The Holiday Franchise Company


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‘Sell me this pen…’

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A common sales question asked in job interviews for decades.

I was asked this question at age 17 whilst interviewing for a role selling water coolers. I spent 15 minutes keenly explaining to the interviewer how a cheap-looking plastic biro would be the best thing they had ever bought. I believe the phrase ‘life-changing’ was even mentioned! Whilst the interviewer probably appreciated my efforts, it was not necessarily the answer they had been waiting for.

So, what should my answer have been?

This ‘pen riddle’ was made prominent in the Hollywood film, The Wolf of Wall Street, based on the turbulent real-life story of Wall Street stockbroker, Jordan Belfort. Whilst his life as depicted in the film was controversial to say the least, the real-life Belfort is a self-made multi-millionaire and regarded by some as one of the world’s greatest ever salespeople. 

The pen riddle – posed by Leonardo Di Caprio playing Belfort’s titular character – features several times throughout the film. In the final scene, a reformed Belfort has become a motivational speaker and sales coach. Stood before a large audience, he hands the pen to a startled onlooker he urges them to, “sell me this pen.” Just like 17-year-old me, the candidate starts reeling off reasons he thinks the pen is desirable. Clearly dissatisfied with this response, Belfort takes the pen from him and hands it to the man sat next to him who also starts extolling what he believes to be the pen’s benefits. Still not content, Belfort again hands the pen to someone else and the same thing happens. As the camera pans out over the packed auditorium, the question reverberates on unanswered in our minds. In a later televised interview with the real-life Jordan Belfort, an audience member – clearly as desperate as we are to find out the real answer – puts the question back to Belfort

“The real answer is, before I’m even going to sell a pen to anybody, I need to know about the person, I want to know what their needs are” Jordan Belfort

Belfort continues explaining there is no point unleashing a myriad of information that you believe is relevant until you understand why they want it. It is stabbing in the dark and a waste of your time. A seller could try and sell every benefit they believe the pen has, but they might not be relevant to the individual client. It is much easier to sell something once you have identified a need for it!

Have 30

“The only one rational thing can you do when someone asks you to sell me this to pen, is to start asking them questions. So, tell me how long have you been in the market for a pen?” Jordan Belfort

This is exactly the approach we take at The Holiday Franchise Company in our accredited Sales Through Service Training. It is essential when our franchisees speak to potential customers about their holidays, they find out their needs before making suggestions. By asking questions we can discover; what is important to them; what they like doing; and crucially, why they want to go.

I have worked as a sales coaching in the travel industry for over a decade and have consistently found that the best sellers always start a conversation with great questions. When asked about their favourite questions, top sellers always say, ‘what’s’ and ‘why’s’. These sorts of questions open out the conversation and provide them with crucial information about the customer and their needs. This then enables them to come back to them with a holiday itinerary individually personalised to them.

Two ears and one mouth

Of course, there is no point asking questions if you are not listening to the answers. In our training, we talk about ‘active listening’, where we encourage franchisees to focus on what the customer is saying. By taking note of these ‘tiny noticeable things’ a franchisee can personalise the itinerary, then highlight the fact they were paying attention when presenting, e.g. “I know you love golf, so I have purposely chosen a fantastic hotel with one of the world’s best golf courses next door”.  It is a proven fact that if a customer has a personalised itinerary that is right for them, they are much more likely to book.

‘You can make more friends in two months by showing interest in others than you can in two years by trying to get others interested in you’ Dale Carnegie

Questions are not just there for finding things out. Think back to a first date – the key to building an initial relationship with someone is to ask questions and simply show an interest in them. Questions help you build rapport with customers and get them to like you – and people buy from people they like! This is also a particularly good way to gain repeat customers – when I was an agent some of my regulars were more like friends than customers.

What is more, conversation makes the process much less corporate and robotic and makes it more fun and enjoyable. We are lucky too that travel is literally the best thing on earth, it is not like we are selling insurance or double glazing… (or pens!).

So, by asking these questions you are having more fun, building rapport and finding out key facts that help you offer their perfect trip. Which in turn is maximising your chances of converting the enquiry into a booking.

This is just a glimpse of our Sales Through Service Training, where we have developed a proven sales process which if followed ensures our franchisees convert more bookings.

Oh, and for those wondering, I didn’t get the job!

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