Using Questions to Take Control of Sales

A few years back, I was sitting in my office at AdRoll when I received a phone call I’ll always remember. 

It was right around 8 AM and the call was from a local number, so I assumed someone had been locked out of the building and was trying to get in. This wasn’t the case, though. It was the founder of a startup that sold sales rep calling software. He wanted to speak with my friend Ben.

It took me a second to figure out why Ben was the person he was calling for. I knew it wasn’t Ben’s job to buy this type of software, so what made this kid think that he was calling the right person?

Putting two and two together, I came to the conclusion that this founder had simply typed “AdRoll” into LinkedIn and clicked on the first profile that showed up. Being first alphabetically, Ben’s profile appeared and this founder put him on his list of calls for the week. 

Being 8 AM, though, the office was pretty empty and Ben hadn’t come in yet. I told the founder that he was unavailable and we hung up the phone. 

What that founder didn’t realize, however, is that I was the one responsible for buying sales software. Since I was running Sales Operations (along with my team of mid-market closers), I’d been actively looking for some new software, too. 

It goes without saying that he had no idea I was his buyer. It also goes without saying that we never met and we never bought. 


The Value of Customer Interactions

I included the story above to illustrate an important concept: every prospect interaction is valuable. 

As a salesperson myself, I’m always excited to talk to other salespeople. I’ve literally spent hours on the phone conversing with telemarketers just to see how well they pitch (I know, it’s not exactly normal behavior). As you can imagine then, I was more than willing to give this founder a few minutes of time, especially when I was in the market for what he was selling. 


If he’d simply asked me who I was, he’d have learned instantly that I was the person he wanted to talk to. The problem, of course, was that he didn’t ask any questions. 

And it’s questions that can turn every interaction into a learning experience. If you know what to ask (and how to ask it), you can learn a lot about your target customer and what it takes to sell something to them.

Don’t ever make assumptions about who you’re talking to. Whenever possible, ask who you’re speaking with and what their role is. Even better, ask them questions that help you to gauge whether or not the company needs your product. 

For example, even if I had been a Head of Marketing for AdRoll when I received that phone call (assuming he asked who I was), he could have carried on the conversation by asking about the efficiency of our pipeline. He could have asked whether or not we were using certain pieces of marketing software that were compatible with his. He could have asked any number of questions to get any idea of what our company needed at that point.


Asking Questions to Identify Your Target Customer

A repeatable sales process is built by targeting one specific type of customer at a time. If you’re able to get on the phone with the VP of Sales at an advertising company that has roughly 100 employees, there’s a good chance that other people in the same position at similar companies will be interested, as well. 

Why? Because they all struggle with the same problems. They all go through the same issues on a daily basis. 

If you can figure out why that first VP was interested in talking to you, you can use that information when you reach out to their competitors. 

The way that you figure this out is by asking them directly:

How happy are you with your current sales software?

What kinds of problems are you having with it?

On a scale of 1-10, how happy are your reps with the current software?

Where is new sales software on your list of priorities?

Of course, it’s important not to make the conversation feel like a game of 20 questions, so be natural. But the better you’re able to assess the needs of the person you’re talking to, the better you’ll be able to sell to them and their competitors. 


Asking Questions to Lead the Conversation

If you’re making cold calls all day, having a list of questions next to you is going to be much more valuable than a scripted list of statements. People get sick of being pitched at all day. Asking questions, on the other hand, is a way to let your prospect know that you’re interested in the problems that they’re struggling with.

The best sales calls feel less like cold calls and more like free consulting sessions. Like a good consultant, though, you need to wait until you understand the problem before you can provide a solution.

There are four main types of questions I like to have on-hand for sales calls. Each of these has a different function in the conversation:

Closed Questions

Example: Have you eaten today?

Closed questions are “yes” or “no” questions. When you ask these types of questions, prepare for the response to be close-ended. 

These questions work best when you already know the answer. They also work well if you phrase them in terms of a correction (i.e “You haven’t eaten today, right?). They’re a great way to bring a certain problem to the front of a person’s mind, to remind them that they have the problem without stating it outright. 

Open Questions

Example: How do you decide what to eat for lunch?


When you ask closed questions, it’s likely that you’ll receive longer, more specific answers. They leave a lot of space for your prospect to articulate their feelings on a certain topic.

Pay close attention to how your interlocutor responds. Their answers will give you insight into both the company itself and the buyer’s role in that company. 

Scale Questions

Example: On a scale of 1-10, how hungry are you right now?

Scale questions can give you an idea of whether or not your customer even needs your product.

These work very well if you’re asking someone to answer on behalf of someone else. If I was talking to the Head of Sales, I could ask them, “On a scale of 1-10, how interested do you think your CEO is in…?”. Their answer might help me to determine whether or not the company is a good fit. 

Rank Questions

Example: Rank these four sandwiches in order from best to worst. 

Ranking questions enable you to determine your customer’s priorities. 

If I ask a founder, “Say you had to choose between a great calling solution or a great CRM software, which would you pick?”, I’ll be able to figure out how likely they are to buy my product. Like scale questions, these are great for analyzing whether the company is worth pursuing as a client. 


Never Stop Learning About Your Customers


Remember, the more you know about your customers and their organization, the easier it’s going to be to gain traction. Whenever you get the opportunity, ask your customers as many questions as possible. 

Even if they don’t plan on making the purchase, you can learn a lot about how a company and their competitors operate, the types of problems they deal with, how they decide to buy a product like yours and why they’re not interested. Ultimately, asking better questions will help you close more deals. 

Christopher Zacher