May 17, 2025 | Read online
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Everyone says “there are no stupid questions”
I disagree.
There are plenty of stupid questions. Just ask one of my favorite coaches and post game interviewees Greg Papovich 😂
Well, maybe not “stupid” because people probably get offended by that these days, but definitely lazy.
Here are three common sales questions and statements I hear all the time and I think are lazy and we need to stop:
- Tell me about your business
Companies spend thousands, if not millions of dollars on Marketing to tell the WORLD about their business and you’re not going to spend the 5 minutes it takes to review that information before the call?
- What are your priorities?
You can’t do a quick search using AI to understand what the main priorities and challenges are for someone in their position at a company/industry like theirs so you can ask clarifying questions instead of generic ones?
Any my absolute least favorite….
- What keeps you up at night?
My daughter. Next question.
We need to do better or our value/relevance as sales professionals is going to continue to erode.
Let’s talk about how.
(p.s. JB Sales Members, this is the first week of the “Member’s Only” section of the newsletter so make sure you scroll down to check it out for upcoming events.)
TACTICAL TIPS:
Anchoring
We’ve all been told to make sure we ask “open ended” questions, especially throughout the Discovery process.
I’ve always said that the only group of people that answer “close ended” questions with open ended answers are…Sales reps.
We’re the only ones who, when asked a “yes” or “no” question, will say yes or no and then go on for another 10 minutes about something. Most other people will simply say “yes” or “no.”
However, open ended questions aren’t always the best types of questions to ask. One of their challenges is that they tend to put a lot of pressure on the person being asked. They need to:
- Process the question
- Prioritize from a long list of answers
- Translate abstract thoughts into a clean response
Think about it. When we ask an open ended question like “what are your priorities?” people usually have multiple different priorities for different things they’re working on and they change all the time.
That’s why when we ask that question we usually get vague answers.
We need to evolve our open-ended questions into anchoring statements looking for clarification instead.
“In psychology and behavioral economics, anchoring refers to the cognitive bias where people rely heavily on the first piece of information offered (the "anchor") when making decisions. In negotiation, it’s often used to influence pricing, but in sales conversations, it applies to framing and hypothesis-driven discovery.”
(see more information about anchoring with my customized JBs Content Assistant GPT).
For instance, instead of saying something like “tell me about your priorities” you should do a little homework and say something like “We’re working with other VPs of SaaS in the SaaS industry and they are telling us their main priorities right now and moving into next year are X, Y, and Z. Are those similar to yours or different?”
The client’s desire (and ability) to correct or confirm and add more detail are far greater than they are to answer an open ended, vague question.
(P.S. - If you want to learn more about how I prepare for meetings, develop a hypothesis and come up with better questions you’ll want to join me for this week’s Free Training Friday where I’ll be covering the exact process and tools I use to prep for meetings.)
TECH/RESOURCES:
Questioning Skills
I don’t care how “experienced” we are in Sales, we can all learn to ask better questions.
Below are some books I recommend to help improve your questioning skills.
I recommend buying and reading each of them but I’ve included a link to the summary and key tak-aways for each book using JBs Content Assistant GPT that includes links to buy each book.
- GAP Selling by Jim Keenan (summary)
- A More Beautiful Question by Warren Berger (summary)
- Questions That Sell by Paul Cherry (summary)
BONUS TIP:
If you want to know if you have a good question, always make sure you have a REASON for your question.
Assume every time you ask a client a question they are going to push back on you and say - “why do you need to know that?”
If your reason isn’t about helping them figure out the problem then it’s probably a “qualification” question that is more about you trying to figure out what you can sell them. If your reason is about them then it’s probably more of a “Discovery” question that helps both of you learn about the problem.
SALES FROM THE STREETS:
How My Questions Got Me a Job at Xerox
My first job out of college was with DeWalt Power Tools. I was under the “Sales” umbrella but it was really more of an Event Marketing position.
I didn’t really start learning about Sales until I got my second job at Xerox.
