How to Ask Prospective Clients Deal-Closing Questions
Updated: May 17
One of the most powerful tools you can use to close more consulting deals is asking questions.
But not just any ‘ole questions…
Questions that close deals are specific and strategic, not generic and random.
The key is to never ask questions that any run-of-the-mill consultant can ask. Questions like, “What keeps you up at night?”
Questions like that scream, “I couldn’t be bothered to find out anything about you before this meeting, and I’d rather have you do the work to make me understand what’s going on with you and in your market.”
Clients can tell by the question you ask that you haven't put the effort in. That in turn shows them what it will likely be like working with you. And it sure doesn't make them want to hire you!
Asking questions also helps you keep the meeting focused on them and not on yourself. It can stop you from going on and on about yourself, which shows the client that you will put them first if they hire you.
But not every question should be asked for the same reason. Different types of questions serve different purposes when you are first meeting with a prospective client. It is essential to know the difference so you can question strategically!
Each and every question you ask should be for one of three purposes:
Reveal what they need and are willing to pay for and capture enough nuance to pinpoint what you could do to solve their problems and achieve their aspirations
Demonstrate that you have the right knowledge and expertise about them and the context in which they operate
Pivot the conversation to discussing how you can help them achieve outcomes they most want
Ask Revealing Questions
The goal of revealing questions is to get a client to open up about what their problems and aspirations are. You want to find out information that you can’t find on their website or through other means. This includes what frustrates them and makes them feel good.
These types of questions will allow you to suss out the specifics of their situation, what they’ve done or tried so far, and their top priorities. They reveal what you can do to help them and let you identify outcomes they are willing to pay for. These questions also help you develop a scope, pricing model, price, and timeframe for a proposal.
What outcomes do you have to achieve no matter what and why?
If you achieved X, what would that do for your company that you can’t do otherwise?
What’s the risk of not addressing this issue?
What is this problem costing you from a [financial, operational, personnel, or cultural] perspective?
What haven’t you been able to achieve yet that frustrates you more than anything else?
Ask Value-Demonstrating Questions
The goal of these questions is to demonstrate your value, not generally but specifically to them. You want to show that you get them, you know what’s happening in their market and industry, and you know what it takes to be successful. These types of questions also get them to reveal even more.
X is happening in your market now. How have you been responding to that?
You’ve grown in X ways in the last X years. How has that enabled you to reach your goals? What’s still missing or falling short?
In the next X years, it looks like you’ll have to be ready to do X. How have you been preparing for that?
The primary risks companies like you are facing in the near-term are X, X, and X. Which ones do you feel the least ready for and why?
X is a significant opportunity in your market. What would taking advantage of that do for your company? What would happen if you didn’t go for it?
Ask Pivoting Questions
The goal of these questions is to allow you to transition the conversation to talking about a specific engagement with you.
It’s important to ensure that you don’t come across as manipulative or icky when you ask these types of questions. Like you’ve been holding your breath until you can say, “Give me money!” Nothing kills trust faster than that, and clients rarely hire consultants they don’t trust.
If you ask enough revealing questions, you should have a better understanding of how you could help them and what they care most about. And their answers should have ignited your desire to help them! So show them that authentic understanding and desire.
You can think of these questions as bridge questions—bridging from discovering more about them to discussing ways you can help them.
What have you tried before to solve the problem and what happened?
Of all the things we have been talking about, what rises to the top of your priorities?
If you don’t address anything we talked about, what are the risks you’d be taking?
What would you lose if you did nothing or kept doing what you’re doing now?
Here’s what I heard matters most to you: X, X, and X. Is that right?
You can then pivot to an offer question. My favorite: I heard you say 3 things that I could help you with. They are X, X, and X. Do you want to talk about how I could help and what that could look like?
That opens the door for you and the prospective client to talk about the specifics of an engagement.
And that is the power of asking questions strategically!
If you want to dive into more ways to prepare to wow prospective clients, check out my free Initial Prospective Client Meeting Checklist.