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Pop quiz! Which would you rather do: Have an insightful conversation about your business with a good friend, or be grilled about your business needs by a salesperson?
Most of us would rather have a good conversation — yet when it comes to sales calls, many salespeople have been trained to fire off a list of questions, hoping to make a sale. The result? Poorly qualified leads, missed opportunities, deals that never close and a lot of wasted time.
“Time is a limited resource,” said Tanya Gray, author and sales coach at Getting Clients Today. “If you don’t ask qualifying questions, then you’re spending time on unqualified leads — and that’s a disaster. The salesperson who is wasting time on a tire kicker is just sabotaging their sales career.”
To Umar Hameed, CEO of No Limits Selling, the ability to ask the right questions stems from building a quality connection with the buyer. “The stronger that relationship is, the more we have permission to ask interesting questions,” he said. “Because when we don’t ask the right questions, or we don’t have enough of a relationship built to allow that person to answer them honestly, it takes us away from the sale.”
Making sure your sales team is being effective when questioning prospects isn’t about having a list of perfect qualifying questions for your company — it’s about training them to focus on and engage with their buyer.
Otherwise, they may be missing out on valuable information that would allow them to turn a ho-hum sales call into a chance to have a meaningful conversation with the customer — and get better sales results.
#1 Develop a Guide for Meaningful Conversation

When Gray works with clients to develop guideline questions for their sales teams, she works backward from the value the business brings to the customer, then designs a series of questions to take the customer on that journey. “I literally do it step by step,” Gray said. “But if I don’t ask them questions to ascertain how much time they’re losing right now and what else they could be doing with that time, I’ll never make it important to them.”
Gray cautioned against using the questioning guide as a firm script. “One client I worked with had all these pre-qualifying questions, but they weren’t conversational,” she said. The result was that the company’s salespeople were trained to listen for specific answers and move on to the next question, rather than engaging the customer on a deep enough level to uncover real needs.
When a salesperson is just working down a list of questions that may not seem to be logical in the course of the conversation, the subliminal message that the customer gets is that the salesperson isn’t really listening, Gray said. “Then the salesperson loses the opportunity to drill down deep enough in that conversation, and they never get that deep information about the customer’s needs.”
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#2 Train Your Team to Use that Guide Meaningfully

It’s not as easy as just supplying your team with the right questions — you need to make them understand why it’s important.
Hameed frequently sees this problem in the clients he works with. “There are two parts of sales excellence: One is knowing what to do, the other is actually doing it,” he said. “A lot of salespeople get into a stalled state when they don’t follow the prescribed thing they should do because of fear or reluctance or anxiety.”
As a neuro-linguistic programming (NLP) practitioner, Hameed works with salespeople to get to the bottom of what’s causing them to stall. “What I’ve found is that underneath every single behaviour is a belief that controls it,” Hameed said. If a salesperson is resisting asking the right questions, it could be due to a fear of being seen as rude or pushy — beliefs so deeply held that the person may not realize they have them.
“At one level, they want to ask the questions, because that’s how they were trained,” Hameed said. “On the other level, they may have been raised to think that only people with poor manners ask personal questions.”
Gray agrees that a lack of self-awareness can keep a salesperson from making lasting changes in their behaviour. When trying to train a salesperson to listen more actively and ask better questions, she suggests recording the sales call, then asking the person to listen to that call and identify the behaviours that showed when they were and were not listening.
The next time they make a call, Gray would have them choose specific active listening behaviours (like clarifying their statements and repeating their concerns back to them), then make note that they done them. “The first part of behavioural change and training is self-awareness,” she said.
#3 Changing the Dynamics of the Sales Call
Armed with a questioning guide focused on their company’s value and active listening skills focused on deeply engaging with a customer, the dynamics of the sales relationship change.
“If you take people on a journey of awareness and self-discovery through questions that are logical, by the end of it they’re just desperate for the solution,” Gray said. “At that stage, you haven’t had to sell anything.”
By Jessie Kwak. Originally published on Pipedrive Blog
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