We’ve all been selling since we could string a sentence together. And, we’ve all been negotiating since we could connect those paragraphs into a sentence.Don’t believe me? Spend five minutes with any 3 year old and you’ll change your mind on that belief.

Then why is selling so hard? Why are some people terrible at selling and some so good? Why do some people hate selling? And, some get fired up deep into their core at the prospect of closing a deal.

I’ve never considered myself a salesperson. I don’t feel comfortable in the traditional sales scenario. I do consider myself an extrovert and I think I can influence people around me to make certain decisions. But, for me, that’s always come from empathy and active listening. Understanding other perspectives and then communicating context around my opinions. For me, that then can lead to a “sale”.

I'll take you back to my first “real” sales job. I worked at a Brazilian restaurant in South Africa while I was in university. Like many kids in uni, you need cash to fund parties and bad behaviour. Being a waiter is a relatively easy transition into the workforce. You need minimal experience and it’s not a complicated process. But, the owners of this restaurant had different ideas on how to run things. It was a party venue. Weekends were filled with large tables of 20-30 people celebrating a hen's night, bucks parties and birthdays. That meant chaos, instigated by the waiters and some well-timed shots.

Each waiter/waitress was expected to entertain their guests not just serve them. And, that meant selling drinks. Yes, selling. Our goal was to get our guests shmangled which in turn, ended in them having the best night ever. As an incentive, the owners gave us a 3% commission on every alcoholic drink we sold. And, I was good. To be honest, I think I was better at the entertaining part and the sale came as a byproduct of that. Rather than being a pushy salesperson, I focused on building relationships with the key person at each table.

A little later in my career, I became a franchisee at a purified water and cooler company. In my early twenties, I didn’t have the money to invest in becoming a franchisee. The franchisors knew this so they offered me full support and admin from the head office. But, I’d have to build up my own book of clients, no sales team or me.

This was a major step up from being an incentivised waiter selling good times. The money I now needed to earn wasn’t only for drinking and Xbox games. I needed to make a salary. This meant I needed to sell. A lot.

So I split my day into 2 parts. In the morning I would open a yellow-pages. I assume most of you will know what that is but, for my younger audience, the Yellow Pages was(is) a business directory phone book. If you don’t know what a phone book is, then damn I’m older than I thought!

Anyway, I would sit with the Yellow Pages and call companies in alphabetical order and try to sell them a cooler and purified water subscription. I won’t go too deep into this but those first 6 months of cold calling were some of the lowest points in my career. I was petrified! I was terrible at it and it never got any easier. I got more rejections in any one day than an entire month's worth of picking up girls at clubs.

Every afternoon I would load 5 coolers and 5 bottles of delicious, purified water into my VW Golf and hit the road. I would drive into large office parks and walk into offices cold. A water cooler under one arm, a 22L bottle of water on the other shoulder and sometimes a bunch of flowers for the boss's PA. No wonder my guns were impressive in my twenties.

Door-to-door selling wasn’t easy but it was 1000x easier than cold calling. That’s when I realised my “sales” ability came from relationship building, not from direct selling. When I was in front of a prospect and I could get personal for a bit, I often got the outcome I was looking for. I ended up closing bigger deals and longer contracts. Again though, these came about because I’d been working on the relationship for weeks.

So I have paid my school fees when it comes to sales. I’ve pushed the sled, piled with crap for miles and miles. Since working in startups and tech I’ve loved not having to be in sales. The pressure, the rejection and the incentives. Fuck I hate incentives! (See here for more on that topic).

But, now I sit as CEO of a tech startup and I realise that I am selling every day. I am doing more sales now than I did in all my years as a salesperson.

As a CEO you always need to be selling. Selling culture and values to your team. Selling strategy to your leadership team. Selling your product to partners and enterprise companies. Selling yourself and your company to investors.

Sell! Sell! SELL!

So why doesn’t it feel the same? Why am I now "OK" with it?Because I don't have a choice. Because the stakes are higher than just earning a salary? In fact, quite a few salaries now rely on my ability to sell. I’ve struggled to put my finger on the reasons. Then, this morning driving to work it hit me.

Don’t sell. Educate.

I believe in what we do. I believe in the problem we’re trying to help businesses solve. So now it’s more of an education piece to get everyone on board.I’m educating our team on how a tech startup can work together and operate. I’m educating our leaders on good practices and habits to grow culture. We're educating our customers and partners about the future of tech in their industry.

What I’m getting to (in my long-winded way) is that there are two takeaways I’d like to leave you with.

First, as a CEO, experienced or beginner, you better learn how to sell. You’re going to have to sell many things to different stakeholders. The upside is that there are many ways to close deals or sway opinions. Find what works for you.

Second - relationships. Compounding relationships is a secret weapon! You’ll need to leverage relationships from your past to help guide you when you’re lost. And, you’ll need to leverage relationships to drive sales in your business.

Most important, you’ll need strong relationships with your crew if you want the ship to make it out of the harbour.

Peace, love and Muscles.

JarrenThe Beginner CEO

Book I’m Reading This Week

No Rules Rules - Reed Hastings & Erin MeyerAs I go on the journey of creating a meaningful culture in a business I am trying to learn from the best. This book is the Netflix story of how they’ve reinvented culture in tech.

Additional Reading on Sales

Never Split the Difference - Chriss VossThis is the ONLY book I re-read every single year. I’ve also recommended this a few times already. Chris is an ex-FBI hostage negotiator turned business and sales trainer. It’s a great read for anyone. I give this to my sales and retention teams to read.

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