Careerfile: Simon Bailey, Winning Pitch

Simon Bailey was told he had 10 seconds to decide if he wanted to be a trainer. After seven, he said he would. Twenty years later, he’s more than made his mark.

What particular challenges does your job as head of sales talent development pose?

I design and deliver learning and development programmes for sellers and their leadership teams. Popular programmes like The Apprentice and Natural Born Sellers, although great TV, send out the message that you need to be aggressive and self-centred to be successful whereas, in fact, you need to be a caring person driven by the customer’s needs rather than your own. Until the UK wakes up to this, sales will continue to be a dirty word and will not attract the calibre of people it really needs.

What areas of learning and development are you currently addressing?

We are running a number of programmes called the ‘DNA of Great Sellers’. Unlike conventional sales training programmes, we really get into the hearts and minds of the sellers, re-invent their mindset so they are focused on the right things and then re-fire their professional and personal ambition.

How and why did you get into training?

In 1988, I spent time in the training and development team at Alliance & Leicester. It seemed a great environment, full of enthusiastic people who clearly enjoyed what they did. One day, I mentioned my observations to the head of training, who said: “OK, you’ve got 10 seconds to tell me if you want to be a trainer”. He pressed the button on his digital watch and just stared at it. We got to about seven and I said “go on, then”. That was 20 years ago, so I guess it must have been the right decision.

What’s the best or most memorable training event you’ve attended?

A three-day residential event that got deep inside my psyche. The trainers made some fantastic discoveries about what goes on in this head of mine that energises me and other things that hold me back. Enlightening and invaluable.

And the worst?

All of them where the so-called trainer just turns up and runs through the same old stuff they’ve always delivered in the same old boring way. It shows that the trainer is focused on themselves and making a quick buck rather than the needs of their audience.

What’s key to putting on a successful course?

Spending time with the sellers, managers and customers of a company before designing the event. This gives you such amazing insights and makes the training come alive.

How do you measure the impact of training?

In three ways: the quantity of increased sales, the quality of increased sales – making sure that the motivation for the sale is the customer, not the seller’s bonus – and then the things that the sellers go on to achieve in their professional and personal lives.

When you were a youngster what did you want to be?

A bit weird this, but I wanted to run my own crocodile farm.

What, in life generally, really annoys you?

People who don’t know what they’re talking about, people who never deliver on their promises. And technology when it doesn’t work.

What was the first record you bought?

Queen’s A Night at the Opera. And it’s still one of the best five albums ever.


Simon Bailey is head of sales talent development at sales training specialist Winning Pitch

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