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My Basic Toolkit of 16 Open-Ended Consulting Questions

13 min. read
November 24, 2023

I used to talk too much in sales meetings. Sometimes, I would get excited about the project and start riffing on how the client could accomplish her goals. At other times, I would warm up to a question she asked and use up all of our time talking about myself. (Not good!) These days, I rely on a list of tried-and-true consulting discovery questions to draw out my prospect and get her talking about her goals, challenges, and budget.

Instead of giving prospects a firehose to the face, I prove to them that I can listen well, make interesting new connections, and bring clarity. And isn’t that exactly what she needs in our first meeting?

This post will cover two approaches to sales before making a case for why talking less and listening more is the BEST approach to closing more big-ticket freelance and consulting projects. Toward the end, I will share with you the 16 consulting questions that help me to stay focused on the ultimate goal of finding good-fit clients, solving their painful problems, and getting paid handsomely.

Who’s with me?!

Table of Contents

If you’d rather skip the post and go straight to my 22 open-ended consulting questions, I’ll send you the swipe file.

Two Basic Approaches to Sales

Before you can stop jabbering and start listening, you may need to revisit your core beliefs about sales. Here are the two basic approaches to sales:

  1. You talk to sell; or
  2. You listen to sell.

I have tried both, and I now endorse the latter approach. Your soon-to-be clients will sell themselves on working with you if you simply shut up and listen.

At this point, you might be thinking, “Wait! Don’t my prospects need to know a lot about me before they will put their confidence in me?”

It’s true that a client’s money will follow her trust. It’s also true that you need to earn her trust.

However, the question above assumes that your prospect already knows what her problem is. If she does, you can sometimes close a sale through clever persuasion or pummeling your client with your expertise.

Some people will stroke a check to shut you up or bribe you to turn off the firehose. “I get it, I get it, take my money already.”

Most people don’t have clarity around their problem or the various ways they can go about solving it.

That’s why, in order to buy, people need an itch, not a pitch.

Asking open-ended consulting questions enables both parties to get clarity and draw a circle around the itch. Meanwhile, this listening-focused, consultative approach sales often increases the project scope. Instead of stopping with one or two symptoms, you can dig down to root causes.

For example, your prospect may not really have a marketing problem if she has a large email list. She may have a strategy-and-content-and-consistency problem. Were you to help her warm up her list, produce valuable content, and drip that value out twice a week, you could help her 10x her investment in you. She might have been happy to pay you $2,500 for a marketing plan, but now she’s thrilled, over the moon, to pay you a $2,500 per month retainer, for 12 months, to manage all of her content creation and email marketing.

So yes, these interview questions to ask clients will help you peel back the layers, push past the symptoms to the painful, expensive problem underneath, and frame up a project of significantly higher value—both to the client and your consulting business.

Fewer Headaches & Higher Profit Margins

As counterintuitive as it may seem, you build a prospect’s confidence when you talk less. Insightful questions testify to your competence more than your clever monologues. Consultative sales also positions you as the expert. You display more poise.

While you’re busy nodding and taking notes, clients feel heard and understood. They most certainly do not feel like you’re selling at them.

Down the road, these clients make fewer demands and accept the marketing medicine that you dispense without suspicion, skepticism, or complaint.

Remember this: How you sell, more than what you sell, determines the outcome of the meeting and value of the project.

Hopefully, I have already convinced you of the benefits of the consultative approach to sales, but here are several more to drive home the point:

  • Less pushback. If you listen well and take the time to identify deeper needs and root causes (rather than simply pin a quote to surface-level symptoms and requests), you will receive less pushback during the project. Why? The client won’t second-guess her decision as much. She will have greater confidence that you’re working together to solve an important problem.
  • Faster decisions. Clients who have more clarity going into the engagement have more confidence in taking the proposed path. This confidence results in quicker decisions on their end and less explaining and personality management on mine.
  • Higher margins. Once the client is focused on achieving the desired outcome, the amount of time required to produce that outcome becomes irrelevant. My overall time investment can decrease without affecting my client’s satisfaction in the process or overall experience. With flat-fee engagements, less time spent on bringing the project to a successful conclusion means a higher effective hourly rate and higher profit margins.

In short, consultative selling produces bigger projects with higher profit margins and happier clients.

Umm… what’s not to like?

