Consult Carson 6/7: “What fact-finding questions should I ask?”

From today’s mailbag: “My manager tells me I need to ask ‘fact-finding questions’ but I’m not really sure where to get started. What questions should I ask?”

Carson: Your success in any given sales transaction that hopefully begets a business relationship hinges quite a bit on first contact and how you choose to follow (or not follow) a selling process.

Once you are granted access to ask questions and have a conversation, thanks to maneuvering through the gatekeeper as a friend rather than foe and by capturing enough attention to advance from the decision-maker, it is time to start gathering clues. Like Sherlock Holmes and Doctor Watson, you must advance stealthily but methodically; one false step and you’re toast. Proper and proficient use of your time, however, in ascertaining your customer’s needs and wants, their current method of doing whatever you’re trying to convince them to change (either non-existent or a competitor) and what they do and don’t like about that current choice will determine practically everything going forward.

1. Don’t ask a question just to be asking a question. Many times, I’ve heard sales reps just ask a myriad of questions with no real purpose. Certainly, it does help to know how long they have been in business, but right now I don’t necessarily need to hear a litany of their entire career. Be able to inquire without interrogating; be able to figure out what you really need to know to uncover where you can be the solution to their problem.

2. Think big picture. Where does this customer want to go? What are potential new forays they can make? What’s something they are missing in their current arsenal? To uncover these, think about what you have to offer. What does your solution often cure? Try to find any potential holes or points of discontentment in your customer’s current way of doing business. Then find out what they have done to address it, or why they have not addressed it. Not only will you need to overcome objections like lack of belief and price, but you will need to uncover hidden objections as well – past failures in the very line of work you’re in – to actually proceed.

3. Ask the questions that will allow you to prove return on investment. Find out the worth and value of a proper solution. Utilize this information when you are justifying the price and cost of your solution – “Mr./Mrs. Customer, you indicated previously that landing a new client/ remedying your efficiency issue/ the cost of acquiring a new employee, etc., was $$$$. By applying our tried and true strategy, you increase the probability of landing that client/ resolving that issue by XXX% for a mere $$$$$ investment. That said, just how quickly do you make a profit?” Work with them to uncover the solution you want them to uncover.

4. Realize that a customer’s primary objection is lack of belief. In reality, it’s the only one; it’s the very reason they throw obstacles like price and partners out to you. If they believed this would work, they’d be selling their partner and they’d be spending the money to fix a problem they have already identified (or that you’ve helped them find! Elementary, my dear Watson!). Knowing this, and knowing you don’t really sell anything – they make the decision to buy! – ask the questions that will lead the horse to the water that they will be enticed to drink. You want them to draw conclusions, so make them see the inadequacies of their current comfortable (or uncomfortable) ways of mediocrity or failing. Show them that it’s possible to “have it all” – to dive into the new forays or ventures they want to eventually pursue.

5. Check with them along the way. Remember, we don’t close every customer the first conversation. We rarely do. That said, ask the questions that show you’re there as a trusted advisor. Point out the current state of the union and ask, “How may I be of additional service?” “How may I further support you at this point?” “What additional questions exist, or what can I shed further light on so we may provide the added efficiency we discussed?” Open-ended questions, not questions that end in a yes or a no, that position you as someone with their best interests at heart and make clear you are offering respectful service rather than a hard close will make the environment conducive to the sale.

Ask the questions that will enable you to overcome stated or hidden objections before they even surface. Use your experience and mistakes in sales conversations to figure out where you stumbled before. Odds are, asking more questions and having more facts would have and will enable you to solve the case of what specific combination of facts prompt your customer to respect you, trust in you, and buy from you.


Carson V. Heady posts for “Consult Carson” serving as the “Dear Abby” of sales and sales leadership. You may post any question that puzzles you regarding sales and sales leadership careers: interviewing, the sales process, advancing and achieving. You will also be directly contributing to his third book, “A Salesman Forever.”

Question submissions can be made via LinkedIn to Carson V. Heady, this Facebook page: , Twitter via @cvheady007 or e-mail at or you may post an anonymous comment as a reply to my WordPress blog at the bottom of this page:

Carson V. Heady has written a book entitled “Birth of a Salesman” that has a unique spin that shows you proven sales principles designed to birth in you the top producer you were born to be.

If you would like to strengthen your sales skills, go to

About cvheady007

I am a Christian, Husband, Dad, workaholic and author. Biography Carson Vincent Heady was born in Cape Girardeau, MO, graduated from Southeast Missouri State University and moved to St. Louis in 2001. He has served in sales and leadership across Microsoft, AT&T, Verizon and T-Mobile. Carson is best-selling author of the Birth of a Salesman series, the first book of which was published by World Audience Inc. in 2010. He released The Salesman Against the World in 2014, A Salesman Forever in 2016 and Salesman on Fire in 2020. He is also featured in Scott Ingram’s B2B Sales Mentors: 20 Stories from 20 Top 1% Sales Professionals. Carson is a 7-time CEO/President’s Club winner across 5 roles at AT&T and Microsoft and National Verizon Rockstar winner. He has been recognized as a top social seller at Microsoft and is consistently ranked in the top 25 sales gurus in the world on Rise Global. He is included among the Top 50 sales authors on LinkedIn. With over 330K social followers, Carson has also been interviewed on over 30 sales and leadership podcasts, by such luminaries as Jeffrey & Jennifer Gitomer, Jeb Blount, Brandon Bornancin, Sam Dunning, Larry Levine, Darrell Amy, Scott Ingram, Thierry van Herwijnen, Jim Brown, Sam Jacobs, Luigi Prestinenzi, Donald Kelly, Marylou Tyler, George Leith, Pat Helmer, Eric Nelson, Ron Tunick, Jeff Arthur, Mary Ann Samedi, Jean Oursler, Andre Harrell, Marlene Chism, Bill Crespo, Matt Tanguay, Josh Wheeler and Chad Bostick. He has also co-hosted the Smart Biz Show on EG Marketing Radio. His articles have appeared in several noteworthy publications such as SalesGravy, Smash! Sales, Salesopedia and the Baylor Sports Department S3 Report. Carson lives in St. Louis, MO, with his wife Amy and daughters Madison, Sidonia and Charlotte.
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