I Don't Know How to Do Sales

Purpose is a snow plow. Three thoughts on sales.

This week in Greenpoint it’s blazing hot. I’ve been talking to some really talented folks about their new companies and the barriers they are facing. One of the phrases that comes up again and again when I talk to creative founders is that they are concerned about their lack of ‘business’ or sales experience.

When I hear “I don’t know how to do sales” it might mean one or more of the following concerns:

  • I don’t have a mental framework for how to think about sales

  • I’ve never seen a functional sales organization in action

  • I don’t have domain experience

  • I am lacking personality traits I think I need for sales

There are countless good books written about sales, and countless YouTube videos, events and seminars.

I wanted to share just 3 things about sales that I’ve learned while scaling Gengo, Farm.One and my previous work, things that are not often discussed when we talk about sales.

1. Find purpose to overcome barriers

Learning any new skill is about being persistent and overcoming barriers.

Gabby and I play Fortnite, the dumb and wonderful online combat game where players are dropped onto an island and compete to be the last one standing, all while the play area shrinks over time. In the game’s latest ‘Season’ you can drive cars which are modifiable with guns and other add-ons.

The Cow Catcher - a mega plow for your car

My favorite add-on is called the “Cow Catcher” - it’s a kind of heavy duty snow plow. The plow turns what is normally a fragile vehicle into an unstoppable demolition force. It’s great fun. But more importantly:

The plow allows you to behave completely differently:

  • You do not have to slow down for anything except for a mountain.

  • You can use it as a tool to destroy things.

  • You can go up against enemy vehicles with complete confidence.

  • You can take less care over your exact route because you know that whatever you come up against, you can knock down with the plow.

  • SO: It changes your mental attitude about the game.

Purpose is a magical snowplow.

I remember meeting Jeff in the lobby of an identikit Hilton in central Manhattan in 2012. We were hiring for a senior sales leader at Gengo, the translation technology startup I founded in Japan.

Jeff was just five minutes early to our meeting, but in that short time he had got to know the doorman, the hotel staff and a couple of other guests in the lobby before I even got there. Very quickly I learned that was simply who Jeff is - he is genuinely curious about people and brimming with positivity and energy. These kinds of personality traits are common in good salespeople - being interested in people. But this wasn’t actually the thing that gave Jeff his superpower. His superpower was purpose.

What gave Jeff purpose was that every deal we signed at Gengo meant more jobs and income for our thousands of translators around the world. The idea of getting jobs for real people was the biggest motivator for Jeff. The more deals he signed and the more revenue he created, the more he felt good that he was creating meaning and value for real people around the globe. While other aspects of our culture and company were also important to Jeff, this underlying purpose helped to smooth over some of the turbulence and tribulations of a growing startup. This purpose helped motivate him to learn new things and to overcome difficulties.

For new founders, purpose is a magical snowplow that can help you figure out anything and everything. If you haven’t done sales before, but you find incredible personal meaning in closing a deal, you will figure out how to close a deal. If you haven’t built a complex business development partnership before, but you are trying to improve access to healthcare, you will figure out how to do it. And so on.

This is why I spend a lot of time with my coaching clients trying to find their true purpose. Some founders think they have figured this out already. Most haven’t. Purpose can often be confused with things like envy, or competition, or prestige, or simply to make a million dollars — but folks who are driven primarily by these things always seem to find that once they achieve their goal, they have a huge gaping hole where their effort and attention used to be, and not much to show for it. True purpose is something that will keep you going long beyond any small hiccups, and keep driving you forever.

In general, finding ways to help people is a good purpose that will last forever. Being really interested in every single person you meet, with genuine curiosity, will overcome most inexperience or ignorance. Love it.

2. Prioritize relationships over transactions

I coach Japanese startups on US market entry, in collaboration with JETRO, the trade organization that helps many Japanese companies go overseas. This work is a pleasure due to the high quality of the companies and the high quality of the materials and expertise that they put together. It’s also difficult, because I am working with founders and executives who are often relatively new to their own markets, and completely new to US ways of doing business.

They often come from a traditional Japanese business culture which emphasizes long-term relationships and stability, over rapid growth and transactional mindsets. They want to enter the US market (risky, big opportunity) but have a short timeframe for ‘success’ which means they must understand, at least in part, some of the US “Wild West” way of working.

The Wild West

The "Wild West" period in the US was from the end of the Civil War in 1865 to around 1900. It was marked by westward expansion, rugged frontier life, cowboys, outlaws, and the push for law and order in the western United States. Think gold rushes, the transcontinental railroad, and iconic gunfights. This era shaped the adventurous and rebellious spirit we often associate with American history. And it has also cast a toxic shadow over American commerce that still shows up today in startup culture:

  • You must move quickly 

  • Everyone is a stranger

  • People aren’t around long enough to form trusting relationships

  • All of “this” might disappear 

  • There is a land-grab

This mindset is still prevalent in American commerce. Apply this paradigm to many startups and much startup behavior over the past 10 years, you’ll see a lot of resonance. Behaving like this seems like it makes a lot of sense in the short term, and creates a lot of waste and destroys value in the long term. Most of the time it means that folks are focused more on transactions, rather than relationships.

