I have made so many mistakes working in sales.

All for good reason though… so I can share those experiences with you and help you avoid them at all cost.

Yes, these mistakes lost me business but they also taught me valuable lessons that I will never forget.

When I first got my start in marketing/sales- I was in a call center. I came into that cubicle with a hot head on my shoulders from the aggressive interactions I had on the car lot.

Let’s just say- the pushy salesman was a BIG no when customers could quite literally hang up on me.

Scroll down to discover the 7 mistakes you should avoid at all cost while working in sales:


Seems simple right!?

Not so fast. Have you ever really listened to someone and if so how often do you do it?

Some people are naturally gifted at this and usually they are low-toned, quiet individuals, who are less outgoing. Not exactly your run of the mill candidate for working in a sales job.

Listening did not come naturally to me, but it is absolutely vital to your success in sales.

When I got my start in small business marketing selling over the phone, my trainer was working with me and he started timing how much I was speaking during each call. Once in an eight minute phone call, I spoke for more than six minutes of the conversation.


This was a huge wake up call, I needed to let the prospect speak and part of getting that person to speak involved not just dialing back the “Chatty Kathie” inside me but it also required asking the right questions.


This comes down to open ended responses vs close ended ones.

How, what and why.

These are your bread and butter in a sales conversation.

It not only helps you get discovery started quickly and easily but it also keeps your client talking and allows you the time you need to strategize what to say next.

Back at the beginning of my time working over the phones selling, I would say “So you want to send some emails?” The answer is obvious, “Yes.” This left me dead in the water.

Instead when I asked “Why do you want to send emails?”

The answer was not close ended. It opened an opportunity for the prospect to think, respond, and engage authentically.

Some of the things my prospects would say is “I have a launch of my new website that is about to happen and I really need to get the word out,” or “I have a lot of customers coming into my store but once they leave it is hard to get them back in the door.”

Both of these answers created leverage for me in the conversation.

In the first example this information the client provided would help me to know they have a deadline.

A deadline for the launch of their new website and they wanted it to go smoothly. In order for that to work they needed an email marketing company to help them get the word out and fast.

The first example highlighted their time line/urgency; and in the second example I discovered the pain point: they are struggling to get repeat business.

Ask the right questions, get them talking and pay attention for the pain points, so you can use it as leverage later on in the interaction.


Businesses and individual customers move quickly when it is finally time to make the purchase.

Be on time with your follow up.

If you tell the prospect you will be calling at a specific time, have a calendar that you fill out immediately and one that reminds you when that time frame arrives.

Set that sucker to go off five minutes early so you have time to finish up anything you are working on in that moment.

Then do yourself a favor and call that client immediately!

Additionally, this is a great way to build trust and respect.

My team listened back on a sales call by one of our top reps at our company wide training and the first thing the prospect said was “I didn’t think you were actually going to call me.” He responded by saying sarcastically “Of course, I’m on top of this kind of thing and I mean business.”

The call immediately transitioned into gathering payment information.

Don’t be like me all those years ago, with a calendar that was mismanaged, not attended to and poorly utilized.

Be responsible and call your leads when you say you are going too. It could mean gaining a sale or completely squandering a perfectly good opportunity.

The competition knows how to use a calendar.


When I was working in application sales I was involved with a prospect in an attempt to bring his restaurant onto my marketing application but he was a difficult client to work with. He made it hard to build value.

I could tell he was just nodding his head in hopes I would end the meeting and leave.

He told me he needed to redo his website before he could consider my platform and to follow up in a few weeks. I had my doubts about this one.

I got in touch with him a few weeks later, the stuff about his website didn’t really seem to matter anymore and he was clearly “Keeping me on the hook” if you will.

He told me that “I could follow up with him in a few months if I wanted.”

I immediately responded, “No, I actually don’t want to follow up with you in a few months if you aren’t actually interested. I don’t do that, your time matters and so does mine. Are you at all interested in growing your business with my app?” He immediately told me that he wasn’t really that into the whole idea and I told him to take care.

The point to this story is, sometimes you just need to let go.

You can’t win them all and in sales that happens far more often than anyone would like to admit.

