Asking the RIGHT Questions that Actually Close the Sale

Do the questions you ask in your sales conversation give you information that actually moves the sale forward?

Asking the RIGHT questions is CRUCIAL to winning the sale.

And most people are losing sales by wasting each precious one on either information they don’t really need or digging into pain.

  • Instead, when you design your questions around uncovering whether someone is a fit or not for you – you’ll win an absolute minimum of 2x more business
  • I’ve gone on at great length about pain digging questions…so for the sake of variety, let’s focus on the other type of questions that aren’t good for a successful sales conversation.
  • They’re the types of questions you would ask someone if you were already working together and you were solving their problem.
  • You’re going straight into expert/education mode – usually because you’re genuinely excited about and an expert in your craft.
  • But they’re not the kind of questions that give you the information you need to be effective in a sales conversation.

So, for example a health specialist might be asking questions about time of day the person eats, frequency of meals, types of food they currently eat, how much exercise they get, etc.

The answers to these questions give you no idea on whether their goal is realistic or they’re someone you can help.

They’re in-the-weeds questions you would ask once you’re working together and crafting a plan for their goals.

So, by the end you’re unable to assure them of how you’d be a good fit to work together.

Instead, you would want to focus on questions like:

  • What are you struggling with right now?
  • What have you tried to solve this before?
  • What’s your goal and expectations with someone like me?
  • On what timeline? Etc.

Because when you get answers to these questions like:

  • I can’t keep up with all the activities my kids want to do because I’m overweight
  • I’ve tried a couple diets but nothing sticks because it’s so drastic so I yo-yo
  • I would love to lose 20 lbs in the next 4 months

Then you would know this person is a good fit for you and very clearly be able to differentiate yourself (or “sell”) to them.

You’ve got the information you need to customize your “pitch” by emphasizing “I’m not about fad diets, drastic sacrifice and pain to achieve your goals because those things aren’t realistic or sustainable. I’ve got a few simple ways to get you back in hiking/kayaking shape to join your kids on all their latest adventures just like (give client examples). “

Another example could be a copywriter or marketing expert.

They can get pretty excited to dig into “Who is your target audience/ideal client? What are your differentiators/marketing angles? What’s your overall brand/vibe that you want?”

But again, these aren’t going to help you understand what their goal is and how you’d help them reach it.

When you get to the end of the conversation and you try to “sell” yourself you would be guessing at what they wanted to know and hear.

Instead if you focus on questions more like

  • What do you need help with?
  • What’s your overall goal?
  • What timeline?
  • What have you tried to achieve that goal before?
  • What was the experience/result?


The answers to those questions could sound like:

  • A paid funnel for my high ticket offer
    I’d like to get to at least 5 new clients/month in the next 90 days
    I’ve tried a webinar before with high attendance but had very low conversion to booking calls
  • Then those questions will give you a higher level picture of whether this is someone you can truly help.
  • AND the valuable information you get from those questions will allow you to position yourself better as their ideal solution – instead of guessing at what their ideal solution is because you don’t have the right info.

You’re able to say – “That’s an extremely realistic goal! Sounds like there might be a gap in the content of the webinar we can tweak as well as the copy on the page to get you what you’re looking for. This is an area I have expertise like with (give client examples).”

This also makes the best use of your time.

Your prospect has a limited patience, time and attention span and can easily grow tired and irritated with the conversation when there’s too many questions (you really don’t want to ask more than 10 at an absolute maximum).

So, you want to focus ONLY on the questions that allow you to understand if they’re a good fit for you.

All my clients see an immediate increase in sales when we revise their questions like this.

Re-positioning your questions with the intention of uncovering whether someone is a fit vs. getting lost in the weeds or uconvering pain is something I focus on in my 6 month Matchmaker Sales™ Mentorship.

I’m helping solopreneurs sell something that is $3k+ 2x-10x the number of people saying “yes” to their offers (most start seeing results within a few short weeks).

  • In the mentorship, we’ll uncover how to effectively win sales without pain, pitching or pretending to be someone else.
  • We also dive deep on how to “pitch weave” so your prospect never feels ‘sold’ and you never have an extended period of time in the conversation where you’re the only one talking (AKA “pitching”).
  • And I also show you how to help people overcome their own objections without ever getting defensive.
  • I even help you with tweaking your pre-qualification process so that you’re getting better prospects on your calls in the first place.
  • You’ll walk away with a custom plan for your sales calls that fits your personality, audience and product like a glove to consistently and predictably convert 80% of your leads.

If interested in my mentorship, please book a call and we can discuss the details to make sure it’s a fit for you 🙂


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