Beyond the Pitch: Game-Changing Questions For Sales Meetings

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If you ever have to sell anything, especially services, you know that you’re trying to ANSWER several questions for yourself or your company:

  • Can we help this person?
  • Do we want to work with this person?
  • Will this person pay us?

Just as important, though, you need to answer questions for the POTENTIAL CLIENT:

  • Do they see us as different from all their other options?
  • And… do they want to hire us/work with us?

Guess what? Most people get this wrong. After 12,000 hours working with professionals and salespeople, and hundreds of hours reviewing client consults and sales calls, it’s not even a question for me anymore. People screw this up all the time.

They rarely ask more than 3-4 questions before they pitch. That pitch may simply be about their background, their experience, or telling the potential client that they can help. But it’s a pitch either way.

Or, if they do ask more questions, they’re asking the wrong questions. They’re asking “How?” questions and not “What?” or “Why?” questions.

The result? “I’ll get back to you.” “Send me information.” “We’ll think it over.” “Thanks for your time.”

Hearing this is so frustrating when you know that client should’ve signed with you. Because you can help them, and as well as or better than others.

There’s a different way to go about this.

The Problem with the First Meeting or Consult

The first meaningful conversation with a potential client or customer is where 80% of deals are won or lost. Everything thereafter is about details, logistics, and wrapping up what a customer has decided what they want to do. But that’s a post for another time.

Whatever you call your first substantial meeting, your goal is the same:

  • Find out if you can help
  • Determine if you WANT to help
  • Discover if they want your help
  • Understand if they qualify for your help

That’s really it. We all overcomplicate it so much.

Software salespeople – sometimes compensated the wrong way – push for next steps, demos, or free trials. Even with people who aren’t qualified. I know. I’ve been a potential customer who wasn’t qualified and had to tell a sales rep, “You don’t want me in your pipeline.”

Professionals (attorneys, accountants, insurance brokers, etc…) screw it up by 1) talking too much about themselves, 2) assuming the prospective client knows more about the subject area than they really do, and 3) forgetting they’re dealing with people, not just the facts of the situation.

For example, when I train attorneys to win more clients, they believe they need to determine EVERYTHING about the matter in the consult, and know in their heart of hearts they’ll get a great outcome for the potential client. Once they feel confident of this, they believe the client will sign because, logically, they themselves are convinced. Their close rates are rough.

Let’s be clear: finding out if you CAN help doesn’t mean you know with 100% certainty you will solve the person’s problem perfectly. When dealing with people, there are few guarantees. What you want to know is if you can help them through a certain situation. Doctors don’t give guarantees, and attorneys know it’s unethical to give them. Because so much is unknown. You just want to know, “Can I help on this? Can I get them closer to their goal?”

Do you want to help them? You have to find that out. Some customers or clients just aren’t worth the headache. Are they going to be calling you at all hours? Will you have to track them down for payment? Will they treat you or your staff poorly? Will they do what you need them to do for you to both succeed? Gotta figure that out.

Do they want your help? It’s laughable how rarely people actually ask this. They look for buying signals, or assume, or just send over some information without asking, “Do you want my help?” Asking that one question will lead to more closed business than said Jedi mind tricks.

And…you want to find out in that meeting if this person qualifies for your help. Can they choose you? Can they pay? Will they pay? That’s the crux of what you want to know. In B2B situations, there may be a few more, but essentially, this is what you want to discover.

Now, the questions you need in your toolkit.


The Questions You Need

This is why you’ve read this far. Here we go.

I break these down by categories and put them in the order I typically ask them in a consult.

Commentary included.

Questions about their thinking and my positioning








  • What are you looking for in a (fill in the blank – attorney, consultant, software product, etc…)?
  • I can’t be the first person you talked to. Tell me what you’ve heard from others.
  • Sounds like you haven’t found what you’re looking for.

