Questioning techniques - Not a dark art from a Sith Lord

The first time I truly understood the power of questioning techniques was during my first full-time job as a Mixer Suit Salesperson for a fashion retail chain in the UK—River Island (then known as Concept Man in the late 80s). While everyone else had general shop assistant duties, I was given the role of selling mix-and-match suits to customers. I suppose my Area Sales Manager, who hired me, saw a confident young guy and assumed I’d naturally be able to "sell ice to the Northern Territories" or "sand to North Africa."

Far from the truth! I was expected to approach complete strangers and start conversations. "Hi... can I help you?" The usual responses? "No, thanks," "No," or, in some cases, I’d receive a look so intense it felt like I was about to be incinerated by dragon fire—a proper Game of Thrones death stare. I loved every aspect of the job—except actually trying to sell suits. Then Christmas came, and my boss gave me an ultimatum: sell or be fired. Each Saturday, I had to total up the value of the apparel tags and report weekly sales figures. Up to that point, they had been disappointingly low.

The thought of losing my job—and therefore my income—was worrying. I needed to act fast. Determined to improve, I started going in on my day off to spend extra time practising my approach. But I still needed more insight. My first step was reaching out to my counterpart in another store, who happened to be the top salesperson in the country. What made him so successful? His advice was simple: talk about anything, add a little humour, and remember—it’s a numbers game. The more people you engage with, the greater the chance of making a sale.

But what did he mean by “talk about anything”? It wasn’t just about saying the usual, “Hi, can I help you?” Instead, it was about opening a conversation:

• “Hi, how are you?”

• Followed by a favourite British topic—the weather: “What do you think of the weather today?”

• Then leading into: “What are you looking for?”

The key difference? Switching from a closed question to two open ones.

The impact was immediate—my sales increased significantly! This, in turn, led to a promotion to Assistant Store Manager, then Store Manager, and eventually a management role in a flagship city store.

In the professional sales world, or for those aspiring to enter it, training often covers different types of questions—when and how to use them. Open questions (How, Who, Why, When, Where, What) encourage conversation, while closed questions (e.g. “Red is a colour?”) elicit a simple yes or no response, which can kill a conversation. In a sales meeting, the real skill lies in blending open and closed questions effectively, guiding the conversation towards the ultimate goal—a sale.

Over the years, many training sessions have focused on questioning techniques and their inextricable link to listening skills. I’d bet my last pound or Canadian dollar that if you asked any top sales professional, they’d say listening is the most crucial skill to master!

In summary, the ideal approach is:

1. Lead with an open question.

2. Listen carefully.

3. Confirm understanding with a closed question.

4. Follow up with another open question.

   
   

And the final question? Always ask for the order or confirm the next action

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