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The Power of Open-Ended Questions in Sales & Sales Management

Posted by Tony Cole on Thu, Sep 15, 2022

Conversation is much more pleasant than interrogation.  This is important for an effective coach to remember because after two or three questions, a salesperson is going to feel like they are being attacked.  This is also true for prospects.

Great coaches ask great questions like “Bill, how did that linebacker get past you?”  If the coach tells him, “You’ve got to keep that linebacker from getting past you”, does Bill learn anything? Chances are he already knows he shouldn’t have let this happen.  By asking the right question and reviewing via the post-call debrief (similar to viewing the game film together), Bill will better analyze his own actions and discover what he failed to do. 

Note that the coaching question, “Bill, how did that linebacker get past you?” is an open-ended question.  In sales and sales management, it is best to avoid asking “yes” and “no” questions. They are not effective during the sales process or when working with and coaching salespeople.  Phrase your questions as open-ended. This will help to engage the salesperson, make him/her think before answering and get him/her involved.

Let’s say that you have a sales person who frequently fails to uncover the competition during the sales process.  You could ask him/her, “Did you find out about the competition?” or “When you asked the prospect about those firms being considered, what did he say?”

Can you tell which question is going to get a better answer and provide more insight?  Open-ended questions make coaching sessions more conversational and more engaging.  Open-ended questions will help the salesperson identify the gaps between what they are doing and what they should be doing. Open-ended questions gather more information.  

Let’s parallel this to a conversation with a sales prospect. Your salesperson has secured a first meeting and over the phone, identified a specific issue or pain that is the reason for the meeting. Are they equipped with a meaningful series of open-ended questions that are conversational in nature, so that the prospect does not feel like they are being interrogated?  Here are some of the open-ended questions we recommend in a first meeting sales conversation:

  • What has to happen today so that you feel that this was a great meeting?
  • Tell me more about that (assume you have uncovered some problem or issue).
  • How long has that been going on?
  • What have you done to fix it?
  • When you spoke to your current provider, what did they say? or
  • What has your current vendor done to make this problem go away?
  • What happens if you don’t fix this?
  • What is this problem costing you?
  • Is that a problem?
  • Do you want to fix it?

While there are several Yes/No questions at the end of that series, for the most part, that questioning technique is conversational and open-ended. The salesperson is genuinely interested in the answers to these questions so that they will understand if they can help the prospect.

Now back to the coaching parallel. Once the gaps between expectation on the call and actual execution during the call are uncovered with your salesperson, you need to gain agreement from the sales person that there is a gap before moving to the next step. Sometimes the salesperson will not see this immediately. Upon agreement, identify specific solutions and objectives to improve performance.  The key here is to identify solutions that will help the salesperson learn and grow. Do not just set data or results-based goals. 

An example of a learning objective would be to improve the percentage of contacts to appointments.  An increase in this percentage would indicate improvement in an initial-call skill. Improving the quality of initial calls would be a measurable objective because there would be a corresponding increase in opportunities created.  Be sure to document the identified, agreed-upon objectives and note the specific action items and corresponding necessary behaviors so that you enhance the salesperson’s probability of success.


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Topics: open ended sales questions, asking sales questions, asking the right questions

Why Great Salespeople Are Like Curious Children

Posted by Tim Shanahan on Thu, Sep 06, 2018

Child: "Can I have ice cream for dinner?"

Parent: "No."

Child: "Why?"

Parent: "Because ice cream isn’t good for you."

Child: "Why?"

Parent: "Because it has no nutritional value."

Child: "Why?"

Parent: "Umm … I guess because its makers wanted to make sure it was tasty."

Child: "Why?"

Parent: "So, they could sell more of it."

Child: "Why?"

If you’re a parent, you know this scene all too well. And if you’re an honest parent, you know that at times all those incessant questions can be downright annoying.

But you also know that asking those questions is a critical part of the child’s developmental process. Children have no built-in knowledge base, so asking questions – and getting answers – is the way in which they begin to make sense of the world around them.

It’s similar to great selling, actually – minus the “annoying” part.

Great salespeople always ask the extra question. They know that the more knowledge they can gather about the customer’s situation, the better they can serve him or her.

6463827_xxl kid hand raised-1

Ask, Then Listen

It’s not enough, though, to just fire away with question after question. Great salespeople listen – really listen – to the answers their customers give.

That may sound simple, but if you’ve ever watched a locker room interview after a big game, you’ll see how often people who are paid to ask questions – sportswriters – fail to do this.

Locker room interviews don’t always produce thoughtful questions.

Reporter: “Johnny, tell us about your game-winning hit.”

Player: “Well, I was just looking for a pitch to drive. But I really think the key was the week I spent in a sweat lodge before the game. That really cleared my mind.”

Reporter: “Uh huh. So, what are your thoughts about tomorrow’s matchup?”

We exaggerate here to make a point. But often writers are so intent on getting through their list of questions (and getting back to the press box to file a story before deadline) that they fail to listen to answers that, if they followed up on them, would give them a much better story.

What’s the Customer Really Saying?

At PrecisionLender, our software is designed to help bankers have these better conversations with borrowers by supplying them with insights from our virtual insights coach, Andi®. So, consider this hypothetical situation …

Let’s say you’re trying to win a deal with a borrower for a $3,000,000 commercial real estate loan. But the borrower says he’s planning to go with a competitor bank that’s offering a rate that’s 50 basis points lower.

Some bankers throw up their hands right then. The deal doesn’t meet their target so, then, oh well.

But great bankers start asking questions. “What can you tell me about this deal?”

Perhaps then you find out how, exactly, the competitor bank is offering such a low rate. Maybe it’s because part of the loan is guaranteed. That could be the end of the story. But the great banker channels his inner annoying child and asks about the guarantee: Who’s providing it? What are the details?

In this hypothetical scenario, the guarantor is the borrower’s father-in-law. Again, this could be the end of the line. But the great banker – unlike the mediocre sportswriter – is listening to the answer, and he detects that the borrower is less than thrilled at the prospect of “owing one” to his father-in-law. So, the great banker asks more questions and finds out that the borrower would be more than willing to cut a few months off the length of the loan if it means he can get the same low rate and not have to rely on his father-in-law’s guarantee.

By asking questions and listening to the answers, the great banker has gathered enough information to turn the tables and win another deal for his bank.

With this approach, the only people truly annoyed are the bankers working for the competition.


About Tim

As SVP of Enterprise Client Success for PrecisionLender, Tim’s significant career experience in commercial banking makes him uniquely qualified to partner with bank executives to increase revenue and profitability, as well as improve the customer experience and colleague experience. Prior to joining PrecisionLender, Tim spent over 10 years at Citizens Bank (NYSE: CFG) in various line and support roles, including National Sales Director - Franchise Finance, Chief Operating Officer - Commercial Finance, Director of Commercial Banking Strategy and Growth, and Head of Commercial Excellence. In addition, Tim served as Director of Credit Product Management for BMO Harris Bank.

Topics: Qualifying skills, asking the right questions


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    Anthony Cole Training Group has been working with financial firms for close to 30 years helping them become more effective in their markets and closing their sales opportunity gap.  ACTG has mastered the art of using science-based data and finely honed coaching strategies to help build effective sales teams.  Don’t miss our weekly sales management blog insights from our team of expert contributors.


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