Tough Questions Sales Professionals Must Ask...and Why


Every successful sales process needs to start with what might be called the “tough questions.” You know them—questions that are so direct they make you sweat and shake in your shoes, that can make you so uncomfortable you’re wary about asking them. 


Why? Because you’re afraid you might offend the buyer. Or, perhaps you fear the buyer will not like you once you ask. Remember that people buy from people. If you offend your buyer or give them reasons to not like you, you might be hurting or killing your chances of winning the sale.


What questions do this to you? Well, here are a few I thought of:

  • Is there an approved budget for this purchase?
  • How much is it? (i.e. your budget)
  • Who has final approval authority in your company to buy products like ours?
  • Who are gatekeepers? (i.e. people who can block the sale whether or not they have approval authority)
  • What potential objections to our products and services are out there?
  • Who can sign a contract?
  • Is there a defined process for buying products like ours? What is it?
  • Will you draw me an organization chart showing gatekeepers and decision makers?
  • Will you introduce me to the key decision makers?


If you think asking these questions and others like them is uncomfortable in the early stages of the sales cycle, rest assured they only get harder as the process moves forward. And having the answers is absolutely essential to your success. Which brings us to a cold hard fact of the sales profession: if you don’t ask the tough questions during the initial discovery phase, you’re unlikely to get answers later on. When you really need those answers to proactively make sure you have the right influencers on board, identify and address objections, and close the deal, it may be too late to get them. At best, you can come off as begging or sounding unprofessional. At worst, your deal can be derailed by gatekeeper issues you didn’t even know about.


So, how do you overcome the fear of asking the tough questions upfront, during discovery?


First, you need to change your mindset from that of a sales professional to being a person who is  helping another person solve a problem they are experiencing. You are not “selling” this prospect, you are helping them with a big problem they have. You have the solution, and you are working with your prospect to better understand how to help them resolve their issue. (If this is not the case, you may want to revisit the qualification questions for this prospect to make sure engaging with them is a good use of your time and effort.)


Second, you need to realize you aren’t insulting the buyer by asking these questions. Again, you are helping them bring a solution to their company by explaining to you how the buying process works, including budgets and who is likely to be involved. 


Approaching the discovery phase with a collaborative toolset like a Discovery Wizard, that lets you share the questions you want to cover with your buyer before you meet with them, means you aren’t just dropping these tough questions on your buyer when you meet. If your buyer came to you through your outbound lead tools like an ROI Calculator on your website, Discovery Wizard is already populated with that information. The organized series of questions in a Discovery Wizard, as opposed to a list on a yellow pad, shows you are professional, organized, and educated as you seek to gain a better understanding of the buyer’s issues, pains, and goals. Seeking to better understand the buying process and who the decision makers are are natural extensions of this discovery process.


With the tools and technologies available today, asking the tough questions doesn’t have to be the challenge it has been in the past. I find that a Discovery Wizard helps get tough questions answered and, by integrating with your existing SFA systems, gets you started and keeps you on the right track for a successful sale.


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Michael Nick is Vice President of Growth and Strategy for ValueCore. He has published several bestselling books, including ROI Selling, Why Johnny Can’t Sell, and Amazon’s Top 10 Business book, The Key to the C-Suite. Michael has been mentioned and published in Selling Power, The Huffington Post, Sales & Marketing Magazine, and featured in Top Sales World magazine. Michael was named for four straight years in a row as a top 50 “Most Influential” people in sales and marketing in the world by TSW. In addition, Michael ranks in the top 50 top sales gurus from Sales Guru. To contact, call 262.338.1824 or email him at [email protected].


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