Top 5 Sales Mistakes You're Probably Making

“A loss ain't a loss, it's a lesson

Appreciate the pain, it’s a blessin”

- Jay-Z

First off, as a sales professional you should be obsessed with constantly improving your skills. Unlike nearly every other profession, sales reps are paid based on their value to the company. The more valuable you are - the more you’re paid.

Now, think about all of the sales calls you’re currently making and answer a simple question - how much would you earn if you won 20% more of your deals? What about 40%? Yeah, it probably comes out to a lot of money.

That’s why every single call is an opportunity to get better. I promise that if you actually practice this mentality, you will grow personally, professionally, and of course financially.

Good news is that there are probably countless ways you can improve. The bad news is that it takes a lot of discipline and conscious effort. When I first started out as an entry level SDR at Citrix Systems, I was lucky to be surrounded by coworkers and managers that called me out on my shit. And trust me, there was a lot.

Sure, at the time it sucked hearing that I wasn't confident, sounded “too salesy”, or that I was scared to ask for their business. But six years later I'm pretty damn glad they did. Most of the time people don't know they're making mistakes, and sales people are no different.


Hands down the single most effective and easiest way to improve in sales is to listen to your damn calls. I promise you that no matter how perfect you think your call went, there are at least twenty things you could have done better.

Record your calls (most CRM’s and call systems have the functionality now), and listen to them. Religiously. Walking to Starbucks for your overpriced coffee? Listen to a call. Commuting to work? Listen to a call. Doing cardio at the gym? Listen to a call!

To make this even more effective you should be listening to your coworkers calls, especially the top salesperson on your team. But don’t stop there - listen to nearly everybody. I bet somebody on your team handles an objection better than you do, or pitches pricing in a way that’s more creative. There’s always something to learn.

The final (and most effective) step is to grab some coworkers and listen to calls as a group. Again, they might have some input that you have never thought of. However, this does require you to work with sales professionals that know what they’re talking about.


In college, everyone is beaten over the head to ‘sound professional’ and ‘communicate effectively in a professional capacity’ (whatever that means).

What they don’t tell you is that people buy from people. This means that you should just be yourself. Stop trying to live up to expectations of ‘sounding professional’ because it will simply come off as fake.

If you listen to your call recordings, there’s a good chance you’ll realize that you have a “phone voice”. If done properly, this can be great. However, most people end up sounding like a high pitched squirrel.

Next time you’re on a phone call - pretend you’re talking to your best friend. How would your voice sound? What words would you use? Now imitate that.

When I was selling software at Citrix, we were taught to investigate client problems for at least 20 minutes, and then offer a solution (conveniently, our product) for the next 30 minutes. That's exactly what most of us did, and it worked about 20 percent of the time.

Except Chris. Chris would spend 45 minutes talking about the most random things (mostly golf and fishing) with his prospects. The funniest part? Most of the time he didn’t even show the product we were selling!

Since people like to buy from people, they respected his authenticity. This built rapport and trust, which allowed him to deliver a great customer experience, and win more deals (over 50 percent of the time, actually). Chris had a conversation that typically went like this:

Prospect: So what about this Citrix ShareFile product you were gonna show me?

Chris: Oh yeah, I can definitely show it to you - but honestly I spend all day working with companies like yours, and I can say that it's gonna be a game changer for you. Want to go ahead and get your account set up?

Prospect: Sure, let me go grab my credit card.

This blew my mind. Here I was showing the same damn product demonstration every hour, and he's was spending his day talking about golf and some big ass fish that he caught? Time to start being authentic.


"Trust me boss, that deal is 100% coming in tomorrow night and it'll get me to quota. Bill gave me his word."

Sound familiar? I bet. Guess what? Bill's a damn liar.

Until the contract is signed, and the invoice has been paid, you don't have a deal. It doesn't matter what Bill told you, or how many promises you were given from their purchasing department.

This ended up biting me in the ass one month with a deal that would have gotten me over quota. I wasn’t worried, after all they promised the contract would be signed. You can probably imagine how it played out.

In fact, your prospect’s main job isn't to purchase whatever you're selling. It's to do their job. Your quota and the annoying call reminders ("just to check in") are probably getting in the way of that - and that's okay.

What's not okay is allowing your prospect to steamroll you. If you both agreed that something would be done by next Wednesday and it hasn't happened, then you need to find out why.

Sometimes this could be solved with a simple "Are you still interested in implementing this in your company?"

If you were authentic in your conversations, then you will have the trust and rapport to get a truthful answer. It's that simple. Sometimes they'll tell you the deal isn’t happening. And that's also okay.

If you're seeing this happen a lot with your deals, then maybe you're...


I strongly believe that at the beginning of a sales call you should make it obvious that's exactly what it is. You're not "just showing a product" and you're not a marketer that "just want to get their thoughts". You're a sales professional that's figuring out their pain points, offering a solution, and if it makes sense for them - you're going to ask for their credit card.

Not setting proper expectations is actually a clear sign of a larger picture - lack of confidence.

Confidence is one of the most important traits in sales. Hell, it's one of the most important traits in life. Why? Because it impacts everything. Not being authentic? Lack of confidence. Not calling your prospect out for going back on their word? Lack of confidence. Not setting proper expectations? Yeah you guessed it - lack of confidence.

You can set proper expectations pretty easily with something like:

“For today's agenda - I want to make sure I’m respectful of your time. To do that, I’d love to find out more about your business, figure out your biggest pain points, and then show you exactly how we can help. If you like what you see, we can talk pricing and implementation. How does that sound?"

You can be even more straightforward, but this at least gets your point across.

What if they're not comfortable with that? Then you should respectfully say you'll send an email with more info, because if you're wasting time talking to somebody that will never buy then you're..


This is probably the hardest to implement properly, because it actually requires a lot of discipline and hard work. But you can always control how hard you work.

For example, I've had a similar conversation more times than I can count:

Great Rep: I don't know what's going on, my pipeline is completely empty. Maybe it's just seasonality?

Mediocre Manager (me): Yeah, maybe. How’s your prospecting going?

Great Rep: Oh I didn’t think I had to, since there were so many opportunities at the beginning of the month

Mediocre Manager (me): So did you backfill them with calls?

Great Rep: About that...

Your pipeline is the result of the last 30 days of your prospecting. Let me say that again. Your pipeline is the direct result of the last 30 days of your prospecting.

If you have an empty pipeline, it's because you stopped picking up the phone. Sorry to break it to you, sweetheart. Sometimes seasonality and budgets do play a role. But you can control how many calls you've made. Plus, what are you doing in sales if you aren't willing to outwork everybody?


Hopefully you've enjoyed reading (skimming) this post, and can crush your quota by implementing some of these tips.

Interested in hearing about a specific topic? Leave a comment and I’ll try my best to cover it in a post. Feel free to share this post!

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- Mark

#sales #advice #coldcalling #closing