5 Things I Didn’t Know I Was Doing Wrong In Sales

For 6 months in my first sales role I thought my sales manager was my enemy.

I battled with him almost daily to prove I was, as he would put it “man enough for the job”.

He was bald, angry and a little bit psychopathic.

He would slap my back so hard that it hurt my belly when I closed deals and stare me down into a seeping puddle of embarrassment when I lost them.

He attempted to get me riled up to the point of testosterone shooting out of my eyeballs each time we spoke but all he did was the opposite.

I would avoid wanting to speak to him at all costs, never mind ask him for assistance.

Which is the whole point of his job. To help his sales team hit their targets (so he can hit his own).

It took many months for me to tell him that his style of management wasn’t working and that I just wasn’t naturally as angry as him. Instantly we had rapport for the first time and he became a huge asset in helping me succeed.

From helping out with sales calls when I was getting overwhelmed to managing the internal staff when I’d yet again not done my monthly paperwork, he took a huge weight off my shoulders when I stopped trying to battle him on phone call.

Here are 4 other things I didn’t know I was doing wrong in sales that you might be doing too –


A) I didn’t track my electronic communication

I now use ClearSlide (partner of the Salesman Podcast) to track when prospects open my emails, read the documents I’ve sent them and most importantly it gives me the analytics to know when people are ready to close the deal.

For a number of years I didn’t track any of this and I was constantly being reactive and predicting where my prospects were within the sales cycle.

I had no data other than what they were saying (which is never reliable) to put close dates in place within my CRM.

clearslide engagement salesman

Now with ClearSlide I can see when there are flurries of open activity, when the emails are getting opened by other people higher up the decision food chain and a whole bunch of indicators which tell me now is time to close the deal.

Additionally as I’m sending way more content to prospects as is the most powerful tool that salespeople have to keep communication open with their customers, I couldn’t live without it.


B) I didn’t hustle hard enough

When I worked in medical device sales I used to think that making cold calls at 4pm on a Friday was hustle.

I remember thinking this because no-one within the NHS would answer the phone after 3.30pm on a Thursday as they’d be “wrapping up for the weekend”.

I felt like I was pushing myself hard in comparison to the people I was selling to (which was never a good indicator).

I then starting spending more time with a salesman called Steve.

Steve would be in hospital theatres, after traveling to the other side of the country, at 7am on a Sunday morning to help surgeons with their new equipment.

He would work 7 days straight and never complain about it at our weekly sales meetings. He would embrace it.

That year he earned £90k more than me and in my mind, it really put his hustle into perspective.


C) I didn’t plan far enough ahead

I still have this problem now.

Even with years of sales experience and the vision of hindsight I still close a way higher percentage of deals when I’m hungry.

This isn't my Maxda RX8 but those are the side skirts that will be going on mine soon.
This isn’t my Maxda RX8 but those are the side skirts that will be going on mine soon.

I don’t mean physically hungry, I mean when I want a new part for my RX8.

Or when I’ve an opportunity to travel to record a Salesman Podcast episode in person but there isn’t the budget in the company bank account.

3/4 days later I’ve closed enough deals to make it happen.

But why didn’t I do this in the first place? It’s because I don’t plan my pipeline far enough a head.

I’m likely leaving thousands of dollars worth of commissions on the table by doing this.

And I’m still slightly guilty of doing this now.


D) I didn’t develop long term relationships

For many years all of my deals were one offs.

I think this is a classic, green salesman mistake. I would close one deal, get the invoice paid and then instantly move to the next prospect on my list.

I assumed that once I’d secured the deal and collected the funds it was down to the company I worked for to service the customer.

We had a customer service and fulfillment team for a reason, right?

What was the point in paying them good money to sit in an office all day if I had to keep in touch with the customer and make sure they were happy.

“If we can keep our competitors focused on us while we stay focused on the customer, ultimately we’ll turn out all right.” ― Jeff Bezos

How dumb was I!

Selling more products or services to existing customers is approximately 999993% easier than chasing brand new ones. Your company has given you a sales target to hit and they don’t care  how you do it.

These days you are much more likely to see me calling a current customer and laughing about what their kids have been upto over the weekend or gossiping about that new Mazda rotary engine that has been rumoured than me cold calling for new business.

The most important thing I’ve learnt about sales over the past 12 months is that if you look after your customers, they will look after you. 

They want you to succeed as you are helping them make money too!



Will Barron is the founder of Salesman.Red and host of the Salesman Podcast where he entertains hundreds of thousands of millennial salespeople every month. If he isn't recording or editing shows he's racing his RX8 or riding bicycles down mountains.

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