The Question To End ALL Conversations

Written by Jeff Bittner

7 Min Read  

Sometimes, one question can change the entire dynamic of a conversation by eliciting information that otherwise would have been left unsaid or missed.  If you have ever heard the statement, “Finish Strong” then this particular article will apply well to you.

In my years of teaching questions inside both Customer Support and Sales Teams, so many times we spend all of our energy on how we open and then maintain the momentum through the conversation, that we forget to “Finish Strong”.  I have seen good conversations come to an abrupt end where one last effective question could have opened doors that remained closed throughout.  

So what if there was a question that could be used in most situations that would allow you to gain any last piece of information that could be useful to know but may have been skipped.  The great thing is, there is such a question and if you begin to use it in your life, you will see what I mean.

I have used this question not just in sales, but in all of the following instances:

  • Interviews
  • Dealing with new vendors
  • Conversations with Customer Support
  • And much more

This ONE question will give you insight into what may have been overlooked and what may be still important that you did not or did not know to ask about.  It allows the conversation to end with either you getting confirmation that you have all you need or it opens up an opportunity for you to gain additional knowledge.  Here is the question:

So you come to the end of the conversation and you bookend it with this EVERY time you can…

“What question did I not ask, that I should have which would be helpful for me to better understand…(fill in the blank)”

Let’s break this down and walk through why it is so effective.

“What question did I not ask”.  

This question within the question does a few things.

  1. Hands the reigns back to them
  2. Forces them to assume one was not asked that should have been.  
  3. Validates that you know they potentially may have more to offer

“that I should have”

Humbleness is a powerful tool.  Don’t assume you know everything or assume that the expectation is that you asked all the key questions.  By saying this you admit that you might have missed something important you are asking for their help in identifying it.

“which would be helpful for me to better understand…” 

If the conversation had gone well up to this point, regardless if it is sales or support, if a connection is made, individuals want to be helpful.  Asking this closing part while stating it’s to understand again validates that they have the knowledge you may still want, and not know it.

Inside our Braintrust Academy, we train individuals and sales teams on how to make sure that your conversations are the most effective they can be, and asking the right questions at the right time is an important part of that equation.

Not long ago I had a call with a  potential vendor who was not doing a great job explaining their product in terms that pertained to my needs.  We were looking for specific SAAS-based software and this individual was sharing bells and whistles I could have cared less about and I needed a very specific solution.  I asked all kinds of questions trying to ferret out if the software did what I needed and could not get the answer I needed.  The call came to a close and I ask this person, “look I don’t think this is what we are looking for but let me ask…

“What question did I not ask, that I should have which would be helpful for me to better understand if this software is right for us?”

The person said, “Great question and yes actually, it might be helpful to know that it does X, and Y.”  I just sat there.  Both features were exactly what I needed this software to do.  Seriously, I felt that I was crystal clear about what I wanted so I asked why they did not share this earlier?  They apologized and admitted they should have.  We ended up using them and it has been a great fit for us.

This question is not about being an “Aha, gotcha” question.  It really should be used with a curiosity mindset and trust me, I have never had anyone say, “What a dumb question.”  They always say, “That’s a great question, I’m going to steal it from you.”  

For more on how we help individuals, small businesses, and Enterprise corporations, check out our Braintrust Academy at and find out what thousands of others just like you are doing to have a more effective customer conversation.