"Sell me this pen."
Asking the right questions to maximize the customer relationship and accelerate the sale.
Any sales professional who has been around for a while may have heard the age old interview question: “Sell me this pen.”
Anyone who jumps into talking about the pen and the way it writes immediately fails.
You’re supposed to ask questions:
What do you value in a pen?
How do you like the pen to feel in your hand? How do you want it to write?
What do you use pens for in your daily life?
Then, based on their answers, you start talking about the pen in front of you and selling it to the interviewer.
Every good introductory sales call should lead with questions, not solutions.
Now we all know, pens are pretty simple.
If you’re selling B2B SaaS, medical devices, real estate, or engineering hardware, you’re in a more complex world.
You need to be able to frame your questions in a way that helps you holistically understand your customer’s ecosystem, challenges, and start connecting the dots about how you can help.
Before formulating questions make sure you have a solid understanding of the challenges your product or services solves and/or how it can help your prospect accelerate your growth.
Then spend some time on your client’s website, reading their 10-K and earnings data, learning about what they are focused on.
Finally, try to understand the priorities of the person you’re meeting with and how they’re compensated. Use your questions to figure out how to make them the hero.
Now, you can start drafting your questions:
What are they doing today? What are their challenges with that current approach?
What are their goals?
Where do they see the org going in the next 1-3 years. How can you help them move towards this direction?
Are there any organizational changes that will impact decision making and buying power?
Are they using any competitive tools today? What has been their experience with them?
Their CEO has talked about X priority - how do they see that impacting the decision?
Sell with your ears, not with your mouth and watch the deal accelerate.
✨ AI Magic ✨
The coolest thing is that AI can now take a lot of the pain out drafting smart prospecting questions and asks some pretty remarkable questions.
Try using Claude to write your prospecting questions for you using the following formula:
“I am a [your role] at [your company] trying to sell [your product] to [your prospect’s title] at [your prospect’s company]. Please give me five discovery questions specific to [prospect customer].
🔔 Ring the bell! 🔔
Katie Winterfield is an Account Manager at ATI focused on onsite healthcare and just crushed a deal!
Customer Industry: Light manufacturing, pharmaceutical, automotive
Problem: The customer had needs in occupational medicine, injury prevention and ergonomics.
How she won: This was a true case of leveraging strong relationships to land and expand. Katie worked with an existing client and used her trusted relationship to branch into a new location. She spent time learning about their specific needs in this new facility through her corporate client contacts before approaching them to do business together. Through mutual trust, she was able to grow ATI’s footprint and staff an ergonomist for their office/lab buildings.
Creative Selling: Katie’s style is true solution selling. She focuses on building a relationship so she can get to the root of the needs of the client. From there, she was able to provide a custom tailored solution that actually solved their problems. That relationship and industry know-how can go a long way.
Katie’s Inspiration: She is inspired by her former boss and mentor Sheila Denman!
*We want to celebrate sales leaders, wins, creative ways you’ve used AI, and share anything else this community might benefit from.
Comment or DM us and nominate your sales peers, share your wins, or anything else!
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