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21 Killer Sales Questions To Boost Your Confidence And Close Any Deal Faster

This week on the Wednesday Edition of Talk Business With Howard, the guest on the radio show will be David Newman. David is the author of the book, Do It! Marketing: 77 Instant-Action Ideas To Boost Sales, Maximize Profits And Crush The Competition. To listen to the live broadcast on Wednesday, May 15 at 11 AM/ET, click here. Or bookmark this page and listen to the replay when it is posted to the top of the page. Thank you, David, for being a guest on the radio show show and for the guest blog post. -Howard-

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David Newman - Do It! Marketing21 Killer Sales Questions To Boost Your Confidence And Close Any Deal Faster

As a marketing speaker and marketing coach, my clients often ask me for advice on sales. Naturally, this makes a ton of sense because the MORE and BETTER marketing you do, the FASTER and EASIER your sales process becomes.


Nothing frustrates me more than when my clients DO a lot of the great marketing we work on together ONLY TO BLOW IT during the sales process!
So… don’t let this happen to YOU.
Let’s talk about what you need to close the deal: the steps you need to get from the first solid marketing conversation to the final signed contract.
Depending on your particular business, this could take anywhere from 10 days from first contact all the way up to a year or more. The sales process can be a long and winding road.


And along the way, it’s all too easy to lose confidence, let your resolve and motivation slip, and eventually lose control of the sales process – which ends up in chasing the prospect, unanswered emails and phone messages, mounting frustration for you and your sales manager, and a sales pipeline that is gummed up worse than an Alaskan oil spill.
BUT there are several factors totally within your control that make your sales process go faster and easier – and some of these can even get you unstuck, unstalled, and moving again for sales opportunities that you had long given up on.


The most important factor within your control – by far – is asking smart questions early and often.
Think about it: delays in your sales process come from one main source…
You don’t want surprises on their end – and they don’t like surprises on your end.


Each surprise or question or unexpected element can add anywhere from a week to a month to your sales process – and you don’t want that.
Understanding this, you’ll want to ask your prospects some key selling questions early on in your conversations and throughout at every major step and milestone.


The questions you’re about to get are not your typical “sales robot” questions that your prospects have heard a million times – totally inept and inappropriate questions like “What keeps you up at night?” “What would it take to earn your business” and others of that stripe.


Rather, these are smart questions – they are process questions – they ask about your prospect’s real-world buying process. What’s important to them? Who are the players? What’s their buying culture? What will raise red flags? What ammunition will they need from you to make the whole internal political sales process go faster, smoother, and easier? Questions that get to the heart of the one thing that matters most: How do they BUY?
Let’s cover them together now so you can begin using these 21 killer sales questions to close more deals – more easily and more often. This will boost your confidence, restore your motivation – and help you get your sales mojo back!


1.    If you were to decide this is a good idea, how do you buy things like this?

2.    How do you implement?

3.    What should I know about your timing? Signoffs?

4.    When do you budget for things like this?

5.    Do you think this deal is going to work?

6.    What’s missing or what should we add?

7.    Are you going to pitch it?

8.    What else do you need to see from me?

9.    Can I help you put together some numbers?

10. Do you have some numbers I could include?

11. Who else besides you will be making this decision?

12. Are “they” going to like it?

13. WHAT are they going to like?

14. WHAT are they going to push back on?

15. What else is going to be in our way?

16. How would YOU respond to that?

17. What answers do you need from me to so you’re prepared to answer their questions?

18. How much detail do YOU want?

19. How much detail will THEY want?

20. Are there any surprises we should be prepared for?

21. If this were just you and me, how excited would you be to move ahead on a scale of 0-10?
Hint: If they answer 9 or 10 – you’re good; If they answer 7 or 8 – ask, “What would need to change to get us closer to 10?” If they answer 6 or less, you have a problem. Go for no with “I don’t think we can make this work. Do you?”


Bonus idea: Dan Pink, author of To Sell is Human, offers the following pair of “irrational questions” to help you overcome a negative response at any point in your sales process and sell more effectively:


  1. “How ready are you to [take the desired action], on a scale from 1 to 10, where 1 means not ready at all and 10 means totally ready?”
  2. Next, ask your prospect, “Why didn’t you pick a lower (yes, lower) number?”


This will get them to reveal all the reasons buying your product or service might not be such a terrible idea after all. And you’re back in the conversation. Brilliant!
Be relentless and follow up like a friendly bulldog.
Never let an active prospect get more than 10 days away from you.
Always show up in their world like a happy squeaky wheel: Circle back. Send more value. Ask more questions. Offer more engagement. Invite further dialogue. Come back with more ideas to genuinely help them.


More and better and faster sales will follow.
I guarantee it.


David Newman is a marketing expert, professional speaker and founder of Do It! Marketing, a marketing strategy firm dedicated to making thought-leading entrepreneurs and executives more successful. David’s book, Do It! Marketing: 77 Instant-Action Ideas to Boost Sales, Maximize Profits, and Crush Your Competition is available at Free resources are available online at Contact David directly at or call (610) 716-5984.


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