TT#007 - A couple online sales bloopers (and how to avoid them)...

Apr 19, 2022

I’ve been in sales for 20 years, so I tread lightly when it comes to calling out shitty sales practices. We’ve all been guilty of slip ups, mistakes, and bad days, right?

But, we can learn from other people’s mistakes.

Why are they mistakes?

Why were they made?

How do we avoid them?

It’s for that reason that I’m going to share a couple online sales bloopers with you.

Each of these is representative of something I see quite a bit. So, I’ll share what happened with context, why it’s a mistake, why that mistake is usually made, and how you can avoid ending up on this list.

Out of respect for the sales profession, and knowing I’ve made plenty of mistakes in sales myself, I’ve protected the identity of the people and companies whiffing at these sales tactics.

Blooper 1: How not to get calls scheduled with Sell By Chat...

Sell By Chat (SBC) is selling via direct message, chatbots, email, SMS, and other text channels. The typical SBC playbook consists of casually opening up a conversation, qualifying a prospect, and closing right there in the chat, or booking a sales call to continue the conversation.

Here’s how not to do this...


Ok, so far, not bad. It’s a couple of casual messages with a bit too much time in between, but a good introduction and follow-up trying to elicit a response.

Then, with no additional action taken from me...

He promised he wasn’t trying to bother me in his second message, yet here we are.

3 things to note at this point:

  1. If you open SBC conversations with statements like, “...not trying to bother you I promise...” and, “If you’re not interested, no worries and I hope you have a great day...” and continue following-up despite no response, you violate trust with prospects.
  2. If prospects don’t respond to layup questions as simple as, “Is there anything specific you were looking for?...” don’t escalate to personal questions that are more difficult to get answers to.
  3. When you make inaccurate assumptions about a prospect, such as they are struggling to get in shape, and you’re wrong... you destroy your credibility forever. Ask clarifying questions before making statements that make you look stupid.

I’m a sales professional and I’ve helped build SBC processes and playbooks. So, out of respect I reply and politely let this person know I’m not struggling to get in shape.


And we could’ve ended things well there, right?

Yes, but 2 minutes later…


Wait, what?

Why in the hell would you send me a calendar invite? Better yet, why would you want me to use it if I said I don’t have a need for your product or service?

Keep in mind, all I’ve done at this point to indicate any interest is look at this person’s profile (because they are in my target audience to sell to) and inform them that I don’t need their services.

So, I asked why they sent a calendar invite to me.

So, at some arbitrary point in the future when I’m no longer in shape, and I’m struggling with fitness, I’m going to remember this conversation, rifle through my direct messages on LinkedIn, and find this link to ask for your help?

Let’s recap our SBC blooper...

Why is this a mistake?

It’s a smart move to engage people that view your profile on LinkedIn. However, you have to put this in context. This may or may not indicate interest. And treating someone that may have stumbled on your profile like a high intent buyer is like assuming the girl who may have been looking at you across the bar is ready to go home with you right now.

Don’t be that person.

Not only are these subpar sales practices, they put you at risk on platforms like LinkedIn because it’s easy to flag you as a spam, which gets your account shut down.

Overall, the tactics here violate trust, erode credibility, and hurt this person’s brand.

Why does it happen?

The primary reason conversations like this happen is a misunderstanding of what the real goal is.

All too often I see salespeople and processes so fixated on activity metrics, like number of booked calls, they lose sight of the real goal, which is quality conversations with qualified and interested prospects.

In this example, the worst case scenario is that I book a call. I’m not qualified or interested. So I’m a waste of time.

Getting a call booked may give you a dopamine hit, but dopamine hits don’t pay the bills.

How do you avoid it?

You avoid these types of bloopers by engaging people with strategic, targeted questions that are easy to respond to. Then leverage that engagement to qualify, conduct discovery, and move interested people through your sales process.

Most importantly, listen to what they say. Avoid getting so fixated on the “next step” in the process that you lose sight of where that step is supposed to take someone.

Blooper 2: Automation gone wild...

Like it or not, automation on social media platforms is increasingly common.

You can use automation to scale finding new connections, opening up new conversations, and executing full-on drip campaigns.

That sounds great, until your automations make you look bad.

Let’s see how that plays out here...

Well, this is great for me, right? I have a prospect interested in my coaching programs.

Excellent, let’s chat.

Then, 4 hours later…

Uh oh, looks like there’s a ghost in the automation machine.

Automation isn’t AI. It’s efficient, but it’s not very smart. And unfortunately for Gabrielle, it doesn’t make her look very smart either.

Here’s what I mean:

  1. There’s no response to, or acknowledgment of, what I said. Because there can’t be. It’s automated. So it comes off as awkward (at best).
  2. It takes one click to see that, yes, I have thought about packaging my knowledge into a course and selling it worldwide. In fact, you can buy some of that knowledge right here. So if I thought this was a real person, I’d think she was lazy.
  3. It’s a sales pitch disguised as an inquiry about my services. Pretending to be interested in someone’s services in order to create an opportunity that allows you to pitch your services is misleading, shady, and ineffective.

So, I don’t respond.

Then, the following day...


Hell yes! Let me jump at the opportunity to hop on a call and learn how to sell just like this.


Let’s recap our automation blooper...

Why is this a mistake?

Gabrielle’s initial outreach was really creative and strategic. By asking for information about my coaching services, she’s qualifying me as a coach.

She’s also using a question that has a very high likelihood of getting a response. As a coach, if someone is asking about my services, they’re going to get a response.

But it’s deceptive. And it doesn’t work. Most rational people aren’t going to buy from you after being duped by you.

The tactics are clever, but violate trust, erode credibility, and hurt this person’s brand.

Why does it happen?

There are two mistakes to address here.

First is the conversation starter that’s misleading. This happens when people are either too lazy or not creative enough to come up with ice breakers that work without pretending to be a prospect.

Second is the automation that fails to deliver an authentic vibe of a conversation. This happens when people exchange efficiency for effectiveness. Automation can certainly reply to more people than you can manually, but the tradeoff isn’t worth it if conversations go like this.

How do you avoid it?

One obvious way to avoid this type of blooper is to not mislead prospects into thinking you want to buy their stuff. Invest the time into coming up with ice breakers that are both effective and not slimy. Easy enough.

Another obvious way to avoid this type of blooper is to simply not use automation.

But automation can be an effective tool, when it’s used properly. Using automation properly means recognizing its advantages and its limitations. For example, you can use automation to start conversations, and step in to engage when someone responds.

Conclusion & Takeaways

There you have it. A couple online sales bloopers and how you can avoid them.

Key takeaways:

  1. Don’t lie, mislead, or be deceptive.
  2. Don’t be shortsighted in your sales process.
  3. Don’t become ineffective in order to be efficient.

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