The "Rules of Selling" All the Best Salespeople Ignore

Unlike most new starters in sales who land an SDR role straight out of college, I was being groomed for a career in sales since the day I could walk. My father was a VP at what is now HP Enterprise. I remember listening to call after call as we drove to school each day. After seven years in selling roles, here are the seven rules of selling I would tell my 18-year-old self to ignore.

1) You can sell anyone

As a younger sales rep, I watched all the movies and was inspired by the sales leaders around me who appeared to close every deal they touched.

The reality is that all the great fighters pick their battles.

To truly succeed as a salesperson, it isn’t about finding a style that can win every deal. It’s about knowing which deals are worth pursuing.

I’m not saying you should pursue a more holistic method of closing deals; I’m simply stating that your energy should be focused on closing more of the right deals.

2) You need to study the product more

The rep who knows the most about the product is never the most successful one. Your ability to ask insightful, provocative questions, and use the answers to uncover what matters to the prospect, is far more important than product knowledge.

Younger reps (including me when I was younger) are prone to “feature dumping,” or bombarding prospects with all the offering’s bells and whistles. They believe this is a way to appear like a subject matter expert, despite their age and lack of experience.

When training my teams, I often draw the analogy to medicine: A doctor doesn’t begin the consultation by listing out their areas of expertise. Instead, they ask questions and if unsure of a diagnosis, call on other peers or run more tests.

Similarly, salespeople shouldn’t be afraid to ask for help when we don’t know the answer to a question. The best performers leverage people inside their team who have more specific knowledge and bring them into discussions, making prospects feel like they are getting a high-quality experience.

I used to feel ashamed bringing my CEO into deals, feeling helpless for not being able to close them myself. However, if I have a guaranteed winning play in my back pocket, I am a lesser salesperson for not using it.

3) You need to dress or look a certain way

As salespeople, we’re often scrutinized on our appearance. If we appear too well-groomed, with slicked-backed hair and a gold Rolex, our customers instantly become cautious, careful not to become the next “contributor” to our monthly pay check.

On the other hand, if we dress too casually, we are guaranteed to create a poor impression.

I was so concerned over my appearance that as a teenager I once spent more than $3,000 of my own hard-earned money on a Boss suit.

Fast-forward to 2017, and I have found a unique appearance has a distinct strategic benefit.

Not only can you break the ice with prospects, who frequently comment on your style (in my case my cowboy hat), people usually feel like they know you already after seeing your face in various places online, like LinkedIn, Facebook, or Twitter.

And people you meet only briefly are more likely to take your call or respond to your email if you mention your style, for example, “I’m the guy who was wearing the cowboy hat.”

4) You should start at a great company

When you work at a great company, everything is provided for you: Training, corporate swag, and the salesperson’s favorite commodity, leads.

Compare this to a scrappy, yet well-positioned start-up. The lack of, well, everything, can be extremely beneficial for a junior sales professional.

First, you learn how to do business in the real world without the comfort of a logo behind you. Master this skill, and you will never go hungry.

Second, the amount of variety in the role allows you to explore a range of skills outside the conventional sales realm that may come in handy later in life. For example, I was exposed to development, data science, and project management. These skills now help me engage with software firms who serve those industries.

Third, in a younger company, age is just a number. Smaller firms tend to value ability over experience, while larger enterprise firms forgo meritocracy at the expense of politics. Sell well, and you can command your future.

5) You need to follow a script

My first few sales managers hammered on the importance of a script. But no one was selling. Was it because of the product, or our mediocre talk track?

A script can be a good stepping stone, but it’s critical to develop a customizable strategy for each individual call rather than a one-size-fits-all approach.

This strategy should center on building trust and rapport, diagnosing pain points, and adjusting your messaging to the customer’s specific needs.

6) You need technology

When my father taught me to drive, he insisted I learn with the most challenging car. If I could drive my 6,000-pound stick-shift Land Cruiser, he said, there wouldn’t be much else I couldn’t handle.

Just like starting at a large company can be detrimental because it’s easy, I think reps are overly reliant on technology. Consequently, they’re not building up the core skills required to be a successful salesperson.

For instance, overreliance on web conferences doesn’t fully prepare you for the pressures of a live boardroom environment. Email automation technology is promoting a scattered, volume-based strategy rather than a carefully crafted strategic selection of accounts. Dialers and phones are quickly disappearing from desks as cold calling techniques go away.

Most of the best deals I have closed have come from less-conventional methods: Meeting people on public transport, intentionally dining in hotel buffets once a week, or going to corporate events. The art of the sale is so much more than just email: It is about getting creative and having the tenacity to do whatever it takes to open doors. Technology can sometimes limit your potential rather than enable you.

7) You need a leader with a proven track record

I used to feel I could only respect leaders who had done it all before -- seasoned sales veterans who had closed the biggest numbers.

It dawned on me the best sales performers didn’t become the best managers. Many were extremely egocentric, unaccustomed to internal politics from being free in the field for years, and viewed by management as obstacles to higher earnings (most senior AEs out-earn even the CEO in the world’s leading software companies.)

I now have one key requirement for my leader: A passion for sales enablement. I would pick a manager who's focused on providing tools and resources (like data and customer references) to help me shorten deal cycles over a seasoned veteran from the field any day.

Not all sales "wisdom" is worth listening to. Now that I've drawn my own conclusions, I'm more successful -- and you will be too.