable. Is that okay?
  • May I ask a personal question?


  • Do you mind if I push back a bit on what you just said?
  • Are you okay with a few more questions?
  • May I offer a suggestion?

How/when else have you asked for permission? Has doing so worked for you? Please add your thoughts in the comments section below.



  1. R. Mallory Starr, Jr.
    June 15, 2016 at 8:36 am Reply

    The ask for permission to ask some hard perhaps, too frank, and, maybe socially impolite questions is essential in a serious diagnostic interview meeting. Doing so shows guts and a high level of confidence. It also shows that one is not afraid. The consulting relationship is not a social one and that assumes that the exchange between a trusted advisor in a consulting role with a client is a very deep one often requiring exchange of knowledge that can make a difference in the action path to higher level success.

    David, you do come up with great information and such nformation is a gift — thank you!!

    • David A. Fields
      June 15, 2016 at 8:59 am Reply

      You’re right, Mallory. To do our job well we often need to ask impolite, uncomfortable questions. The “easy” questions have landed our clients where they are now; the hard questions are often the way out. Asking for permission allows us to assume a trusted advisor role where difficult questions are explored. Thank you for bring that piece to the fore, Mallory.

  2. Karyl Innis
    June 15, 2016 at 9:09 am Reply

    I love the simplicity of this approach….and I think you are right. Thanks for the clarity.

    • David A. Fields
      June 15, 2016 at 9:34 am Reply

      Simple works! No reason to over complicate things, right? Thanks for highlighting that aspect of asking for permission, Karyl.

  3. Doug Loescher
    June 15, 2016 at 9:17 am Reply

    Brilliant… simple… memorable. I love these type of tips! I especially find it useful to apply later in the process, when we need to get real with clients about the core issues, (often involving them directly). Thanks, David, for this universal strategy!

    • David A. Fields
      June 15, 2016 at 9:35 am Reply

      Exactly, Doug. In fact, this is a strategy that works well throughout engagements and (surprise) at home too! Let me know how you fare with it.

  4. Mary Drotar
    June 15, 2016 at 11:33 am Reply

    Nice post, especially a good point on sharing unfavorable results. Unfortunately, we do have negative findings that we have to share with our clients, and some clients react to honesty better than others. It is important to soften the blow.

    • David A. Fields
      June 16, 2016 at 10:25 am Reply

      Mary, long ago (before the years sanded away some of my rougher edges) a wise person told me, “David, give people a chance to put on their armor before you shoot them.” That’s proven to be an extremely useful rule of engagement.

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