David A. Fields Consulting Group How to Gain Critical, Delicate Information From Prospective Consulting Prospects
Consulting is largely about inquiry. Training yourself and your team to initiate inquiry optimally will help your consulting firm immeasurably.
Unless you’ve limited your practice to responding to RFPs, winning new consulting projects involves asking questions. Many questions.
Such as, “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?”
At times, probing for information can feel uncomfortable, intrusive or even rude. You may worry at those times whether merely asking the question will shut down any possibility of winning a project.
You’ve probably been told you “should” be able to ask about anything, even the most sensitive information. Your prospect’s budget, their personal gains, who the decision maker is, and more.
It’s supposed to be easy!
It’s often not easy at all.
If asking uncomfortable questions were easy, you wouldn’t find it uncomfortable and wouldn’t dodge important questions that you know would help you and your prospective client.
Clearly, therefore, there are daunting, internal impediments preventing you from blurting out some questions.
Part of your resistance is fear that your prospect will be offended or taken aback by your request. That you will be perceived as rude, uncouth, insensitive and not worthy of a project.
Those are legitimate concerns.
Were you to blithely fire off whatever questions flit through your mind, unfiltered and unfettered, you could irreparably harm the relationship and eliminate any chance of winning the consulting engagement.
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 offer (or are assumed to have) a good reason, you’re likely to get the information you’re seeking.
This is called presumptive permission, and works extraordinarily well with some variation of “May I…” or “Do you mind if…” before virtually any inquiry.
Asking for permission demonstrates that you’re thinking Right-Side Up. That you’re putting your prospect’s interests first.
Presumptive permission 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, presumptive permission opens the door for deep, trust-laden communication, and long-lasting consulting relationships.
Below are a few examples of asking for permission that usually work with consulting 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?
Those are just a few examples of presumptive permission.
What turns of phrase have you used to start constructive inquiry, particularly around difficult or sensitive topics?
Text and images are © 2025 David A. Fields, all rights reserved.
One I find myself using often is “Do you mind if I give you another way to think about that?”
That is a fantastic, Right-Side Up way to ask for permission to dissent.
Thanks for contributing, Belden!
I like question! I may have to borrow that one. 😊
I learnt at an early stage of my consulting career to treat meetings with prospective clients like doctor’s visits. I had a one minute overview of our consulting work and capabilities to share as an introduction but then asked them to talk about their program. Once they started providing information it was typically easy to talk about their most critical issues and what they would like to be able to change. Very often they almost “wrote the proposal” for us! Asking questions in a friendly non judgmental manner is key.
Kudos for shifting the focus back to your prospects while making them feel heard, safe, and valued. You practically outlined two core frameworks of discovery: the 30-Second Firm Overview and the Context Discussion.
Thank you for sharing your experience here, Roger!
It is really important to ask the “right” questions. I’ve seen people hit up clients with a laundry list of questions that “must” be answered before starting the project. I’ve been on the receiving end of that scenario. Personally, I would rather ask 2 or 3 open ended good questions that can drive a dialogue and conversation. My point is that less is often better.
Good insight, Joe. Moving through questions as if it was an online survey makes for a terrible client experience. Balancing the right questions with deep listening is the hallmark of effective consulting.
Thanks for chiming in!
Being driven by a sincere curiosity shines through and avoids the ham-fisted ‘move-the-sale-along’ vibe. I have always liked using the Begin with the End in Mind question around business and buyer outcomes. For example, “If you don’t mind my asking, if we achieve the desired results for the business, what will that do for you?” Understanding this linkage makes the business more personal for me.
Jeff, that is a very good question to ask, and nothing beats genuine curiosity and interest in helping your clients!
Thank you for your comment, Jeff.