The Power Of A Love Letter


For many of us, the earliest time we’ve ever had to ‘put ourselves out there’ is when we’ve had to ask someone out. In the school yard – this is fraught with risk, mainly of the consequences of getting it wrong. Enter the ‘love letter’. An arms’ length approach.

Interesting, this is a first real foray in to writing a proposal document of any description. As a supplier (of affection) toward the target of that affection we have to a) see if they reciprocate and b) wish to act on it. It is a sales document no different than many we write to potential clients every day – just with a different outcome and, arguably, greater personal risk.

Now, this was all fun and games until I found out my 10 year daughter got a love letter. Instantly the paternal instinct kicked in and the hackles went up. Who is this boy? Tell me more…..

Then my partner told me to read the letter…

Dear …….

I know a lot of boys like you but I don’t care, it would be enough to be your best friend (well, one of your best friends).

Strong start, acknowledged a/the objection (although, who are all these other boys!! A question to explore later). Also, provided an optional outcome, allowing for a gracious, albeit acceptable exit.

You are a kind and caring person and that’s what I need to keep me company everyday.

Brilliant – lead with the key features you admire and why that is important to you. Compliments, when sincere, are powerful. My ‘Dad Mode’ is softening as this boy has skills.

If you don’t want to be my best friend, it’s okay I understand. I’m sorry that I told you I liked you but it was the truth!

Nearly lost me here but closed strong with the ‘I like you even if you don’t like me back’ line. Same is true in prospecting – just because they say no today, it doesn’t mean they are any less attractive as a potential client tomorrow. And, as this boy so succinctly put it, if you don’t tell them you like them, you aren’t risking anything, therefore you may not get anywhere.

Now I put an end to it and I just want you to be my best friend! ( + some emoticons I am too uncool to understand)

In for the close. Direct and ‘asking for the business’. Well done. Too often we do great things in sales but fail to ask for the business.

PS: Please don’t show this card to anyone because they will tease and embarrass me

No, son – this letter is awesome! We put ‘commercially sensitive’ or ‘private and confidential’ on ours in the work place…same thing. In this case, I love this as it is about being vulnerable. He’s exposed himself and asked my daughter to be empathetic to this.

No proposal is complete without a somewhere to sign, just as no love letter to a 10 year old is complete without:

Bless his cotton socks – he even closed with ‘handwritten by my big sister, sentences by me’. Nice, honest disclosure. I have little doubt that his big sister also helped in write this – but I think this is brilliant. If you have a big sister – why not enlist her help. Why not get someone to help you who is experienced on the ‘buy’ side of the conversation. Something there we can learn from maybe? My good friend, Cian McLoughlin of Trinity Perspectives always talks about Win Analysis. Here, this 10 year old boy started ahead of the curve by engaging the help of his sister. He increased his chances of success dramatically.

To understand how best to sell, understand why your clients buy. I wish I thought of this when I was at high school!

The only thing he missed in this whole letter was what he could bring to the relationship (he’s 10) and this is what I told my daughter to ask him, nicely.

As a Dad – my first reaction was ‘No!’ – but dammit, once I finished that letter I was actually on the boy’s side – eventually. A telling point to remember given I wasn’t even the intended audience. Mainly because I know what was involved in writing that letter. He also reminded me that even a love letter is a sales document.

As you can see above, my daughter said yes (after some consternation). It worked.

We don’t always tell our prospects (let alone our clients) we would be proud to be their supplier and the reasons why. We are often good at telling them why they should choose us, but not so good at telling them why we chose them. We don’t always ask outright for the business – we hope they know we want it. We can learn from a 10 year old’s love letter like this.

This boy and my daughter had a conversation at school and the cards didn’t fall in his favour. He regrouped and wrote this letter and won in the end. Interesting.

This reminded me that, when approaching prospects, we undertake a very similar activity as this 10 year old did, whether written or verbal. Sometimes with less skill unfortunately. We simply just often don’t write ‘love letters’ to our prospects like this. Often we aren’t this explicit – we dance around the fact we’d like to do business and drop subtle hints. We don’t always open up and tell them we’d be proud to do business with them, in any form, if given the opportunity and, importantly, can we? Sure, this boy may have gotten shot down (hopefully I raised my daughter better than that) but at least he would have known, rather than wondered. As we saw, he picked his socks up once and re-assessed his strategy, and it paid off. This 10yo just showed us what great skills reflection, agility and tenacity are here.

As sales people, we can often be guilty of being a one trick pony and always relying on a single means of prospecting – we don’t always adapt our approach to our audience or try different and/or multiple ways of engaging. We do the same thing, every day and often expect the same results with every client, or worse, different (ie better) results. Why is this?

Some clients don’t like cold calls – but it doesn’t mean that they don’t like being approached in a different manner. It may just mean they don’t like being rung. This letter is an example – giving my daughter the time to read, reflect and consult resulted in a far better outcome than simply blurting it out in the playground (a cold call). Some people don’t like being ‘sold’ – but do nearly all like value being added.

How we approach someone can be incredibly important – you only have to go to the animal kingdom to realise the incredibly complex and often ostentatious rituals that exists around finding a partner. Yet, with business, we seem to ‘dumb it down’. We just rush in and often kill the opportunity before it’s started and don’t even know it.

An example is the prospect who never returns your phone call. Ever. We often simply blame them and move on. Our technique is perfect surely – why change? Now you can keep dialing…or maybe not. Try an email. Try a text. Get an intro.

Write a love letter.


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