However, I might have never gotten that job if I did what most other reps do in an interview by focusing on their pitch versus being curious and asking questions.
I was 22 years old going on my first interview for a new position at Xerox that a friend of mine had recommended me for.
I updated my resume, put on my 3-piece suit from Men’s Wearhouse, shined up my shoes and headed to their office expecting to meet with the hiring manager.
When I got there and went into the room for the interview, there were 6 executives lined up on the other side of a long board room table with one seat on the other side of the table waiting for me to sit in it.
To say I was a little intimidated was an understatement. Thankfully I was wearing a dark colored suit so they couldn’t see the sweat stains that were starting to form under my armpits.
When I sat down, I barely had a chance to pull out my resume before one of the executives slid a copier spec sheet across the table to me and said: “Here’s our newest copier model. You have 5 minutes to go back out into the lobby to learn about it and come back in and pitch it to us.”
Ummm…excuse me?
I knew absolutely zero about copiers other than you pushed a green button on the top of the machine and paper came out the bottom.
Also, have any of you ever seen the font size on a copier spec sheet? It’s like .02 font and none of it makes any sense to a normal human being.
I don’t love reading that much and I have a terrible memory so I knew there was no way I was going to be able to read that entire sheet and come up with a presentation worth a shit in less than 5 minutes.
So, I went back out into the lobby, threw the spec sheet in the trash and waited 4 minutes and 59 seconds to go back into the board room.
When I went back in, here’s how it went:
Them: “alright kid, what do you got for us?”
Me: “I’m not sure actually.”
Them: confused looks on their faces
Me: “I do have some questions for you though.”
Them: “sure, fire away.”
Me: “do you use copiers in your office?”
Them: “yes”
Me: “on a scale of 1-10, how happy are you with your existing copiers?”
Them: “7”
Me: “What would make it a 10?”
Them: “if they scanned to email, did duplexing and had a lower cost per page.”
Me: “I have a showroom around the corner with some copiers that scan to email, do duplexing and have a lower cost per page. Would you be interested in coming by to check them out?”
There was an awkward silence when I asked that final question as they all looked at each other with raised eyebrows. Then one of the executives asked me if I would step back outside and give them a minute to talk.
When I came back in they offered me the position and asked how soon I could start.
There was obviously a little more to the story than that but that’s how I got my job at Xerox and it taught me a valuable lesson.
It doesn’t matter how great your product is or how perfect your pitch is, it’s about finding what matters to the person you’re talking to and focusing your solution on what they need instead of what you think is important to them.
The only way you can do that is by learning how to ask better questions and be genuinely curious about their responses and wanting to learn more.
By the way, that 1-10 question is still one of my go-to’s because you can apply it to almost anything.
(Level up your questioning skills today by joining the JB Sales Membership using coupon code “JBNEWSLETTER for 20% discount)
Speaking of membership……
MEMBERS ONLY
Last Month’s Free Training Friday (Intro to AI in Sales) was a huge hit and got great feedback so I’ve decided to bring in my AI coach (Chris Briest) to do a 3 part workshop series on AI for Members only.
Use the link to Session1 above to register for one or all three.
Also, I’m bringing back my AMAs but instead of doing open AMAs that anyone can join, I’m offering 15 minute 1:1 sessions to members only. There’s only a couple left so sign up now if you want some 1:1 time with me to help address some of the challenges you’re facing right now.
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ADDITIONAL WAYS YOU CAN LEVEL UP YOUR SALES GAME
- The JB Sales Membership 2.0 is where you’ll get access to my live training, workshops, AMAs and OnDemand catalog so you can level up your sales skills every day! 3000+ Sales pros have already joined. Are you next?
- The industry-leading Make it Happen Monday Podcast where you’ll get insights and inspiration from some of the most interesting and influential people in the world of Sales and business. (this is where you’ll hear the Guy Kawasaki episode on May XYZ)
- The JB Sales YouTube channel with practical tips that you can apply immediately to drive results along with interviews and content that is guaranteed to get you to think differently.
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