3 tips on asking good sales questions

During my first week at Magestore, I enrolled in a LinkedIn Learning course called Asking Great Sales Questions by Jeff Bloomfield, thinking the course would help me prepare better for my new role.

It’s a good course overall. However, for experienced salesmen, they might think this course is a bit basic for them. And even for me, as a newbie, many parts of the course sound pretty common sense and intuitive. Yet, I was still able to find some solid advice and insights from the coach, which I will sum up 3 most useful points that I learnt in this story.

1. Goal confirmation

One of the mistakes many salespeople make is to go too granular too quickly in trying to understand the customer’s goals. It’s not wrong to try to know what goals your customer is trying to achieve. However, good sales people don’t ask their customers what their goals are because customers might give you unfocused answers, which confuses everyone in the meeting or lead the project to a wrong direction.

Instead, what you should do is tell them what they think their goals are and ask them to confirm whether that is true to 1) control the conversation and 2) keep both you and the customer stay focused. Once the goal is clearly identified, you’ll be able to ask laser focused, effective questions around the problems, which eventually will lead to the need for a solution.

Jeff Bloomfield, trainer of the course, said that most of the time throughout his years of experience working with C-level executives, leaders mainly have one or more of these 4 top common goals (in no particular order): 1) grow revenue; 2) increase profitabliity; 3) shorten sales cycle; 4) create and foster a culture of high performance.

You can frame your goal confirmation questions around these goals or list down the most common goals in your industry and apply this tip in the next meeting you have with customers.

2. Create connection

When starting a conversation with customers, most salesmen are taught to built rapport first before moving on to the main business.

Unfortunately, that often leads to salesmen asking textbook rapport questions like: “I see you like tennis. I like it too!” or “You went to university XYZ. I have a cousin who went there too!”. There you have rapport, right? Not quite. Because so many people have used these opening lines inelegantly, customers are now sick of them and know that after this part, you’ll continue with a product introduction just like everyone else.

That’s why Jeff thinks textbook rapport questions no longer work, and instead, it’s sometimes useful to just be vulnerable and authentic to customers, making it easier to gain empathy and build trust because trust is not just built on credibility but also the ability to connect on a personal level.

What if you’re not naturally good at small talks and showing your raw, vulnerable self? Jeff recommends that salesmen who rank high in terms of expertise and credibility but low on ability to connect would be more suitable for serving existing customers.

3. Problem quantification

I wish I could sum up this point well but I couldn’t. So I’ll insert an excellent example made by Jeff below so it’s easier for you to get this point.

A recent survey determined that 58% of qualified deals were put into sales pipeline tracking systems, such as salesforce.com across industries that ended up going to the dreaded no decision.

You (the salesman) would ask the prospect: “When you look at the ratio of qualified deals in your company’s pipeline, is that percentage close to your experience?”

Now, let’s say they say: “No, not really. We only have around 40% no decision deals in the pipeline.” They might think they just pushed back on your insight and stopped your questioning in its tracks.

The reality is, you’re just getting started. Now that you have a bonafide prospect-driven number to work from, you can continue on with the quantification process.

You: “Oh, I see. Well that’s certainly better than the industry average, Mr. Customer. Just out of curiosity, what is your average sale worth in revenue terms?”

Customer: "Well roughly $10,000.

You: “Okay, so how many deals does your company have in a given month?”

Customer: “Roughly a hundred.”

You then have what you need to really drive the impact of your questioning relative to the problem that you know that they’re going to want to address.

You: “Okay, so Mr. or Mrs. Customer, so you average a hundred deals in process per month, but 40%, or 40 of those deals end in no decision, is that correct?”

Now, they already told you that it was, so if they disagree, they’re actually disagreeing with themselves.

Then the real impact to your business of those 40 deals is actually $400,000 in lost revenue per month. Which was simply the 40 deals going to no decision times the $10,000 average per deal value.

Next, you might say something like, so the reality is even a modest 10% improvement, or just four of those 40 deals per month, actually saying yes, versus going to no decision, could add $40,000 directly to your bottom line. Does that sound about right to you? Get them to agree. If they don’t, go back through the numbers until you settle on a solid number that they agree with.

Do you see what we’re doing here? We have provided valuable information to them using third party insight, then we see if their experience tracks with this, and then finally, we assign a value to that information based on deeper questioning.

By following this questioning model, you’ve allowed the prospect to tangibly quantify what’s at risk to them in their own words with their own example.

A prospect isn’t looking for solutions unless they perceive a tangible, concrete problem that needs to be solved. By validating the impact of the problem, and quantifying the cost to the prospect, you elevate the urgency in their mind to solve it.