Before we move on, though, I want to define the term.

photo frame text saying "ask for more questions"
Photo Credit: Jonathan Simcoe via Unsplash

What exactly do I mean by “consultative selling”?

Consultative selling is facilitating a process of self-discovery for the client.

  • She takes time out of her day to meet with you and discuss a project.
  • You ask questions about what she would like to see happen, and a problem, need, or goal comes into focus.
  • Addressing the underlying problem or root cause may look different than the initial project.
  • Regardless, your presence and willingness to ask open-ended questions creates space for the client to gain clarity.
  • Increased clarity leads to increased confidence, which invites decisive action.

You will of course talk some. You may need to summarize or punctuate your prospect’s rambling thoughts or briefly interject: “Let me put you on pause for a second to make sure I understand….”

You may repeat back what you’ve just heard for the sake of gaining a more accurate understanding: “Let me repeat back what I heard you say.”

Mostly, however, you simply ask questions and take notes.

During consulting interviews, open-ended questions strip away uncertainty, anxiety, and ambiguity. Without the murkiness of indecision and excuses clouding her judgment, your prospect can recognize a clear path forward. As the impromptu guide, who has already proven knowledgeable and trustworthy, you become the obvious choice as ongoing pathfinder.

Here’s another nuance here worth special emphasis: As a consultative seller, you don’t have to have all the answers. No, your role is to use the tools at your disposal to uncover what your prospect already knows.

If consultation is archaeology, then open-ended consulting questions are toothbrushes, not jack hammers. On the other hand, your strong opinions may be jack hammers. They seem to do the job faster than questions but do more harm than good.

When you flap your jaw in a sales meeting (or even a get-to-know-you meeting), it’s up to you to deliver a convincing pitch, to give an applaudable performance, so to speak. But you can take the pressure off yourself by asking thought-provoking questions instead of going through your script.

A prospect’s conviction about the right course of action is a better pitch than your pitch.

Yes, go ahead and tweet that!

What does this look like in action?

What I’m saying is hold off on the impressive acrobatics routine of expertise for a second and instead help your prospects excavate goals, desires, and problems. Sales-as-consultation—or call it “discovery” if you like—creates an opportunity for clients to sell themselves.

Your part in this discovery process will go something like this:

  1. Say hi.
  2. Go through the requisite get-to-know you stuff. Keep it brief without being awkward about that brevity.
  3. Transition with a question like, “So how can I help you? From your point of view, what brings us here today?”
  4. Shut up and ask open-ended consulting questions. Whether or not clients are aware of it, open-ended questions loosen them up and get them talking about deeper stuff that drives their decision-making.
  5. Ask more specific, clarifying questions as needed.
  6. Take notes. Later, toward the end of your meeting, you can review your notes aloud: “Okay. I’m going to repeat back some of what I’ve heard to ensure that we’re on the same page. See if this sounds accurate to you… .”
  7. Then, um up what you have discovered together to build consensus.
  8. Then, identify next steps by explaining a couple of different ways that you and the client can work together to accomplish those steps.
  9. Ask the client which options she prefers.
  10. Once you know the approximate scope, you can discuss compensation—usually a couple of days later on a follow-up call.
  11. Once you define the scope and agree upon compensation, you send over your master service agreement and a payment link for the deposit.

But I’m getting ahead of myself. You might be wondering, “What client discovery questions should I ask?” Keep reading…

trees in forest with question marks painted on them
Photo Credit: Evan Dennis via Unsplash

My Basic Toolkit of 16 Open-Ended Consulting Questions for Consulting Interviews

Here are 16 interview questions for successful client discovery, in no particular order:

  1. If you could accomplish only one thing by the end of this meeting, what would that be?
  2. That’s pretty broad. Which part would you like to focus on? Okay, and which part of that?
  3. So if we were to get you some clarity around that, then you’d walk away feeling good about our time together today?
  4. Can you help me see how that connects to the outcome you’re after?
  5. Let me put you on pause for a second. I heard you say you wanted to talk about BLANK. This seems to be a new direction. Do you want to go this new direction or stick to BLANK?
  6. What is the project?
  7. By when are you looking to have it finished?
  8. Tell me how you came up with the project. What changed or what happened that made you realize, “I need to do X”?
  9. Can you tell me more about the “something” that this project will solve? What itch will the project scratch?
  10. What’s your biggest challenge with your business?
  11. What would you like to see happen? What does a home run look like in this situation?
  12. If you were to achieve that, what would that mean for your business?
  13. What happened that made you think, “I need to do something about X”?
  14. Have you worked with someone like me—in my case, a marketing consultant—before?
  15. How did that go?
  16. Is there anything that could keep this project from being successful? Are there any risks and/or opportunity costs if you were to do nothing?

