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Hey Reader,
Can I ask you a weird question?
When was the last time you went on an interview?
The reason I ask is...
Whether it’s been years or just last week, you probably noticed something:
The company interviewing you trying to see if you were a fit for them—as expected.
But they weren’t necessarily as prepared for you to vet them in return.
Sales calls are no different.
Prospects expect to assess you, your product, and your company. But they don’t often anticipate you flipping the script.
They don’t expect you to evaluate them.
That’s where confident salespeople set themselves apart.
Confident sellers operate with a mindset of equal footing. They don’t chase prospects.
They qualify opportunities.
They set the tone early by making it clear: “This is a two-way street.”
It all starts with a simple shift in how you approach the conversation.
Imagine opening a discovery call with this:
AE: "Would it be okay if I asked you some direct questions to see if we’re even a fit for your goals? Not everyone is, and I want to be mindful of your time."
Cool no?
This one sentence does so much:
- It positions you as a professional, not a product-pusher.
- It creates curiosity and respect.
- It sets the tone for a partnership, not a one-sided sale.
Once you’ve set the tone, you’re free to ask deeper questions that truly qualify your prospect.
Here are a few examples:
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Goals and Priorities:
- Can I ask what specific goals are you hoping to achieve by using a tool like ours?
- Curious, how have you been addressing [specific problem] up until now?
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Challenges and Friction Points:
- If I can be direct, what’s been the biggest hurdle in solving [problem] with your current approach?
- To what extent have you tried other solutions before? Curious what didn’t work?
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Decision-Making Process:
- Who else on your team would have to weigh in on a decision like this, even if you say no?
- Would it make sense to discuss the criteria you'll use to determine if this is the right fit?
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Budget and Timeline:
- I can't imagine there is budget allocated for a solution like ours currently. Is that wrong?
- How quickly do you need to see results, or is this not a big priority for the team right now?
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Cultural or Philosophical Alignment:
- What’s most important to you should we decide to move forward?
- Not sure how to ask this, but how open are you to trying a different approach if it delivers better results?
The moment you start asking these kinds of questions, the dynamic shifts.
You’re no longer just another vendor trying to “make the sale.” You’re now a professional evaluating whether this opportunity is worth your time and effort. T
his creates respect, positions you as an expert, and—most importantly—ensures that you’re working with prospects who are genuinely aligned with what you offer.
Want to get better at flipping the script?
Go on a job interview. Seriously!
The next time you’re in that setting, pay attention to how the interviewer expects you to sell yourself.
Then, start asking them tough questions:
- What makes this company a great place for someone in my position?
- What’s the biggest challenge you’re facing as an organization?
- How do you define success for someone in this role?
You’ll notice how the dynamic changes when you start vetting them. And you’ll realize just how powerful this technique can be in your sales calls.
Use the questions above to guide the conversation. Notice how it feels to approach the call from a position of confidence and partnership. Not only will you have more fun, but you’ll also find yourself closing more deals with clients who truly value what you bring to the table.
Stay curious!
Charles
📘P.S. Version 2 of my Actionable Discovery Guide is releasing soon! Get on the waitlist here for free bonuses and special discounts! Can't wait to help you crush 2025!
Charles Muhlbauer
Find me on LinkedIn
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