I am a sales person. Man up.

It’s surprising how large a role whiskey and beer play in my personal development


  • You never know if you don’t ask
  • The best way to fail at negotiating is to negotiate against yourself
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Onto the debrief

A couple months back I was at a bar with a good friend and ex-colleague, Ryan. He had just left the sales team at Google to pursue his dream of being an entrepreneur; he co-founded a B2B robotics startup and we were reminiscing about our time in sales (I had left sales after 2 years and joined the marketing team in 2018)

My first client workshop as a sales rep back in 2016

The bar had a deal that night and so we paid an equivalent of US$ 50 for 5 vouchers, and the brochure explicitly said each voucher can only be redeemed for craft beers

Halfway through the drinks, Ryan, noticed a brand of bourbon on the shelf - Buffalo Trace - and mentioned it was a great bourbon for the price

I, being an obviously very adventurous soul, wanted to give it a try and was going to pay but Ryan stopped me and said:

Let’s use a voucher to redeem a glass each

I immediately responded with:

Yea right, the whiskey is for sure more expensive the beer. There’s no way they’ll go for it

Ryan said: “Let’s ask”

You probably know how this plays out so I’ll skip to the end: the waiter we asked brought the manager over and after a bit of back-and-forth, the manager shrugged and said “Ok, sure”

I was pleasantly surprised with the response, impressed with Ryan’s “audacity,” and ashamed of myself

I had, after all, spent 2 years in the sales team, AND I had read Chris Voss’ book “Never Split the Difference”

I should have been comfortable with negotiation, why was I so afraid?

It would be simple for me to just summarize with a cliche: “you never know until you ask,” and include a Michael Scott meme (actually I’ll include the meme anyways)

But, I realized there’s a much more practical tip I can apply in the future: I “lose” the negotiation the second I start to argue against myself

When Ryan brought up the idea, I basically had already convinced myself that “the value of the beer is for sure less than that of the bourbon, there’s no point, so let’s not even bother asking”

Had I thought about it from the manager’s point of view - “Hm, the bar is pretty empty tonight, I want these 2 guys to keep drinking, I don’t really mind them getting a bit more tipsy and potentially spending more” - I would have been confident the question would have worked!

If Ryan ever reads this post he’ll probably think I’m trolling him since it’s such a “small” thing from his point of view (he’s a few years older than me) but to this day, whenever I want to ask for something but hesitate, I literally remind myself “you were in sales, man up”

And 9 out of 10 times, I end up getting what I ask for.

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