Why Sales Sucks
Three problems holding your team back and giving a great career a bad name
Trial by Fire
My first day in sales — November 17th, 2008 — was not a good day.
I was 23. I had moved to Manhattan a week earlier, shoehorning my possessions into a tiny Murray Hill apartment with one window and a single bedroom creatively carved into three. I entered our office, on the 51st floor of Rockefeller Center. Our head of HR met me and walked me to the sales floor. I heard the sales team before I saw them. The din of chattering male voices and a backing track of CNBC filtered around the corner. It was loud. Energetic. Intimidating.
The sales team was straight out central casting. A room almost entirely populated by 30-something men in well-pressed shirts with clean haircuts and strong handshakes. As I introduced myself, I flashed back to college and a short-lived experiment with fraternity rush. I felt a familiar inadequacy blanketing me—an un-ignorable signal that I was being warmly welcomed into the lowest level of a rigid hierarchy. Message received. I could stay, but I was not yet part of the tribe. Not yet one of them.
After a short 1:1 meeting, my head of sales walked me to my desk and plunked down a post-it note. On it was a phone number and two names: A person and an investment firm. He pointed to the post-it and said:
“Give this guy a call. See if you can get a meeting.”
My pulse quickened. I had just walked in. I was barely an employee. I had no training, no orientation, and no script. I didn’t know how much our research product cost, how it worked, or the sectors we covered. I was awash with uncertainty and fear. I wasn’t ready.
But this was the job. So I picked up the phone.
I don’t remember how I opened the call, but I do remember what happened 30 seconds into it, with the rest of the sales bullpen listening in, mere feet from my desk.
The guy hung up.
So I kept talking. Just me and the dial tone. The head of sales stood over me, casting a shadow of anxiety as I clumsily brought my one-sided conversation to a close. “No I understand… it sounds like it isn’t a fit,” I stammered into my handset. “But I appreciate you taking the time. I’ll send you a bit more on what we do, and I would be more than happy to follow up.”
I exhaled a quiet, raggedy breath. My face felt hot. I could hear my blood in my ears.
Welcome to your new job, kid.
Time to buckle up.
What Sucks About Sales
Thankfully, my first day in sales was also my worst day. Things got better. Eventually.
Over the next 6 months, I listened in on calls, learned what our customers cared about, and cobbled together a talk track about who we were, what we sold, and how our team could help. I booked a bunch of meetings, closed some deals, hired two teams of junior salespeople under me, and eventually ran a territory of my own before leaving to get my MBA. I figured it out. Eventually.
That’s the thing. Every good salesperson figures it out — eventually. But trial-by-fire stories like mine — cold starts with no onboarding, no guidance, no coaching — are all too common. Weirdly enough, we salespeople seem to cherish them. There’s pride in escaping the jungle armed with only a phone and a machete. Against all odds, you made it out. On your own.
But why start with the odds stacked against you? This is a business, not Naked and Afraid. The goal is to grow, not to simply survive. It isn’t fun for someone to stumble through their first 100 pitches without the context of what their prospects do all day. It isn’t smart to hand a new salespeople a territory without a plan of attack. A high bar should come with the resources required to meet it.
My first day in sales sucked for three specific reasons. They’re the same three reasons that any day, job, or career in sales can suck.
1. You don’t know who to call.
2. You don’t know what to say.
3. You sound like everyone else.
That’s it. If you’re a CEO, a CRO, a Head of Sales, or just someone intent on growing your business, you can’t just let these happen. Face and fix these problems, and a life in sales — and your team’s trajectory — can improve immediately. Let them persist, and your salespeople will flounder.
Sure, some will figure it out. Eventually. But by ignoring these problems and letting your team fend for themselves, you’ll be willfully complicit. Guilty of being asleep at the wheel. An accessory to the invisible crime of unfulfilled potential.
You’ll never know how good you could have been.
And that really sucks.
In the rest of this upcoming series, I’ll go deeper on “why sales sucks”, how to fix these three universal problems, and the simple tools you can use to rescue your sales team from their own character-building “figure-it-out” experience.
If you want to help your sales team ramp quicker, close deals faster, and achieve their potential, I think you’ll like where this is going.