Try a little of the Japanese approach

Of course, it’s not just Japanese companies that think this way. There are plenty of examples of US sales approaches that prioritize relationships - the old adage that it’s better to sell a customer multiple cars over their lifetime, than to just sell them one vehicle.

But if you have been brought up in the US sales and startup environment, it’s worth taking inspiration from the Japanese approach. It’s worth thinking about how you might foster relationships, in contrast to thousands of folks around you who are thinking only in the short term. Ask yourself:

  • How might I act if I would be in this industry for the next 25 years?

  • How might I build a lifelong network among this community?

Companies may come and go. But you will persist. So thoughtful sales leaders do the work to build relationships while conducting transactions. This means that each time you work with someone, you are building a relationship, strengthening your network, and creating valuable trust for the future. In this way, a little of the Japanese way of doing things can help.

3. Collect ways of doing

Read, watch, discover

Personally, I started my career with a British private school education’s disdain for sales, which I associated with showmanship, jocks, lying, cheating, stealing. I wanted to grow my business but avoid the squalor of Glengarry Glen Ross, the pathetic figure of Willy Loman, idiots with a heart of gold like Del Boy in Only Fools and Horses, the soft untrustworthiness of Lovejoy, the anger and impatience of our discount Donald Trump, Alan Sugar, the market traders shouting out prices, the mobile phone salespeople on Oxford Street impervious to questions of honesty.

So I read a ton of sales books. I read books like Coaching Salespeople into Sales Champions, The Accidental Sales Manager, The Challenger Sale, Predictable Revenue. I took my time. I started to appreciate the craft. I started to understand the dynamics of leading indicators versus lagging indicators, of seeing the shape of a funnel, of defining a qualified lead, of the practice and calm and continual effort of a successful sales machine. Through a combo of reading a ton of books and working with some incredibly smart and talented salespeople, I shed the disdain for sales and started to love it. I still had trouble shaking off the woozy off-balance sense of vertigo when cycling quickly back and forth in a day between creative tasks and management fire-fighting and the necessary drumbeat and focus of sales.

I also started to learn that (like any craft) there are infinite ways of doing it.

There is no one way of sales

You will be introduced to many startup sales folks who have done the same type of sales over and over and over again. But there are very few folks who have done different kinds of sales, in different cultures, in different stages of a company, in different verticals. So be careful - sales advice from ‘experienced’ folks might be completely counter-productive for your specific business, and you should not assume the first advice you receive is relevant.

As a founder, it is your job to find the sales methodology for yourself and your company that ‘makes sense’ — as in, it is most in touch with reality. So you need to make sure you are turning over every stone to find the ways of working that suit you and your company. Reality is about you, and about your team, and about your market.

Talking to many people about how they have scaled their specific businesses in specific markets will show you how many approaches there are. For example, here are some broad descriptions of different sales styles. And this is by no means an exhaustive list.

  • Consultative Selling - Often used in B2B services
    Focus on understanding the client's needs and offering tailored solutions. Act as a trusted advisor rather than just a salesperson.

  • Solution Selling - Often used in technology, software, industrial products
    Identify a problem the customer has and position your product as the solution. Emphasize how it solves their specific issues.

  • Transactional Selling - Often used in retail, e-commerce, FMCG Focus on quick, one-time sales. Highlight convenience and efficiency to close deals fast.

  • Inbound Selling - Often used in online businesses, SaaS, digital marketing
    Attract customers through content marketing and SEO. Let potential customers come to you after engaging with your content.

  • Relationship Selling - Often used in real estate, luxury goods, financial services
    Build long-term relationships with clients. Focus on trust and repeat business rather than just immediate sales.

  • Social Selling - Often used in fashion, beauty, lifestyle 
    Use social media platforms to connect with potential customers. Share engaging content and interact with your audience to build a loyal customer base.

  • Value-Based Selling - Often used in finance, consulting, enterprise solutions
    Emphasize the value and ROI your product or service offers. Show how it will save money or provide significant benefits over time.

  • Challenger Selling - Often used in consulting, enterprise sales, professional services
    Challenge the customer's thinking and offer new insights. Position yourself as an expert who can help them achieve better results.

  • Event-Based Selling - Often used in software, education, tech startups
    Host webinars, workshops, or live events to demonstrate your product. Engage with customers directly and answer their questions in real-time.

  • Collaborative Selling - Often used in healthcare, construction, large-scale projects
    Work closely with the customer to understand their needs and co-create solutions. Emphasize partnership and cooperation.

Just as you use a process of customer discovery early on to create a compelling product, that process of customer discovery is also sales discovery - it’s about uncovering how, where, and when to locate your customers.

  • What are the best ways to find these folks?

  • What’s the best way to talk to them?

  • What does respect mean to them?

The more you learn about your customers, the more it will become obvious how to work with them, help them, help them be happy.

During the early days, it’s important to try a bunch of things, each time measuring what works and what doesn’t. This might feel dispiriting at the beginning, when nothing seems like it is working. But you will find activities and ways of measuring them that work. And then you can double down on them.

Successful sales teams do not bounce around from one method to another. They have identified the key activities that work for them — and they keep doing them. They work on perfecting the craft. This is the state you aspire to reach as an early-stage startup — the state where you all know what you are doing, and your team can concentrate on doing it well.

I coach CEOs, founders and executives on how to reach their full potential, become great leaders, and scale strong, impactful companies. It works.

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