Bad Questions, Stupid Answers, and Wasted Sales Effort.


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The ebb and flow of selling hinges on your crafty ability to ask and answer key questions.

To be truly great at sales you need to be good at both sides of the question and answer process.

No matter how good you think you are, you always need to be refining the type and style of questions that you ask prospective buyers.

And this isn’t anything particularly new.

There are countless sales training programs that focus on helping us manage this questioning process better.

How to reframe a question. How to avoid answering a question. How to style a presentation so that we avoid potentially damaging questions that we don’t want to answer.

There is Sandler Sales Training, SPIN Selling, Dale Carnegie Training, Customer Centric Selling, Action Selling, Seductive Selling, and dozens of hybrid sales training systems from companies like Richardson, Miller Heiman, and Franklin Covey.

So you would think that with all the training and focus on the question -nd-answer process that we would get really good at turning questions into detailed opportunities that have a clear finish line.

Right? We would expect that our questions lead us to close the deal.

So why don’t they?

Why is it that we go through our qualification process, check all the right boxes in our CRM, and then up walking away from a conversation with a buyer thinking “Boy, that sure was a stupid answer….”?

We’re confused by the answers we get back from potential buyers. And too late in the selling cycle we find out that we’ve just wasted our time…

And it didn’t have to happen in the first place.

Too many times we forget about the most important part of the question-and-answer process.

We forget to ask if the questions being asked are even the right questions.

We forget the obvious — that bad questions always get “stupid” answers.

And calling them “stupid” answers isn’t really accurate. It’s probably a bit unfair. These are perfectly reasonable answers if you factor in the crazy questions that we love to fire off at our prospects.

  • We ask how soon the buyer is looking to make a decision when the buyer isn’t even sure what decision they need to make.
  • We ask if the buyer has a budget and how much it is instead of asking the buyer why they want to get rid their pain right now.
  • We ask “who else” the buyer is considering purchasing from without honestly asking ourselves if we can deliver on the buyer’s expectations.
  • We ask the buyer why they have objections to our solution instead of caring about the buyer’s success from the outset of the engagement.
  • We ask the buyer to invest in us when we haven’t invested in them.

And one thing becomes abundantly clear.

We’re wasting our sales effort.

We think that by doing what’s easy, we can avoid having the hard conversations. That we can half-ass empathy and still produce the outrageous success we want for ourselves.

We’re only fooling ourselves with our bad questions.

Our questions stay selfish, buyers find us annoying, the elephant stays in the middle of the room, and what could have been an amazing career is limited by our inability to love and learn.

And that just seems unnecessary.

Asking better questions solves the problem.

And maybe that’s not entirely right either.

Maybe it’s just about caring more.

Republished with author's permission from original post.

Dan Waldschmidt
Speaker, author, strategist, Dan Waldschmidt is a conversation changer. Dan and his team help people arrive at business-changing breakthrough ideas by moving past outdated conventional wisdom, social peer pressure, and the selfish behaviors that stop them from being high performers. The Wall Street Journal calls his blog, Edge of Explosion, one of the Top 7 blogs sales blogs anywhere on the internet and hundreds of his articles on unconventional sales tactics have been published.


  1. Dan: Although you’re a bit hard on salespeople, this is a great blog. I’ve met some–well, many–salespeople who are excellent at asking questions.

    Others are badly coached–told to ask questions like “What other vendors are your company considering?” As you point out, an idiotic question if you don’t know whether you are actually being considered!

    But the unsaid point is that many salespeople fail by not understanding what information they’re after to begin with–risks and opportunities.

    Instead, salespeople are offered a set of go-for-the-jugular questions, that annoy the bejeebers out of buyers because they’re used to hack away at closing the deal instead of methodically discovering the key information. “Hey, my boss told me that the shortest distance between two points is a straight line!”

    Would it be OK if I added this link to a related article, “The Right Sales Questions Will Get the Right Answers”? Oh, what the heck . . .

  2. Andrew,

    Great point. There are some emotionally intelligent creatures in the sales and marketing forest… 🙂

    While I am being somewhat “cheeky”, I do recognize that there are some great “questioners” out there.

    Link away my friend.

    Dan Waldschmidt


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