The Power of Asking Uncomfortable Questions

The Power of Asking Uncomfortable Questions

Welcome back to the 27th issue of Disrupting Conversations! 

I remember sitting in a sales seminar several years back, listening to some of my contemporaries speak prior to my turn on stage. There were some really interesting takes on the topic of trust, but one in particular caught my attention: “Don’t ever ask a question you don’t know the answer to.” 

Unfortunately, I will never forget that moment; it was the worst piece of advice I’d ever heard. 

It reminded me how misguided and misaligned some sales training can be. I remember feeling angry. As coaches, our job is to know our sh!$, and this was the recommendation? 

Since then, I’ve doubled down on my mission to help empower sales professionals to become more courageous and purposeful in the questions they ask. And yes, the most powerful questions are often the ones you don’t know the answers to.  

In sales—and life in general—the most impactful questions are often the ones that make us squirm a little. The ones that create a little tension, but ultimately help us get clarity. So, let’s talk about why—and how—we should do this for our prospects.

Remember, good questions build trust. Competency only matters after the trust has been built.  

Breaking Sales is my podcast to connect with those who are ready to break free from the chains of old sales methodologies that don’t work.

Title of Episode: Building Credibility with Questions

🎙️Think of your favorite comfort food, restaurant, music, or sneaker. What would happen if someone tried to convince you to try a different snack, or go to a different place to eat? 

Say they invested heavily in telling you how good the alternative was, and listing out all the impressive features and benefits. How do you respond? Do you listen objectively or with biases? 

You already know the answer. There is very little chance you would try something new. So why would it be different for your prospects, teammates, or kids? How many times have you had the answers to the test (what the prospect needs) and led with your credentials, but the prospect did nothing different? 

In this episode, Pam and I break down the pitfalls that sales professionals run into with credentials and offer a better solution for building real credibility: asking the right types of questions in the right way.

The Power of Uncomfortable Questions

Imagine you're in an exploratory conversation with a prospect. You’re realizing that the prospect may benefit from your services, but there's a potential roadblock—their boss has a long-standing relationship with your competitor. Your urge to progress a sale might push you to pitch your services and expertise, hoping to convince the prospect how you’re better. In truth, how many times has this approach worked? Is this really the pathway to success? The answers are clear: few and no. 

But what if you took a different approach?

What if, instead of focusing on your own agenda (to advance a sale), you asked the questions that truly serve your prospect? Questions that help your prospect to do the more meaningful thinking right there in the conversation. Think about it, there are two parts to this puzzle:

1. Could the prospect benefit more from your services?  

2. Are they ready, experienced, and/or equipped to champion your services? 

👉 If they would be better served by your offering, it’s important not to get lost in the euphoria of that realization. Why? 

Because #2 is where the real trust and conviction lie. Here’s some questions to help you understand how and if your prospect is ready to go to the mat for you… 

1. "How do you think your boss will respond to this proposed change?"

2. "What risks do you see for yourself if this doesn't go well?"

3. "What potential gains do you see if it does go well?"

4. "Do you think the potential gains outweigh the risks?"

You may be hesitant to ask these questions. They require you to step back from your own needs and wants and truly align with your prospect’s thinking. But they serve a crucial purpose: they help your prospect think through their situation more thoroughly, and they demonstrate that you're genuinely interested in their success, not just in making a sale.

This approach goes hand-in-hand with a concept we talk about all the time: not labeling situations as "good" or "bad." When we approach conversations with an open mind, free from preconceived judgments, we create space for these powerful, perspective-shifting questions.

The result? A deeper, more meaningful conversation. One where your prospect feels truly heard and supported. And one where you gain invaluable insights that can help you tailor your approach and ultimately provide better solutions.

👉 Remember, the goal isn't to make people uncomfortable for the sake of it. It's to ask the questions that need to be asked—the ones that lead to real understanding and meaningful progress.

So the next time you're in a crucial conversation, whether it's with a prospect, a colleague, or even a family member, challenge yourself to ask the uncomfortable questions, even—and maybe especially—if you don’t know the answer. You might be surprised at how much you—and they—can gain from it.

Thanks for reading!

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