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10+ Open Ended Questions Every Sales Rep Should Ask

Asking great questions is an art, skill, and science

Good Morning and Welcome to The First Follow Up of 2024. It’s officially time to follow up with all of the prospects that told you to ‘check back next year’, and start every email with “Happy New Year”. 60% of prospects say ‘no’ 4 times before saying yes, which means you’ll need to get a no every week in January to get the ‘yes’ in February. 😁 

In today’s Follow Up:

  • 11 open ended sales questions❓️ 

  • A sales pitch tip 🗣️ 

  • Sales around the internet 🤌 

  • Sales jobs, LinkedIn & a sales meme 😂 

10+ Open Ended Sales Questions to Ask

At its core, therapy sales is all about listening and asking questions.

Listening is important, but today, we’re talkin’ questions.

Asking great questions is an art, skill, and science.

A good question can help you get leads, negotiate, and close deals.

Questions come in every shape, size, and form, but using open-ended questions is one of the best ways to extract the most info from your prospect. Rather than getting a simple “yes” or “no”, they require the prospect to think deeper about their answer and provide additional details.

So today, we’ve got 11 open ended questions to start using in your sales meetings.

Let’s dive in. 👇️ 

Rapport Building 🤝 

Rapport building is all about connecting and building trust with your prospect. The right question can help uncover what matters most to your prospect, and how you can use that to build rapport.

What needs to happen today to make this meeting/time a win for you?

This is a great question to break the ice at the beginning of a meeting. Use the answer to guide the rest of your call.

I saw [insert recent company news/announcement]. Were you involved in that?

This requires research before the meeting but is a great way to show that you’re invested in them. Find news like recent fundraising, acquisitions, notable hires, or notable new customers they signed.

What does a typical day look like for you?

This question should help you understand how your prospect would personally interact with your product or solution in their day-to-day. And since most people love talking about themselves, this will typically open up the conversation.

Discovery 🤔 

Discovery happens at every step of a sales cycle. It’s all about uncovering information that can help you drive the sale and close the deal. Asking the right questions is the key to good discovery.

Can you walk me through your current situation/process?

Understand their current situation and the problems they face. If their current situation isn’t *that* painful, they may not have a need.

Can you tell me more about the problem you’re trying to fix?

Dig into their pain points and the severity of the situation. The more detailed and severe the problem, the more need they have.

Have you tried to solve this before? If not, why now?

This is great for understanding the timeline and severity of the issue. There’s often a recent change at their company that you can use to drive the sale.

If you didn't solve [insert the problem], could you live with it?

This is a great question to measure their pain and urgency. If they can live without a solution, their pain and urgency is low.

If you could wave a magic wand, what would the perfect solution look like to you?

This question can be used for selling almost anything by swapping out the underlined half of the question. It forces the prospect to visualize the solution they want and helps you understand their point of view.

Qualifying Questions  

Qualifying questions help you understand if a prospect is a good fit for your product or service. If they’re not, you’ll save a lot of time by disqualifying them early in the conversation.

As my old sales manager said: “Disqualify early and often”. Unless your pipeline is empty… then you talk to whoever will take your call. 🙃 

In an ideal, but realistic world, when would you have this solution implemented?

This question will take care of the ‘timeline talk’ for you. Once they’ve given you a firm date/time, use it to build urgency in the deal.

How does the evaluation and decision-making process typically work at your company? 

Use this question to understand what will need to happen on their end to get the deal done. It’s your job to keep them accountable and make sure things are moving.

If you found the perfect solution, what blockers would prevent you from moving forward?

This can be a great segway into the ‘budget talk’, or closing questions. In most cases, even if the solution is exactly what they’re looking for, you’ll still have objections to overcome (budget, pricing, stakeholder buy-in, etc.). The sooner in the process you can uncover those blockers = the better.

What is your favorite part of the sales cycle?

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Sales Tip of The Day 💡 

Try front-loading the negatives in your sales pitch.

🗣️Our tool does take a few weeks to implement, but that’s because it will replace all of the tools your team is using and save you $X per year.

🗣️This house is the most expensive on the list, but that’s because it’s in the nicest school district and was fully renovated last year.

When you bring up the negatives in the front of your pitch, you’re able to combat and justify them at the end.

Sales in the News 🗞️ 

Cool Jobs at Cool Companies  

Checking in on LinkedIn 👀 

Are “late night party leaves” a thing….? 🤔 

Sales Meme of the Day

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