In the past I would hound customers that I knew in my heart were not going to buy.

I would leave them voicemail after voicemail and endless emails. I was holding onto hope and that death grip that I had was interfering with me focusing on those people that actually wanted to work with me.

Prospects are far too nice and they will not tell you the truth. Sometimes you have to ask and in this situation I did. I could have easily followed up with him in a fews months but why? Just so I could find out what I already knew. The chances of anything changing were slim to none.

If you know in your gut that person is not going to buy, allow yourself to be frugal about how much mental capital you are willing to part with.

Mental capital is the currency of your own mental health. Selling can take it out of you, why waste time on someone if you don’t have to. I am not saying never follow up again, but read your audience and remember that at times it is okay to be conservative.


This one is important.

Know your customer, the type of person that you sell to on a regular basis and pay attention to what they consistently say as objections to your product/service.

When I worked for the mobile application that I mentioned earlier and brought on busy restaurant owners to host content and drive in traffic with my app; I put in a ton of work behind the scenes to prepare for objections.

I wrote out each objection and then thought up the best cushion response and rebuttal to help neutralize the situation smoothly.

Initially I heard “I don’t want to discount my food” from several restaurant owners. I didn’t know how to respond and ultimately I’d walk away without a sale, and without a good response. I felt embarrassed and disappointed like I hadn’t properly prepared for the conversation.

This is your job, you know those objections are coming so be ready for them.

Write all the most common objections down and practice your rebuttal to them in the mirror several times a week or when you are driving home from work. Anytime you can talk to yourself without interruption is best.

Better yet, practice them with someone if they are willing.

You will want your response to come off naturally even though it’s rehearsed, so you will want to know these rebuttals like a second language.

l guarantee you this will help you transition a potential prospect to an eventual paying client.


This one piggy backs off the last one.

If you sell high ticket tractors to farmers, sell like a farmer.

If you sell beauty supplies to older women in a department store, sell like a refined, classy, older lady.

If you work in B2B sales and you work with countless people in one decision making process, sell like a business owner.

A good example of what not to do- Don’t spout off product details on rapid fire to a business owner who has zero time on their hands, over-complicating the sale and confusing the prospect so much they just hang up the phone.

Small business owners wear many different hats in their business and probably have quite literally NO TIME TO TALK TO YOU. Hook them with intriguing information at the beginning, figure out 1-2 pain points and solve them with a quick solution utilizing your product.

Don’t tell them anymore than what they need, and don’t make it sound complicated, they don’t have time for complicated.

Know your audience, respond to their unique needs and be ready ahead of time to predict how they are going to behave.


Sales is a grueling activity.

Some days, no matter how you spin it, you have to be willing to take the heat.

There will be many ups and downs. It is vital that you can hold your head up and continue pushing forward.

I regretfully have let customers get under my skin from time to time.

One time I ended a confrontational conversation at the call center and scoffed loudly with an obnoxious exhale.

My manager approached and asked what the problem was, I expressed my frustration and he, of course, had zero sympathy to offer stating “This is a sales job, you’re just going to have to get over it.”

That is exactly it, when you work in sales, it is a lot like being a gold miner.

Did any gold miner ever discover gold after digging for just the afternoon?

Did a gold miner ever find gold talking about how much was hiding underneath the top soil and how they were destined to find it?


This is where the rubber meets the road or in this case the shovel meets the ground.

A gold miner just keeps digging. A gold miner puts in the work through so many countless days of nothing but dirt in order to find the gold.

They didn’t curse the heavens every time it didn’t happen, they just kept digging, until it DID happen.

Sometimes whether it’s a door to door sales job, a car lot or a pipeline inside an online database, no matter how you get your leads, you are going to come up on a ton of bad ones before you get to the gold. That’s okay!

That’s to be expected, and this took a long time for me to realize.

Instead of expressing my frustration with my manager I should have ended the phone call, reflected on what I could have done better and immediately gone back into my pipeline and started dialing.

You have to get through the NO’s before you get to the YES’s

There you have it, my top 7 things you should avoid at all cost working in sales. I hope you will take this information and consider your own process, are you making any of these same mistakes?

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