3 New Rules for Selling in 2018

Brandon Healey
Bootkik
Published in
6 min readJul 12, 2018
“Convince me.”

I regularly find myself hearing a smug “really?!” when I tell people I’m in sales. Their tone generally suggests a note of sarcasm and surprise. This used to eat at me.

What’s so embarrassing about being in sales? I’m not that stereotypical salesperson, am I? These are common internal questions for a salesperson focused on self-development. The world is becoming more oppositional to conventional sales tactics, and a salesperson needs to adapt to survive.

Sales in 2018 is undergoing a new level scrutiny. With deepening cultural skepticism, changes in consumer buying habits (less in-person), and a shorter attention span, the sales department has its work cut out for it.

So how do we modernize our sales approach? How can we make real connections and continue to close deals in this new environment? How can we avoid being labelled as “too sales-y” in a culture that is increasingly skeptical of sales people?

With a decade of sales experience behind me in small business and startups, I’ve learned that a new set of rules are required to sell in 2018. I don’t claim to be a perfect example of a modern-day-sales-machine, but these three new rules have totally changed my approach.

If you keep these rules in mind, I promise you’ll close more deals, and develop healthier relationships with your clients (both of which are equally important).

Fun Tip: Don’t take yourself too seriously as a salesperson. No one else does.

Rule #1: Real Relationships Last Longer than One Pitch

Sales is about connection. We need to develop real relationships and trust with our clients, 2018 hasn’t changed this fact. We know that customer attention spans have dropped; I have noticed that this has affected sales departments too. Many sales departments’ “customer attention span” has become atrocious.

Commonly heard in sales offices:

“They’re a bad fit.”

“That guy was an (expletive).”

“This customer just isn’t worth pleasing, you can’t win them all.”

We criticize customers’ shortened attention spans, while we as sales people face the same challenge. We’re “done” with tough customers pretty fast at times.

We should know better than this, right? Due to hyper-connectivity, you can’t get away with treating people poorly anymore. It was only a matter of time before this reached the sales desk.

In 2018, we are seeing combinations of technology and industries occuring at increasing speeds. Amazon is getting into healthcare, Uber is working with NASA, and your business is ripe for major disruption too. Good or bad, your business is changing. If you selectively respect your customers, it will come back to haunt you.

Ask yourself:

“Did you respect and value that person, even if they were a bad fit?”

“How would you treat this client differently, if you knew you would be selling to them again in 6 months?”

“Did you develop a real relationship with them, beyond your first pitch?”

I hope so.

Fun Tip: Most people are nervous meeting new people. If this part of your psyche is gone (numbed away by thousands of client meetings), fake being nervous. It’ll show others you’re not a robot. They don’t trust robots. Nobody buys anything from a sketchy robot.

Rule #2: Solve Problems Tenaciously

Everyone’s a problem solver nowadays. A quick glance at a stack of fresh resumes will tell you that we have a society that produces hordes of “master” problem solvers. Similar to our society’s delusion that we are all above average drivers, we simply are not all great problem solvers. What we can control is how motivated and tenaciously we strive to solve problems. That matters.

For as long as I can remember, it has bothered me if I can’t solve a problem. I have spent countless hours on puzzles, riddles, and rubix cubes. My insatiable need to solve problems gets me in trouble. It doesn’t always go over well with work colleagues and it can certainly make my personal life a bit dicey.

Fun Tip: Some bad dates can’t be problem solved.

As a salesperson, your role is to advocate for your customers. Your job is to find solutions to the problems your customers face. Hearing “no, we can’t do that” should be common during an open brainstorming session.

Salesperson during brainstorming session:

“Can we put ads on this page?”

“Can we rebrand? I think our company webpage looks out of date.”

“What would be involved in offering twice as much of our service for the same price?”

At times, tenaciously solving problems can be a bit tough on your colleagues or your dating life, but it won’t be tough on your customers. They love it.

For non-sales people, I know it can be annoying hearing your sales department regularly asking for new features on your product, service, or doohickey. Don’t ignore this. They’re trying to make you money.

Fun Tip: Sales people are very likely to ask for silly additions to your doohickey that are utterly ridiculous. Yes, they are messing with you.

An appropriate response to hearing a ridiculous idea from the sales department.

Rule #3: Know yourself

Sales people can be some of the least self-aware people on the planet.

The typical sales persona is extroverted, light hearted, and tenacious, but unaware of themselves. The benefit of being unaware, is that a salesperson can keep trucking forward in the face of adversity. They didn’t even notice that they blew that sale. Really. The downside however, is that sales is about developing lasting relationships. You can’t do that if you are damaging those relationships without realizing it. Focusing on self awareness can pay incredible dividends and allow a salesperson to quickly differentiate themselves.

Don’t expect a bunch of praise or accolades about the work you’ve done on self-awareness. This basically just chills you out to the level of most non-sales people, so your coworkers probably won’t even notice. Where this pays off in spades is in long-term relationships. Your clients will have an easier time relating to you and will feel more comfortable when you reconnect months (or years) down the road. Your staff will grow a deeper respect for your healthier leadership.

If that’s not enough pay-off, you go-getter you, I assure you that your friends and significant other will appreciate the self-work you’ve done. The improved health in these relationships will be all the pay-off you’ll need. You can ask them for a trophy if you’re still not satisfied.

Fun Tip: Want to differentiate yourself significantly? Don’t be a jack of all trades. You’re not. Pick two or three things and let those be your schtick. I fly fish, love trendy cafes/diners, and have travelled extensively. In everything else, I try to be a learner (especially if I feel relatively confident in that topic). Salespeople have a habit of being a jack master of freaking everything.

The world needs sales people to be trustworthy problem solvers who are self aware. Up to the task? Good. Go sell something!

Recommended Reading:

  1. Looking for a tool to improve your self-awareness? I found the Enneagram personality test & this book really helpful. If it doesn’t make you more self-aware, it’ll certainly humble you a bit.
    The Wisdom of the Enneagram — Don Richard Riso & Russ Hudson
  2. Looking for a shiny new book on the changing climate of technology and culture? Check out Jim Gibson’s book (referenced under Rule 1).
    The Tip of the Spear — Jim Gibson

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