Being Salesy

Sales is evolving, but the perceptions are slow to change

Most people do not see themselves going into sales. Very few ever imagine that sales will be what they do for a living. Yet here you are reading this newsletter about sales, along with the over 13 million people in the US that are in the sales profession.

We all have a story about what led us to sales. My path was perhaps a bit more jarring than most. I was a software engineer at a tech company in NYC. I transferred to the San Francisco office to work at customer sites at a consultant when in the span of one month, all the sales reps and the sales director quit. I was the last person standing, so the VP of Sales nominated me to head up sales for the western half of the US.

I had no training or experience. I was literally thrown into the fire to figure things out. One day I was writing code, the next I was calling prospects, contacting customers for renewals, setting up meetings and demos, and tracking things in the CRM system (that I built). My saving grace was perhaps the fact that I knew the product inside and out, and that I also hate failing.

Without any guidance, I simply interacted with prospects and customers the way I would like to be engaged. I asked lots of questions. I listened to what people were telling me and took copious notes. I followed up when I said I would follow up. I never pushed for a meeting if it was clear there was no interest. I definitely screwed up a bunch, but I was at least competent and was able to generate sales.

Later I would go to companies with much more mature sales cultures. A lot of what I was taught and the things I observed had little to do with the hard charging tactics I thought sales was about. I learned about consultative selling, earning trust, building relationships, generating business cases, and establishing long term mutual value. I dug deeper into understanding motivation, internal and organizational drivers, and cognitive biases in decision making.

There were plenty of things that I did not necessarily enjoy. The paperwork & processes, the CRM systems, the internal battle for resources, the forecast calls, and the prospecting blitzes. What I discovered however over time was a career and profession that is both vital and impactful in a way that few other jobs can ever be. Sadly, very few outside sales see this.

An article in the Wall Street Journal piqued my interest about the perception gap in sales. Those just entering the workforce are not apparently not interested in sales jobs. Ziprecruiter notes that the number of sales roles on their platform has increased 65% to more than 700,000 open positions around the US over last year. The jobs are plentiful, the candidates are not. As the CEO of ringDNA shared:

“People don’t go to school and think, ‘I’m going to be in sales’. It’s the lifeblood of every organization, but talent is limited.”

Sales is still often seen as a boiler room. It is heavy cold calling, high pressure, and huge stress every month to make your number. People think sales is just for extroverts or for those that are naturally pushy and aggressive. Plenty of sales “gurus” and “thought leaders” do not help sway those perceptions with their rah-rah, hard charging tactics.

The term salesy is the word that comes to mind. One site defines it as a salesperson who sells a product to someone in the wrong stage of awareness in an aggressive or superficial manner, making the prospect feel uncomfortable. There were certainly times in selling when I became acutely aware that I was pushing a prospect away because of my approach.

We all tend to fall into the trap of being salesy. Whether it is pressure from sales managers, anxiety about hitting numbers, or other stress that causes us to lose empathy, we will have moments where we slide from helping our customer to pushing them. So, how do we stop doing the things that come off as salesy?

It starts with self-awareness. The fact that you feel you are being salesy is a good sign that you are aware of your words and actions. The signs are not hard to pick up. Customers ghost you. Prospects are quick to get off the phone. Conversation in meetings is limited and information not forthcoming. When this is happening, you need to hit the pause button and understand what habits and behaviors are causing customers to not trust you.

The first point of interaction with a prospect has a lot to do with your success in building trust. Your approach to cold calls and emails will set the stage for the relationship. Do you take time to personalize your approach, or does it feel formulaic? Does it sound like you care about the person and the problems they face? That is an important bridge in establishing trust.

It is hard to earn trust from the onset with a prospect because there is no prior basis to form trust. This is even harder for sellers because there is already a heavy burden of distrust when first engaging. The best way to earn trust is to earnestly listen. Buyers want to feel they are being listened to, so make sure you are giving prospects a space talk about their needs.


One barometer for engagement is the percentage of time a prospect is speaking. Who is doing the talking? If it is you, then you are probably not doing a good job listening and verging into being salesy. You need to interweave more questions into your sales conversations and be willing to dig in further to explore the challenges your customer is facing.

One sure fire way to lose trust is in how you fulfill commitments. The first commitment is to tell the truth about the solution you are offering and the capabilities. The second commitment is to do what you say you will do. I am baffled when salespeople will say they will follow up, and never follow through. That is a signal to prospects that they do not matter.

The last thought to share on being salesy is the motion between buyers and sellers. The natural tendency is to be cagey and deflect when engaging a salesperson, to keep things close to the chest. This makes some sales reps want to push harder. Instead, you want to create gravity and pull buyers to you. This happens when you have earned trust, have rapport, and demonstrate credibility built on being knowledgeable and consultative. I will talk more about this in a future post, but for now it is important to recognize this push-pull dynamic in your own selling.

Thanks again for reading. Let me know what topics you want to read more about and what you feel would be most helpful. Take care and have an excellent rest of the week!

Mark Birch, Founder of Enterprise Sales Forum

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The Enterprise Sales Forum is a professional community championing the practice of sales through monthly sales talks at chapters globally. Our chapters provide an open, collaborative and diverse environment to share new ideas, network and learn actionable insights for professional sales development.