3 Life Lessons I Learned as a Salesperson.

Cover photo credit goes to Monica Lie

I didn’t leave my previous company, Skyscanner, because it was bad.

In fact it was the very opposite.

I had fantastic colleagues, managers and growth opportunities.

In many ways, my experience in sales was critical to building up not just the financial means, but also the confidence to take my year off work.

These are three lessons that have really stuck with me.

1. The only impossible sale is the one you don’t try to ask for.

Shortly after starting my sales role in Skyscanner, I found my team of three had shrunk to a team of one:



I was now the sole person to grow the business in the whole APAC region.

The most junior, fresh-faced greenhorn.

I was horrified.

“There’s no way anyone would speak to a n00b like me.”

In my first couple of weeks doing outreach, I didn’t even try to connect with more senior individuals.

But, as anyone in sales knows, the greatest chance of success was to speak with decision makers.

I won’t tell you how many times times I revised my LinkedIn messages when sending my first few out to those I considered “the Impossibles“, ie the C-levels.

The self-doubt barrage continued.

“Will they think I’m impertinent sending this?

Am I going to make them think less of Skyscanner?

Have I ruined all future potential of a partnership!?

Oh god. Here goes.”

Palms sweaty and mom’s spaghetti rumbling in my stomach, I clicked send.

Within a few days, I got a response:

“Thks for the msg. This sounds interesting. When can we talk?

Sent from my iPhone

I was in shock. I’d actually gotten a reply. (!!!?!?!?11!!)

Professional #FreshoutofUni photo

As more and more of these happened with partners that I initially deemed completely out of my league, I learned that it pays to just ask.

No matter how ‘impossible’ something may seem, in asking, there’s a 50-50 chance of getting what I hope for.

Don’t ask?

I’m the only one limiting myself and making sure it’s 100% no.

2. Use an Agenda.

Using an agenda (ie, a list of discussion points shared beforehand) is the easiest thing to do but can have enormous impact.

Agendas have the benefits of:

  1. Providing clarity: why are we having this meeting?
  2. Prioritising: making sure the most important things are covered first

Even when meeting friends, I sometimes ask for an agenda.

Okay, so I don’t call it an ‘agenda’. .

With friends I say, “is there something on your mind?”

If it turns out that a friend has an issue to discuss, I then ask for a quick summary in order to think more deeply about it before we meet.

It’s actually been incredible helpful in making my catch ups with friends even more meaningful.

3. It is better to be respected than liked.

The feeling I hated most as a salesperson was walking out of a negotiation feeling like I had given away more than I should have.

I realized I was going above and beyond just to get a smile from partners, even when it was counter-productive.

I was prioritising ‘being liked‘.

Respect is quite different from being liked.

Being respected means I am firm in my convictions and will protect my interests.

This was a really important lesson for me.

I’m very high on “agreeableness” and the fear-laden thought “omg what if she / he doesn’t like me” is constantly running through my mind.

To be liked, or not to be liked, that is the question. Photo credits to Monica Lie!

This is tricky when this fear shapes my actions no matter what the context is.

For example, I wouldn’t return food with hair in it, or wouldn’t reschedule a fitness class because I was afraid of being disliked by the service provider.

I was putting up with inconveniences for nothing other than a desire to be “liked” — by someone I wasn’t even invested in.

It’s still something I’m working on, but I’ve now started to prioritize being ‘respected’ instead.

Have you worked in sales before?

What are some your biggest learnings?

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