On Selling

8 minute read

I find it surprising when people seek my guidance on how to sell because selling isn’t what I consider part of my identity. I see myself as an individual contributor who enjoys hands-on problem-solving and tinkering. This inclination makes me more chaotic and creative, traits that differ from the arguably more predictable nature required in sales.

I thrive in ambiguity and uncertainty and I love to operate like an unsupervised learning agent. Still, I do get satisfaction when I create something that mirrors the world and affects it in a positive way (e.g., education, science, ESG, space exploration, etc.). Those who see me in my everyday life will know that I commit time everyday to exercising and staying fit, homeschooling my kids with heavy emphasis on engineering, creativity, and experimenting. That I’m a clown who likes joking around and keeping a white belt mindset. And that I’m a father figure to my family first and foremost. I feel like that’s what I’m good at.

But the fact that people seek my advice on selling prompted me to write this blog post, because perhaps during my tinkering over the years, I have learned a few things that make me efficient at it. So here’s a framework to help you learn how to sell.

1. Situation: who, what, what, who, what, where, and what?

First and foremost you have to understand the situation. Think about who you are selling to, what their functional role is, what incentives they have, who they report to, what industry they operate in, where they live, and what is the biggest challenge they are facing right now. And many other such questions.

Convincing a 4 year old

For example, you could be selling to a four-year-old who has no job and who effectively reports to her big sister (with a dashed line to her parents), who loves mermaids, and really is excited about learning how to write/read/jump on a trampoline/ride a bicycle/dance like a ballerina. She’s young and her focussed attention span is no more than a few minutes.

Convincing a 44 year old

Another example would be a vice president of digital transformation at a fortune 100 company who functionally reports to the technology organization, but in practice really reports to the senior VP of supply chain, and the chief operating officer of the company.

You can fill in the blanks with your imagination for the rest of the questions.

2. Complication: what keeps them up at night?

Next is to form a series of hypotheses about a complication or an opportunity for them. And you keep going until you’ve found one that is good enough. And this is probably the single biggest point of failure where you’ll think that this is obvious, but you will forget to do it.

Understanding the situation is not enough. It’s a bit like a designer who is expert at typography and design systems, but won’t make something people want because they aren’t listening or using common sense. Selling what you have to offer by describing it is not enough. You need courage to have thought leadership. You need to be able to guess, test and iterate on what it is that this person cares about and has as a problem in front of them. Sometimes they are unaware of the problem/opportunity, and sometimes they refuse to acknowledge it. Doesn’t matter. It’s your job to figure it out for them if you want to sell to them.

Help people discover what they want

A common fallacy is that people know what they want and that if they could only give you the requirements you could make it for them. So therefore, it’s their fault and not your fault that you built the wrong thing. Similarly, it’s easy to say that you are a victim of your environment and that’s a poor mindset. A rich mindset is to refuse to accept this situation and instead believe that you can reframe your mental models and proactively shape your environment to make it better.

Educators, from people who have raised kids to Professors at University know well that people will change their minds about what they want/love/desire once a spark is ignited inside their minds. The reality is that successful people achieve success by making something that people want. It’s never obvious because if it was obvious, then someone else would’ve already created it. Hindsight is 20/20.

Use all information and your imagination

So if you want to sell something to someone you better get good at leveraging all the information at your disposal and the full might of your brain to make good hypotheses on what people want. It doesn’t matter whether it’s for dating or helping your child with a problem or helping the director of operations getting a promotion.

3. Resolution

Understanding the problem is half the solution and it’s easy to jump into and fall in love with a (suboptimal) hypothesis. So it’s always good to take time to form a good mental model of the situation and the complication. Sometimes it’s clear that you have found something worth solving, and when you do, then you should get very tactical because formulating a resolution is not easy.

Think like the CEO

Tactical advice when selling to someone (whether it’s a 4 year old, a venture capitalist, or a manager of an HR department overseeing 7,500 people) is to think like their CEO (e.g., their parents, their limited partners, or literally the CEO of a public corporation). If you read the annual report and you pay attention to the specific words that the CEO has used, you will be able to align your vision with the CEO’s vision and provide thoughtful suggestions to anyone who is working in this organization.

This perspective on what matters and where the wind is blowing will give you leverage like a Jedi superpower. It doesn’t take long to do and it doesn’t require much effort. But for most people, it seems like it never makes it to the top priority when it should be a top priority.

Recall the example of a vice president of digital transformation. In 2024 it seems likely that they will have important items such as:

  1. How to cut cost (high interest rates and inflation make this fashionable)
  2. How to improve the quality of delivery at scale
  3. How to leverage more the talent inside and outside their organization
  4. How to innovate using large language models, machine learning, and AI
  5. How to mitigate risks and proactively engage on environment, social, and governance issues (ESG)

Rule of thumb

A good rule of thumb is that what sells the most is to reduce variable cost because it’s tangible. Second in line is to reduce real risks, especially things that have gone wrong recently (e.g., cybersecurity incident). And third is to increase revenue.

Once you have 1, 2 or 3 of those, the next question is budget. You need to make sure that there’s some kind of purchase order and approval for the product/service you are selling. At this point, the most important thing is that you have built a shared vision and aligned incentives with the person you’re trying to sell something to. They are your champion and want to make it happen.

4. Closing

You know you have a champion inside the organization once they start to show impatience and complain about the slowness of their organization to buy and get going. A bit like the frustration of waiting in line at Apple to buy the iPhone 15 Pro Max with 1TB because you want to shoot ProRes Log Videos.

But even if you have your champion, you still don’t have a sale. It is so easy to underestimate all of the things that could go wrong to prevent a sale from happening: procurement, insurance, compliance, politics, and geopolitics just to name a few.

This is true, whether you’re selling equity to fundraise for your startup (sometimes even “yes” still means “no”) or whether you’re trying to get your daughter to eat broccoli. Closing is hard, it’s frustrating, it’s disappointing, and it can crush your soul.

When it’s closing time, you better be ready to accept that despite every effort you put in this, it might still not work and, yes, it’s not fair. There are numerous occasions where legal documents have been signed, but until the money is in the bank account, you haven’t completed a full cycle. And even if you deliver everything you promised, your respectable client might fail to raise their Series A and tell you fuck off after you ask them why their are ghosting you on email.

That is partly why selling is better done as a team sport so that you learn from people who have done it before.

5. Mindset

I once heard a tongue in cheek comment that the best salespeople have credit card debt, are paying alimony, and have an expensive lifestyle. That may be true, but that also sounds like a stressful life and it definitely is not my approach.

Perhaps part of the reason why I’m good at selling is that when I do, I do it for fun and not by necessity. It’s something that is interesting. It’s a puzzle to solve, and the act of tinkering with it is rewarding in and of itself.

I hope that this was somehow insightful to you. I welcome new ideas and approaches to selling.

Disclaimer: this was not written by artificial intelligence (e.g., an LLM). I did use it, however, to check my syntax and small errors to improve readability. I prefer to avoid it as much as possible to stay more authentic and credible.