I ask these to get my head around what someone wants in a solution or the expert they’re hiring. Maybe not what they need, but at least what they believe they want. If I don’t know this, I won’t know if I want to help them, or if I’m the right person to help them.

Quick example: people hire attorneys for a variety of reasons, but often they want someone who will A) fight for them, B) be available and communicative, or C) fix the mess the last attorney made. Knowing which one they want determines what said attorney shares in a consult.

These questions also ferret out if competition is in play, and why said competition hasn’t been hired. These are things you want to know if you’re a solo business owner, or on a large sales team and having to enter everything into Salesforce for your manager.

You position yourself and your firm in that meeting based on the answers to these questions.

Questions about the situation

  • Why are you here today?
  • How are you hoping I can help?
  • Tell me what’s going on
  • What are you trying to do/achieve?
  • How long has this been an issue?

These aren’t going to be revelations to you, but they aim to open up the conversation on their situation. We want as much information as possible to get our hands around what the prospect thinks and what may be the root cause.

A lot of the situation is about understanding the GAP between where people are – personally, financially, emotionally, strategically – and where they want to be. Often, they’re buying a bridge to get them across that gap.

Questions about what’s really going on

The questions here are designed to unpack those above. These have to be tailored by industry and market, but they’re almost always some version of the below:

  • Tell me more about that
  • What does that mean?
  • Why?
  • How did you end up here?

The aim here is NOT to solve the problem, but to understand the real issue. It’s also not necessarily to educate the prospect, but for now, you.

Questions about costs

We want to understand the financial impact of the prospect’s situation, whether what’s happened up to this point, or what’s at stake. Why financial? Because it’s measurable vs. other factors, and money is the unit of exchange we trade in. This may involve a little math on your part, which is fine, as long as you’re using the prospect’s numbers.

The below need to be tailored to the situation and market.

  • How have you tried to address this?
  • What has this cost to date?
  • What will it cost if this goes wrong?
  • What happens for you and the company if this goes well?

Questions about what’s at stake

It’s easy to believe money is the only thing at stake. Nope.

Often, non-financial factors drive people. Clout or status. Being right. Sleeping easier at night. Working less. Feeling more secure. Questions like the below help you get there:

  • What if this doesn’t get resolved? Or doesn’t get resolved the right way?
  • Why is this so important?
  • What does this mean to you?
  • If you get the outcome you’re talking about, how does that impact you? Other than in dollars and cents?

It’s okay to get personal. It’s why people buy.

Questions about alternatives

  • Why not ___________?
  • You know you could __________. I’m curious why you’re not doing that.
  • What about the other ___________ you’ve looked at? They are good at this, right?

Every time I suggest someone ask these questions, they look at me as if I have 2 heads and say, “But I’m giving them an out.”

To which I reply, “They knew they had an out when they started the conversation. You’re asking these to understand why they aren’t opting for one of those options.”

You want to take alternatives off the table. For both of you.

Questions about commitment

  • Is this a nice-to-have, or a must have?
  • Is doing nothing an option?
  • Why not?

Before we get to discussing money (which is really much simpler than these sorts of questions), we need to know, “Is this person all-in on solving this problem?” If not, there’s really no point in talking money.

Questions about moving forward

I’ve only got one for you:

  • Do you want my help?

Get this one answered in the affirmative, and everything hereafter is details.


Why this matters

Most people are PUSHING their products or services by detailing what they do, how they do it, and their accolades.







Guess what? Everyone else is doing the same thing.

As a result, prospects can’t tell anyone apart. They can only differentiate on price, tenure, or the client list. Those may or may not work in your favor.

When you run a different type of meeting or consult, even if your products or services are the same, the prospect PERCEIVES you differently. And that makes you stand out.

They trust you more because you listen more.

They believe your diagnosis more because you have a better understanding of their situation.

They like you more because you’ve shown more interest in them.

Want to know one more thing?

They choose you more often because they trust you, believe you and like you more than their alternatives.

Take it to the bank.

It’s not hard. It’s just uncommon.


Adam Boyd