Sales Tweak of the Week #3: Ask the Hard Questions

This week I’m at Fort Benning, helping our soldiers get back into the workforce via American Dream U and I am blown away and inspired by our troops. I wanted to send you this very relevant sales training Tweak of the Week. Massive success comes from massive action. You need to make time your slave—so when you’re out on the road, use technology to keep up and stay connected; don’t use “out of office” as an excuse to take a break.
This week’s strategy is about asking hard questions.

3. Ask the Hard Questions
It is my experience that salespeople miss opportunities to build trust due to not asking the hard questions. I was on a sales call with one of my top representatives and sensed that the decision maker wasn’t buying the presentation. I interrupted with, “You don’t believe a word he is saying, do you?” The client started laughing and said that was exactly what he was thinking. You have to ask these types of questions: “How do you feel about our price?” “How do you feel about our terms?” “Why would you do business with me, when you have dealt with our competitor for so long?” If you don’t get the answers to the hard questions, you will find yourself not closing deals and never knowing why.

And in the real world you will lose out for not knowing the right questions to ask at the right moment. So identify what those hard questions are for yourself. Then drill asking them. The mother of all learning is repetition. The number of times you are able to repeat those questions, the more you will know the information, own it, and make it second nature to you. That second nature presence will propel you into massive success and domination in your industry.

I’d love to see the hard questions you ask or have been asked in the comments below.

Be great, nothing else pays,


  • John W says:

    There is a difference between good profits and bad profits…
    The Ultimate Question Fred Reicheld

  • William Ballard says:

    Great Post Grant!

    Keep the inspiring and motivating messages coming (They are changing lives ;))

    In order to be successful in business you have to be willing to deal with and do the hard things in life. It is the only way to achieve greatness.

    Massive action on the hard areas creates massive success soft areas.

    Here is a hard question to ask: “Are you ready to make a decision to change your future today?”

  • Warren says:

    Hi Erick,
    Your comments are dead on. I love the specific examples you gave on your feedback to help tweak what was said to come across best to the customer. Here’s one I have just started. “If the price was the same, wouldn’t you rather get our product?” If yes, then, “How much more would you be willing to pay for the quality/convenience/customer service of our product?”

  • Jaxi West says:

    If my price is the same, what’s your biggest reason for not wanting to sign this contract?

    This isn’t about you. ‘why wouldn’t you provide me the business’. This is about them not understanding the value of your product/service or something else, but it’s rarely about you.

  • Jaxi West says:

    Hi Bobby

    You are making it personal and putting the prospect in an awkward situation to explain what it is ‘about you’ that they are not moving forward. Keep this to business.

    Yeah, they are buying you so to speak, but they are really buying the product, so keep it about the business/product.

    Better suggestion:
    “What is it about our company, or they way we have discussed this product that is making you hesitant to sign this contract? I want to cover anything that you aren’t comfortable with.

    Let the prospect talk.

    If you sense they aren’t giving you candid answers or still would not sign the contract, THEN come back with:

    “If it’s me, be frank, I won’t take it personally, I just need to know so I can bring my boss in to finish this with you, and we will find another rep to handle your account.”

    Show you are real, not just about ‘making a sale/money’, you really want to help them

    Also, keep your sentences more natural in conversation.Your sentence was long and you will loose the prospect by saying so much in professional talk (ex: price is supported by the guaranteed multiplied ROI)

    Better suggestion:
    Make sentences short and get verification after each big ‘potential issue’ :

    “Okay, so you like the product and you know what it will do for your business, right? Is there anything about this product you don’t like?”

    “And we went through the price, how over time it’s going to save you time and/or money, right?”

    “Do you really see this? Does the price make complete sense to you for the ROI you will get over time?”

    “What would be the one reason you wouldn’t sign this contract, today or any other day this week?”

    Didn’t intend this to be a critique- just tips to help.

    Your learning from the best – so you are gonna have tremendous success!

  • Filiberto says:

    Fees are…For a total of $….

    Please let me know if the price is fair to

  • Jaxi West says:

    Hi Erick,
    not sure if you are joking or not, but
    “do you really think it will magically appear?”

    Geez, talk about insulting your prospect!

    You don’t win by insulting. You win by complimenting or uplifting.

    “You seem like a smart/sharp guy, not the type to leave this up to chance when you will already be going through an emotionally tough time if this really did happen. I am sure you won’t want to be stressing out about “how am I gonna pay for this”.

    “So let’s just get you set up on this, so this is in place and you don’t have to ever think about this again.” You’ll be really glad you did. Many of my clients let me know days later that they were glad they got this because it was a mature, responsible thing."

    Again, not sure if you were joking,

  • Kerwin says:

    If my price is the same, why would you not provide me the business?

  • Bobby says:

    We have determined that this product will satisfy your needs and that the price is supported by the guaranteed multiplied return on your investment, what is it about me that is keeping you from moving forward today?

  • Erick says:

    If your spouse died today how would you pay the funeral? Do you really think it will magically appear?LISTEN for x amount a month i can get rid of this problem for you fair enough?

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