Consultative selling is not coloring inside the lines.

This way of thinking about sales will require a paradigm shift for freelancers and creatives who expect their clients to say, in effect, “Here are the lines. Color inside them.”

In consulting interviews, you may be more comfortable when a client gives you a site map for a website or a bullet point list of blog post topics. But once you make the right mental shifts, as the situation demands, from vendor to advisor, specialist to consultant, you can move upstream and capture more high-value projects. (You can read more on those mental shifts here.)

Some prospects will know what they want, but the majority will need some assistance in figuring out what they want. They need a safe space where they can express doubt and frustration, fear and hope, resignation and enthusiasm.

By setting aside the acrobat leotard and becoming the archaeologist, you won’t be leaving money on the table.

Here is consultative selling in two verbs: Listen, dig, and describe.

Don’t stop with the 16 consulting interview questions. Close the sale!

The 16 interview questions I just shared won’t do you any good if you don’t save them. My swipe file will save you the effort, and I’ve also included 6 more questions that will help you to steer the conversation to a decision and to close the sale.

To get the swipe file with the 22 questions, put in your name and email address below, and I’ll send you the download link.

Key Takeaways

  • Whoever is doing the talking is doing the selling. If you ask good questions then shut up and listen, your soon-to-be clients will tell you exactly what they want to buy and how they want you to sell it to them. So listen to sell instead of talking to sell. 
  • A consultative approach to sales enables you to peel back the layers, push past the surface-level symptoms to the painful, expensive problems underneath, and identify prescriptions (aka, projects) of greater value.
  • Clients may lack clarity about their problems or needed solutions. Open-ended consulting questions help both parties gain clarity, accurately define the problem, and figure out the most effective solution.
  • Open-ended questions create space for the client to gain clarity, which boosts their confidence and supports decisive action.
  • Consultative selling now leads to stronger proposals, faster decisions, fewer headaches, higher profit margins, and happier clients later.
  • Listen attentively to notice when the client becomes more energetic or shows emotion and ask clarifying questions so that you can later repeat back to them what you’ve heard and ensure that both parties are building consensus around the core problem.


How to prepare for consulting interviews?

First off, remind yourself that the pressure is off. As a consultant, your job isn’t to produce novel insights like a magician pulling rabbits out of a hat. Rather, your job is to facilitate a process of self-discovery for the prospect through open-ended questions, a willingness to listen more than you speak, and relentless curiosity.

Remind yourself also that your initial objective is to bring clarity and begin formulating a “problem statement.” None of us can propose an effective solution until we have accurately diagnosed the problem. Effective discovery (diagnosis) summarizes the problem to be solved (problem statement) so that you can help the client determine the best path forward (prescription).

Finally, take some time to research the prospect before the meeting. Familiarity with their industry, company, brand, and business model will help you build rapport quickly.

What are the wrong questions to ask during consulting interviews?

The wrong questions to ask are leading questions. If you ask questions to which you think you already know the answer, you’ll miss the most important discoveries. Take, for example, this question: “Don’t you think that the real problem is BLANK?” Instead of creating and holding space, this question piles on assumptions.

Better questions create bigger surface area for new and better insights. Here’s an alternative to the question above: “Have you put any thought into the root cause?”

You’ll make a better impression and bring more clarity if you assume that the client already holds the most valuable expertise, insights, and answers and you’re there to help them diligently dig.

This post may contain affiliate links. Please read my disclosure for more info

Austin L Church portrait photo.

About the Author,
Austin L. Church

Austin L. Church is a writer, brand consultant, and freelance coach. He started freelancing in 2009 after finishing his M.A. in Literature and getting laid off from a marketing agency. Freelancing led to mobile apps (Bright Newt), a tech startup (, a children's book (Grabbling), and a branding studio (Balernum). Austin loves teaching freelancers and consultants how to stack up specific advantages for more income, free time, and fun. He and his wife live with their three children in Knoxville, Tennessee.


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