5 Pieces of Terrible Sales Advice (& What to Do Instead), According to Coursedog's Director of Sales

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Zach Drollinger
Zach Drollinger


Welcome to "The Pipeline" — a weekly column from HubSpot, featuring actionable advice and insight from real sales leaders.

salesperson receiving terrible sales advice

As a salesperson, you've probably gotten your fair share of career advice — and it goes without saying that some of those tidbits have definitely been more valuable than others.

Sometimes, the insight you get can help you shape more sound, thoughtful sales efforts — giving you a framework to help you better understand your prospects and how to cater to them. But there's a flip side. Some insight you get winds up being dated, disjointed, or detrimental to your overall sales acumen.

So to help give you perspective on some fundamentally flawed sales advice, I‘ve compiled five terrible sales tips that might put reps on the wrong course — along with the necessary wisdom to set them straight. Let’s dive in.

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5 Pieces of Terrible Sales Advice (and What to Do Instead)

1. “You want to cast as wide a net as possible — prioritize volume over personalization when communicating with prospects.”

The Bad Advice

“Sales is a numbers game, above all else. You're best off throwing everything at the wall and seeing what sticks. A solid mass email blast is going to generate the highest volume of productive responses — prospects don't care whether or not your email went to a billion other people. The soundness of your general messaging and the quality of your product will speak for itself.”

The Right Advice

Sales is an inherently personal practice, so naturally, prospects are going to be most receptive to communication that has some kind of personal touch. Very few (if any) prospects are going to respond to a sales email that brings “to whom it may concern” energy.

Do your homework. Conduct some research to get a sense of who your prospect is, their role at their company, what their business does, and what their organization is up to.

This doesn‘t mean you have to scour their Instagram and reference their last vacation (as we’ll cover later in this post) — but being able to reference something like a recent career milestone or a piece of content they've published can go a long way in potentially generating a productive response.

2. “Haven't you seen Glengarry Glen Ross? Always be closing, baby!”

The Bad Advice

“No way. Shut up. You haven't seen Glengarry Glen Ross? And you're in sales? Are you kidding? Al Pacino, Alan Arkin, and Ed Harris? What about Alec Baldwin's speech? Come on, man. You have to know that scene — the one where Alec Baldwin says 'Second place is a set of steak knives,' and then tells all of the guys in the office to 'Always be closing.' That's how you sell. That's how you live. I'm not kidding, dude. I literally structure my entire life by those words.”

The Right Advice

It might be a hot take, but I‘m of the school of thought that the "always be closing" mentality is dated at this point. The high power, low empathy approach that the mindset entails doesn’t really play with the modern buyer.

“Always be closing” revolves around being aggressive, extremely persistent, and consistently on the hunt for the next new customers. It positions a salesperson as an external force that pushes a prospect through a sales process.

But buyers today are much less receptive to that kind of pressure than they used to be — they're more interested in a salesperson acting as a helpful, consultative resource who assumes more of an advisory role in a sales engagement.

Aim to educate your prospects and tailor your approach to suit their personal interests and preferences. It's obviously easier said than done — but you can get there by leading with empathy, understanding where a prospect is in the decision-making process, practicing active listening, conducting research, and ultimately aligning your efforts with their specific pain points.

3. "Never take ‘no’ for an answer. Prospects always respect persistence."

The Bad Advice

“Prospects respect a salesperson who keeps at it. Don't take 'no' for an answer — so much of sales is about powering through.”

The Right Advice

Now, the right advice here isn't to not be persistent at all in sales. You want to approach sales engagements with assertiveness and gumption — and that generally means not tucking your tail and retreating at the first sign of friction.

Objections are par for the course in any sales effort — so when you get some pushback, you need to be prepared to entertain, diagnose, and ultimately remedy the pain points prospects might bring up. And doing that often takes some thoughtful, measured persistence.

But there's a fine line and massive difference between “thoughtful, measured persistence” and obnoxious hounding. And in many cases, that line is the word “no” — especially when it's repeated.

It‘s not your job to force a relationship with a prospect when there’s no potential there, and a buyer is much more likely to circle back after doing some more research on their own time — and if you don't respect their boundaries the possibility of them “circling back” is going to disappear.

4. “Under-promise, and over-deliver.”

The Bad Advice

“If you set expectations low, you look great when you deliver results that inevitably exceed them. Prospects won't know any better — and you'll position yourself as someone who goes the extra mile with an offering that works especially well for them.”

The Right Advice

You should never make excessively lofty promises to prospects to posture and hype yourself up, but you don't want to radically undersell yourself either — doing that is disingenuous and ultimately detrimental to your efforts.

It can be tough, but this is the best advice I have on this front — promise realistically, and work hard to deliver more.

Let's consider an extremely streamlined example — imagine you sell curriculum scheduling software, and you‘re working with a regional college in the southwest called XYZ University. They’re interested in your software and struggling with class scheduling conflicts.

Let‘s say you’ve sold to institutions of similar size and structure in the region before. Some of those schools also used the same kind of legacy curriculum scheduling platform that XYZ does. In your experience, those similar institutions have reduced scheduling conflicts by an average of 60% with your software.

When selling to XYZ University, you wouldn't want to sell on the basis of, “We can likely reduce scheduling conflicts at your institution by 40%” — hoping that they'll see the results you actually expect and be so impressed that they say, “Gee whiz! Look at those numbers! We're never going to churn! Yippee!”

In doing so, you might immediately sell yourself too short or read as shifty. Instead, trust your solution, sell honestly, and work to produce results that are as impressive as possible.

5. "Get personal when researching prospects — really let them know you did your homework."

The Bad Advice

“Do your homework as thoroughly as possible. Get to know a prospect on a deeper level before you engage with them. Take a look at their personal social media, and be able to reference certain aspects of their life like a friend of theirs would. People trust the people who know them intimately!”

The Right Advice

Thoughtful, well-structured sales communication is central to establishing and sustaining productive relationships with prospects — and having a sense of who a prospect is, how their business is faring, and how their organization presents itself are all key on that front.

And in many cases, having a tidbit of slightly more personal information to start the conversation or keep things interesting is a good move — but if you go that road, you want to still keep things professional.

There's a difference between congratulating a prospect on a recent promotion or complimenting a piece of content they published and asking them whether their kids — little Tanner and Shawna, those gosh darn adorable goofballs who look just like their mom — enjoyed their recent family vacation to Cancun that you saw pictures of on Facebook.

At the end of the day, sales engagements are professional interactions — don‘t lose sight of that by getting overly personal. In most cases, demonstrating an intimate knowledge of a prospect’s life creeps them out more than it impresses them.

Now, the terrible advice I listed here might be a little overblown — but at each one's core is an issue that a lot of sales reps might struggle with. Hopefully, this list will offer sales professionals some perspective to help them better cater to, assist, and ultimately delight their prospects.

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